Home Vacation Rentals By Owner In Key West, FL

Showing 20 Of 1997 Vacation Rentals
Slider Thumb

$669.38

/ Nightly
Condo

WATERFRONT PENTHOUSE! Galleon Resort Key West, Sleeps 6, Private Beach

Key West, Florida, United States

WEEK 39 PENTHOUSE UNIT D-51 ! 9/26--10/3/26.brEnjoy 7 nights in downtown Key West at The Galleon Resort!brbrThe Galleon Resort is located in the heart of Old Town Key West in the Historic Seaport District. This resort overlooks the Gulf of Mexico with a private marina, private beach, pool, hot tub, with a restaurant and tiki bar. Relax in the hot tub or workout in the onsite fitness center. Enjoy fishing off the dock, or rent bicycles and take in all that Old Town Key West has to offer.brbrMel Fisher Museum, Mallory Square and Duval St are just a 5 minute walk from this conveniently located resort. The Ernest Hemingway Home & Museum is 1 mile away.br.brWe have one week to offer in 2026 with guaranteed unit number as follows:brWeek 39, 9/26--10/3 is Unit D51 PENTHOUSE marina side unit. The 2nd bdrm here has two twins that can be pushed together to make a queen.brbrOverlooking the marina and historic seaport. This two bedroom condo sleeps six, and features a fully equipped kitchen. The primary suite has a king size bed, jetted tub, shower, two vanity sinks and large closets. The guest bedroom features either two twins and has access to the full guest bathroom with a shower. The living room has a TV with cable, dining area for six, and a queen sleeper sofa. Large balcony from the living room overlooking all of the boats & restaurants in the marina.brbrOther than the rent paid to VRBO, there will be a $80 resort fee to be collected by the front desk upon check in. This is in addition to the rent already paid. A $150 refundable security deposit is also secured on your credit card and is released by resort after checkout as long as no damages occur during your stay.brbrOne free mid week cleaning! Housekeeping changes linens and towels on Wednesday only at no additional charge. If daily housekeeping is desired, there is an additional fee imposed by the resort.brbrParking for one vehicle, per unit only. No oversized vehicles, RV's or trailers are allowed to park on property. Parking is extremely limited and multiple vehicles are not able to be accommodated.brbrMinimum Age: 21 years oldbrPet Policy: No PetsbrAn ID and credit card for a refundable security deposit will be required.brCheck-in is after 4 pm;brcheck-out by 10 am.brNo Smoking. Penalties will apply.brNon-Refundable Cancellation and Refund Policy:br$80 Resort Fee Due at Check-in *Pricing Subject to changebrGuest check-in certificate will be email to you directly from the resort once VRBO releases full payment to me, the owner.brPlease look over the lease document uploaded in VRBO.brbrNote that we do not accept liability for any inconveniences beyond our control including but not limited to temporary defects or outage of utilities, closures of resort amenities, or limitation of any other service. We will not provide refunds, reimbursements, or compensation for inconvenience or interruption of utilities, resort amenities, or any other service. Trip/Vacation insurance is highly recommended and may be included as part of VRBO's fees.brbrPictures are representative of the unit, layout and decor may vary.
Bed 2

Bed

Bath 2

Bath

Sleep 6

Sleeps

Slider Thumb
Exceptional(4)

$202.02

/ Nightly
Condo

Stunning Ocean View 2BR/2BA Condo in Exclusive 1800 Atlantic Community

Key West, Florida, United States

CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 AtlanticbrStart Date: May 2025-Estimated Completion: Spring 2026brPlease be advised that a balcony restoration project will be underway at 1800 Atlantic from May 2025 through Spring 2026.brImportant Notes:br-Units available for booking will not be under construction.br-All amenities, including the pool, spa, and sunning beach, will remain open and fully operational throughout the project.brbrbrbrbrStunning Ocean View 2BR/2BA Condo in Exclusive 1800 Atlantic CommunitybrbrWelcome to your beautifully renovated, second-floor oasis in the prestigious 1800 Atlantic community in Key West. This stunning 2-bedroom, 2-bathroom condo features custom tile work throughout, an expansive private balcony, and breathtaking views of the Atlantic Ocean and lush gardens.brbrThe primary suite includes a luxurious king-sized bed, while the guest bedroom offers two twin beds that can be converted into a king upon request—ideal for families or couples traveling together. A queen sleeper sofa in the living room adds extra sleeping space, and all rooms are furnished with brand-new beds for maximum comfort.brbrThe fully equipped kitchen, in-unit washer and dryer, high-speed internet, and cable TV ensure all the conveniences of home. A dedicated desk area allows you to send a postcard or take care of work while away.brbrStep out onto your private balcony and enjoy al fresco dining with ample seating and tranquil views of nature and the ocean. Relax in the Olympic-size heated pool, unwind in the large hot tub or sauna, or take advantage of the lighted tennis courts and nearby beach access.brbrLocated close to Key West’s vibrant nightlife, city center, and airports, this condo blends the perfect balance of serenity and accessibility. Ideal for families, couples, or business travelers, this property is available for monthly rentals.brbrResort-Style Amenities Include:br Heated Olympic-size pool & jacuzzibr Sauna & tennis courtsbr Lush tropical landscapingbr Secure, exclusive community settingbrbrYour tropical escape awaits—book your stay today!
Bed 2

Bed

Bath 2

Bath

Sleep 6

Sleeps

Slider Thumb
Exceptional(3)

$224.24

/ Nightly
Private Vacation Home

Booty Caye - Fun & Energetic - 2BD/1.5Bath - Golf Club Drive

Key West, Florida, United States

Escape to your private oasis at Booty Caye, nestled within the exclusive enclave of the Key West Golf Club. This beautifully appointed 2-bedroom, 1.5-bath condominium offers a lively retreat for those seeking a longer stay amidst the lush landscapes of a golfer's paradise. With a minimum lease of 29 nights, indulge in the serenity of island time and the luxury of a thoughtfully curated home.brbrFrom the moment you step in, the dynamic, colorful tiles on the staircase set the tone for a home that's as lively and vivacious as Key West itself. The terracotta tiles underfoot keep the vibe warm and inviting as they sweep through a living space that's open, airy, and eager for entertainment.brbrThe heart of the home, a fully-equipped kitchen, boasts sleek, modern appliances juxtaposed against the classic subtlety of white subway tiles. A commercial-grade refrigerator, dishwasher, and a large electric flat-top stove/oven stand ready to fuel your culinary exploits, while the adjacent dining area, with seating for four, promises intimate dinners or a spot for engaging conversation. This is complemented by additional deck seating for al fresco moments.brbrUnwind in the living room, where a plush sofa invites you to enjoy your favorite shows on a 77-inch Smart TV, or transform it into a queen-size sleeper for visiting guests. brbrAscend the spirited staircase to the tranquil haven of your bedrooms, each boasting plush queen-size beds and ample storage. The front bedroom extends the invitation to the outdoors with a private balcony, an idyllic nook for solitude and reflection. For entertainment, a guest room has a projector screen, ready to turn any night into a movie night.brbrThe gated community ensures privacy and security, with the added convenience of your own parking space.brbr* Dive into two inviting pools.br* Explore a whimsical butterfly garden.br* Keep active in the fitness center.brbrVenture beyond the gates, and you're just 15 minutes from the pulsating heart of Key West—Duval Street and the Historic Downtown Seaport. Here, the spirit of the Keys is palpable in the bustling streets, brimming with local eateries, boutiques, and cultural landmarks.brbrAt Booty Caye, every detail is curated to create an unforgettable vacation experience—where luxury meets comfort, and the charm of the Keys is your daily reality. Book your month-long stay and let Booty Caye be the canvas for your Key West memories.brbrImportant Notice: Some booking platforms may not correctly display our security deposit requirements. This contract is based on a $125 non-refundable damage protection plan in place of a $5000.00 refundable security deposit; if you prefer to pay the $5000.00 deposit instead, please let us know. brbrGuests are subject to a 2% credit card processing fee. In order to avoid that fee, we encourage you to pay by check. brbrLocated inside the gated Key West Golf Club communitybrPets consideredbrCommunity Poolsbr15 Minutes to Duval Street/Historic Downtown Seaport
Bed 2

Bed

Bath 1

Bath

Sleep 4

Sleeps

Slider Thumb

$178.12

/ Nightly
Private Vacation Home

The Coral Cottage in Historic Key West

Key West, Florida, United States

Spend time in beautiful Key West and live like a local in a true Conch Home!brbrThe Coral Cottage is perfect for groups with 4 guests and a furry friend. A fully-renovated 2 bedroom, 2 bath home on the 1st floor.brbrLocated in an historic local neighborhood in downtown Key West near beaches, parks and cafés. Enjoy beautiful foliage on your private porches with seating and a grill.brReserve its sister cottage, the Sea Glass Cottage, to accommodate parties of 8-10 in separate units within the same home.brbrThis is a beautiful, floor fully-renovated (2022) home with a classy coastal beach house decor with wood floors, lots of windows, and an open floor plan for entertaining indoors or on the large porch with a grill and views of the garden and flowering fruit trees.brbrWe offer free, off-street parking, however, our central location allows for biking or walking as well.brbrThe living area has high ceilings, a 70 flat screen Smart TV, a comfortable couch and seating and a dining table all adjacent to the kitchen which is fully equipped with stainless appliances. There is a Keurig coffee maker and a full range of appliances and kitchen tools for your cooking needs.brbrThe AccommodationsbrbrThe beautifully appointed bedrooms include one king and one queen-sized bed, dresser, night stands, and a 65 inch flat-screen Smart TVs with large windows and closet space.brbrThere is lots of natural light with beautiful windows with views of our foliage and fruit trees. The two completely renovated large bathrooms have showers and a full-sized washer and dryer.brbrThe AmenitiesbrbrThree split unit ACs, Washer/Dryer, three flat-screen SmartTVs, wireless high-speed internet throughout the property. Fully-appointed kitchen. Linens, bath and beach towels provided. This property has ample off-street parking, a large porch with seating and a grill, and will accommodate four guests along with your furry friend!brOther things to notebrAccess to the pool at our sister property is also available.
Bed 2

Bed

Bath 2

Bath

Sleep 4

Sleeps

Slider Thumb
Exceptional(87)

$1149.3

/ Nightly
Private Vacation Home

**CASA SERENDIPITY @ OLD TOWN** Historic 3BR/2BA Home & Pool + LAST KEY SERVICE

Key West, Florida, United States

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!brbrSometimes in life a 'stroke of good fortune' leads you to discover something so delightful at a moment when you're not even looking for it. When strolling through the streets of Old Town Key West, you may be fortunate enough to stumble upon a home with the perfect combination of quintessential charm and the conveniences of modern amenities. CASA SERENDIPITY is a tastefully restored historic home featuring every coveted amenity you can think of: an unbeatable location, spacious indoor and outdoor living areas, a private pool, a fully equipped kitchen, off-street parking, and a classic wrap-around porch. CASA SERENDIPITY coupled with Last Key Realty's Five-Star Guest Services is a recipe for a Key West vacation that you'll be treasuring for years to come. brbrTHE LOCATION... brbrImagine your vacation home being just steps in either direction from all of the shops, restaurants, and sites of Duval Street and the Historic Seaport. Take a short stroll or ride your bike down to the best of Key West, six blocks down Angela St to hit local favorites like Mangoes, DJ's Clam Shack, and Antonia's. Just a few blocks down Frances Street and you'll find yourself at The Waterfront Brewery, Schooner Wharf, and all of the local favorites of the Seaport. brbrTHE LIVING AREA and KITCHEN... brbrDesigned in Key West's famous 'conch cottage' style, this cozy island home welcomes you with vibrant furnishings and décor and exudes that familiar feeling of home from the moment you walk through the front door. The living area boasts a large flat screen TV, which you can watch from the comfy living room furniture, or from the kitchen thanks to the open layout of the first floor. The kitchen is fully equipped with every tool needed to prepare a meal at home when you decide to take a break from the beloved restaurant options of Key West. The kitchen bar seating is perfect for a casual bite or for keeping the cooks company. The formal dining room is located just around the corner from the kitchen, with a dining table for six. brbrTHE OUTDOOR LIVING and PRIVATE POOL AREA... brbrFully fenced for privacy and surrounded by lush tropical greenery, the outdoor living and pool area of this home will undoubtedly be a favorite gathering place for your group. There are comfortable chaise lounges on the pool deck for you to soak up the sun, or retreat to one of the multiple lounging options on the spacious wrap-around porch in the shade. Spend those hot South Florida days relaxing in your private pool or switch on the pool heat in the cooler months. The backyard is complete with a large propane grill and outdoor dining set that seats 4. brbrTHE ACCOMMODATIONS... brbr• Master Bedroom: Located on the First Floor with a King bed, a flat screen TV, direct access to the back yard, and access to the master bathroom with a walk-in shower, located across the hall.brbr• Second Bedroom: Located on the Second Floor with a King bed, a flat screen TV, and access to the shared full bathroom on the second floor. brbr• Third Bedroom: Located on the Second Floor with a King bed, a flat screen TV, and access to the shared full bathroom on the second floor. brbrALL LAST KEY VACATION HOMES INCLUDE:brbr• Washer and Dryerbr• Central Heat and A/Cbr• Ceiling Fansbr• Flat Screen TVs in Living Room & All Bedroomsbr• Fully Equipped Kitchenbr• Basic stock of spicesbr• Starter supply of paper productsbr• Starter set of cleaning productsbr• Linens and Towels providedbr• Wireless high-speed Internet access and full cable includedbrbrIn addition, this fully stocked home also includes, but is not limited to the amenities on this list:brbr• Fully Fenced and Lushly Landscaped Private Yard br• Private Pool with available Pool Heatbr• Off-street Parking in Drivewaybr• Propane BBQ Grillbr• Home OfficebrbrOther notes:brbr• Interim housekeeping provided upon requestbr• This property will accommodate up to 6 adultsbr• Max of 2 Pets Allowed with Additional Fee of $200 per petbr• Last Key Realty vacation homes are rented to family groups and responsible adult groups only. Groups who expect they may cause after hours noise will not be a good fit for this home and should be aware they may incur additional penalties when in residence for violations. There will be a $500 charge for after-hours dispatch of our staff in response to calls resulting from verified noise complaints for violations by our guests in residence.
Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps

Slider Thumb
Exceptional(1)

$478.65

/ Nightly
Condo

Atlantic Parrot | Oceanfront Condo w/ Pool

Key West, Florida, United States

This vibrant beachfront condo is the perfect home base for soaking up the sun and sea breezes of Key West. Located directly along the shoreline, this colorful coastal escape pairs relaxed island style with unbeatable ocean views, creating an inviting retreat just moments from beaches, bike paths, and iconic island attractions. With resort-style amenities and a private balcony overlooking the water, this condo sets the tone for a memorable Florida Keys getaway.brbrThe Ambiance:brDesigned with an open and airy layout, this fourth-floor condo offers plenty of space to unwind after a day in the sun. Step out onto your private ocean-view balcony to enjoy morning coffee or sunset skies over the Atlantic. Inside, the living area is bright and welcoming, complemented by a fully equipped kitchen and updated furnishings. The cheerful décor and beachy palette reflect the laid-back rhythm of island living.brbrGuest Perks:brGuests enjoy access to a variety of shared resort amenities, including a large outdoor pool, relaxing hot tub, fitness center, and on-site tennis courts. A digital E-lock provides secure, contactless entry with a unique code for each stay. The condo includes air conditioning, WiFi, and one designated parking space in the building's garage (parking fees apply). Whether you're lounging poolside or heading out for a day of adventure, convenience is built into every detail.brbrNeighborhood Highlights:brWith the Florida Keys Overseas Heritage Trail right outside the building, exploring the island is effortless. Bike or walk to Smathers Beach just steps away, or head west to the popular spots at Higgs Beach, including the pier and historic West Martello Tower. Old Town Key West attractions like the Ernest Hemingway Home and Museum and Mallory Square are just a short drive away, offering endless dining, shopping, and cultural experiences.brbrGetting Around:brOne vehicle parking is available on-site for an additional fee, making day trips and excursions simple. Explore Key West effortlessly by bicycle, scooter, golf cart, or on foot, as many attractions are easily accessible from the property. This area is ideal for biking and walking, with direct access to scenic paths along the beach. Guests can easily reach beaches, parks, and attractions without needing to drive far. Feel free to ask for local recommendations!brbrOther Things to Note:br- This home is located in a noise-sensitive area and participates in a Good Neighbor programbr- Quiet hours are enforced from 10:00 p.m. to 8:00 a.m.br- No smoking is permitted anywhere on the premisesbr- No pets are allowedbr- Guests must be 25 years of age or older to rentbr- This rental is located on the 4th floorbr- One parking space is available for a feebrbrCheck-in time is 3:00 PMbrCheck-out time is 11:00 AMbrbrBook your stay today and enjoy beachfront living with resort-style amenities in one of Key West's most scenic coastal locations. Whether you're here to relax by the pool, bike along the shoreline, or explore the island's historic charm, this colorful oceanfront condo offers the perfect blend of comfort, convenience, and coastal adventure.brbrAt Colocada Vacation Rentals, we're committed to providing a smooth, relaxing, and unforgettable Key West experience. Have questions or need local tips We're always happy to help make your stay
Bed 2

Bed

Bath 2

Bath

Sleep 6

Sleeps

Slider Thumb

$182.96

/ Nightly
Condo

Authors Retreat - Downtown Key West

Key West, Florida, United States

This 2 bedroom, 1 ½ bath condo in the Campbell historic building offers a new translation for the word “vacation.” The vocabulary begins behind a white picket fence with a courtyard of cozy cottages nestled around a sparkling pool. The setting is perfect as a postcard: quiet yet located two blocks from Key West’s world-famous Duval Street. Walking, biking, a pedi-cab, or uber work nicely as ways to get around. A coveted parking space for one small vehicle (must be under 16 ft.) is provided. brbrThe story starts at the compound gate. Right inside is a bike rack and lots of green and flower plantings to remind you that you are in paradise. A few steps more bring you to the entrance of this residence. If you turn around, you get the full aha! view of the shared pool. Straight head is the small porch area and another larger, quite charming porch to the side. brbrOnce inside the door, you’ll find the living and dining area which has plenty of natural light, high ceilings, and a glass brick accent wall reflecting light back into the room. There’s plenty of comfy couch and chair seating to make a congenial conversation area. If you are more up for being entertained, there’s a smart TV w/ high speed internet access perfectly positioned for streaming from the seating arrangement. It is equipped with the YouTube TV streaming service which includes the typical expanded basic TV channels plus the ABC, CBS, NBC, Fox and PBS network affiliates from Miami (our broadcast TV market). You can also stream your TV subscriptions or log into your Netflix or Amazon Prime TV accounts. The flatscreen TV sits on an artisan, three-shelf cabinet with ratan-weave doors. The shelves provide space for important things that you want close at hand but don’t want creating clutter in the open. Also in one corner is a table and chairs suitable for meals or for playing cards or board games. Overhead a ceiling fan creates tropical ambience and air circulation. Of course there’s central AC, high-speed internet, three flat-screen TVs, with efficient and attractive ceiling fans throughout. brbrNext in the floor plan is a guest half bath. Then comes the full bath opening out to the den. Here also is a second streaming TV sitting on a roomy storage cabinet. A wardrobe provides room for clothing and office supplies. A daybed provides extra seating or a comfortable accommodation for a third guest. An upholstered conference chair with arms provides the perfect place if someone wants to consult or chat. Also a bookcase stands nearby. It’s a compact, multifunctional room with many windows letting in plenty of Key West’s naturally beautiful light. brbrNext comes the King bedroom again flooded with natural light. A chest with many drawers stands ready to store whatever you need stored and serves as a perch for the third TV. A closet for hanging this and that is partially formed by the unique glass brick wall. brOn to the kitchen…all the appliances you’ll need for cooking and cleanup are supplied in stainless. Cabinets and shelving above and below help avoid clutter. Pots and Pans are artistically hung from the ceiling, as are utensils on the wall. The windows give glimpses of the soothing pool just outside. Faustos, a local grocery store since 1926, is less than a block away if you want foodstuffs to fill up the refrigerator or pantry. All appliances are new in 2024. Or maybe the kitchen will be mostly for warming left overs from meals out at one of the island’s myriad eating establishments.brbrIf you like to swim or are a sun worshiper, you still haven’t explored the best part of this condo: the courtyard and pool. The pool, which is for the exclusive use of Campbell Courtyard guests, is no small dipping or cocktail pool as is prevalent in Key West. Rather, it’s heated (in winter) and generously sized. The pool and deck area are ringed with a white picket fence and plenty of tropical foliage to create beauty, privacy, and a kind of tranquil peace-of-mind that only nature can provide. Chaise lounges and chairs sit invitingly next to the pool, as does a dining table and chairs. If shade is more appealing, claim your spot under the gazabo-style seating area at one end.brbrThe whole set up at Campbell Courtyard is alluring but there’s more--a whole storied island awaiting your exploration: the emerald water of the Atlantic and of the Gulf of Mexico, beaches, conch-style houses, civil war forts, museums, famous hangouts like Sloppy Joe’s, Elvis look-alikes, an expansive waterfront park, and sharks for petting at the Aquarium. From your central Old Town location, most things are easily accessible by foot or bike or the Duval Loop bus. For example the island’s main artery—Duval Street where you’ll find shopping of all sorts, art galleries, tours, open-air restaurants, bars and much more—is less than two blocks away.brbrA few blocks in another direction you’ll find the Historic Seaport with tall ship sunset sails and water sport opportunities like diving, fishing, parasailing, snorkeling, jet-skiing, and more. Or try one of the waterfront restaurants that ring the harbor. Set your timer so you don’t miss the nightly Sunset Celebration at Mallory Square where visitors and locals alike gather to applaud gently as the sun slips below the horizon. It’s a MUST experience.brbrMaybe your taste runs more towards the arts. If so, you’re in the right place for music, movies, plays, art galleries, lectures, and more. If you like beaches, your accommodations are within biking distance to a favorite locals’ beach, Fort Zachery Taylor, where you can rent chairs, umbrellas, and snorkeling equipment. Bathrooms, showers, a snack bar, and picnic tables are also available. Or maybe you’ll decide to skip the beach in favor of exploring the adjacent Civil War-era fort, which was designated a National Historic Landmark in 1973.brbrIf this is your first trip to the Conch Republic, a guidebook from Books & Books on Eaton Street or a stop at the Chamber of Commerce Information Center on Greene Street will help make sure you don’t miss anything. Other info on the current music scene, movies, plays, gallery openings, and charitable events can be found at milezerokeywest.com (calendar section). Historic Hideaways' informative Area Guide/Events page located on our website also has a Calendar of Events. We DO NOT guarantee that the information VRBO (and affiliated sites) scrapes from our site to display on theirs is 100% accurate, particularly the amenities. If you come to us through them, be sure to look at all the information on our site related to your rental once you book to be sure you have accurate and up to date information. Campbell Courtyard COA does NOT allow renters to have pets.
Bed 1

Bed

Bath 1

Bath

Sleep 3

Sleeps

Slider Thumb

$287.54

/ Nightly
Condo

Sun, Sea, & Citrus - Bright 2-Bedroom Monthly Rental in Old Town Key West with Private Pool. Sleeps 5-6

Key West, Florida, United States

Our guests are in for a treat at such a bright and beautiful entire first-floor unit in Key West. This inviting two-bedroom bungalow is perfectly situated on a calm and quiet street in Old Town, yet just steps from the historic cemetery and a stroll from ever-buzzing Duval Street. You’ll also have your own off-street parking within the property’s gate, perfect for a smaller vehicle or your golf cart for further cruises (contact our concierge to help you arrange all your rental needs).brbrThe unit itself shines with fun color and vaulted, sunlit interiors. Rocking chairs await you on the front porch, and a sparkling private pool and grill are all yours to enjoy out back. The vibrant citrus orange kitchen is as energizing as a Cuban coffee, and comes fully equipped with a stainless steel refrigerator/freezer and all the cooking essentials. Gather around the dining table for a homemade meal or favorite Key West take-out, then mix a drink under the neon cocktail sign at your personal mini bar.brbrThe open living room is airy and easygoing, with a comfy pull-out sofa ready for weekend visitors or kids tagging along on a longer stay. On either side of the living space, you’ll find two king bedrooms, each designed for maximum comfort and reprieve. Both feature plush king-sized beds, smart TVs, closets, and split-unit ACs to personalize your climate control. The primary suite has immediate access to the pool deck and a sun-drenched en-suite bath. Another full bath is available to the other bedroom and common area.brbrBright, spirited, and simple, this Angela Street retreat is a fantastic place to call “home,” throughout your Key West trip. We look forward to making sure you have a great stay at Sun, Sea, & Citrus. brbrRestrictions: Smoking permitted only outside please. No pets. We do not accept guests less than 25 years of age unless accompanied by a family group or guardian.brbrPAYMENT: Payment for the rental will be processed outside of VRBO according to the terms of your rental agreement (sent for review upon reservation). Payments by credit card are subject to an additional 2.95% merchant processing fee.
Bed 2

Bed

Bath 2

Bath

Sleep 5

Sleeps

Slider Thumb

$1793.26

/ Nightly
Hotel

Windward Point Beachfront Resort, Hot Tub, Pool

Key West, Florida, United States

Set along the Atlantic Ocean, Hyatt Windward Pointe Resort blends the laid-back Key West style with a modern, upscale resort ambiance. Here is a retreat where you can slow down and forget the rush and stress of your day-to-day life. Bask beside the lushly landscaped pool that gives you the illusion that you're softly floating on the open sea, grab a snack at Abbey Road poolside sandwich and snack bar or get your blood pumping at the fitness center at site resort Hyatt Key West Resort & Spa.brbrAll of the ultra-spacious, ultra-plush residences at Hyatt Windward Pointe features two bedrooms - the master bedroom with a king bed and adjoining bath outfitted with a walk-in shower and spa tub, and the guest bedroom with a queen bed. Ocean, pool and courtyard views are available, and everyone is sure to take advantage of the convenience offered by a full kitchen, dining area, living room, TV, fully-furnished balcony and complimentary Wi-Fi access!brbrHyatt Windward Pointe Resort's convenient location puts you just minutes from the free-spirited art, music and entertainment scene of Old Town. Or, head over to nearby Smathers Beach, the biggest white sand beach in Key West to rent windsurfers or go parasailing. The keys are also a haven for anglers - shallow flats, mangrove islands, inland channels and open blue waters offer world-classing fishing opportunities. Hoping to test your skills on the green You're in luck - Key West Golf Club is located nearby and is the only Caribbean inspired course in the U.S.brbrRoom TypesbrAll rooms are identical at Hyatt Windward Pointe Resort:brbrbr2 Bedroom Condominiumbr2 Bathrooms, Full kitchen, Sleeps 6brbrOn-Site Features & AmenitiesbrAccessible unitsbrBarbrClubhousebrInternet accessbrMovie rentalsbrOutdoor poolbrRestaurantbrSaunabrShared laundry facilitiesbrWhirlpool/hot tubbrNearby AttractionsbrBoatingbrDrug storebrFishingbrFitness centerbrGolfbrGrocery storebrHikingbrLive entertainmentbrMedical facilitiesbrPlayground areabrRiverbrScuba divingbrShopping areabrSpa servicesbrTennisbrWater skiingbrWind surfingbrPoliciesbrNo PetsbrNo SmokingbrMinimum check-in age: 21brCheck-in time: 4:00 PMbrCheck-out time: 10:00 AMbrbr1. **24-Hour Front Desk & Concierge Services**br- Our dedicated front desk team is available 24/7 to assist with any inquiries, provide information about the resort and local attractions, and ensure your stay is comfortable. Our concierge can help you plan your activities, make reservations, and offer recommendations for dining and entertainment.brbr2. **Housekeeping Services**br- Our housekeeping team ensures that your residence is impeccably maintained. Daily housekeeping is available, as well as turndown service upon request. We also offer additional amenities such as extra towels, toiletries, and bedding.brbr3. **Dining and Room Service**br- Enjoy a variety of dining options, including our Road Poolside Sandwich and Snack Bar. For those who prefer to dine in the comfort of their residence, room service is available, offering a selection of delicious meals and snacks.brbr4. **Recreational Facilities**br- Relax by our lushly landscaped outdoor pool, which offers an illusion of floating on the open sea. Our fitness center is equipped with state-of-the-art equipment to keep you active during your stay. We also have a sauna and whirlpool/hot tub for ultimate relaxation.brbr5. **Activities and Entertainment**br- We offer a range of on-site activities, including movie rentals, and organized events at the clubhouse. For adventure seekers, our concierge can arrange water sports, fishing trips, and scuba diving excursions.brbr6. **Family Services**br- Families are welcome at Hyatt Windward Pointe Resort. We provide cribs and high chairs upon request, and our playground area is perfect for young children. Babysitting services can be arranged for parents who wish to enjoy some private time.brbr7. **Business Services**br- For our business travelers, we offer complimentary Wi-Fi access throughout the resort, as well as fax and photocopy services. Meeting rooms are available for small gatherings or business meetings.brbr8. **Transportation Services**br- We provide shuttle services to and from Key West International Airport. Additionally, our concierge can arrange car rentals, taxi services, and provide information on local transportation options.brbr9. **Laundry Services**br- Shared laundry facilities are available on-site, and dry cleaning services can be arranged through the front desk.brbr10. **Special Requests**br- Our team is here to cater to any special requests you may have, whether it's celebrating a special occasion, dietary requirements, or arranging for in-room spa services.brbr**Local Attractions and Excursions**brbrOur resort's prime location puts you minutes away from the vibrant culture of Old Town, Key West. Explore the art, music, and entertainment scene, or head over to Smathers Beach for water sports like windsurfing and parasailing. Fishing enthusiasts and golfers will find plenty of opportunities to indulge in their favorite activities nearby.brbrAt Hyatt Windward Pointe Resort, our goal is to provide you with a memorable and enjoyable stay. We are here to ensure that every aspect of your visit exceeds your expectations. Should you need any assistance or have any questions, please do not hesitate to contact our front desk or concierge.brbrbrPlease be advised that we cannot assume responsibility for any inconvenience, unavailability,bror interruption of services due to necessary repairs, ongoing improvements, on-sitebrconstruction, closure of amenities, or other circumstances beyond our control. Guests will bebrpromptly notified of any such issues as they come to our attention. Please note that room viewsbrand bed configurations may vary at some resorts while accommodating the same number ofbrguests. We encourage guests to seek clarification prior to booking and to inform us of anybrspecial requests, which we will endeavor to accommodate if feasible. Additionally, all resortsbrrequire a valid ID of the person on the reservation and a major credit card at check-in to coverbrpotential charges for damages, liabilities, and incidentals.
Bed 2

Bed

Bath 2

Bath

Sleep 6

Sleeps

Slider Thumb

$1430.23

/ Nightly
Private Vacation Home

~CALIFORNIA DREAMING~ Enjoy an extended vacation in this posh home and pool.

Key West, Florida, United States

MONTHLY RENTAL: Requires a minimum stay of 28 nights occurring within the same month. Stay a month and live like a local!brbrTHE PROPERTY: From its people watching front porch to its private heated pool, this home will surround you in tranquility. On the right side of the home’s entrance is a comfortably furnished living room with plenty of natural light. A wet bar with cabinetry is nearby and outfitted with filtered and carbonated water taps, a beverage fridge and a Breville espresso machine. There is also a convenient first floor bedroom and bathroom as well as a laundry area with full size washer/dryer, cabinet storage and a folding counter. If you need to work or school from home, California Dreaming has a large office to the left of the entrance with two work stations. br brLove to cook or re-heat take-out It’s easy to do either in this breathtaking chef’s kitchen with stainless steel appliances, stunning cabinetry, and quartzite countertops. A window above the farmhouse sink provides a sunny view. The 6-burner Italian Bertazzoni slide-in range with griddle is a dream to use. It is flanked by wall sconces and adorned with a custom hood. The large contrasting kitchen island provides additional work space and seating. Sliders lead the way to your heated, saline pool. Complete with loungers and a propane grill, this newly landscaped pool area affords the ultimate in privacy.br brAscend to the second floor where you will find three additional bedrooms. The primary ensuite is beautifully furnished and includes a reading nook, an extra-large walk-in closet, and balcony access for morning coffee. It’s bathroom is stunning and includes custom plaster dual sinks, storage, a Zellige tiled walk-in shower and soaking tub. The other two bedrooms are equally attractive. One has access to the balcony, and they share a hall bath. The bath includes a walk-in shower whose tile is designed in a palm tree motif. A solid surface vanity with storage is also provided.br brThis completely restored designer dream home with lush landscaping, covered porches and a rejuvenating pool, will provide you with a relaxing respite in paradise. Come see for yourself and start ‘California Dreaming’ today! brbrBED CONFIGURATION: The primary bedroom has a king bed. Two of the guest bedrooms have queen beds. The third guest bedroom has a twin bed. Please note the twin bedroom does not have a TV.br brOUTDOOR AMENITIES: Abundant landscaping provides privacy around the saline, kidney-shaped pool. The pool is heated seasonally (November-April) for an additional fee which will be assessed at the time of booking. Lounge chairs, a propane grill and a bicycle shed are also provided. brbrPARKING: This home includes off-street parking for two small vehicles.br brLOCATION: Within walking distance to the White Street Pier, this Old Town location provides easy access to the Southern end of Duval Street. brbrPETS: This home is NOT pet-friendly. (If you have pets, please browse through our many homes that are pet friendly).brbrSMOKING: This is a non-smoking home and property.brbr***Guests must be 25 years of age or older unless accompanied by an adult.brbr***Please note that the cleaning fee includes a full mid-stay clean***brbr***Managed by Historic Key West Vacation Rentals***
Bed 4

Bed

Bath 3

Bath

Sleep 7

Sleeps

Slider Thumb

$974.25

/ Nightly
Hotel

Charming Bungalow Perfect for Families! Free Breakfast and Pool Access

Key West, Florida, United States

This listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms.brbr✦ Each room is 270 sq. ft, equipped with complimentary toiletries, high definition 55-inch TV, available with Premium cable.brbr✦ Rooms are not adjoining and possibly not next to each other. Spaces are assigned upon arrival based on availability.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm.brbr✦ Outdoor shared pool available all year, opened from 7:00AM to 10:00PM.brAdditional features:br • Heated poolbrbr✦ Paid parking lot, available for $30 per day.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $100 per night refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $45.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome. $50 per pet per night. No breed or size limitsbrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ The required refundable security deposit is charged per unit, per night, on a valid credit card.
Bed 2

Bed

Bath 2

Bath

Sleep 8

Sleeps

Slider Thumb
Exceptional(1)

$596.01

/ Nightly
Private Vacation Home

**TRUMAN’S TROVE @ THE ANNEX** Private Home & Pool + LAST KEY SERVICES…

Key West, Florida, United States

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival!brbrHunting for the perfect Key West vacation home can feel like a daunting task. However, once you discover TRUMAN’S TROVE, you’ll know that you’ve struck gold! This two-story private home has been beautifully furnished and designed to the highest standard. In addition, TRUMAN’S TROVE offers an ideal location within Truman Annex, Key West’s most exclusive Gated Community. TRUMAN’S TROVE combined with Last Key Realty's Five-Star Guest Services and Complimentary Concierge, is guaranteed to be a treasured Key West vacation experience.brbrTHE LIVING AREA & KITCHEN…brbrTRUMAN’S TROVE has an open and airy layout. The spacious living room features a large flat-screen TV and comfortable seating options. The plush sofa pulls out to a Queen sleeper to accommodate extra guests. The indoor dining area has a large dining table with seating for six and there is an additional three seats at the kitchen bar. The fully equipped kitchen has top-of-the-line stainless steel appliances and all the tools you'll need to prepare meals at home. There’s also a wine chiller next to the kitchen bar. A convenient powder room is located on the first floor.brbrTHE BACKYARD…brbrSwing open the double French doors and step outside to the tropical backyard. The covered outdoor lounge area is perfect for relaxing in the shade. Feeling competitive Challenge your group to a cornhole tournament. Once you’ve worked up an appetite, treat everyone to a BBQ of today’s fresh catch using the propane grill and outdoor dining table that seats six. The backyard is fully fenced and landscaped for ultimate privacy. Tiki torches and landscape lighting allow the backyard to be enjoyed both day and night. The back walking gate opens to Eaton Street, for easy access to all the downtown action from your vacation home.brbrTHE GATED COMMUNITY…brbrTruman Annex is the most exclusive private residence community in Old Town Key West. Located just off the main drag of Duval Street, Truman Annex is an oasis of calm, quiet streets lined with palm trees and beautiful Floridian homes. Within Truman Annex, Admirals Lane is even further tucked away down a small cul-de-sac with ultimate privacy. The entrance to Truman Annex is secured by a 24-hour staffed guard gate and you can use the residential entry gate keys to come and go on foot at night.brbrTHE COMMUNITY POOL & FORT ZACHARY TAYLOR STATE PARK…brbrThe landscaped community pool is located at the end of the lane, with chaises and a cabana with restrooms. Or you can walk to Fort Zachary Taylor State Park, with the prettiest beach in Key West, just a half mile away from your front door.brbrCompliance with Truman Annex Community Rules & Regulations is expected of all Last Key guests. This includes “Quiet Time” in all outdoor areas, public and private, after 10PM.brbrTHE ACCOMMODATIONS…brbr** Master Suite: Located on the Second Floor with a King bed, two closets, a flat-screen TV, a private balcony, and an en-suite bathroom with double sinks and a walk-in shower.brbr** Second Bedroom: Two Twins OR One King bed, a full closet, a flat-screen TV, and access to the hall bathroom with a shower and tub combo.brbrALL LAST KEY VACATION HOMES INCLUDE: brbr** Washer and Dryer br** Central Heat and A/C br** Ceiling Fans Throughoutbr** Flat Screen Cable TVs in Living Room & Bedrooms br** Fully Equipped Kitchenbr** Basic stock of spicesbr** Starter supply of paper productsbr** Starter set of cleaning productsbr** Linens and Towels provided br** Wireless high-speed Internet access and full cable is included br** Full Time Concierge Service brbrIn addition, this fully stocked home also includes, but is not limited to the amenities on this list: brbr** Fully Fenced & Landscaped Private Yard br** Community Pool Accessbr** Propane BBQ Grillbr** Sleeper Sofa br** Assigned Off-Street Parking for One Vehiclebr** Cornhole SetbrbrOther notes: brbr** Interim housekeeping provided upon request br** This property will accommodate up to 6 adultsbr** No Pets Allowedbr** Last Key Realty vacation homes are rented to family groups and responsible adult groups only. Groups who expect they may cause after hours noise will not be a good fit for this home and should be aware they may incur additional penalties when in residence for violations. There will be a $500 charge for after-hours dispatch of our staff in response to calls resulting from verified noise complaints for violations by our guests in residence.
Bed 2

Bed

Bath 2

Bath

Sleep 6

Sleeps

Slider Thumb
Exceptional(2)

$483.23

/ Nightly
Private Vacation Home

Atlantis House Main Residence

Key West, Florida, United States

Summary:brbrBeautiful Key West Residence close to Higgs BeachbrbrbrbrThe Space:brbrWelcome to the Atlantis House, a beautiful vacation rental located in the heart of the charming island town of Key West. This exquisite property has everything that you could want in a vacation rental home - elegantly designed interiors, high-end amenities, and an unbeatable location close to everything that the island has to offer. The main house of Atlantis House features 3 bedrooms and 2 bathrooms, with elegant modern coastal design elements found throughout. The spacious and beautifully designed open floor plan invites guests to entertain in style, with a large chef's kitchen boasting high-end appliances that include a huge sub-zero fridge and freezer. Attention to detail and a carefully curated color palette welcome even the most discerning traveler, creating an atmosphere of laid-back luxury that is perfect for your island getaway. One of the highlights of Atlantis House is the bonus second-floor bedroom, which boasts stunning ocean views and offers yet another option for dining and entertaining. The nice upstairs terrace is the perfect spot to relax with a book or enjoy an evening cocktail, taking in the sights and sounds of this vibrant island community. The location of Atlantis House is truly unbeatable - located just steps from the Whitestreet pier and within walking distance of Higgs and Smathers Beach, which are two of the most popular beaches on the island. Additionally, the nearby farmers markets and free bikes provided by the property make it easy to explore and experience everything that Key West has to offer. If you are seeking a monthly vacation rental that truly embodies the essence of island living, then Atlantis House is the perfect choice. With its unbeatable location, elegant design, and thoughtful amenities, this vacation rental is a true island gem. We invite you to come experience the best of Key West living at Atlantis House.
Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps

Slider Thumb
Exceptional(9)

$669.86

/ Nightly
Condo

TortugasHarbor Light Suite

Key West, Florida, United States

Summary:brbrLuxury 1BD/1BA Suite with Two Oasis Pools, Pergola, Outdoor Bar and Grill and Private Porch with Amazing Views.brbrbrbrThe Space:brbrEscape the Ordinary...brbrbrbrThe Tortugas Harbor Lighthouse Suite offers a luxury king bedroom that can accommodate up to 4 guests and was completely refurbished in 2024. This beautifully appointed second floor suite, located in a renovated 1930s Historic Key West building, offers a private exterior entrance and a spacious front porch offering Key West Lighthouse, breathtaking pool and amenity views, and a partial view of the famous Hemingway House, tucked away on a quiet Key West Lane. The Suite is located steps away from the two brand new oasis pools and brand new amenities on the property.brbrbrbrSuite Amenities:brbrbrbr•           Luxury king bed with premium linensbrbr•           Queen sleeper sofabrbr•           Fully equipped kitchen with granite countertopsbrbr•           Spa quality stone rain shower bathroombrbr•           Hardwood flooring throughout the suitebrbr•           Amazing second floor porch with seating areas and pool and garden viewsbrbr•           Smart TVs with the latest Roku device for apps and streamingbrbr•           High-speed Fiber Wi-Fibrbr•           Washer and dryerbrbr•           Luxury well-appointed furnishing and artworkbrbr•           Reserved parking space for one vehiclebrbr•           Luggage hut to store luggage and belongings in before check in or after check outbrbrbrbrLocation:brbrThe Tortugas Lighthouse Suite offers the perfect blend of convenience and tranquility, located just a half-block from world-famous Duval Street. While you’re steps away from the vibrant energy of Key West’s best shops, restaurants, and nightlife, the resort is tucked away on a peaceful, picturesque lane, providing a quiet retreat. The iconic Hemingway House Museum, just behind the property, is only a 2-minute walk away, and Fort Zachary Taylor Park and Beach are also within easy walking distance. Experience the best of both worlds—close to the action, yet an oasis of peace and quiet.brbrbrbrAbout the Property:brbrWelcome to The Lighthouse Suites Collection, an exclusive six-unit luxury vacation rental resort offering in the heart of historic Old Town Key West. Just steps from Duval Street and a short walk to Fort Zachary Taylor Park beach, our location places you at the center of Key West’s most iconic attractions and vibrant nightlife.brbrbrbrThe Lighthouse Suites Collection is truly one of a kind.  This mini resort is defined by its luxurious suites, on-site parking, and exceptional location. Our immaculate 5-star accommodations are enhanced by a unique outdoor experience featuring two tropical oasis pools with spacious pool decks, a pergola with a cozy seating area and fire pit, and a fully equipped outdoor kitchen and BBQ grill with a Brio filtered water and ice maker station.brbrbrbrWhether you’re planning a romantic escape, a memorable family vacation, or an unforgettable group retreat, the Lighthouse Suites Collection offers the ultimate Key West experience, blending luxury, comfort, and first-class amenities.brbrbrbrIn March 2025, we completed a full renovation of our outdoor common areas, exclusively accessible to guests of our six suites.brbrbrbrThe property now features two brand-new oasis plunge pools, each with its own sundeck, offering the perfect spot to sunbathe or unwind by the pool. Guests can relax on our teak chaise loungers or indulge in one of our two luxury double chaise cabanas. We also added a 200-square-foot pergola, separated into two areas: one half features a cozy seating area with a swing and fire pit, perfect for enjoying an elegant evening cocktail. The other half houses a fully equipped outdoor kitchen, complete with a BBQ, sink and two refrigerators. To top it off, the kitchen includes a Brio filtered water and ice maker system to keep you hydrated on warm Key West days.brbrbrbrProperty Amenities:brbrbrbr•           Two brand-new heated oasis plunge pools, each with waterfalls and pool showerbrbr•           Brand-new spacious pool decks around each poolbrbr•           Six luxury teak chaise loungers with umbrellas and pillowsbrbr•           Two brand-new double chaise luxury resort cabanas seating two guests eachbrbr•           Two in-pool chaise ledge loungers to sunbathe and cool off simultaneouslybrbr•           A brand-new 200 SF teak pergola with a louvered open or closed ceilingbrbr•           Luxury couch and daybed swing under the pergola with an elegant fire pitbrbr•           Fully equipped outdoor bar, BBQ grill with a sink and fridge under the pergolabrbr•           Covered bar kiosk for enjoying a cocktailbrbr•           Key West tropical foliage throughout the property with lighted step-stone pathsbrbr•           Exclusive on-street parking spaces with room for six vehicles and 1 per suitebrbr•           Schlage smart lock security on all Suites and gate access to the propertybrbrbrbrGroup Accommodation:brbrIf you need more room for your party, contact us about renting one or more suites for your stay. We have 3, two-bedroom suites, 2, one-bedroom suites, 1, one-bedroom bungalow accommodating a maximum of 30 guests. The property is perfect for weddings, other large gatherings, and events.brbrbrbrFrequently Asked Questions:brbr1. Are the pools and amenities shared brbrYes, the 6 Suites share all the amenities above which are exclusive to only guests staying with us on property and is secured with smart locks on the gate access to the property common areas.brbrbrbr2. What is the parking situation Can I bring more than one vehicle brbrParking in Key West can be challenging, but we’ve made it easier for our guests. Our property includes five reserved parking spaces and one exclusive off-street parking space for the Carysfort Light Suite, all conveniently located on Eanes Lane, right next to the Suites. Each space is clearly marked with signage along the buildings.brbrbrbrWe can accommodate one vehicle per suite. If you rent multiple suites, you’ll be assigned the corresponding number of parking spaces. For your convenience, a property map showing the location of all six parking spaces is included in the photos. Additionally, we will send the property and parking map in your welcome packet for easy reference.brbrbrbr3. Where is my Suite located brbrPlease refer to the property map in the pictures, which will show you the location of your Suite on the property. All three properties are adjacent to each other and the property is fenced in with smart lock gates.brbrbrbr•           The Alligator Reef (2BD, 1BA), American Shoal (2BD/1BA), Sombrero Reef (1BD/ 1BA), and Tortugas Harbor Suites (1BD/ 1BA) are located at 419 Truman Avenue in the same historic building, with Sombrero Reef and Tortugas Harbor Suite located upstairs.brbrbrbr•           The Key West Lighthouse Suite is a separate individual queen bungalow with a loft featuring a queen bed, located at 215 Eanes Lane.brbrbrbr•           The Carysfort Light Suite is a separate individual 2BD/ 2BA with its own exclusive off-street parking space, located at 217 Eanes Lane.brbrbrbr4. Do I need a vehicle or transportation brbrIf you have a vehicle, we have rare parking available that most lodging on the island cannot offer but you do not need a vehicle to enjoy your stay with us. The property is located one-half block off Duval Street on quaint and quiet Eanes Lane delivering one of the best lodging locations on the Island close to everything but in a peaceful and quiet location. Here are the distances to some Key West Landmarks:brbrbrbr•           Key West Lighthouse Museum, 2-minute walkbrbr•           Ernest Hemingway Home and Museum, 2-minute walkbrbr•           Blue Heaven Restaurant, 5-minute walkbrbr•           Southernmost Point Buoy, 8-minute walkbrbr•           Key West Butterfly Conservatory, 8-minute walkbrbr•           Sloppy Joe’s Bar, 12-minute walkbrbr•           Key West Amphitheater and Park, 12-minute walkbrbr•           Mallory Square Sunset, 12-minute walkbrbr•           Fort Zachary Taylor State Park & Beach, 12-minute walkbrbrbrbrWe look forward to welcoming you to paradise!
Bed 1

Bed

Bath 1

Bath

Sleep 4

Sleeps

Slider Thumb
Exceptional(14)

$823.15

/ Nightly
Condo

American Shoal Light Suite

Key West, Florida, United States

Summary:brbrLuxury 2BD/1BA Suite with Two Oasis Pools, Pergola, Outdoor Bar and Grill and Private Patio.brbrbrbrThe Space:brbrEscape the Ordinary....brbrbrbrThe American Shoal Lighthouse Suite offers separate King and Queen bedrooms and was completely refurbished in 2024 that can sleep up to 6 guests. This beautifully appointed ground floor suite, located in a renovated 1930’s Historic Key West building, offers a private exterior entrance and a spacious private outside patio area offering Key West Lighthouse views tucked away on a quiet Key West Lane. The Suite is located steps away from the two brand new oasis pools and brand-new amenities on the property.brbrbrbrSuite Amenities:brbrbrbr•           Luxury king and queen beds with premium linensbrbr•           Full sized sectional couch with pull out bedbrbr•           Fully equipped kitchen with granite countertopsbrbr•           Spa quality stone rain shower bathroombrbr•           Hardwood flooring throughout the suitebrbr•           Spacious back porch with dining tablebrbr•           Smart TVs with the latest Roku device for apps and streamingbrbr•           High-speed Fiber Wi-Fibrbr•           Washer and dryerbrbr•           Luxury well-appointed furnishing and artworkbrbr•           Reserved parking space for one vehiclebrbr•           Luggage hut to store luggage and belongings in before check in or after check outbrbrbrbrLocation:brbrThe American Shoal Lighthouse Suite offers the perfect blend of convenience and tranquility, located just a half-block from world-famous Duval Street. While you’re steps away from the vibrant energy of Key West’s best shops, restaurants, and nightlife, the resort is tucked away on a peaceful, picturesque lane, providing a quiet retreat. The iconic Hemingway House Museum, just behind the property, is only a 2-minute walk away, and Fort Zachary Taylor Park and Beach are also within easy walking distance. Experience the best of both worlds—close to the action, yet an oasis of peace and quiet.brbrbrbrAbout the Property:brbrWelcome to The Lighthouse Suites Collection, an exclusive six-unit luxury vacation rental resort offering in the heart of historic Old Town Key West. Just steps from Duval Street and a short walk to Fort Zachary Taylor Park beach, our location places you at the center of Key West’s most iconic attractions and vibrant nightlife.brbrbrbrThe Lighthouse Suites Collection is truly one of a kind.  This mini resort is defined by its luxurious suites, on-site parking, and exceptional location. Our immaculate 5-star accommodations are enhanced by a unique outdoor experience featuring two tropical oasis pools with spacious pool decks, a pergola with a cozy seating area and fire pit, and a fully equipped outdoor kitchen and BBQ grill with a Brio filtered water and ice maker station.brbrbrbrWhether you’re planning a romantic escape, a memorable family vacation, or an unforgettable group retreat, the Lighthouse Suites Collection offers the ultimate Key West experience, blending luxury, comfort, and first-class amenities.brbrbrbrIn March 2025, we completed a full renovation of our outdoor common areas, exclusively accessible to guests of our six suites.brbrbrbrThe property now features two brand-new oasis plunge pools, each with its own sundeck, offering the perfect spot to sunbathe or unwind by the pool. Guests can relax on our teak chaise loungers or indulge in one of our two luxury double chaise cabanas. We also added a 200-square-foot pergola, separated into two areas: one half features a cozy seating area with a swing and fire pit, perfect for enjoying an elegant evening cocktail. The other half houses a fully equipped outdoor kitchen, complete with a BBQ, sink and two refrigerators. To top it off, the kitchen includes a Brio filtered water and ice maker system to keep you hydrated on warm Key West days.brbrbrbrProperty Amenities:brbrbrbr•           Two brand-new heated oasis plunge pools, each with waterfalls and pool showerbrbr•           Brand-new spacious pool decks around each poolbrbr•           Six luxury teak chaise loungers with umbrellas and pillowsbrbr•           Two brand-new double chaise luxury resort cabanas seating two guests eachbrbr•           Two in-pool chaise ledge loungers to sunbathe and cool off simultaneouslybrbr•           A brand-new 200 SF teak pergola with a louvered open or closed ceilingbrbr•           Luxury couch and daybed swing under the pergola with an elegant fire pitbrbr•           Fully equipped outdoor bar, BBQ grill with a sink and fridge under the pergolabrbr•           Covered bar kiosk for enjoying a cocktailbrbr•           Key West tropical foliage throughout the property with lighted step-stone pathsbrbr•           Exclusive on-street parking spaces with room for six vehicles and 1 per suitebrbr•           Schlage smart lock security on all Suites and gate access to the propertybrbrbrbrGroup Accommodation:brbrIf you need more room for your party, contact us about renting one or more suites for your stay. We have 3, two-bedroom suites, 2, one-bedroom suites, 1, one-bedroom bungalow accommodating a maximum of 30 guests. The property is perfect for weddings, other large gatherings, and events.brbrbrbrFrequently Asked Questions:brbr1. Are the pools and amenities shared brbrYes, the 6 Suites share all the amenities above which are exclusive to only guests staying with us on property and is secured with smart locks on the gate access to the property common areas.brbrbrbr2. What is the parking situation Can I bring more than one vehicle brbrParking in Key West can be challenging, but we’ve made it easier for our guests. Our property includes five reserved parking spaces and one exclusive off-street parking space for the Carysfort Light Suite, all conveniently located on Eanes Lane, right next to the Suites. Each space is clearly marked with signage along the buildings.brbrbrbrWe can accommodate one vehicle per suite. If you rent multiple suites, you’ll be assigned the corresponding number of parking spaces. For your convenience, a property map showing the location of all six parking spaces is included in the photos. Additionally, we will send the property and parking map in your welcome packet for easy reference.brbrbrbr3. Where is my Suite located brbrPlease refer to the property map in the pictures, which will show you the location of your Suite on the property. All three properties are adjacent to each other and the property is fenced in with smart lock gates.brbrbrbr•           The Alligator Reef (2BD, 1BA), American Shoal (2BD/1BA), Sombrero Reef (1BD/ 1BA), and Tortugas Harbor Suites (1BD/ 1BA) are located at 419 Truman Avenue in the same historic building, with Sombrero Reef and Tortugas Harbor Suite located upstairs.brbrbrbr•           The Key West Lighthouse Suite is a separate individual queen bungalow with a loft featuring a queen bed, located at 215 Eanes Lane.brbrbrbr•           The Carysfort Light Suite is a separate individual 2BD/ 2BA with its own exclusive off-street parking space, located at 217 Eanes Lane.brbrbrbr4. Do I need a vehicle or transportation brbrIf you have a vehicle, we have rare parking available that most lodging on the island cannot offer but you do not need a vehicle to enjoy your stay with us. The property is located one-half block off Duval Street on quaint and quiet Eanes Lane delivering one of the best lodging locations on the Island close to everything but in a peaceful and quiet location. Here are the distances to some Key West Landmarks:brbrbrbr•           Key West Lighthouse Museum, 2-minute walkbrbr•           Ernest Hemingway Home and Museum, 2-minute walkbrbr•           Blue Heaven Restaurant, 5-minute walkbrbr•           Southernmost Point Buoy, 8-minute walkbrbr•           Key West Butterfly Conservatory, 8-minute walkbrbr•           Sloppy Joe’s Bar, 12-minute walkbrbr•           Key West Amphitheater and Park, 12-minute walkbrbr•           Mallory Square Sunset, 12-minute walkbrbr•           Fort Zachary Taylor State Park & Beach, 12-minute walkbrbrbrbrWe look forward to welcoming you to paradise!
Bed 2

Bed

Bath 1

Bath

Sleep 6

Sleeps

Slider Thumb
Exceptional(61)

$723.98

/ Nightly
Private Vacation Home

Key West Lighthouse Suite

Key West, Florida, United States

Summary:brbrLuxury queen bungalow suite with twin beds in the loft and a private porch with amazing views. Share two oasis pools, pergola, outdoor bar and grill.brbrbrbrThe Space:brbrEscape the Ordinary...brbrbrbrThe Key West Lighthouse Suite is a cozy queen bungalow home with a double twin loft that sleeps up to 4 guests. This beautifully appointed stand-alone suite remodeled in 2024 is a perfect romantic retreat or ideal for those traveling with children. The suite is directly in front of one of our two new oasis pools with rear pool views. There is also a private front porch with Key West Lighthouse and partial Duval Street views on a quiet Key West Lane.brbrbrbrSuite Amenities:brbrbrbr•           Luxury queen-size bed with premium linensbrbr•           Upstairs loft with 2 twin beds - can be set up as king upon request - with premium linensbrbr•           Luxury well-appointed furnishings and artworkbrbr•           Private bathroom with a glass showerbrbr•           Private secure entrancebrbr•           Spacious front porch with views of the Key West Lighthouse and Duval Streetbrbr•           Smart TVs with the latest Roku device for apps and streamingbrbr•           High-speed Fiber Wi-Fibrbr•           Well-equipped kitchen with refrigerator and icemakerbrbr•           Parking space for one vehiclebrbr•           Hardwood flooring throughout the suitebrbr•           Washer and dryer combo unitbrbr•           Luggage hut to store luggage and belongings in before check in or after check outbrbrbrbrLocation:brbrThe Key West Lighthouse Suite offers the perfect blend of convenience and tranquility, located just a half-block from world-famous Duval Street. While you’re steps away from the vibrant energy of Key West’s best shops, restaurants, and nightlife, the resort is tucked away on a peaceful, picturesque lane, providing a quiet retreat. The iconic Hemingway House Museum, just behind the property, is only a 2-minute walk away, and Fort Zachary Taylor Park and Beach are also within easy walking distance. Experience the best of both worlds — close to the action, yet an oasis of peace and quiet.brbrbrbrAbout the Property:brbrWelcome to The Lighthouse Suites Collection, an exclusive six-unit luxury vacation rental resort offering in the heart of historic Old Town Key West. Just steps from Duval Street and a short walk to Fort Zachary Taylor Park beach, our location places you at the center of Key West’s most iconic attractions and vibrant nightlife.brbrbrbrThe Lighthouse Suites Collection is truly one of a kind.  This mini resort is defined by its luxurious suites, on-site parking, and exceptional location. Our immaculate 5-star accommodations are enhanced by a unique outdoor experience featuring two tropical oasis pools with spacious pool decks, a pergola with a cozy seating area and fire pit, and a fully equipped outdoor kitchen and BBQ grill with a Brio filtered water and ice maker station.brbrbrbrWhether you’re planning a romantic escape, a memorable family vacation, or an unforgettable group retreat, the Lighthouse Suites Collection offers the ultimate Key West experience, blending luxury, comfort, and first-class amenities.brbrbrbrIn March 2025, we completed a full renovation of our outdoor common areas, exclusively accessible to guests of our six suites.brbrbrbrThe property now features two brand-new oasis plunge pools, each with its own sundeck, offering the perfect spot to sunbathe or unwind by the pool. Guests can relax on our teak chaise loungers or indulge in one of our two luxury double chaise cabanas. We also added a 200-square-foot pergola, separated into two areas: one half features a cozy seating area with a swing and fire pit, perfect for enjoying an elegant evening cocktail. The other half houses a fully equipped outdoor kitchen, complete with a BBQ, sink and two refrigerators. To top it off, the kitchen includes a Brio filtered water and ice maker system to keep you hydrated on warm Key West days.brbrbrbrProperty Amenities:brbrbrbr•           Two brand-new heated oasis plunge pools, each with waterfalls and pool showerbrbr•           Brand-new spacious pool decks around each poolbrbr•           Six luxury teak chaise loungers with umbrellas and pillowsbrbr•           Two brand-new double chaise luxury resort cabanas seating two guests eachbrbr•           Two in-pool chaise ledge loungers to sunbathe and cool off simultaneouslybrbr•           A brand-new 200 SF teak pergola with a louvered open or closed ceilingbrbr•           Luxury couch and daybed swing under the pergola with an elegant fire pitbrbr•           Fully equipped outdoor bar, BBQ grill with a sink and fridge under the pergolabrbr•           Covered bar kiosk for enjoying a cocktailbrbr•           Key West tropical foliage throughout the property with lighted step-stone pathsbrbr•           Exclusive on-street parking spaces with room for six vehicles and 1 per suitebrbr•           Schlage smart lock security on all Suites and gate access to the propertybrbrbrbrGroup Accommodation:brbrIf you need more room for your party, contact us about renting one or more suites for your stay. We have 3 two-bedroom suites, 2 one-bedroom suites, 1 one-bedroom bungalow accommodating a maximum of 30 guests. The property is perfect for weddings, other large gatherings, and events.brbrbrbrFrequently Asked Questions:brbr1. Are the pools and amenities shared brbrYes, the 6 Suites share all the amenities above which are exclusive to only guests staying with us on property and is secured with smart locks on the gate access to the property common areas.brbrbrbr2. What is the parking situation Can I bring more than one vehicle brbrParking in Key West can be challenging, but we’ve made it easier for our guests. Our property includes five reserved parking spaces and one exclusive off-street parking space for the Carysfort Light Suite, all conveniently located on Eanes Lane, right next to the Suites. Each space is clearly marked with signage along the buildings.brbrbrbrWe can accommodate one vehicle per suite. If you rent multiple suites, you’ll be assigned the corresponding number of parking spaces. For your convenience, a property map showing the location of all six parking spaces is included in the photos. Additionally, we will send the property and parking map in your welcome packet for easy reference.brbrbrbr3. Where is my Suite located brbrPlease refer to the property map in the pictures, which will show you the location of your Suite on the property. All three properties are adjacent to each other and the property is fenced in with smart lock gates.brbrbrbr•           The Alligator Reef (2BD, 1BA), American Shoal (2BD/1BA), Sombrero Reef (1BD/ 1BA), and Tortugas Harbor Suites (1BD/ 1BA) are located at 419 Truman Avenue in the same historic building, with Sombrero Reef and Tortugas Harbor Suite located upstairs.brbrbrbr•           The Key West Lighthouse Suite is a separate individual queen bungalow with a loft featuring a queen bed, located at 215 Eanes Lane.brbrbrbr•           The Carysfort Light Suite is a separate individual 2BD/ 2BA with its own exclusive off-street parking space, located at 217 Eanes Lane.brbrbrbr4. Do I need a vehicle or transportation brbrIf you have a vehicle, we have rare parking available that most lodging on the island cannot offer but you do not need a vehicle to enjoy your stay with us. The property is located one-half block off Duval Street on quaint and quiet Eanes Lane delivering one of the best lodging locations on the Island close to everything but in a peaceful and quiet location. Here are the distances to some Key West Landmarks:brbrbrbr•           Key West Lighthouse Museum, 2-minute walkbrbr•           Ernest Hemingway Home and Museum, 2-minute walkbrbr•           Blue Heaven Restaurant, 5-minute walkbrbr•           Southernmost Point Buoy, 8-minute walkbrbr•           Key West Butterfly Conservatory, 8-minute walkbrbr•           Sloppy Joe’s Bar, 12-minute walkbrbr•           Key West Amphitheater and Park, 12-minute walkbrbr•           Mallory Square Sunset, 12-minute walkbrbr•           Fort Zachary Taylor State Park & Beach, 12-minute walkbrbrbrbrWe look forward to welcoming you to paradise!
Bed 1

Bed

Bath 1

Bath

Sleep 4

Sleeps

Home Most popular vacation rentals in Key West