Vacation Rentals By Owner In Key West, FL

$385.88

Key West Charm | 3 Pools, Complimentary Breakfast, Near Duval Street!

Key West, Florida, United States

This listing is for a room within a hotel.brbr✦ Your room is 240 sq. ft, equipped with complimentary toiletries, high definition 55-inch TV, available with Premium cable.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 $50 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.

1

Bed

1

Bath

2

Sleeps

$4567.51

/ Nightly

Private Vacation Home

Lighthouse Suites Collection

Key West, Florida, United States

Summary:brbrSix Luxury Suites Creating 9 BD/ 7 BA, Two Oasis Pools, Pergola, Outdoor Bar and Grill and Private Porches and Patios. Sleeps up to 30.brbrbrbrThe Space:brbrEscape the Ordinary...brbrbrbrThe full offering of all 6 luxury suites of the Lighthouse Suites Collection delivers 9 bedrooms, 7 bathrooms in 3 buildings accommodating up to 30 guests all recently renovated and refurbished in 2024 and 2025. Each unit contains balconies, porches or patios with stunning views of the Key West Lighthouse, partial Duval Street views and a partial view of the famous Hemingway House. By reserving the entire Lighthouse Suites Collection, all of your guests will have exclusive access to the two brand new oasis pools and all of the property amenities in a contained boutique compound environment located on a quiet Key West Lane.brbrbrbrSuite Amenities:brbrbrbr • Luxury King and Queen beds in all units with premium linensbrbr • Sleeper sofas in each unit except Key West Light Suite which has a Queen loft bedbrbr • Six fully equipped kitchen with granite countertopsbrbr • Six spa quality rain shower bathrooms and one half bath in the Carysfort Suitebrbr • Hardwood flooring throughout the suitesbrbr • Spacious private and porches balconies and patios for each suite with amazing viewsbrbr • Smart TVs with the latest Roku device for apps and streaming in every roombrbr • High-speed Fiber Wi-Fibrbr • Washers and dryers in every unitbrbr • Luxury well-appointed furnishing and artworkbrbr • Reserved parking space for six vehiclesbrbr • Private entrances for all units and lockout doors for two of our combo unitsbrbr • Luggage hut to store luggage and belongings in before check in or after check outbrbrbrbrLocation:brbrThe Lighthouse Suites Collection 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.brbr brbrThe 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.brbr brbrWhether 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.brbr brbrIn March 2025, we completed a full renovation of our outdoor common areas, exclusively accessible to guests of our six suites. brbr brbrThe 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.brbr brbrProperty Amenities:brbr brbr • 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 ceiling brbr • 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.brbr brbrFrequently 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.brbr brbr2. 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.brbr brbrWe 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.brbr brbr3. 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.brbr brbr • 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.brbr brbr • The Key West Lighthouse Suite is a separate individual queen bungalow with a loft featuring a queen bed, located at 215 Eanes Lane.brbr brbr • The Carysfort Light Suite is a separate individual 2BD/ 2BA with its own exclusive off-street parking space, located at 217 Eanes Lane.brbr brbr4. 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:brbr brbr • 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 walkbrbr brbrWe look forward to welcoming you to paradise!brbrbrbrGuest Access:brbrPrivate entrances to all 6 suites.brbrbrbrThe Neighborhood:brbrLocated on a residential street just a half-block off of world-famous Duval Street.brbrbrbrGetting Around:brbrKey West is a very walkable city. We also have bicycle and scooter rental companies, city buses, taxis and ride-share services.brbrbrbrOther Things to Note:brbrPlease see the welcome book inside your suite for any other information you need, including how to use the grill and fire pit.brbrbrbrInteraction with Guests:brbrContactless check-in using smart locks. We are available 24/7 by phone. Staff will be on the property daily and weekly to clean the outdoor area and service the pool and landscaping.

9

Bed

7

Bath

30

Sleeps

$187.34

/ Nightly

Apartment

Birkenstrasse 52 Wohnung 2 by Interhome

Engelberg, Canton of Obwalden, Switzerland

55 m2. More information by the provider: The 2-bedroom apartment is located in an apartment building on the 2nd floor. In the immediate vicinity of the Titlis cable car station. Modern and bright open kitchen (renovated in 2022) with oven and Dolce Gusto coffee machine. 1 double bedroom. Living room with pull-out double sofa, TV, radio. Free WiFi. Bath-toilet. Balcony. Parking and garage. Washing machine in the house for shared use. Ski storage. Pets not allowed. Non smoking.br2-room apartment, 2nd floor: living-/dining room with a sofa bed, kitchen, 1 double room, bathroombrIncluded: Bath- and kitchen towels, garage parking, local tax. Excluded: Baby cot CHF 20.00, key deposit CHF 300.00 with credit card.brbrIncluded in price:brBed linen (initial supply) (2026-06-01 - 2027-12-02)brERV cancellation insurancebrFinal cleaning (Basic cleaning is always carried out by the guest) (2026-06-01 - 2027-12-02)brLocal taxbrInterhome plants 100'000 m2 of flowering fields to save the beesbrbrDeposit information: brBreakage deposit by credit card Visa / Mastercard (2026-06-01 - 2027-12-02): 300.0 CHFbr #CH6390.925.1

Bed

Bath

Sleeps

$789.8

/ Nightly

Private Vacation Home

Luxury Key West Compound with Pool, Guest Cottage, and Walkable Access to Duval

Key West, Florida, United States

Located in the coveted Historic District of Old Town! Situated on a quiet residential street, close to the Atlantic Ocean, beachfront restaurants, the Southernmost Point of the United States, the South end of Duval Street, and the White Street gallery and shopping area.brbrTHE MAIN HOME…brAs you enter the main home, you will be captivated by the huge high-end chef’s kitchen, natural light, and hardwood floors. A white, quartz waterfall island has seating for four and a built-in microwave. Custom cabinets, recessed lighting, and stainless-steel countertops complement this unique home. Stainless steel KitchenAid appliances and a large refrigerator are sure to impress the chef in your group.brbrThe adjacent open-concept living room/dining room and convenient powder room are accented with Dade County pine and designer décor. A large L-shaped sleeper sofa, a chair, and two swivel chairs provide views of the large-screen TV and the pool. The dining area seats 6 comfortably at the trestle table.brbrA lighted staircase at the entry leads to the primary bedroom, a luxurious retreat, and an immense spa-styled bath, complete with private access to the front porch and a large, oversized 2nd-floor back deck accessed through double French doors and a bank of windows! It is adorned with a woven rattan bed, nightstands, lamps, a dresser, and a large screen TV. Two large closets are also provided for your extended stay. The oversized ensuite bath features a double walk-in shower, multiple showerheads, a soaking tub, a water closet, and dual sinks with lighted coral mirrors. The stackable full-size washer and dryer are conveniently located on the 2nd floor of the home.brbrThe 3rd floor has two additional ensuite bedrooms flanking the hall. The first guest bedroom includes a queen bed, nightstands with lamps (each with built-in USB charging), built-in open shelving, a dresser, a closet, and a desk, as well as an ensuite bath. The second guest bedroom has a canopy bed, side tables with lamps, a closet, and its own cozy, modern ensuite bath.brbrTHE BACKYARD & POOL…brStepping outside through the double French doors, you’ll be transported to your very own private oasis. The backyard is surrounded by privacy fencing and features lush tropical landscaping. You’ll have plenty of room for everyone to lie out, relax, or enjoy an outdoor meal. Taking a dip in the heated saltwater pool and spa is the perfect way to relax after a day of exploring the island. Treat everyone to a poolside BBQ using the propane grill and outdoor dining table. There’s even a convenient outdoor shower located by the pool area. brbrTHE GUEST COTTAGE…brSteps away from the pool is the guest cottage, which is like no other! The 1st floor includes an open-concept family room, a wet bar, and a wall of windows overlooking the pool. Ample seating, a large-screen TV, a washer/dryer, and a powder room provide all the comforts of home. Sleek stainless steel appliances include a microwave, refrigerator/freezer drawers, a sink, an ice maker, and a wine cooler to ensure refreshments are close to the pool and guests. The 2nd floor bedroom is cozy and comfortable. Reading in bed is no problem with two nightstands and lamps. Complete with a closet, ensuite bath, and walk-in shower, this charming space is perfect for guests.

Bed

Bath

Sleeps

$405.38

/ Nightly

Cottage

Sunshine Siesta Cottage~Great Old Town Location, Pool, Private Hot Tub!

Key West, Florida, United States

BOOK NOW! Walk down the secluded brick path of the 4-unit compound, past the tropical foliage to Unit B, adjacent to the shared pool. Enjoy being surrounded by the unique quietness in the midst of Old Town. Enter the great room with all the kitchen accoutrements needed to prepare the perfect meal. Dine inside at the kitchen island or outside under the palms. Two spacious bedrooms connect to the private backyard where the hot tub awaits. All 5 star reviews on AIR. Video Tour https://youtu.be/yb9BnYwXPrYbrThe spacebrVibrant island vibe a short walk from Duval! Close to the party, far enough to relax. Borrow our bikes to visit the iconic White Street Pier, Southern Most Point, and any of the fabulous restaurants. Everything Key West has to offer, just minutes away!

Bed

Bath

Sleeps

$459.52

/ Nightly

Condo

Magical Sunrises on the Atlantic, Upgraded Condo & 10 minutes to Downtown.

Key West, Florida, United States

**About...** brDream Maker on the Atlantic is a two-bedroom condo conveniently located near beaches and restaurants, just minutes away from Duval Street. Nestled in a gated oceanfront community, it offers a peaceful retreat with beautiful ocean views from the private balcony.brbr**Furnishings...** brUnwind on the cozy couches while enjoying a movie or gather around the dining table that seats six for a home-cooked dinner.brbr**Sleeping Arrangements...** brThe primary bedroom features a king-size bed, while the guest bedroom has both a queen and a twin-size bed. Both bedrooms offer ample closet space and stunning ocean views. Additionally, the living room includes a queen sleeper sofa, making it perfect for accommodating families, friends, or couples.brbr**Details and Amenities...** brDream Maker on the Atlantic is a third-floor renovated unit featuring two bedrooms and two full bathrooms. One bathroom includes a large tiled walk-in shower, a soaking tub, and a double sink vanity, while the guest bathroom has a tub. The well-equipped kitchen boasts beautiful countertops and amenities, including a drip coffee maker, as well as a washer and dryer. Step out onto the private balcony to enjoy the ocean view and refreshing ocean breeze. The balcony is furnished with comfortable seating, perfect for soaking up the morning sun while sipping a warm cup of coffee to start your day.brbr**Pool and Outdoor Living...** brCommunity amenities include a heated Olympic-sized pool and a bubbling 20-person hot tub, as well as three tennis courts, one of which boasts the only clay surface in Key West. There are bathrooms near the pool for convenience, whether you want to enjoy a sauna soak or a quick rinse before heading back to the condo. A small community library and fitness center are also available. Spend your evenings under one of the many pavilions while grilling your dinner and enjoying the refreshing breeze from the Atlantic Ocean. Plus, bask in the sun on the property’s private beach or take a short two-minute walk to Smathers Beach, the largest beach in Key West! brbr**Parking...** brEach unit comes with an assigned parking space in the garage, subject to height restrictions. Limited outside parking spaces are available on a first-come, first-serve basis. brbr**Concierge Services...** brTake advantage of our concierge services to help plan activities for your trip. We can assist with bikes, scooter, and golf cart rentals, as well as a variety of excursions, including snorkeling, sunset cruises, jet ski rentals, parasailing, kayaking, fishing, paddleboarding, and much more. We can even stock your fridge with all the necessities before your arrival. brBook Activities /keywestattractionsfishingdiving/brbrbr **Cancellation...**br Bookings canceled at least 30 days before the start of the stay will receive a refund, minus a $250 cancellation fee.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.

Bed

Bath

Sleeps

$647.63

/ Nightly

House Boat

40ft Sailboat, 3 Bdrm, 2 Bath, sleeps up to 6

Key West, Florida, United States

Experience the ultimate escape aboard our 40’ yacht, docked at the exclusive Perry Marina. This unique yacht is perfect for families or friends, seeking a memorable getaway. Sleeps up to 6 guests, with 3 private staterooms and 2 full baths. Marina amenities, including 2 pools, 3 restaurants and bars, fitness center, free parking, free shuttle downtown and many more.

Bed

Bath

Sleeps

$281.25

/ Nightly

Private Vacation Home

Eliza Street Retreat, 2 bedroom, 2 bathrm, + loft, private pool, great location

Key West, Florida, United States

Adorable historical conch house 2 bdrm, 2 full bath and outdoor shower on quiet street with all the modern day amenities & decor in convenient location, relax by your private heated/chilled pool surrounded by decking and palm trees. Enjoy your morning sitting on the front porch watching the breeze travel through the palm tree leaves.Central location, walk or ride a bike to Duval.brbr1. Duval Street - 0.6 mibr2. South Beach - 0.7 mibr3. Higgs Beach - 0.6 mibr4. Key West Cemetery - 0.5 mibr5. Simonton Beach - 0.6 mibr6. Key West Butterfly and Nature Conservatory - 0.7 mibr7. Locals' favorite market, Fausto's, is just one block away

Bed

Bath

Sleeps

$739.84

/ Nightly

House Boat

SPECIAL OFFER! 50 Foot Luxury Sailing Catamaran in Five Star Resort, Key West!

Key West, Florida, United States

This yacht is new to our fleet and VRBO! Boasting 6 staterooms with each having its own private bath and shower, sleeping up to 12 adults. You will not find a more luxurious yacht on VRBO than this.brbrYou and your guests will have exclusive use of this 50 ft yacht all to yourselves. The yacht stays docked, the entire reservation, at the Perry Hotel and Marina, which invites you to complimentary use of two swimming pools, two poolside bars/restaurants, shuttle service to downtown, and more. You and your guests can come and go on the yacht anytime, day or night.brbrDue to local regulations, it is required that you choose at least one of the following options during your reservation: a two-hour excursion, a four-hour excursion, an eight-hour excursion, a ten-hour excursion, or a 24-hour excursion.brbr- 2-hour excursion: $1100+ tax & gratuitybr- 4-hour excursion: $1800+ tax & gratuitybr- 8-hour excursion: $2600+ tax & gratuitybr- 10-hour excursion: $2900+ tax & gratuitybr- 24-hour excursion: $3400+ tax & gratuitybrbrThe prices listed above are per excursion and not per person. The cost of the excursions must be paid directly to our company at the time of booking. The prices listed above include the captain's fee and fuel.brbrThese excursions are highly recommended by our previous guests and are sure to provide you with a memorable experience. During these outings, you may have the opportunity to learn how to navigate the yacht, snorkel around the coral reef, fish from the yacht, spot dolphins and sea turtles, and much more. (Snorkeling and fishing gear is not included, but it is available for rent).brbrOur 24-hour charter is particularly popular as it combines the activities of a day excursion with the unique experience of spending a night anchored on the ocean. You can even enjoy multiple excursions during your reservation period if you desire.brbrJust imagine sleeping under the stars with no neighbors next to, above, or below you like in a hotel room. You can spend your days and nights fishing from the boat, relax on the deck while listening to the sounds of tropical fish jumping in the water, and experience the thrill of being away from the marina, anchored on the ocean. If you're seeking an adventurous and extraordinary vacation surrounded by breathtaking ocean views, wildlife, and fish, this is the perfect choice for you. You might never want to return to land again!brbrThe weather in this area is ideal throughout the year for activities such as snorkeling, fishing, lobster catching (seasonal), kayaking, paddleboarding, learning to sail, scuba diving, or simply enjoying a relaxing sunset cruise.brbrIn addition to our excursions, we provide an exceptional concierge service that brings luxury directly to you. For an additional cost, our offerings include VIP packages, chef services, catering, provisioning, limo service, golf cart rentals, sporting goods rentals, and much more.brbrThis unique yacht features large windows that offer breathtaking ocean views from every angle. The spacious cockpit, with its sliding glass door opening to the galley, provides ample seating for all your guests and creates the perfect space for entertainment. Moreover, the expansive flybridge deck and helm station, complete with an outdoor kitchen (sink, fridge, and BBQ grill), add to the yacht's impressive features. Additionally, it offers a fully furnished kitchen, where you can prepare your own meals. Whether you're inside the modern and elegant interior or up high on the bridge deck, this yacht will undoubtedly create lasting memories.brbrThis yacht is remarkable for the seamless circulation between inside and outside. In the passageway, the private spaces, all with a full view of the sea, combine intimacy and pleasure: six magnificent cabins. This Sailing Yacht is set to satisfy your wildest demands for the highest level of comfort. 12 guests can stay overnight at the marina, with 12 passengers being the maximum for charters that spend the night away from the marina. brbrIf you're interested in a bareboat charter to the Dry Tortugas, please note that a minimum of five nights is required. In addition to the payment made through VRBO, you would need to purchase three 24-hour excursions, allowing you to spend one night at the Dry Tortugas. On your way to and from the destination, you would also stay at the Marquesas Islands, which are located halfway. This charter is truly a once-in-a-lifetime experience that will provide memories to cherish forever. Due to the distance, it is not possible to make the trip to the Dry Tortugas and back in just one day. brbrWe also offer charters to popular destinations such as Little Palm Island, Bahia Honda State Park, Marathon, Islamorada, Key largo, and more.brbrThe excursions and charters offered are discounted from the regular prices and must be paid directly to our company outside of VRBO at the time of booking.brbrWe also offer bareboat day charters, which do not require an overnight stay on the yacht. To book this type of charter, please contact our company directly, as VRBO is solely set up for overnight accommodation bookings.brbrOur company also offers snorkel gear, wet suits, fishing gear, e-bikes, scooters, golf carts, kayaks, and paddle board rentals, for an additional cost, to truly take in Key West. brbrIf you wish to operate the boat or tender yourself, you must book directly with our company and go through an approval process. Taking control of the vessel yourself (without hiring a captain) is subject to prior experience on similar boats.brbrThe advertised price on this listing covers the cost of insurance that covers you and the crew during your reservation period as well as the cost to survey the boat after you leave. You will be required to undergo a bareboat contract and will take full responsibility of the operation and safety of the yacht, crew, and all passengers.brbrThere is a $50 charge per night per person over four prior to your paperwork being processed. Additional fees after the paperwork is sent. Additional rules listed in house rules. brbrGuests must be able to walk up & down stairs inside the boat and be able to make a longer than usual step at times to get on and off the boat.brbrIf this yacht does not meet your specifications we have other yachts that may.

6

Bed

6

Bath

12

Sleeps

$247.31

/ Nightly

Private Vacation Home

COCKTAILS ON THE CORNER- 2 Bedroom / 1 Bathroom W/ Pool - Old Town Key West

Key West, Florida, United States

Welcome to Cocktails on the Corner — Your Tropical Oasis in Old Town Key West!brbrStep into the perfect blend of historic charm and modern luxury at this beautifully renovated 2-bedroom, 1-bathroom Conch-style home, ideally situated on the corner of Southard and Margaret Streets. Nestled just minutes from the vibrant heart of Old Town, this residence invites you to experience the laid-back Key West lifestyle with all the comforts you desire.brbrHighlights:brbrPrime Location: Just 4 blocks from iconic Duval Street and 3 blocks to the Historic Seaport waterfront — perfect for exploring on foot or bike.brbrCharming Conch-Style Home: A seamless mix of historic character and contemporary upgrades.brbrSpacious & Comfortable: Two beautifully appointed bedrooms plus a sofa sleeper in the living room, comfortably accommodating guests.brbrFully Renovated Kitchen & Bath: Quartz countertops, stainless steel appliances, breakfast bar with stools, and a modern bathroom with a large shower.brbrPrivate Outdoor Paradise: Enjoy your own 12 x 15 ft heated (optional) in-ground pool surrounded by lush tropical foliage and mature canopy trees.brbrInviting Outdoor Living: Fenced corner lot with high-top seating, sun loungers, rocking chairs, and a gas grill—perfect for relaxing or entertaining.brbrEntertainment Ready: 50” TV with Firestick, ceiling fans, and a cozy open floor plan for socializing.brbrLaundry Convenience: Full-size stackable washer and dryer tucked inside the primary bedroom.brbrParking: Street parking available on a first-come, first-served basis.brbrSleeping Arrangements:brbrPrimary Bedroom: King-size bed, large dresser, closet, ceiling fan, and TV with Firestick for your comfort and entertainment.brbrGuest Suite: Queen-size bed with plenty of natural light streaming through large windows.brbrLiving Room: Sofa sleeper offers additional sleeping space for guests.brbrRelax and Unwind:brbrWhether you're soaking in the pool under the tropical sun, grilling your fresh catch poolside, or exploring the lively streets of Key West, this home is your sanctuary. The fully fenced yard ensures privacy while the mature trees offer refreshing shade — making every moment spent outside simply unforgettable.brbrAdditional Details:brbrGuest Age Minimum: Primary guests must be at least 30 years old and remain on the property for the entire stay.brbrPet Policy: This is a pet-free home to ensure the utmost comfort for all guests.brbrPool Heating: Available November through April for an additional charge.brbrNo designated parking space: street parking is subject to availability.brbrPerfect for couples, remote workers, or small groups looking to immerse themselves in the best of Key West living. Whether you’re escaping winter or seeking a seasonal retreat, Cocktails on the Corner is ready to welcome you with warmth, style, and all the amenities you need for an unforgettable stay.

Bed

Bath

Sleeps

$842.63

/ Nightly

Condo

Key West, FL - Ocean Front - Coconut Beach Resort

Key West, Florida, United States

A Private Tropical Paradise on the Atlantic Ocean in Key West, Florida that is not only hidden from the street, but is on the quiet side of the island. It’s the perfect blend of old island architecture, lush vegetation and walkways flowing onto white verandahs.brbrHidden from the road, on the quiet Atlantic side of the island, is a resort reminiscent of days gone by in Old Key West.brbrThis private tropical paradise, reminiscent of days gone by, sits quietly and serenely on the Atlantic side of Key West. Here you will find a blend of old island architecture, lush vegetation and quiet walkways flowing onto bright white verandahs. Each of our layouts offers its own touch of uniqueness, be it a high-pitched ceiling, a private balcony or a spectacular panoramic view.brbrCoconut Beach Resort once belonged to the late Senator John Spottswood. He originally purchased the property because of its quiet location, the predominantly Southeasterly Ocean breeze, and a sandy bottom beach.brbrYou'll enjoy everything about our accommodations including the plush comfort of our bedding and of course our Key West charm. Holding true to our colorful island tradition, indulge the senses as you open your beautiful french doors to the balmy breezes of Key West. Our two-bedroom suites all have their own full kitchen and common balcony.

Bed

Bath

Sleeps

$494.67

/ Nightly

Condo

Ocean Front Lower Keys on Stock Island, 3/2 luxury condo at the Ocean's Edge!

Key West, Florida, United States

This ocean front 3/2 condominium is fully equipped with all the amenities you will need for a relaxing stay. The gated community offers a pool, assigned parking and amazing views. The large balcony overlooks the Atlantic Ocean. There is a large open kitchen and living area. The condo comes with Wi-Fi, large smart TV's, all linens and towels needed. The complex is very close to the famous Stock Island restaurants and the adjacent to the Ocean's Edge Marina and Resort. A quick ride will bring you to the sites on the famous Duval Street in Key West. The property has it all. Whether you are visiting to relax on the balcony or by the pool or would rather fish in the Atlantic or Gulf of Mexico, this has it all.

Bed

Bath

Sleeps

$158.76

/ Nightly

Condo

A Pleasant Stay at The Truman Annex in Key West

Key West, Florida, United States

Just inside the Truman Annex's main gate on Southard Street, this well-appointed, very popular one-bedroom, second floor gem features tropical views and breezes and yet it's only two blocks from the heart of Old Town Key West, with an easy walk to restaurants, shops and many other Key West attractions. A Pleasant Stay boasts a large rear deck with a 50% overhang to protect you from the elements while enjoying the shade of lush palm trees and other vegetation. You'll stroll through floral-lined lanes to Shipyard's around-the-corner private pool. Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s old town area. The condos are located 2 blocks from Duval Street and all the Old Town Key West attractions. The properties are also ¼ mile from Fort Zachary Taylor State Park. The property is outfitted with washer/dryer, pots/pans, towels, linens, central air conditioning, off street parking, and pool access. brPlease note: This property has a 28 night minimum stay

1

Bed

1

Bath

2

Sleeps

$329.78

/ Nightly

Private Vacation Home

Renovated Old Town 2 Bedroom with Private Backyard

Key West, Florida, United States

Newly Renovated Townhome in Prime Old Town Key West located just 3 blocks from the beach! Experience the best of island living in this beautifully renovated 2-bedroom, 1.5-bath end-unit townhouse, perfectly situated in one of Key West's most sought-after neighborhoods. Features include a stunning new kitchen with quartz countertops, custom cabinetry, stainless steel appliances, and a handcrafted Moroccan Zellige tile backsplash. The open-concept layout offers bright and welcoming living and dining spaces that extend effortlessly to a private deck - ideal for outdoor dining, entertaining, or quiet relaxation. Upstairs, two spacious bedrooms and a fully renovated bath provide comfort and style, while a convenient half bath serves the main floor. Ideally located off the quiet end of Duval so you have easy access to island's best dining and beaches without the nosy crowds.

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Bath

Sleeps

$376.08

/ Nightly

Private Vacation Home

Paradise on Von Phister, only a 5 min walk to the Beach!

Key West, Florida, United States

Welcome to our charming 3-story Historic Home, nestled in a quiet and desirable neighborhood, just a 5-minute walk from the beach. This spacious and open-concept home is perfect for indoor and outdoor entertaining, offering a truly unforgettable vacation experience.brbrKey Features:br • Large open-concept layout, ideal for family gatherings and socializingbr • Fenced yard providing privacy and a safe space for kids to playbr • Heated pool for relaxation and fun, no matter the seasonbr • Conveniently located just a short walk away from the famous Duval Street, known for its vibrant atmosphere and entertainmentbr • Luxurious primary suite featuring a spacious porch and balcony, perfect for enjoying morning coffee or evening sunsetsbr • Two spacious front porches that invite relaxation and offer a taste of classic Southern charmbrbrAccommodations:br • 3 bedrooms with en-suite bathrooms, ensuring comfort and privacy for all guestsbr • Loft area with 4 twin beds, a cozy retreat for kids or additional guests, accessible by a sturdy ladder. br • 2 dedicated work areas, allowing you to stay connected while enjoying your vacationbrbrWhether you're relaxing by the pool, exploring the nearby beach, or strolling down Duval Street, our historic home provides the perfect backdrop for a memorable vacation. With its blend of modern amenities and timeless charm, it's the ultimate destination for families seeking a comfortable and convenient getaway. Book now to secure your unforgettable stay!

4

Bed

4

Bath

10

Sleeps

$204.56

/ Nightly

Condo

Mariner's Oasis at Sunset Marina- 2bed 2 bath condo w/boat slip for rent

Key West, Florida, United States

AGE REQUIREMENT:brEveryone must be 25 years or older. Families are welcome as long as children are accompanied with their parents and primary renters are 25 years or older. We do not accommodate bachelor parties, bachelorette parties, student groups or construction workers-NO EXCEPTIONSbrbrThis property is a 28 night minimum. Boat slips available for rent! Inquire with us. brbrFEATURES:brBedrooms: 2 (1 king and 1 queen)brBathrooms: 2brLocation: Sunset Marina Gated CommunitybrSquare Feet: 1171brParking: 1 assigned covered parking space (NO ELECTRIC VEHICLES/SCOOTERS/BIKES ALLOWED)brAmenities: Wifi, TVs, in-unit laundry, balcony, shared pool, near the golf course, boat slip availablebrThis unit does NOT have a dishwasherbrbrTHINGS TO KNOW: brRestrictions/Rules: No smoking. No Pets.brbrCheck in: 4PM - We do not guarantee an early check in request will be granted because we need to give the housekeepers time to ready the units for check-in, however, should your unit be ready early, we will notify you from this number that you can check-in. No units will be able to accommodate a check-in earlier than 12pm. brbrCheck out: 10AM - We do not accommodate late check outs. brbrItems provided: All linens, bath towels and beach towels are provided for your convenience. You are provided an initial supply of bath soap, dish washing liquid, toilet paper, laundry detergent and paper towels. Additional supplies are the responsibility of the renter, or once the initial supply is used.

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Sleeps

$168.22

/ Nightly

Private Vacation Home

Monthly Availability beginning May 2025

Key West, Florida, United States

To provide our guests with a clean and sanitized home, our cleaning service cleans AND disinfects all high-touch surfaces in household common areas (e.g. tables, hard-backed chairs, doorknobs, light switches, remote controls, keyboards, handles, toilets, appliances, etc.).brbrWe also feature no contact checkin, no need to go anywhere to get keys or checkin.brbrCome stay in a premier development in Key West. This is a great location to stay with a monthly rental minimum. Reservations must be by the month starting with the first of the month. Yearly rates available. brYou are close to everything Key West has to offer. brbrOur house offers many amenities to make your stay comfortable and convenient. brEach Bedroom on the second floor has a Queen Size Bed, a Flat screen Smart TV, a full size dresser and closet space. The first floor has the Full Size Kitchen, Dining and Living Area that leads out to a large screened-in back porch. Outside is a beautifully landscaped yard with room to enjoy for entertainment or relaxation in the backyard both daytime and with exterior lights at nighttime.brThe Gated Community includes 24-hour security, 2 outdoor pools, fitness center, and beautiful landscaping. Great community for the daily neighborhood walk or bike ride. We have bikes under rear steps in backyard. The Public Golf Course where the property is located is to play at your leisure. From our place, a 15-20 Minute drive to Duval St depending on traffic. A short minute or 2 drive or short bike ride to Lower Keys Medical Center, Gerald Adams Elementary and Florida Keys Community College. But yet everything seems like a short bike ride to everything Key West has to offer. Stay at our place while you enjoy Paradise.

2

Bed

1

Bath

4

Sleeps

$210.1

/ Nightly

Private Vacation Home

Fishpartment South

Key West, Florida, United States

Just a short walk from the Resort style pool and fitness center, our townhome, situated on the 1st fairway of the Key West Golf Club, offers 2 bedrooms, each with en-suite bathrooms, and an office with a queen Murphy bed that can sleep 2 additional people. Upon entering, you'll be met with an inviting and serene space. There is a cozy living area with comfortable furnishings and screened in porch to enjoy your morning coffee or unwind after a full day of activity in key West! Indulge in culinary delights in a full kitchen with stainless steel appliances and everything you need to whip up your favorite recipes.brbrThe community boasts a large resort style pool as well as a second, small pool and a fitness center for your use during your stay!brbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrThings to KnowbrCheck-in time: 4:00 PMbrCheck-out time: 11:00 AMbrQuiet hours are from 10:00 PM to 8:00 AMbrNo smoking is permitted anywhere on the premises.brbrParking notes: There is free parking available for 1 vehicle.

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Bath

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$192.25

/ Nightly

Condo

A Low Tide at The Truman Annex in Key West

Key West, Florida, United States

A Low Tide is a charming first floor end unit in the Shipyard Condominiums in the award winning gated community of the Truman Annex. | Featuring two bedrooms, one with an adjustable king bed and the other with twin beds that can also be made into a king. In addition there is a queen sleeper sofa in the living room. This property has recently been refreshed featuring new appliances, tvs, bedding, etc.! | It is is located 2 blocks from Duval Street and all of the Old Town Key West attractions and includes off street parking for one vehicle. | Enjoy both the front and back rear deck has outdoor dining and lounging all year long. | The refreshing community pool is just steps from the back deck! brPlease note: This property will require a minimum of a 28 night stay.

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Sleeps

$362.39

/ Nightly

Cottage

Colony Sunset- Bright and airy cottage in the heart of old town Key West

Key West, Florida, United States

Located in The Colony, a secluded, gated enclave just steps from Duval Street, Colony Sunset is a colorful and relaxing retreat. Walk up the flagstone path and enter the home through the vivid and cheerful living space, accented with cerulean blue walls and splashes of tropical art. A vaulted ceiling with exposed beams and huge transom windows that extend all the way to the tip of the roof add a bright and airy feeling to the cozy space. Just through the French doors lies a private deck for sunning, relaxing and al fresco dining.brbrThe fully appointed kitchen is attached to the living area and features a sit-down bar, charming open shelving and a bright color scheme. brbrThe bedroom is painted in soothing blue tones and features cathedral ceilings, a king size bed, and flat screen television. brbrJust outside the front door is a porch with Adirondack chairs for enjoying a morning Cuban coffee or a twilight glass of wine amongst the palm trees. The huge Colony swimming pool, which is shared with other residents, is located just steps away. Beaches, shopping, and award-winning restaurants are just a short walk or bike ride from your front door.brbrIf you are staying with a large group, please note that Rent Key West Vacations has two other similar properties to rent within this compound- Colony Calypso and Colony Poolside.brbrBedding: 1 King, 1 sleeper sofa (full)brbrPet friendly- under 40 pounds. Additional fees apply.brbrLocated in The Colony, a secluded compound just steps from Duval Street, Colony Poolside is a peaceful retreat. Enter the home through the serene and inviting living space, accented with blue and white decor, wood floors and pops of color from nautical-themed accents and artwork. A vaulted ceiling with exposed beams and huge transom windows that extend all the way to the tip of the roof add a bright and airy feeling to the cozy space. brbrThe fully appointed kitchen is attached to the living area and features a generous sit-down bar and charming open shelving. Through the French doors lies a private deck for sunning, relaxing, grilling and al fresco dining.brbrThe bedroom is accented with wainscoting and features cathedral ceilings, a king size bed, and flat screen television. brbrBack outside the front door is a porch with Adirondack chairs for enjoying a morning Cuban coffee or a twilight glass of wine amongst the palm trees. The large Colony swimming pool, which is shared with other residents, is located just steps away. Beaches, shopping, and award-winning restaurants are just a short walk or bike ride from your front door.brbrIf you are staying with a large group, please note that Rent Key West Vacations has two other similar properties to rent within this enclave - Colony Sunset and Colony Calypso.brbrBedding: 1 king, 1 sleeper sofabrbrParking: There is a small parking lot for cottage guests and available on a first come first parked basis. If the lot is full, there is on-street parking right on Oliva Street and on surrounding side streets and lanes.

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