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Florida Keys Rentals

From $323 per night (USD)
VRBO
CONCH RETREAT Truman Annex Condo - 2 decks, pool, 2 Bikes, Free parking and WIFI
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
A TRUE CARIBBEAN PARADISE! Location! Location! Location! This is a Saturday-Saturday weekly condo for the rest of 2025. ...
From $323 per night (USD)
VRBO
From $508 per night (USD)
Expedia
**MIDTOWN MOSAIC @ MIDTOWN** Modern Private Home & Pool + LAST KEY SERVICES…
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Spanning an e ...
From $508 per night (USD)
Expedia
From $616 per night (USD)
VRBO
Charming Canal-Front House | WiFi+Swim+Kayak+Fish
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
The whole family will enjoy this tranquil, waterfront getaway in Tavernier, adjacent to Key Largo. With four bedrooms, a ...
From $616 per night (USD)
VRBO
From $1334 per night (USD)
Expedia
Beach Getaway in the Florida Keys
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
If you’re reading this, you’re already on the path to paradise! Thank you for considering us for your dream vacation—we ...
From $1334 per night (USD)
Expedia
From $256 per night (USD)
VRBO
Quiet Conch House in Historic District
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
Discover a piece of paradise with a beautiful conch home located in the historic district of Key West. 4-bedrooms, 2 ba ...
From $256 per night (USD)
VRBO
From $321 per night (USD)
Expedia
Waterfront House - 30' Dock & Pool at Cabana Club
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Relax in this 3-bedroom, 2-bathroom house in the prestigious Key Colony Beach. It is conveniently located near the end o ...
From $321 per night (USD)
Expedia
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VRBO
ISLAND SPA in the Truman Annex
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This Shipyard unit has a Queen bed, one bathroom, very sunny, bright condo.It has a very nice large deck balcony facing ...
Click For Pricing
VRBO
Click For Pricing
Expedia
Luxury Galleon Resort & Marina 2 Bed/2 Bath Marina View
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The Galleon Resort is located in the heart of Old Town Key West and the Marina is one of the most desired harbors in the ...
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Expedia
From $443 per night (USD)
VRBO
BLUE HEAVEN at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s old town area. The c ...
From $443 per night (USD)
VRBO
From $348 per night (USD)
Expedia
P46 - Beautiful updated home on the Gulf side with
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This is a charming 2 bedroom, 2 bath with a loft, single family home is located on the Gulf side. Offering a private, he ...
From $348 per night (USD)
Expedia
From $1034 per night (USD)
VRBO
A Bella Capri in Key West by the Beach! *Monthly rental*
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
This magnificent 5 bedroom Mediterranean villa has a landmark presence, complete privacy and a breathtaking outdoor plaz ...
From $1034 per night (USD)
VRBO
From $374 per night (USD)
Expedia
OYSTER'S PEARL at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This 1BR 1BA condo has an extra large living room with a big screen TV. It sits nestled in the back of the Shipyard back ...
From $374 per night (USD)
Expedia
From $1810 per night (USD)
VRBO
**THE LIME & THE COCONUT @ OLD TOWN** 6BR/6BA Compound + LAST KEY SERVICES..
Bedrooms:
7
Bathrooms:
6
Sleeps:
16
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! According to ...
From $1810 per night (USD)
VRBO
From $698 per night (USD)
Expedia
🌸Home#6 FANTA🐬SEA Full WATERFRONT Home!🌸
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
🌸Home #6 FANTA🐬SEA WATERFRONT!🌸 Look out on the Ocean in your Totally Private😉- Turn-Key and fully Stocked- Single ...
From $698 per night (USD)
Expedia
From $688 per night (USD)
VRBO
A LATITUDE ADJUSTMENT at the Truman Annex in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This Foundry townhouse is a Bostonian style 3 level home located in Old Town Key West. This home has been recently renov ...
From $688 per night (USD)
VRBO
From $2675 per night (USD)
Expedia
A Tropical Luxury Getaway, Your own private resort!!
Bedrooms:
6
Bathrooms:
6
Sleeps:
16
For more pictures on this property look us up on Instagram at sterlingbayhouse. This house is located on the open wate ...
From $2675 per night (USD)
Expedia
From $670 per night (USD)
VRBO
Waterfront beautifully renovated 6 Bedrooms 4 Bath , Gated Private Home
Bedrooms:
4
Bathrooms:
6
Sleeps:
12
This Beautifully renovated Compound / Property Comes With A recently completed and Magnificent Landscape Oasis , That Be ...
From $670 per night (USD)
VRBO
From $258 per night (USD)
Expedia
Keys Deal w/Cafe & Pool Bar! Up to 20% Off Oceanfront 2/2 with Private Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
New Island Grill Pool Bar & Marina Cafe now open! Enjoy our recently renovated Deluxe 2/2 right on the ocean, offering s ...
From $258 per night (USD)
Expedia
Click For Pricing
VRBO
Gorgeous, Breath-taking Sunsets!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Located on the only cut in Key Largo that connects the bay to the ocean. Great fishing and scuba diving Dive shops and w ...
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VRBO
From $655 per night (USD)
Expedia
Snorkel Shack on Sombrero 4 bedrooms 3 baths with
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Vaca-21-495This home is located landside of Sombrero Light. If you take your boat or rent a boat it is a Lighthouse loca ...
From $655 per night (USD)
Expedia
From $500 per night (USD)
VRBO
ANOTHER DAY IN PARADISE at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s old town area. The c ...
From $500 per night (USD)
VRBO
From $599 per night (USD)
Expedia
513 Mariners Club Key Largo | 3 Bed, 2.5 Bath
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Infinite horizons...from this ground floor, luxury, three-bedroom, two-and-one-half-bath villa! A peaceful, relaxing ge ...
From $599 per night (USD)
Expedia
From $1039 per night (USD)
VRBO
A SUNSET BREEZE Beautiful private home with pool!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Enjoy a beautiful private home located in the Historic Truman Gated Community Old Town Key West. Only steps away from Du ...
From $1039 per night (USD)
VRBO
From $555 per night (USD)
Expedia
A SUNSET POOLSIDE in the Truman Annex
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This amazing FIRST FLOOR end unit features two bedrooms and TWO ensuite bathrooms with walk in showers. Each bedroom has ...
From $555 per night (USD)
Expedia
From $500 per night (USD)
VRBO
ARCHIPELAGO ll at The Truman Annex in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This newer renovation is a gorgeous 2 bedroom, 2.5 bath townhouse. The kitchen and baths are new and living room, dining ...
From $500 per night (USD)
VRBO
From $398 per night (USD)
Expedia
ALHAMBRA at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Shipyard Condominiums are located in the Truman Annex Complex which is located 2 blocks from Duval Street and all of the ...
From $398 per night (USD)
Expedia
From $578 per night (USD)
VRBO
SAILOR'S STORY at The Truman Annex in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The Presidents Walk and Southard Court community is located in the Truman Annex Complex which is located 2 blocks from D ...
From $578 per night (USD)
VRBO
From $688 per night (USD)
Expedia
Key Colony Beach 4BD Pool Republic (KCB#19)
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Tropical 4BR pool home in Key Colony Beach with private upstairs/downstairs living. Upstairs: King master, Queen guest, ...
From $688 per night (USD)
Expedia
From $438 per night (USD)
VRBO
AQUA OASIS at The Truman Annex in Key West..
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s old town area. The c ...
From $438 per night (USD)
VRBO
From $586 per night (USD)
Expedia
CONCH ISLAND at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s old town area. The c ...
From $586 per night (USD)
Expedia
From $587 per night (USD)
VRBO
*Casa-Amelia-Key-West* 1/2 block off Duval Street
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to your home away from home! Casa Amelia is a charming Conch house in the historic Gato Cigar Village. Wake up ...
From $587 per night (USD)
VRBO
From $653 per night (USD)
Expedia
412 Mariners Club Key Largo | 3 Bed, 3 Bath
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
No need to search further for your perfect vacation home-away-from-home! This sought-after, 3-story corner townhouse is ...
From $653 per night (USD)
Expedia
From $514 per night (USD)
VRBO
Spacious, waterfront condo w/ a full kitchen, shared pool, & furnished balcony
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Sunset at Harbour Place Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $514 per night (USD)
VRBO
From $204 per night (USD)
Expedia
Poolside Paradise in Key West Golf Club
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to the best of Key West! Poolside Paradise is located in the Key West Golf Club. Our townhome is located direc ...
From $204 per night (USD)
Expedia
From $510 per night (USD)
VRBO
🌸Home (#4) ”A WAVE💦 FROM IT ALL” (Partial Ocean View -approximately 150 ft from beach entrance)🌸
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
#4: A WAVE💦 FROM IT ALL (Partial Ocean View Property-approximately 150 ft from beach entrance)🌸 Totally Private😉- Tur ...
From $510 per night (USD)
VRBO
From $404 per night (USD)
VRBO
Boater's Paradise
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
This incredible property in Islamorada is the ultimate getaway, offering a spacious and flexible layout with 9 beds—per ...
From $404 per night (USD)
VRBO
From $1544 per night (USD)
VRBO
Epic location, Private Parking - Commodore's Cove
Bedrooms:
4
Bathrooms:
4
Sleeps:
12
Summary: Commodore's Cove offers the best of Key West: a prime location and all the amenities of a home. Up to 12 can st ...
From $1544 per night (USD)
VRBO
From $3124 per night (USD)
Expedia
Epic Location Near Duval, Private Hot Tub, Parking
Bedrooms:
7
Bathrooms:
8
Sleeps:
24
Summary: Welcome to Commodore's Compound, an incredible 8 bed, 7 bath home in prime location situated just one short blo ...
From $3124 per night (USD)
Expedia
From $1589 per night (USD)
VRBO
Steps from Duval, Private Hot Tub - Seaport Suite
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Summary: Located in the heart of Old Town Key West, Seaport Suite is the ideal getaway for large groups of up to 12 gues ...
From $1589 per night (USD)
VRBO
From $470 per night (USD)
Expedia
SEASCAPE at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Shipyard Condominiums are located in the Truman Annex Complex which is located 2 blocks from Duval Street and all of the ...
From $470 per night (USD)
Expedia
From $444 per night (USD)
VRBO
TROPICAL VINEYARD at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s old town area. The c ...
From $444 per night (USD)
VRBO
From $272 per night (USD)
Expedia
Two Spectacular Ocean Views from the Living Room and Master Bedroom of the Condo
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Ocean views from living room and master bedroom!! Get your inspiration every morning, directly on the sea from one of t ...
From $272 per night (USD)
Expedia
From $304 per night (USD)
VRBO
Two Panoramic Ocean Views from the Living room and Master Bedroom in this Condo
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Ocean views from living room and master bedroom!! Get your inspiration every morning, directly on the sea from one of t ...
From $304 per night (USD)
VRBO
From $315 per night (USD)
Expedia
Luxurious Top Floor 2 Bedroom Suite w/ Unobstructed Ocean Views
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
With thoughtful and creative touches, both inside and out, mixed with a keen attention to the smallest of details, this ...
From $315 per night (USD)
Expedia
From $923 per night (USD)
VRBO
311 Mariners Club Key Largo | 4 Bed, 3 Bath
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
If this villa has come up in your search for that ‘special’ vacation accommodation…you can stop right now. Villa 311 Mar ...
From $923 per night (USD)
VRBO
From $278 per night (USD)
Expedia
Incredible Views from Ocean Lovers Suite [Ocean Pointe 5413]
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
SEAS THE DAY - OR JUST RELAX - YOU'RE ON ISLAND TIME Classic coastal décor greets you in this one bedroom, one bathroom ...
From $278 per night (USD)
Expedia
From $340 per night (USD)
VRBO
SPECTACULAR OCEAN VIEWS FROM THIS MODERN BEACH CONDO
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Our property is located on 38 acres surrounded by nature and the ocean. The property is gated with 24 hour security. En ...
From $340 per night (USD)
VRBO
From $363 per night (USD)
Expedia
One Of A Kind Ocean Front With Boat Slip
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This one of a kind ocean front property offers much more than just the view. With 3 bedrooms and 2 bathrooms this 1800 s ...
From $363 per night (USD)
Expedia
From $324 per night (USD)
VRBO
Relax & Recharge at our Quiescent 2 BR Condo with Stunning Ocean Views
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Delight in a quiet escape, with open ocean views, from our two bedroom condo located in the 3rd building at Ocean Pointe ...
From $324 per night (USD)
VRBO
From $648 per night (USD)
Expedia
Blue Moonshine upgrades throughout modern finishes, close to Smathers Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 Atlantic Start Date: May 2025-Estimated Completion: Spring 2026 ...
From $648 per night (USD)
Expedia
From $965 per night (USD)
VRBO
Fishermen`s Paradise | Waterfront home with huge pool, 220-foot dock & gorgeous interior
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
Welcome to your perfect island retreat! This freshly remodeled three-bedroom, four-bathroom vacation home on Big Pine of ...
From $965 per night (USD)
VRBO
From $261 per night (USD)
VRBO
Sugarloaf Serenity | Spacious, pet-friendly waterfront retreat on Sugarloaf Key
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Great views of Sugarloaf Sound from this ground-level midcentury-era home that offers expansive sound frontage perfect f ...
From $261 per night (USD)
VRBO
From $1751 per night (USD)
VRBO
**GRAND KEY OASIS @ THE ANNEX** Magnificent Estate & Pool + LAST KEY SERVICES…
Bedrooms:
5
Bathrooms:
5
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! The vacation ...
From $1751 per night (USD)
VRBO
From $336 per night (USD)
Expedia
Amazing Pool & Canal Ground Level Home, Ocean access
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This is an amazing Ground level Pool and Canal home. With stunning concrete ground pool and Jacuzzi tub. (POOL HEAT AV ...
From $336 per night (USD)
Expedia
From $471 per night (USD)
VRBO
ADRIFT in Key West at the Truman Annex
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Stunning, Modern Nautical-themed 2 bedroom, 1 bathroom ground floor condo in the Truman Annex Shipyard Complex completel ...
From $471 per night (USD)
VRBO
From $235 per night (USD)
Expedia
Paradise Found | Pet-friendly 3 bed/2 bath boating home on Cudjoe Key
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Canalfront 3 bedroom/2 bathroom home with excellent oceanside boating access. Open floor plan with a large kitchen, stai ...
From $235 per night (USD)
Expedia
From $225 per night (USD)
VRBO
Blackbeard`s Hideaway | Cozy canalfront cottage is an angler's dream on Cudjoe Key
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Welcome to Blackbeard's Hideaway, your perfect monthly vacation rental nestled in a quiet neighborhood on the oceanside ...
From $225 per night (USD)
VRBO
From $201 per night (USD)
Expedia
Cedar Cottage | Adorable canalfront cottage, lots of dockage on Big Pine Key
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to your perfect slice of paradise in the heart of the Florida Keys! This newly remodeled 2 bed/2 bath home on a ...
From $201 per night (USD)
Expedia
From $274 per night (USD)
VRBO
Foster`s Folly | Gorgeous canalfront pool home close to open water on Cudjoe Key
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Escape to a slice of paradise on Cudjoe Key, where luxury meets tranquility in this stunning 3-bedroom, 2-bathroom stilt ...
From $274 per night (USD)
VRBO
From $290 per night (USD)
Expedia
OPEN WATER PARADISE 2/2 HALF DUPLEX IN KEY COLONY BEACH MARATHON, FL 34
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Open Water Paradise | Key Colony Beach Modern • Clean • Spacious • Walk-Through Layout Relax in this beautifully remode ...
From $290 per night (USD)
Expedia
From $214 per night (USD)
VRBO
Luxurious Key West Pool Home block from Duval! Pool & Patio Recently Renovated!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Old Town refuge barely a block from world famous Duval Street with glimpse of Key West Light House! Located in the Histo ...
From $214 per night (USD)
VRBO
From $348 per night (USD)
Expedia
3 BR/ 2 BA, Canal Front Home, Private Dock for 40' Boat & 1 mi to Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Kickin' Back Reel Time, Your Home Away from Home in Marathon, FL. This beautifully updated, canal front home ...
From $348 per night (USD)
Expedia
From $636 per night (USD)
VRBO
FOREVER YOUNG at The Truman Annex in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
This Harbour Place condominium is in Key West's most prestigious community of Truman Annex offering breath taking water ...
From $636 per night (USD)
VRBO
From $279 per night (USD)
Expedia
Spacious Well-Appointed Oceanfront Suite in Tavernier - Snorkel, Scuba, Fishing!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Our well-appointed condo provides the perfect home away from home. Step onto your private balcony and soak in the mesmer ...
From $279 per night (USD)
Expedia
From $484 per night (USD)
VRBO
ABOUT TIME at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Shipyard Condominiums are located in the Truman Annex Complex which is located 2 blocks from Duval Street and all of the ...
From $484 per night (USD)
VRBO
From $466 per night (USD)
Expedia
HAVANA VIEWS at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Shipyard Condominiums are located in the Truman Annex Complex which is located 2 blocks from Duval Street and all of the ...
From $466 per night (USD)
Expedia
From $460 per night (USD)
VRBO
SAND CRAB CABANA at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Shipyard Condominiums are located in the Truman Annex Complex which is located 2 blocks from Duval Street and all of the ...
From $460 per night (USD)
VRBO
$Key West Condo close to the Ocean. 1 mile to Smathers & 3 miles to Duval St. \n$
From $499 per night (USD)
Expedia
Key West Condo close to the Ocean. 1 mile to Smathers & 3 miles to Duval St. \n
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This 2 bedroom (one King and one Queen, plus Queen size pull out couch in the living room), 2 bathroom unit offers all ...
From $499 per night (USD)
Expedia
From $352 per night (USD)
VRBO
Casa Chiquita - 3/2 Pool - Waterfront - 75’ Dock - Ground Level
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Kick back, unplug, and chum up some yellowtail at one of the best locations in the middle keys! Casa Chiquita is a rece ...
From $352 per night (USD)
VRBO
Click For Pricing
Expedia
Ocean views, great for fishing and kayaking, the best family experience
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Situated just off the historic Florida Keys Overseas Highway, The Hammocks at Marathon™ lets you and your family experie ...
Click For Pricing
Expedia
From $420 per night (USD)
VRBO
Bayview Villa- Pet-Friendly Waterfront Paradise. A fisherman's dream!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
We have recently completed an inside and outside renovation. The Bayview Villa is a private, secluded villa facing Flori ...
From $420 per night (USD)
VRBO
From $288 per night (USD)
Expedia
Ocean Oasis at Ocean Pointe Key Largo Pool Jacuzzi Beach in a Safe Gated Resort
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Photos you are looking at are of our awesome unit. Choose careful because some rentals will assign your unit upon arriva ...
From $288 per night (USD)
Expedia
From $105 per night (USD)
VRBO
Apr 11-May 16 Open, Largo Lookout, Lovely Waterview Unit, MM 99.5, Pets Welcome, 28 Nt Min
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Waterfront 1 Bedroom, 1 Bath Apartment, Located in Heart of Key Largo, Sleeps 4, Pet Friendly Largo Lookout has a minimu ...
From $105 per night (USD)
VRBO
$Oceanfront Luxury Condo\n\n28 night minimum. Book Jan 7-Feb4 for 600 discount.$
From $124 per night (USD)
VRBO
Oceanfront Luxury Condo\n\n28 night minimum. Book Jan 7-Feb4 for 600 discount.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Seagulls Condominiums Islamorada Tavernier Key Largo New Lazy Boy recliner added to our open concept living room. Uppe ...
From $124 per night (USD)
VRBO
From $403 per night (USD)
VRBO
A quiet relaxing place that you can disconnect from real life. Comforts of home
Bedrooms:
4
Bathrooms:
3
Sleeps:
12
Clean, Comfortable, Private, Remodeled, full of amenities, new furniture, relaxing and peaceful. 7+ restaurants at walki ...
From $403 per night (USD)
VRBO
From $394 per night (USD)
Expedia
Direct Ocean View from Your Condo-No Contact Check-In
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Modern 2 bedroom/2 bath condo with nice size balcony overlooks the Atlantic Ocean. California king bed in Master Bedroom ...
From $394 per night (USD)
Expedia
From $451 per night (USD)
VRBO
Beautiful Harbor Front Oceanside Home on the Atlantic Ocean
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Oceanside 3/3 located on beautiful 10 acre harbor. Amazing natural surroundings, harbor & ocean views. New furnishings, ...
From $451 per night (USD)
VRBO
From $1271 per night (USD)
Expedia
Opulent waterfront estate with dock, pool, hot tub & rooftop view - dog-friendly
Bedrooms:
5
Bathrooms:
6
Sleeps:
12
Waterfront Wonder Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $1271 per night (USD)
Expedia
From $445 per night (USD)
VRBO
Conch Republic Consul General's Cottage.-Historic District
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Stay in the Conch Republic Consul General's Cottage. Historic Carriage House is located a few blocks from famous Duval S ...
From $445 per night (USD)
VRBO
From $261 per night (USD)
Expedia
Private Home- Sun-filled Pool- Neighborhood Water Inlet
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This home sits in Key Lime Grove Subdivision which I was born and raised in. It is a neighborhood rich in history and c ...
From $261 per night (USD)
Expedia
From $302 per night (USD)
VRBO
Charming & Tranquil Condo [Ocean Pointe 2208]
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Your vacation starts the moment you step foot into this simply brilliant coastal condo that sits next to the Atlantic Oc ...
From $302 per night (USD)
VRBO
From $326 per night (USD)
Expedia
Conch Republic Consul General's Cottage.-Pool-Historic District-Assigned Parking
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Stay in the Conch Republic Consul General's Cottage. This one bedroom cottage is located in the historic district and o ...
From $326 per night (USD)
Expedia
From $378 per night (USD)
VRBO
Steps To The Beach And The Sunrise-No Contact Check-In
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Nature's boutique offer you an exceptional view of key west's native birds right from your private balcony. It is furnis ...
From $378 per night (USD)
VRBO
From $244 per night (USD)
Expedia
Stone Throw Famous Duval Street Location-No Contact Check-In
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
House is located just steps from famous Dvual Street. Duval Street stretches from the Atlantic Ocean to the Gulf of Mexi ...
From $244 per night (USD)
Expedia
From $748 per night (USD)
VRBO
Hyatt Beach House Resort. Key West. 2 Bedroom. 2 Bathroom WEEK Stay.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Sunday to Sunday WEEK available to book. Limited Boat Slip available onsite. Must be reserved in advance after reserva ...
From $748 per night (USD)
VRBO
From $331 per night (USD)
Expedia
Historic District-Pool View-Duval Street-Beach Nearby-No Contact Check-In
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
This 2 bedroom, fully furnished condominium with brand new living room furniture and dining room table set is located in ...
From $331 per night (USD)
Expedia
From $342 per night (USD)
VRBO
A PLEASANT STAY at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s old town area. The c ...
From $342 per night (USD)
VRBO
From $496 per night (USD)
Expedia
ANGEL FISH at The Truman Annex in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Tropically decorated 2 bedroom 2 bathroom townhouse in secluded area of Truman Annex, complete with updated appliances, ...
From $496 per night (USD)
Expedia
From $652 per night (USD)
VRBO
ABSOLUTE TRUMAN ANNEX in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This Private home is located in the historic Truman Annex of old town Key West, where you can get away from it all while ...
From $652 per night (USD)
VRBO
From $920 per night (USD)
Expedia
TROPICAL EXECUTIVE at The Truman Annex in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This Harbour Place condominium is in Key West's most prestigious community of Truman Annex offering breath taking water ...
From $920 per night (USD)
Expedia
From $380 per night (USD)
VRBO
Keys Villa - Secluded tropical paradise located on the water!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Private, secluded villa faces Florida Bay in view of the fabulous Everglades. Located in a lush tropical hammock in a q ...
From $380 per night (USD)
VRBO
From $246 per night (USD)
Expedia
Waterfront Cottage at Tavernier, Florida Keys
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Our beautiful Waterfront Cottage offers breathtaking views of the ocean, a private deck with a propane grill, and a won ...
From $246 per night (USD)
Expedia
From $358 per night (USD)
VRBO
Gorgeous house, GUARANTEED to beat any price for a 3BR in Marathon
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Three bedrooms and 2 bathrooms in open concept with everything you need in the heart of the Keys. Ample parking spaces ...
From $358 per night (USD)
VRBO
From $800 per night (USD)
Expedia
Paradise Island suite-2 bedroom 1 bath, a block off Duval St w/pool, parking
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
AGE REQUIREMENT: ALL guests staying at the property MUST be 25 years of age or older at this property- NO EXCEPTIONS P ...
From $800 per night (USD)
Expedia
From $973 per night (USD)
VRBO
Bimini suite-3 bedroom 3 bath, a block off Duval St w/pool, parking
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
AGE REQUIREMENT: ALL guests staying at the property MUST be 25 years of age or older at this property- NO EXCEPTIONS P ...
From $973 per night (USD)
VRBO
From $1051 per night (USD)
Expedia
Marlin House @ Tarpon Point
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Summary: Stunning ocean views from all living levels & a waterfront pool! The Space: Welcome to the captivating Marlin ...
From $1051 per night (USD)
Expedia
From $926 per night (USD)
VRBO
Washer & Dryer, Near Downtown - Mesa House, Dos
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Summary: Whether you're lounging on the front porch or enjoying a seafood dinner inside, this 2-Bedroom Suite at The Mes ...
From $926 per night (USD)
VRBO
Click For Pricing
Expedia
2 BR at Hyatt Windward Pointe
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Atlantic Ocean, pool or lush courtyard views and lavish plantation-style decor welcome you to a two-bedroom condominium ...
Click For Pricing
Expedia
From $949 per night (USD)
VRBO
Grand Bahama suite-3 bedroom 2 bath, a block off Duval St w/pool, parking
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
AGE REQUIREMENT: ALL guests staying at the property MUST be 25 years of age or older at this property- NO EXCEPTIONS P ...
From $949 per night (USD)
VRBO
From $771 per night (USD)
Expedia
Nassau suite-2 bedroom 2 bath, a block off Duval St w/pool, parking
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
AGE REQUIREMENT: ALL guests staying at the property MUST be 25 years of age or older at this property- NO EXCEPTIONS P ...
From $771 per night (USD)
Expedia

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