Vacation Rentals By Owner In Key West, FL

$973.13

SEAPORT PANORAMA at Galleon Resort-Beach-Pool-King-BBQ-Kitchen views!

Key West, Florida, United States

GALLEON RESORT LUXURY OCEANFRONT CONDO RENTAL 45 FT FROM THE WATER WITH BREATHTAKING 180 DEGREE FRONT & CORNER BALCONY VIEWS OF KEY WEST HARBOR, SUNSET KEY AND THE GULF OF MEXICO. (These views are also available from the master bedroom, living area and kitchen all day, every day)brbr4th FLOOR OCEANFRONT CONDO RENTALbrSleeps 6 / 1 Master King - 1 Guest Queen / 1 Queen pullout / Large private oceanfront balconybrbrEXCEPTIONAL LOCATION & CONVENIENCEbrThe Galleon Resort is located at the end of North Front St (literally steps from your elevator to Seaport Boardwalk happy hour bar menus, shops & multiple restaurants) / 2 blocks to Duval St + more restaurants, Mallory Square, Front Street eateries, bars and shopping—or cook steaks & seafood on our newly renovated paver picnic patio with 2 extra large Pro BBQ grills and free propane gas on demand + 3 round umbrella picnic tables / 3 HD cable TVs in condo / Free wireless internet / Free private parking / Secluded but very close to all the action / Car not necessary / Rental scooters, bikes, electric golf carts, fishing tour boats, wave runners all on-site to explore Key West from land or water / Oceanfront Tiki Bar & Pirates Cove Marina Bar & Grill on premisesbrbrRECOGNIZED & VOTED IN 2016-17-18 AS A TOP-25 TIMESHARE RENTAL RESORT BY TIMESHARE USERS WORLDWIDEbrbrBEAUTIFULLY LANDSCAPED OCEANFRONT SWIMMING POOL & HOT TUB, LARGE NEW OCEANFRONT COVERED TIKI BAR, NEW SUN DECKS & GAZEBOS, SMALL PRIVATE BEACH & OCEAN SWIM AREA w PLATFORM, PRIVATE FISHING PIER & NEW BBQ PATIObrbrFull-service resort with on-premises concierge, housekeeping, maintenance and security staffing with computerized door entry cards, security cameras, and room safes for guests.brbrChildren welcome. Suitable for seniors and handicapped with four elevators, ramps to pool, outdoor hot-tub, beach, Granite sitting ledges in Master Bathroom and open entry from walk-in shower to JacuzzibrbrThis 96-unit oceanfront property is accessible by car or boat, with free parking and rented boat slips / Great for families & sailboat crews / Marina next to resort to dock your boat / Full laundry, sauna / At the entrance to the Historic Seaport boardwalk / On the ocean in the heart of Key West's incomparable Old Town w tin-roof conch houses, historic museums & homes, unique shops, artist galleries, and quirky Duval Street entertainment / *Don't miss the nightly, world-famous Mallory Square Sunset Celebration (Unique Entertainment-Food-Art-Crafts) just 2 blocks from your condobrbrTHIS CONDO has a full size, fully equipped kitchen, breakfast area, wet bar w wine storage, washer-dryer, dining area, living room with entertainment center (55” TV, DVD player, AM-FM stereo, extra wardrobe closet, drawers) in living area, master bedroom with ensuite 2-sink vanity, closet, makeup vanity with extra device outlets, shower w attachments & jet-tub Jacuzzi, guest bedroom with full bathroombrbrFULL BALCONY with lighting has four chairs & table, and is accessible thru French doors in both the living room and master bedroom with sweeping front and corner views of Key West Harbor, Sunset Key and Gulf of Mexico.brbrEXTRA AMENITIES include 3 HD TVs with cable, DVD player, AM-FM stereo, iron & ironing board, jacuzzi tub, in-room safe and free private/secured wireless internet / Pool towels & bed linens provided / Kitchen and Master bath received complete granite & appliance renovation with new living room furniture in last 2-3 years / There is 1 free parking space for each unitbrbrQuiet and secluded, yet very close to restaurants & shopping / On-premises large oceanfront swimming pool with jetted hot tub / New oceanfront decking, lounges and umbrellas surround the resort / On-premises oceanfront TIKI BAR and Marina-side PIRATES COVE breakfast & lunch bar-grill / On-premises GIFT SHOP with unique, hand-painted & personalized souvenirs at driveway entrance / Small private beach with private fishing pier / New picnic patio with new extra large Pro BBQ grills and umbrella picnic tables / Roof-top observation deck provides amazing 360 degree views of Key West

2

Bed

2

Bath

6

Sleeps

$410.63

/ Nightly

House Boat

Romantic Yacht Stay Key West + Amenities Unit 1

Key West, Florida, United States

Luxury 46-ft Sea Ray yacht in Key West! Sleep up to 6 guests in 2 private cabins, each with ensuite bath and A/C. Perfect for romantic getaways or small groups seeking an unforgettable waterfront experience. Wake up to dolphins, explore pristine waters, and watch stunning sunsets from your private deck. This meticulously maintained express cruiser offers hotel comfort with the freedom of the open sea. Your paradise floating retreat awaits! Discounted ocean excursions available upon request!brbrThe spacebrbrWelcome aboard your private floating hotel in Key West!brbrWe have two identical yachts available on VRBO – perfect for larger parties or multiple families traveling together! This is Grand Admiral 1.brbrThe Grand Admiral is our smallest yacht but it offers plenty of space for up to 6 guests. It has 2 full bed and 2 full baths plus an extra pull out bed that could sleep an additional 2 guests or kids.brbrNote: if you have needs to fit a larger sized group please check out our other listings! We have additional yachts in the same marina that you can book for bigger groups. Just let us know how many beds and cabins you need and we will make you a special offer to accommodate your group size!brbrYou will love waking up on the water in the peaceful Stock Island Marina. A break from the ordinary hustle and stress of a hotel experience.brbrThe Stock Island Marina features tons of amenities which you have full access to:brbrBarbrPoolbrGymbrSaunabrParkingbrLaundry areabrTiki Grilling AreabrBeach (one of the few in Key West)brAccess to public transport (minutes from downtown Key West)brAnd more!brbrOur private on site concierge will help you with any questions you may have and help you plan out your activities for Key West.brbrWe also offer optional ocean excursions for you to take the yacht out for either a sunset cruise or a half day or full day experience on the water. Inquire about the excursions as you can get a discount for being our guest through VRBO.brbrThe Grand Admiral Floating Resort is perfect for:brbrCouplesbrFamiliesbrAnyone wanting a break from the ordinarybrBoat enthusiastsbrbrIf you have questions let us know and we will help you plan the perfect Key West Getaway with our floating hotel and resort!brbr- Vadim from LaRoma YachtsbrbrGuest accessbrGuests have access to the yacht and all the resort amenities including:brbrGymbrPoolbrBeachbrParkingbrTiki Bar PierbrGeneral StorebrAccess Point for public transportationbrbrOther things to notebrThis listing is for your very own floating hotel in Key West. You can use it to explore the area and enjoy the wonderful amenities included.brbrIf you would like to book an additional ocean excursion, just let us know! We will give you a nice discount on either a sunset cruise or full or half day out on the water.

Bed

Bath

Sleeps

$781.93

/ Nightly

Private Vacation Home

Old Town Seacret Paradise! 4 BR with Pool!

Key West, Florida, United States

Charming Key West Oasis – Your Private Slice of Paradise!brbrEmbark on a month-long journey of relaxation and exploration at Seacret Paradise, a hidden gem tucked away in the heart of Old Town Key West. Located just two blocks from the Key West Express and Dry Tortugas ferry terminal, and mere steps from Old Town Bakery, Dive Bar, and Eaton Good, this private retreat blends peace, comfort, and unbeatable access to all the island’s magic.brbrThis charming four-bedroom, three-and-a-half-bath home comfortably accommodates up to nine guests and is ideal for couples, families, or anyone looking to immerse themselves in the Key West lifestyle. Enjoy bright indoor-outdoor living, a sunny balcony, a fully equipped kitchen, and a quiet lane location just minutes from the best dining, music, and waterfront sights in Old Town.brbrBooking Requirements: To ensure a smooth stay, all reservations require a signed rental agreement and a refundable security deposit hold. The deposit hold is $500 for and will be placed on a credit card 2–3 days prior to arrival and released within 5–7 days after check-out, provided no damage or policy violations occur. A Guest Service Fee is included in all reservations and varies based on length of stay.brbrPlease note: In accordance with City of Key West regulations, this property requires a minimum 28-day stay. This allows you to settle in, unwind fully, and explore the island at your own pace.brbrPet Policy: One dog under 30 lbs allowed with owner approval and pet depositbrbrCleaning Fee Breakdown:brTo ensure cleanliness and comfort during your extended stay, the $650 cleaning fee includes a Mid-Stay Clean (A full refresh halfway through your 28-day visit) and a Post-Departure Clean (A deep clean to prepare the space for future guests)brbrSome Additional Amenities (see amenities for full list):brPack-n-play and portable high chair available in upstairs bedroom closetbrFast Wi-FibrSmart TVsbrStrong A/CbrWasher/dryerbrDishwasherbrIce Maker in FreezerbrOne off-street parking spot (compact fit)brbrbrWhether you're here to write your next chapter, chase sunsets, or enjoy fresh croissants every morning, Seacret Paradise offers everything you need to live like a local—luxuriously.

Bed

Bath

Sleeps

$418.26

/ Nightly

Private Vacation Home

TROPICAL PROPERTIES VACATION RENTAL - KEY WEST

Key West, Florida, United States

****This property requires a minimum stay of 28 nights in the same calendar month****brbr***Brand New Pool with waterfall, saltwater, heater, and a chiller to maximize comfort! brbrbrTropical Properties Vacation Rentals invites you to our beautiful historic home located in Historic Old Town Key West. This home is located just two blocks from Duval Street and in the center of all things Key West. This home was originally built in 1929 and has been painstakingly restored to include every modern amenity.brbrbrThe spacebrLOCATION: This tropical destination is a two block walk from Duval Street where you will be dazzled with boutiques, restaurants, nightlife, gallery viewing, shopping and an abundance of other activities, yet the neighborhood is quiet and serene. The homes is located 5 blocks from South Beach, 8 blocks from the North Harbor, a comfortable walk or bike ride to everything Key West.brbrHOUSE LAYOUT: The home is boasts a gorgeous brand new front porch and new pool, with an abundance of patio furniture an outdoors oasis. This home has hard wood floors and modern tile throughout, a spacious family room, central air, washer/dryer located inside the home, a dishwasher all rarities in Key West rentals and makes this a truly enjoyable space.brbrBEDROOMS: This home offers 3 beautiful bedrooms with 2 full bathrooms. Every bedroom on the first floor has a TV, all have tropical décor, new linens and comforters.brThe first floor features 2 bedrooms. The first bedroom boasts a queen bed, dresser, two night tables and a large closet. The second bedroom also has a queen bed, two night tables and large closet. The living room included a brand new sofa queen sleeperbrThe second floor is a loft accessed by stairs as shown in the photographs with a ceiling height of 5'2 and has two twin beds, 2 dressers, night stands, and a clothes rack.brbrCOMMON AREAS: The kitchen contains all brand new top of the line appliances, a refrigerator with an ice-maker, microwave and dishwasher. The dining area contains a comfortable configuration.brbrPETS: No pets are allowed in this home, this is NOT pet friendly.brbrPARKING: There is designated parking space on property for two FULL SIZE vehicles, an absolute rarity in Key West.brbrOUTDOOR AMENITIES: The tropical outdoor space is furnished with several seating areas both in the sunshine and shade. The back of the home offers a quiet respite from the hustle and bustle of nearby Duval Street.brSecurity cameras are installed on the exterior of the house. Front door, side alley, and facing backyard/pool. brbrOTHER AMENITIES: Iron & Ironing Board, 2 x Hair Dryers, Bed Linens, Towels, Beach Towels, Washing Machine, 3 x TV's, Washer dryer, Dryer, Garden (Private), Ceiling Fans, 2 x showers, high speed internet connection, air conditioning, 2x Fire ExtinguishersbrKitchen stove, Refrigerator ,Cookware & Kitchen Utensils, Dishwasher, Microwave, Toaster, Keurig, Blender and BBQ grill and utensils.brbr***Guests must be 25 years of age or older unless accompanied by an adult.brbr****This property requires a minimum stay of 28 nights in the same calendar month****

4

Bed

2

Bath

8

Sleeps

$759.38

/ Nightly

House Boat

Glorious Yacht Stay Key West - 4 BDRMS and Amenities!

Key West, Florida, United States

Spacious 46-ft Lagoon catamaran in Key West! 4 private ensuite cabins sleep up to 12 guests. Enjoy panoramic views from the flybridge, relax in the bright salon, or unwind in the forward cockpit with ocean breezes. Each cabin features A/C and private bath. Perfect for groups and families seeking a unique floating hotel experience with gym, pool, and beach access. Optional sailing excursions available at discounted rates!brbrThe spacebrWelcome aboard your private floating hotel in Key West!brbrSomewhere is a beautiful 46 foot long catamaran which offer plenty of space for up to 8 people! It has 4 queen sized bed and 4 full baths in 4 separate cabins for ultimate privacy.brbrNote: if you have needs to fit a larger sized group please check out our other listings! We have additional yachts in the same marina that you can book for bigger groups. Just let us know how many beds and cabins you need and we will make you a special offer to accommodate your group size!brbrYou will love waking up on the water in the peaceful Stock Island Marina. A break from the ordinary hustle and stress of a hotel experience.brbrThe Stock Island Marina features tons of amenities which you have full access to:brbrBarbrPoolbrGymbrSaunabrParkingbrLaundry areabrTiki Grilling AreabrBeach (one of the few in Key West)brAccess to public transport (minutes from downtown Key West)brAnd more!brbrOur private on site concierge will help you with any questions you may have and help you plan out your activities for Key West.brbrWe also offer optional ocean excursions for you to take the yacht out for either a sunset cruise or a half day or full day experience on the water. Inquire about the excursions as you can get a discount for being our guest through VRBO.brbrOur floating resort experience is perfect for:brbrCouplesbrFamiliesbrCorporate groupsbrBoat enthusiastsbrAnyone wanting a break from the ordinarybrbrIf you have questions let us know and we will help you plan the perfect Key West Getaway with our floating hotel and resort!brbr- Vadim from LaRoma YachtsbrbrGuest accessbrGuests have access to the yacht and all the resort amenities including:brbrGymbrPoolbrBeachbrParkingbrTiki Bar PierbrGeneral StorebrAccess Point for public transportationbrbrOther things to notebrThis listing is for your very own floating hotel in Key West. You can use it to explore the area and enjoy the wonderful amenities included.brbrIf you would like to book an additional ocean excursion, just let us know! We will give you a nice discount on either a sunset cruise or full or half day out on the water.

4

Bed

4

Bath

8

Sleeps

$605.09

/ Nightly

Private Vacation Home

Duval Square Retreat w/ Private Hot Tub, Pool, Parking & Walkable Location!

Key West, Florida, United States

Welcome to Your Tropical Escape at Duval Square brbrDiscover the perfect Key West getaway in this beautiful 2-bedroom, 2.5-bathroom retreat located in the exclusive gated community of Duval Square. Nestled on upper Duval Street—just steps from restaurants, cafés, and island conveniences - this property offers the ideal blend of privacy, luxury, and unbeatable location.brbrProperty Highlights:br~ Spacious & Stylish LivingbrRelax in the bright, comfortable living room featuring a sofa bed, convenient powder room, and easy access to your private balcony.brbr~ Master Bedroom SuitebrUnwind in the serene master suite with a king-size bed and a newly renovated private bathroom.brbr~ Second Bedroom SuitebrPerfect for guests or family, the second bedroom offers a queen bed and its own private bathroom for total comfort and privacy.brbr~ In-Unit Washer & DryerbrPack light and enjoy the convenience of doing laundry right at home.brbr~ ParkingbrA rare luxury on Duval Street—this rental includes one reserved parking space.brbr~ Private Outdoor OasisbrStep onto your private balcony and soak in the tropical breezes while you relax in your personal hot tub - the perfect spot for morning coffee, sunset cocktails, or unwinding after a day of exploring Key West.brbr~ Unbeatable Location - 1075 Duval Street brWalk to galleries, dining, boutique shops, and nightlife… yet return home to a private, peaceful retreat above it all.brbrCommunity Amenities:br• Sparkling swimming poolbr• Lush tropical landscapingbr• On-site restaurants, shops, bank, and convenience storebrEverything you need is right at your doorstep.br________________________________________brReady to indulge in the perfect Key West experience brThis luxurious and ideally located home books quickly—secure your stay today and experience island living at its finest!

2

Bed

2

Bath

6

Sleeps

$605.13

/ Nightly

Private Vacation Home

Luxury Mansion in Old Town Key West – Four Bedrooms, Private Pool

Key West, Florida, United States

Island Dreaming – Your Luxury Key West Getaway - MONTHLY RENTALbrWelcome to Paradisebrbr*** Please note for 2027 High Season rentals Jan- February - Arrival after the 5th of January for 6 week minimum is required in order to get accurate pricing***brbrDiscover the ultimate island retreat at Island Dreaming, a spectacular Key West vacation home nestled between the charm of Old Town and the tranquility of the Meadows District. Whether you're traveling with family or friends, this private oasis blends upscale amenities with the laid-back lifestyle of the Keys.brbr Property Highlightsbrbr Location: Quiet yet central – walk to downtown, yet enjoy serene privacybr Bedrooms: 4 spacious bedrooms including two primary suitesbr Bathrooms: 3.5 modern bathroomsbr Parking: Off-street parking for 1 vehiclebr Size: Comfortably sleeps 8+ guestsbrbr Outdoor Oasisbrbr Private Saltwater Pool: 12’ x 18’, heated (by request), custom-tiled with waterfall & in-pool loungersbr Outdoor Kitchen: BBQ grill, sink, and ice-maker – perfect for entertainingbr Multiple Outdoor Living Spaces:brbr Expansive front porch for morning coffeebr Back deck for cocktails under the starsbr Shaded & sunny lounging areasbrbr Lush Landscaping: Tropical flora, paver walkways, irrigation, and outdoor lightingbrbr Interior Featuresbrbr Seamless Indoor-Outdoor Living: 9-ft ceilings & 16-ft glass doors connect the living area to the poolside deckbr Gourmet Kitchen: Fully equipped for all your culinary needsbr Wine Lovers’ Dream: 600-bottle, walk-in, climate-controlled wine roombr Two Primary Suites:brbr First-floor suite with private bathbr Second-floor suite with vaulted pine ceiling & private balconybrbr Bright Living Room: Natural light and pool views with wall-to-wall glass doorsbrbrAdditional Amenitiesbrbr Whole-house water filtration systembr Custom-designed staircasebr Pool heat available (fee applies; must be requested in advance)br High-speed WiFi & smart TVsbr Washer & dryerbrbrPerfect LocationbrbrLocated in a diverse, upbeat neighborhood, Island Dreaming puts you close to:brbr Duval Street nightlifebr Local restaurants & barsbr Art galleries, shops, and attractionsbr Beaches & marinasbrbrIdeal Forbrbr Familiesbr Groups of friendsbr Extended staysbr Guests seeking a luxury, peaceful vacation with easy access to the actionbrbrAdditional fees may be added after booking:br Pool heating fee of $300 per month for the months of November-March(optional)br Reservations of more than a month require a mid stay cleaning feebr brBook Your Stay Today and Start Living the Island Dream!

Bed

Bath

Sleeps

$298.98

/ Nightly

Condo

Beachy Keen Too at Beach Club in Key West WEEKLY RENTAL

Key West, Florida, United States

WEEKLY RENTAL - Enjoy endless open water views just footsteps away from the tranquil waters and beach of the Atlantic Ocean. br“Beach Club #304” is a serene waterfront oasis located in an upscale gated community within walking and biking distance to the local’s finest spots, including restaurants, beaches, shopping centers, bars and the infamous Duval Street. brbrThe Living room is brightly decorated with spectacular views of the Atlantic Ocean and a wonderful walk out covered dining and lounging deck. The breathtaking view can be seen as soon as you enter this spacious 2-bedroom coastal retreat, which includes combination dining room and comfortable seating for those spontaneous movie nights. The kitchen is fully equipped to make that perfect home cooked meal. brbrBedroomsbrPrimary Bedroom: King bed, flat screen TV, direct access to the balcony, oversized spa-like shower.brbrGuest room (Second room): 2 Twin beds OR One King Bed, flat screen TV, oversized spa-like showerbrbrUnit Features:brCentral A/C, Wi-Fi, washer/dryer, security entry, one reserved parking space in the garage and elevator accessbrbrCommunity Amenities: Resort amenities include two ocean side pools (heated), tennis court, outside cooking and covered dining facilities, and fitness center. Immediate beach and open water access. There are plenty chaise lounges around both pool areas as well as a cabana to enjoy during those sunny island afternoons. Additionally, Rest Beach, Higgs Beach and Smather's Beach are conveniently located nearby.brbrAdditional things to know:brThe Key West Beach Club Condo Association requires additional registration, which includes providing copies of photo IDs for everyone over the age of 17, in advance of your arrival. Details will be provided along with your rental agreement.brbrThis property will accommodate up to 4 adults comfortably, there is an additional sleeper sofa for everyone to spread out:)brSorry, pets are not allowed

Bed

Bath

Sleeps

$699.75

/ Nightly

Condo

Near Duval - Tiki Bar - Private Beach - 2BR Condo - Old Town Key West - Sleeps 6

Key West, Florida, United States

Located in the heart of Old Town Key West. This resort overlooks the Gulf of Mexico with a private marina, private beach, pool, jacuzzi, with a restaurant and bar. Relax in the jacuzzi or sauna during your stay 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.brbrThis spacious two bedroom condo sleeps six, and features a fully equipped kitchen, including a full-sized refrigerator, microwave, toaster, coffee maker, stove and oven. The primary bedroom has a king sized bed, ensuite jetted tub, as well as a full bathroom. The guest bedroom layout may vary, featuring either two twin beds or a queen bed, and has access to the full guest bathroom. Please let us know your preference before booking and we will do our best to fulfill it, though it is not a guarantee. The living room has a TV with cable, dining area for four, and a sleeper sofa. Off the living room is a balcony to enjoy the Key West ocean breezes.brbrGalleon Resort Marina serves breakfast. Guests can enjoy poolside drinks at Sunset Tiki Bar.brbrKey West Shipwreck Museum and Mallory Square are just a 5 minute walk from this conveniently located resort. The Ernest Hemingway Home & Museum is 1 mile away.brbrPlease note, guest bedroom may feature two twin beds or one queen bed. Please let us know your preference before booking. We will do our best to fulfill it, but it is not guaranteed.brbrResort fee in the amount of ($20/per day or $75/per week) plus tax, due at check-in, along with a $150 refundable security deposit. Refundable security deposit is released, as long as no damages occur during your stay. (subject to change)brbrUnits are assigned after booking, in seven night increments. Multiple week stays may be booked, room moves may be required.brbrHousekeeping changes linens and towels on Tuesday only. 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.brbrWe 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.

Bed

Bath

Sleeps

$284.21

/ Nightly

Private Vacation Home

Beautiful Old Town 2 bedroom Cottage on a Private Lane

Key West, Florida, United States

Located in the heart of Key West's historic district on a quiet lane with parking directly in front of the private gated entrance to the home. 3 blocks from Historic Seaport and Duval Street.This is one of Key West's most coveted locations.brPrivate, perfect distance for walking or biking to local shops, bars or restaurants.brSurrounded by beautiful historic homes and mature Key West landscapes. This is a location you will want to visit more than once. Find your Key West home away frobrbrbrLocated in the heart of Key West's historic district on a quiet lane with parking directly in front of the private gated entrance to the home. Close to the beautiful seaport and downtown Duval Street.

Bed

Bath

Sleeps

$1596.38

/ Nightly

Private Vacation Home

4-bedroom resort style home in awesome Key West with large pool and private deck

Key West, Florida, United States

Key West is waiting for you at this superb 4-bedroom resort. Fresh and new inside and out, With 2 king beds, 1 queen bed, 2 twin XL beds, and 1 futon, guests will have plenty of space to relax. The 4 bathrooms feature a large pool and private back deck tub, 4 showers, and jetted bathtubs for a terrific stay. It's easy to see why you'll be able to unwind at our place. Excellent location just a couple blocks from Southern buoy and Duval. Play pickle ball and lounge on the beach just 2 blocks. Includes 4 bikes

5

Bed

4

Bath

10

Sleeps

$599.06

/ Nightly

Private Vacation Home

SOUTHERN CROSS: 3 BR, 3.5 BA home in Old Town Key West with Private Pool & AC!

Key West, Florida, United States

SOUTHERN CROSS:brWelcome to this charming home in Bahama Village - Old Town Key West. This modern and elegant home was constructed in 2021 and features 3 bedrooms, 3.5 baths, off-street parking, and your own private pool! Available for rental stays of 28 days or longer, this home is perfectly situated in the heart of Old Town Key West. Guests are just 1.5 blocks to iconic Duval Street which features some of the best shopping, restaurants, and live music in the country. You're 2 blocks to the historic Key West Lighthouse and Hemingway House Museum, and 3.5 blocks to Southernmost Point or Key West's best restaurant...Blue Heaven!brbrDETAILS & AMENITIES:brEnjoy the enchanting atmosphere of this home which features the perfect blend of luxury, comfort, and island living! The home is complete with modern amenities like a private swimming pool, air conditioning, WiFi, a gas grill, two sets of washers & dryers, tankless hot water heaters for long & relaxing showers, ceiling fans in each bedroom, an EV charging station, and off-street parking, The bright, open layout also features impact-rated doors and windows, solid wood cabinetry, Dade County pine floors, quartz countertops, and professional-grade Viking appliances in a chef's dream kitchen. Each bedroom is spacious and filled with natural light, while the bathrooms are elegantly appointed and strategically placed for convenience--including a half bath with outdoor access, perfect for poolside guests.brbrSLEEPING ARRANGEMENTS:brThis home features a king bedroom suite on the main level with its own private bathroom. The master bedroom suite is upstairs and features a king bed with a large tiled shower with glass surround. The third bedroom suite is also on the second level and contains a full bed and a twin bed...also with its own private bathroom. A half bath is located on the main level and is perfect for pool guests or simple convenience. brbrOUTDOOR LIVING:brEnjoy the best of island outdoor living with a private concrete swimming pool, covered front and rear porches with composite decking, and a gas grill for delicious cookouts.brbrPARKINGbrThis home has two designated off-street parking spots in the front driveway. There is also ample on-street parking in the neighborhood if you have extra guests.brbrPETS:brThis home allows small dogs only.brbrBOOKING DATES:brThe home is only available as a monthly rental (28 night minimum).brbrCANCELLATION:brBookings canceled at least 60 days before the start of the reservation will receive a 100% refund. Cancellations inside of 60 days are non-refundable.

3

Bed

3

Bath

7

Sleeps

$1329.13

/ Nightly

Private Vacation Home

**HALFWAY TO HAVANA @ DUVAL** Two Cottages w/ Pool + LAST KEY SERVICES...

Key West, Florida, United States

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!brbrIf the rhythm of the islands has been calling and you're ready for a taste of the good life, then a stay at HALFWAY TO HAVANA is just what your soul is craving! Situated between the calm waters of the Florida Bay and the vibrant nightlife of Cuba's capital City, this unique vacation home blends the laid-back island vibes with all of the modern conveniences you’ve come to expect.brbrThis 4-bedroom, 4-bathroom property is the combination of 2 side-by-side private homes, reminiscent of the simple cigar-maker cottages that once lined the streets of Key West. The cigar-makers would be quite envious of the modern amenities and thoughtful touches these homes feature, such as the fully fenced backyard with spacious pool and parking for two vehicles. Located ON Duval Street, you'll be steps away from all that Key West has to offer. Paired with Last Key’s exceptional Guest Services & Complimentary In-House Concierge, you’ll be feeling the rhythm of the island in no time.brbrTHE LOCATION...brbrIf you've heard of Key West, you undoubtedly know of the famous 'Duval Street' with its selection of fabulous restaurants, shops, and nightlife. With a prime Duval Street address, HALFWAY TO HAVANA is truly the choice location for a group that wants to be in the heart of it all. You can enjoy unrivaled people watching from your porch or hop down your steps to any of the attractions within walking distance, including the Southernmost Point, Hemingway House, and famous spots like Sloppy Joe's, and any number of delicious restaurants. Should you decide to venture off the island, you do have two off-street parking spaces available.brbrTHE LIVING AREA & KITCHEN...brbrEach home features a living and dining space, complete with a dining table and a flat screen TV. Each living area features a comfortable couch to lounge on. The kitchens feature modern appliances and all of the tools you'll need to prepare meals at home.brbrTHE PRIVATE POOL & GROUNDS...brbrThe property really shines when you get out to the private pool behind the units. Plenty of space to lay out and soak up some sun. Enjoy a swim or sit by the heat-optional private pool in the chaise lounges. Enjoy a poolside meal at the outdoor dining set while using the deluxe BBQ grill. You'll have everything you need for a cookout with the whole gang. The hot tub is a perfect place to end your day with a relaxing soak under the stars.brbrTHE ACCOMMODATIONS...brbr** Master Suite 1: Located in the First House with a King bed and an en-suite bathroom with a walk-in shower..brbr** 2nd Bedroom: Located in the First House with Two Twins OR One King and an en-suite bathroom with a shower and tub combo.brbr** Master Suite 2: Located in the Second House with a King bed and an en-suite bathroom with a walk-in shower.brbr** 4th Bedroom: Located in the Second House with a King bed and an en-suite bathroom with a walk-in shower.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 & full cable includedbrbrIn addition, this fully stocked home also includes, but is not limited to the amenities on this list:brbr** Fully Fenced Private Yardbr** Private Pool with available Pool Heatbr** Hot Tubbr** Two Off-Street Parking Spacesbr** Propane BBQ GrillbrbrOther notes:brbr** Interim housekeeping provided upon requestbr** This property will accommodate up to 8 adultsbr** 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.

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Bath

Sleeps

$180.93

/ Nightly

Apartment

Luxury Island Resort Living at 1800 Atlantic, Pool, Beach, Tennis,in Key West

Key West, Florida, United States

Luxury Island Resort Living at 1800 Atlantic – Key WestbrbrWelcome to resort-style living in beautiful Key West! This updated and turnkey 2-bedroom, 2-bath condominium at 1800 Atlantic offers the perfect combination of comfort, convenience, and tropical elegance—ideal as a primary residence or a vacation getaway.brbrEnjoy open living and dining spaces, an eat-in kitchen with a bonus breakfast bar, ample cabinet storage, and a full-size in-unit laundry. The oversized private balcony offers partial ocean views and is accessible from both bedrooms and the living room. Sun-filled rooms, impact-rated sliding glass doors, and plantation shutters add style and privacy.brbrThe spacious primary suite features large closets, a dressing vanity, glass shower, soaking tub, and a TV sitting area—plus direct balcony access with tropical views. The second bedroom also offers a king-size bed and balcony access. Both bedrooms include flat-screen smart TVs and high-speed Wi-Fi for working remotely.brbrResort Amenities Include:br Private sandy sunning beachbr Olympic-style heated poolbr Jacuzzibr Fitness center & gymbr Three tennis courts (including one clay court)br Community clubhouse & picnic areasbr Lush tropical landscaping throughoutbrbrAdditional Features:br Fully furnished and move-in readybr Covered, assigned garage parking for vehicles under 6’2”br Additional guest parking availablebr Private storage unit includedbr Secure, gated communitybrbrWinter High Season Policy (Dec–Apr):brMonthly rentals must begin on the 1st of the month. Stays longer than one month are welcome, but we are unable to split the rental timeframe during this period.brbrParadise awaits at 1800 Atlantic—your island lifestyle starts here.brbrElevator Upgrade project taking place from June - September 2026 - Please note there will still be one working elevator in both the East and West building while this project is underway.

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Bath

Sleeps

$395.44

/ Nightly

Condo

The Caribbean Suite - 2-K-bedroom /1 bath/ kitchenette/sleeps 6

Key West, Florida, United States

This deluxe Key West Charmer is a beautifully restored Victorian home built in the 1880's that was converted into individual condominiums many years ago, located just one block from Duval Street in the Heart of Old Town Key West. Our casual atmosphere allows you to chill out and enjoy having the best of Key West within easy walking distance of all the restaurants, bars, entertainment and museums that we are most famous for.brbrMingle with other guests around the tropical gardens surrounding the heated pool and sundeck creating the perfect setting for a laid back and quiet afternoon. Enjoy alfresco dining in the tropical gardens while you enjoy the wonderful weather that Key West offers!! brbrThe Carriage House building at the Hollinsed House 2nd Floor - Caribbean Suite is a tropical 2BR/1BA with king beds, full kitchen, living room (with futon), dining area; two balconies with one stretching across the front overlooking the pool and garden area and one located off a bedroom. Sleeps 4 - 6.brbrHave a group coming to Key West Or maybe need just one or two more units Go to Click Here to see All My Rental Listings just above the Map Feature to see the rest of my listings at the Hollinsed House!brbrRATES for SPECIAL EVENTS:brPlease note that rates for Fantasy Fest, Meeting of the Minds (formerly Jimmy Buffet Parrothead Days), Race Week, Thanksgiving, Christmas, New Years, Songwriter's Festival, Memorial Day Weekend, Hemingway Days, and Poker Run all have minimum stays and different rates than are listed on the Rates page of this VRBO listing. brbrDEPOSITS:brA deposit equal to the cost of one half of your stay or one night, whichever is greater, is required to guarantee a reservation. The balance is due 30 days prior to arrival. Sorry, no refunds for early departures. brbrCANCELLATION AND REFUNDS:brCancellations from time of booking to thirty (30) days of arrival date will be charged a $50.00 processing fee per unit rented. All bookings of one week or longer will be charged a $100.00 processing fee per unit rented if cancelled more than thirty (30) days prior to arrival. Cancellations within thirty (30) days of arrival date will be charged for one night per unit rented or may extend their reservation for six months. Cancellations within seventy-two (72) hours to twenty-four (24) hours have a 50% cancellation fee or can be extended for six months. Cancellations within twenty-four (24) hours are non-refundable but will be offered a six-month extension. Sorry, no refunds for shortened stays. We reserve the right, to change your unit number if you are reserving for 3 nights or less.brbrCancellations for Special Events: Fantasy Fest and Christmas/New Years. Reservations of 5 days or longer that are cancelled within 2 weeks of arrival will be charged a $250 cancellation fee. Reservations cancelled within 1 week of arrival will be charged a $500 cancellation fee. Reservations cancelled within 72 hours of arrival are non-refundable. All cancelled reservations will be offered a six-month extension.brbrHURRICANE SEASON CANCELLATION POLICY, EFFECTIVE JUNE 1 -DECEMBER 15TH:brWe do not refund for inclement weather or other circumstances beyond our control. We strongly encourage the purchase of Travel Insurance to protect your vacation investment! In the unlikely event that a hurricane evacuation is ordered while you are a guest, and you have not purchased travel insurance, you will be issued a voucher for the unused portion of your stay. Guests holding a confirmed reservation who are unable to travel to The Hollinsed House because of the closing of the Key West Airport or connecting roadways due to a mandatory evacuation and have not purchased travel insurance will receive a voucher in the amount of the room deposit held. Vouchers are redeemable between June 1 and December 15, up to one year from the issue date, excluding special events and holidays. (Exception: Vouchers issued for cancellations of Fantasy Fest reservations can be applied to future Fantasy Fests in the ensuing two years.) No voucher will be issued if the hurricane is not a threat to Key West and you are unable to travel because of canceled flights or adverse travel conditions outside the Keys. We strongly encourage the purchase of Travel Insurance to protect your vacation investment!brbrKeywords: Guest House, Condo, B&B

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$421.88

/ Nightly

Hotel Resort

Hyatt Windward Pointe, 2 Bedroom Waterfront Resort

Key West, Florida, United States

Hyatt Windward Pointe offers a refined island escape where comfort, serenity, and sweeping open‑water views come together in a beautifully maintained tropical setting. From the moment you arrive, the resort’s lush landscaping, tranquil pathways, and elegant coastal architecture create a sense of calm that feels worlds away from everyday life. Soft ocean breezes drift across the property, and the horizon opens wide in front of you—an ever‑changing backdrop of turquoise water and unforgettable Key West sunsets.brbrThe residence itself is designed with an emphasis on space, privacy, and understated luxury. Thoughtful finishes, generous natural light, and a relaxed coastal palette make the home feel both sophisticated and inviting. A full kitchen with full‑size appliances allows for effortless meals and entertaining, while the in‑suite washer and dryer add convenience for longer stays. The private balcony becomes a favorite retreat, perfect for slow mornings with coffee or quiet evenings with a cocktail as the sky glows over the water.brbrThe resort’s infinity‑edge pool overlooks the shoreline, offering a peaceful place to unwind in the sun or enjoy the gentle rhythm of the ocean. The property’s west‑side location provides a quiet, exclusive feel while still keeping you close to the best of Key West. Within minutes, you can be celebrating the sunset at Mallory Square, exploring the boutiques and galleries of Old Town, or savoring world‑class dining and nightlife along Duval Street. Whether you spend your days relaxing by the water or discovering the island’s vibrant culture, this residence offers a luxurious home base for an unforgettable stay.brbrNOTES: brbrThis property available at a special discounted rate for 3 or 4-night stays for select dates. brbrHyatt will charge a $125 housekeeping fee upon check-out

2

Bed

2

Bath

6

Sleeps

$156.39

/ Nightly

Apartment

STUNNING! HEART OF OLD TOWN!: Walk to Duval and Historic Seaport in minutes.

Key West, Florida, United States

Live like a local in this unique loft apartment in the heart of Key West's Old Town historic district. Walk to Duval Street, Mallory Square and Historic Seaport attractions and restaurants in just minutes. This second floor walk-up features custom Dade County pine woodwork lovingly crafted by local artisans. Full kitchen, private balcony, free Wifi, bedding, cookware, dish ware and towels provided. Minimum Stay 30 days Due to local city ordinance. (Please note that the host is required to collect an additional 5% tourist tax on behalf of the local government upon guest arrival.)

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Bath

Sleeps

$434.62

/ Nightly

Condo

Caroline On My Mind - Paradise, Upgraded - 2BD/2Bath - Prime Location!

Key West, Florida, United States

This beautifully restored, remodeled second-floor 1933 Key West home on Caroline Street offers a unique and inviting experience. The location is highlighted as a key factor, emphasizing the significance of its surroundings.brbrAs you enter Caroline on My Mind, you'll notice a stairway adorned with wainscoting, leading you to the entry. The home boasts an open and comfortable living area, allowing ample natural light to fill the space. The living room features high-vaulted ceilings and cathedral windows, creating an instant vacation-like ambiance.brbrThere is a flat-top electric stove, two-door refrigerator, and dishwasher available to facilitate your cooking needs. The countertop seating for three also provides a convenient space for dining or socializing while in the kitchen. Overall, the kitchen offers functionality and amenities that will allow you to enjoy preparing meals during your stay.brbrThe guest room is located on the same floor, accompanied by a full shower bathroom and a washer/dryer for added convenience.brbrOne of the standout features of this home is the large balcony that overlooks Caroline Street below. Equipped with fans, the balcony serves as a perfect spot for savoring morning coffee or enjoying cocktails. A four-person table allows for al fresco dining, while you can also engage in people-watching and relish the refreshing evening breezes of Key West.brbrTo access the floor above, a spiral staircase takes you to the treetops, providing a unique vantage point. The primary bedroom on this floor features a queen-sized bed that can be converted into two twins upon request. Additionally, for those who need to work while in paradise, there is a functional desk with great views, enabling mental breaks amidst the scenic surroundings.brbrLastly, there's a skylight in the primary bedroom, offering the opportunity for star gazing while lying in bed at night, adding to the enchanting atmosphere of this Key West home.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. brbrMonthly Rental OnlybrbrShared Pool/6 unitsbrbrPets Not AllowedbrVirtual Tour Url: https://my.matterport.com/show/ m=TXf1ngy4X89

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Sleeps

$249.31

/ Nightly

Private Vacation Home

The Gumbo Limbo Cottage - Your Happy Place - 2BD/2.5 Bath

Key West, Florida, United States

Escape to the laid-back charm of Key West with The Gumbo Limbo Cottage, a beautiful and beachy vacation rental. Nestled in the heart of the island, this charming 1933 shotgun house has been impeccably restored and uniquely decorated, creating a tranquil and inviting atmosphere for your month-long getaway.brbrAs soon as you step inside, you'll be greeted by hardwood floors and vaulted ceilings that flow throughout the home. The front reading room, complete with a small refrigerator and desk, is the perfect spot for an early morning coffee or an afternoon nap, while the foyer doubles as a dining room with seating for four.brbrThe master bedroom is just inside French doors that lead to a king-size bed and a separate bathroom, including a private outdoor shower that can be accessed via a side door off of the bathroom. brbrThe guest room features a comfortable queen size bed, and both rooms are located off the main dining area, along with a guest bathroom with a large soaker tub and shower combo.brbrThe open living room and kitchen provide the perfect space for entertaining and cooking for your family and guests. The kitchen is complete with dishware and cookware, ready for you to create your own delicious items. There is countertop seating for two and a gas grill on the lower deck for BBQs. When the living room becomes too warm, you can lower the solar screens to let in natural light without the heat. The sliding glass doors open to the sundeck, complete with a table for six and lounging furniture, making it easy to enjoy indoor-outdoor living.brbrThe backyard is a true oasis, with lush Florida foliage and a large Florida almond tree, and Gumbo Limbo, which are native to Key West. Spend your days lounging on the sundeck or exploring all that this vibrant island has to offer. And, when it's time to wind down, retire to the comfort of your cozy home-away-from-home, complete with linens included and free WiFi. Please inquire about our pet policy. Don't miss out on the opportunity to experience the laid-back charm of Key West this winter - book your stay at this beautiful vacation rental today!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. brbr-------------brFree WiFibrCookware, Dishware, linens, & towels are provided.brMonthly Rental Only: Due to a local city ordinance, the property is not licensed to be rented for less than 29 days

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Bath

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$606.36

/ Nightly

Private Vacation Home

Your own Private Resort! 50ft Dock on Canal w/ Pool, Tiki and RV Hookup!

Key West, Florida, United States

Welcome to your private slice of paradise in the Keys! This exquisite waterfront home offers an unparalleled opportunity to immerse yourself in coastal luxury. Nestled on a sprawling 1/3-acre property, our retreat boasts breathtaking grounds and a mesmerizing ambiance that promises an unforgettable stay.brbrHighlights of Your Stay:brbr Spectacular Indoor-Outdoor Living: Soak in stunning bay views from our spacious patio deck, perfect for al fresco dining or simply admiring the gorgeous Key West sunsets. Lush greenery provides a serene sense of privacy, creating your own secluded oasis.brbr ️ Resort-Style Amenities: Bury your toes in the sand of your private beach-like backyard lounge, or take a stroll through our zen garden, illuminated by captivating bistro lights in the evening. Lounge by the large outdoor saltwater pool or unwind in the resort-style tiki hut overlooking the pool, complete with charming chandelier lighting and a comfortable dining area.brbr ‍♀️ Complimentary Adventure Gear: Explore the bay with our complimentary bikes, paddleboards, and kayaks. brbr ️ Spacious & Luxurious Interiors: Enjoy a generous open floor plan featuring a gourmet kitchen equipped with gas appliances. The dining room comfortably seats up to eight guests, making it ideal for family gatherings or entertaining friends.brbr Elegant Accommodations: The master bedroom features a king-size bed and offers direct access to the patio deck overlooking the channel—wake up to serene water views and start your day in tranquility. Additional bedrooms include one with a queen bed and ample closet space, and another featuring bunk beds and a cozy sofa.brbr Entertainment Galore: Unwind in our bar/game room, complete with a tiki bar and convertible sectional sofa, providing extra space for relaxation and fun.brbr Bring Your Boat & Jet Skis: With a 50ft dock and nearby access to both the Atlantic Ocean and the Gulf of Mexico, you're set for aquatic adventures. Explore nearby sandbars and private islands, enjoy breakfast at Geiger Key, or let us connect you with the best local guides for unforgettable excursions.brbr Ample Parking: Plenty of parking space is available, including room for your trailer or RV.brbrLocal Delights Within Walking/Biking Distance:brbr☕ Famous Baby’s Coffee: Start your day with artisanal coffee and delicious bagels, croissants, and pastries at this local favorite.brbr Baby's Food Truck: Mouth-watering burgers and sandwiches from Baby's Food Truck.brbr Family Park: Enjoy a nearby park equipped with basketball, volleyball, and tennis/pickleball courts and more—perfect for some fun and exercise during your stay.brbrBook Your Dream Getaway Today!brbrIndulge in the ultimate coastal experience—whether it's lounging by the pool, kayaking the bay, or unwinding in our resort-style tiki hut. Just 15 minutes from the vibrant Duval Street, you can enjoy the excitement of Key West while retreating to your peaceful sanctuary.brbrEscape to this luxurious retreat and create unforgettable memories in the Keys.brbrReserve Now and Start Your Adventure!brbr**HOUSE RULES**brbr-No Parties/Eventsbr-No loud outdoor noise after 9pm / before 9am, please be respectful of our neighborsbr-No Diving into Pool or off of Dock, there is no lifeguard on dutybr-No sand in the pool. This could cause expensive damage to the filter. Please use wash bin for feet before entering the pool when coming from beachbr-Please do not leave doors to outside open to avoid letting in insects and to preserve A/Cbr-Additional house rules may apply and will be provided prior to booking check-in date or by requestbrbrbrIt is important to note that water depths and tides may vary in the area surrounding the property. Prior to booking, please consider and verify whether water depths are suitable for your needs. While we are happy to provide answers based on our knowledge of the area, please use extreme caution when boating and use the dock at your own risk. We only allow one docked boat per booking. We can also arrange for an offsite dock for additional boats with access to deeper waters in conjunction with this booking, subject to availability and appropriate fees.brbrPets allowed (smaller dogs and cats) with prior approval of breed and a pet fee (per pet).

4

Bed

2

Bath

8

Sleeps

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