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From $1807 per night (USD)
VRBO
**THE LIME & THE COCONUT @ OLD TOWN** Compound + Last Key White Glove Service...
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 $1807 per night (USD)
VRBO
From $215 per night (USD)
Expedia
Mariners House @ Landings of Largo
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Summary: Beautiful Landings of Largo townhouse centrally located in Key Largo! The Space: Embark on a truly unique vaca ...
From $215 per night (USD)
Expedia
From $858 per night (USD)
VRBO
🌸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 $858 per night (USD)
VRBO
From $415 per night (USD)
Expedia
A LATITUDE ADJUSTMENT @ THE TRUMAN ANNEX
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 $415 per night (USD)
Expedia
From $3107 per night (USD)
VRBO
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 $3107 per night (USD)
VRBO
From $693 per night (USD)
Expedia
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 ...
From $693 per night (USD)
Expedia
From $338 per night (USD)
VRBO
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 ...
From $338 per night (USD)
VRBO
From $748 per night (USD)
Expedia
Snorkel Shack on Sombrero 4 bedrooms 3 baths with pool and 100 Ft of Dockage
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Vaca-25-168 Complete Florida Keys Living – Waterfront Retreat Near Sombrero Reef Heated Pool | 100' Dockage | 4 Kayaks ...
From $748 per night (USD)
Expedia
Click For Pricing
VRBO
Another Day in Paradise at the Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Prime Old Town location meets effortless island living in this 2‑bedroom, 1‑bath first‑floor Shipyard condo. Bright inte ...
Click For Pricing
VRBO
From $585 per night (USD)
Expedia
513 Mariners Club - 3 bedroom luxury ground floor condo with ocean views
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Infinite horizons...from this ground floor, luxury, three-bedroom, two-and-one-half-bath villa! A peaceful, rela ...
From $585 per night (USD)
Expedia
From $822 per night (USD)
VRBO
A Sunset Breeze at the Truman Annex in Key West
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Enjoy a beautiful private home located in the Historic Truman Gated Community in Old Town Key West. This beauty if only ...
From $822 per night (USD)
VRBO
From $299 per night (USD)
Expedia
A Sunset Poolside at the Truman Annex in Key West
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 $299 per night (USD)
Expedia
From $339 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 $339 per night (USD)
VRBO
From $265 per night (USD)
Expedia
Alhambra at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Alhambra is a charming one bedroom, one bath first floor unit with a huge outdoor deck! Shipyard Condominiums are locate ...
From $265 per night (USD)
Expedia
From $357 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 $357 per night (USD)
VRBO
From $847 per night (USD)
Expedia
Republic 4BR Pool Villa - Sleeps 10 (KCB#19)
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
<p>Tropical 4BR pool home in Key Colony Beach! Enjoy private upstairs/downstairs living: Upstairs has king master, queen ...
From $847 per night (USD)
Expedia
From $314 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 $314 per night (USD)
VRBO
From $655 per night (USD)
Expedia
412 Mariners Club - 3 bedroom corner townhome with ocean views
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 $655 per night (USD)
Expedia
From $237 per night (USD)
VRBO
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 $237 per night (USD)
VRBO
From $536 per night (USD)
Expedia
🌸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 $536 per night (USD)
Expedia
From $422 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 $422 per night (USD)
VRBO
From $1002 per night (USD)
Expedia
Commodore's Cove - One block from Duval St
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 s ...
From $1002 per night (USD)
Expedia
From $2069 per night (USD)
VRBO
Commodore's Compound - One block from Duval St
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 bl ...
From $2069 per night (USD)
VRBO
From $1004 per night (USD)
Expedia
Seaport Suite - Steps from Duval Street
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 gue ...
From $1004 per night (USD)
Expedia
From $298 per night (USD)
VRBO
Seascape at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
First floor newly renovated 2 bedroom/ 1 bath corner end unit at the Shipyard Condominiums located in the Truman Annex C ...
From $298 per night (USD)
VRBO
From $427 per night (USD)
Expedia
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 $427 per night (USD)
Expedia
From $369 per night (USD)
VRBO
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 $369 per night (USD)
VRBO
From $410 per night (USD)
Expedia
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 $410 per night (USD)
Expedia
From $341 per night (USD)
VRBO
Stunning Waterfront Condo with Double Balconies
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Summary: Enjoy a spacious two bedroom condominium in Tavernier with stunning ocean and mangrove views. This retreat fea ...
From $341 per night (USD)
VRBO
From $870 per night (USD)
Expedia
311 Mariners Club - 4 bedroom ocean front luxury condo
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 $870 per night (USD)
Expedia
From $329 per night (USD)
VRBO
Birds Eye Loft Perched Above the Marina 1BR 1BA 5413
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: Relax amongst the tropical sights and sounds in this charming oceanfront condo located in Ocean Pointe Suites. ...
From $329 per night (USD)
VRBO
From $351 per night (USD)
Expedia
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 $351 per night (USD)
Expedia
From $391 per night (USD)
VRBO
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 $391 per night (USD)
VRBO
From $342 per night (USD)
Expedia
Bright & Sunny Suite w/ Magnificent Ocean Views
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Relax & Recharge at our Quiescent Condo with Stunning Views of the Blue Green Colors of the Atlantic all nestl ...
From $342 per night (USD)
Expedia
From $515 per night (USD)
VRBO
Blue Moonshine upgrades throughout modern finishes, close to Smathers Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Great top floor 2 bedroom Condo on the Atlantic ocean with views of the ocean and courtyard. The property has a full siz ...
From $515 per night (USD)
VRBO
From $271 per night (USD)
Expedia
Oceanfront Views From Every Room! SEPT. DISCOUNT! RESERVE QUICKLY! Lic #26-0403
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Huge terrace! Right on the water with unobstructed views! Accessible from every room! Spacious and clean. Fully Renovate ...
From $271 per night (USD)
Expedia
From $1039 per night (USD)
VRBO
Fishermen's Paradise | Pool, 220' Dock & Open-Water Views
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
Summary: Welcome to Fishermen's Paradise, a beautifully appointed open-water retreat on Big Pine Key. Enjoy a private h ...
From $1039 per night (USD)
VRBO
From $397 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 $397 per night (USD)
Expedia
From $207 per night (USD)
VRBO
ADRIFT IN KEY WEST at the Truman Annex in Key West
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 $207 per night (USD)
VRBO
From $263 per night (USD)
Expedia
Cayman Cottage | 3 bed/2 bath canalfront home
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Great canalfront 3 bed/2 bath boating home on Ramrod Key The Space: Escape to Cayman Cottage, a charming t ...
From $263 per night (USD)
Expedia
From $238 per night (USD)
VRBO
Paradise Found | Pet friendly, boating on Cudjoe
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Pet-friendly 3 bed/2 bath boating home on Cudjoe Key The Space: Canalfront 3 bedroom/2 bathroom home with ...
From $238 per night (USD)
VRBO
From $307 per night (USD)
Expedia
Bahama Breeze in the Keys
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Summary: Oceanside monthly rental in the Lower Florida Keys with 60 feet of concrete dockage, bait freezer, fish-cleani ...
From $307 per night (USD)
Expedia
From $382 per night (USD)
VRBO
Foster's Folly | Gorgeous canalfront pool home
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Gorgeous canalfront pool home close to open water on Cudjoe Key The Space: Escape to a slice of paradise o ...
From $382 per night (USD)
VRBO
From $234 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 Traveling with a larger group? As ...
From $234 per night (USD)
Expedia
From $225 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 $225 per night (USD)
VRBO
From $383 per night (USD)
Expedia
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 $383 per night (USD)
Expedia
From $342 per night (USD)
VRBO
Oceanside Family Condo with Pool and Beach Access
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Escape to paradise in our ocean-view condo, 3210 at Ocean Pointe, perfectly located between Key Largo and Tave ...
From $342 per night (USD)
VRBO
From $211 per night (USD)
Expedia
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 $211 per night (USD)
Expedia
From $211 per night (USD)
VRBO
Havana Views at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Special Price! - contact us ! Shipyard Condominiums are located in the Truman Annex Complex which is located 2 blocks ...
From $211 per night (USD)
VRBO
From $460 per night (USD)
Expedia
Sand Crab Cabana WEEKLY RENTAL 7 nights minimum!! Truman Annex
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
WEEKLY RENTAL - This property has the ability to be rented weekly (7 night minimum stay) all year long. Shipyard Condomi ...
From $460 per night (USD)
Expedia
From $393 per night (USD)
VRBO
Key West Condo close to the Ocean. 1 mile to Smathers & 3 miles to Duval St.
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 $393 per night (USD)
VRBO
From $426 per night (USD)
Expedia
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 $426 per night (USD)
Expedia
From $510 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 $510 per night (USD)
VRBO
From $408 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
Ocean Pointe is located in the middle of Key Largo and Islamorada that gives you the best way to explore the Amazing Flo ...
From $408 per night (USD)
Expedia
From $106 per night (USD)
VRBO
Nov 18-Jan 1 Open... Live Like a Local*Waterview*Pet Friendly*Key Largo MM 99.5*Manatees
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Waterfront 1 Bedroom, 1 Bath 2nd Floor Unit. Located in Heart of Key Largo, Sleeps 4, Pet Friendly Largo Lookout has a m ...
From $106 per night (USD)
VRBO
From $119 per night (USD)
VRBO
Oceanfront Luxury Condo. Step on to the beach.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Seagulls Condominiums Islamorada Tavernier Key Largo Florida Keys New Lazy Boy recliner added to our open concept livin ...
From $119 per night (USD)
VRBO
From $659 per night (USD)
VRBO
Islamorada Waterfront Paradise with 5 Bedrooms, Pool and Dock
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Escape to your tropical island paradise in the heart of the Florida Keys! Nestled in cross keys location, to Tavernier C ...
From $659 per night (USD)
VRBO
From $1168 per night (USD)
Expedia
Luxury Villa-Infinity Pool-Jacuzzi-Endless Amenities-
Bedrooms:
6
Bathrooms:
6
Sleeps:
14
Villa Murano for 14 plus guests, for families, for gatherings, for corporate retreats for celebrations, for a phenomenal ...
From $1168 per night (USD)
Expedia
From $416 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 $416 per night (USD)
VRBO
From $406 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 $406 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 in a beautiful naturally protected harbor on the Atlantic Ocean. See manatee, tarpon and many bea ...
From $451 per night (USD)
VRBO
From $428 per night (USD)
Expedia
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 $428 per night (USD)
Expedia
From $294 per night (USD)
VRBO
Private Home- Sun-filled Pool- Neighborhood Water Inlet
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Rate reduced to a off season price point. This home sits in Key Lime Grove Subdivision which I was born and raised in. ...
From $294 per night (USD)
VRBO
From $341 per night (USD)
Expedia
Charming & Tranquil Condo at Ocean Pointe-Sleeps 6
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Relax in our 2BR/2BA oceanfront condo at Ocean Pointe Suites in Tavernier. Enjoy designer decor, stunning Atla ...
From $341 per night (USD)
Expedia
From $349 per night (USD)
VRBO
Summer Discounts-Conch Republic Consul Cottage.-Pool-Historic District-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 $349 per night (USD)
VRBO
From $273 per night (USD)
Expedia
Steps To The Beach And The Sunrise
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Explore Key West during the day and evenings are quiet. Nature's boutique offer you an exceptional view of key west's n ...
From $273 per night (USD)
Expedia
From $267 per night (USD)
VRBO
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 $267 per night (USD)
VRBO
From $547 per night (USD)
Expedia
Weekly Rentals Allowed 2026/2027-Pool View-Gated-Duval Street-Beach
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
This condo has been grandfathered in to allow for weekly rentals. One of only a few with City approval. This 2 bedroom, ...
From $547 per night (USD)
Expedia
From $498 per night (USD)
VRBO
Queen Emma at the Truman Annex in Key West
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
This beautifully finished and decorated four bedroom, three bath home has classic Key West architecture and is located o ...
From $498 per night (USD)
VRBO
From $174 per night (USD)
Expedia
A Pleasant Stay at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Just inside the Truman Annex's main gate on Southard Street, this well-appointed, very popular one-bedroom, second floor ...
From $174 per night (USD)
Expedia
From $480 per night (USD)
VRBO
ABSOLUTE KEY WEST in the Truman Annex >>Charming home with a European flair!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This Private home is located in the historic award-winning gated community of the Truman Annex in Old Town Key West, Yo ...
From $480 per night (USD)
VRBO
From $741 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 $741 per night (USD)
Expedia
From $364 per night (USD)
VRBO
Villa located on the water Free marina, and trailer parking.
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 $364 per night (USD)
VRBO
Click For Pricing
Expedia
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 ...
Click For Pricing
Expedia
From $577 per night (USD)
VRBO
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 $577 per night (USD)
VRBO
From $809 per night (USD)
Expedia
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 $809 per night (USD)
Expedia
From $981 per night (USD)
VRBO
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 $981 per night (USD)
VRBO
From $803 per night (USD)
Expedia
Mesa House Dos - One block from Duval St
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 Me ...
From $803 per night (USD)
Expedia
From $764 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 $764 per night (USD)
VRBO
From $577 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 $577 per night (USD)
Expedia
$New listing 3bd/2bt Sleeps 8 \Sunset Paradise Villa\ on canal Big Pine Key$
From $273 per night (USD)
VRBO
New listing 3bd/2bt Sleeps 8 \"Sunset Paradise Villa\" on canal Big Pine Key
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
*Bridge restriction***BIMINI TOPS or Fold down T-tops boats ONLY DUE TO WATSON ST BRIDGE. Sunset Paradise Villa is a ...
From $273 per night (USD)
VRBO
From $547 per night (USD)
Expedia
FULL TIME LIC MGR - LUXURY VIP SUITE - INDOOR PICKLEBALL - STUNNING OCEAN VIEWS!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
An island paradise situated in the heart of Key Largo, adjacent to John Pennekamp Coral Reef State Park and Molasses Ree ...
From $547 per night (USD)
Expedia
From $507 per night (USD)
VRBO
FULL TIME LIC MGR - MODERN 2/2 COCONUT PALM VILLA - OCEANFRONT BEACH RESORT!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
If you want to experience the true meaning of a Key Largo Island vacation, then look no further than our spacious townho ...
From $507 per night (USD)
VRBO
From $476 per night (USD)
Expedia
FULL TIME LIC MGR - INDOOR/OUTDOOR PICKLEBALL - SPEAKEASY - OCEANFRONT RESORT!
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
An island paradise situated in the heart of Key Largo, adjacent to John Pennekamp Coral Reef State Park and Molasses Ree ...
From $476 per night (USD)
Expedia
From $506 per night (USD)
VRBO
FULL TIME LIC MGR - INDOOR/OUTDOOR PICKLEBALL - SPEAKEASY - OCEANFRONT RESORT!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
An island paradise situated in the heart of Key Largo, adjacent to John Pennekamp Coral Reef State Park and Molasses Ree ...
From $506 per night (USD)
VRBO
From $663 per night (USD)
Expedia
FULL TIME LIC MGR - 2/2 OCEANFRONT SUITE! OCEAN & MARINA VIEWS! 2 KING BEDS!
Bedrooms:
2
Bathrooms:
2
Sleeps:
7
You have just discovered one of the most unique properties in the heart of Key Largo. This oceanfront condo is located i ...
From $663 per night (USD)
Expedia
From $664 per night (USD)
VRBO
808 Mariners Club - 4 bedroom townhome, 2 seperate living areas
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Designer upgrades make this luxury, two-story townhouse with over 2600 sq ft of living space the perfect home-away-from- ...
From $664 per night (USD)
VRBO
From $214 per night (USD)
Expedia
Relax in the Keys
Bedrooms:
3
Bathrooms:
2
Sleeps:
4
Completely remodeled 1st floor - 90’ TV, recliner, full size bathroom, kitchen 2nd floor, 2 bedrooms, 2 bathrooms, kit ...
From $214 per night (USD)
Expedia
From $355 per night (USD)
VRBO
September dates w/last minute booking discount, w/Cabana Club Access Included!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Located in the middle Keys on Hawks Cay Resort property, you’ll be perfectly positioned to easily explore Islamorada, K ...
From $355 per night (USD)
VRBO
From $391 per night (USD)
VRBO
Cozy Coastal Villa. Newly renovated private home w/ HEATED pool.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This newly renovated, 3/2 pet-friendly Key Largo vacation home is spaciously laid out over two levels with chic island-i ...
From $391 per night (USD)
VRBO
From $174 per night (USD)
VRBO
SUN, SEA & SKY at Truman Annex in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Located in the desirable Truman Annex community, this beautifully maintained second-story Shipyard condo offers the perf ...
From $174 per night (USD)
VRBO
From $185 per night (USD)
VRBO
A little slice of Heaven
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Comfortable mobile home, located on the canal with 53 ft of dock space, with 20, 000 lbs lift, so bring your boat, full ...
From $185 per night (USD)
VRBO
From $290 per night (USD)
VRBO
A Change In Latitude at The Truman Annex in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
A stay in A CHANGE IN LATITUDE is more than just a rental but will be a part of your Key West vacation experience. In ad ...
From $290 per night (USD)
VRBO
From $341 per night (USD)
Expedia
Beautiful, 2100 sq ft 3/2 w/ocean views & easy ocean & gulf access.
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This is your home away from home. Beautiful 3 story home with spacious master bedroom and bathroom located on top floor ...
From $341 per night (USD)
Expedia
From $550 per night (USD)
VRBO
Luxury 3 bedroom condo overlooking harbor with ocean view, boat slip, amenities
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
1st I want to thank all our past guests for their great reviews. Bay Harbour Starfish is a luxury condo overlooking a la ...
From $550 per night (USD)
VRBO
From $88 per night (USD)
VRBO
Private Home, in the most beautiful, Florida Keys
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
The property is fenced with plenty of car parking. You will book a Family HOME, Our HOUSE is NOT a Trailer or Trailer Pa ...
From $88 per night (USD)
VRBO
From $226 per night (USD)
VRBO
Key Largo-Islamorada area-1 BR, 1 Bath -Privately Owned Condo -Fab Reviews!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
You've found it! No need to look any further. Come on down and explore the beautiful Florida Keys! Picture this... en ...
From $226 per night (USD)
VRBO
From $277 per night (USD)
Expedia
Keys Deal w/Cafe & Pool Bar! Up to 20% Off Beachfront 1BD Sleeps 4.
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
New Island Grill Pool Bar & Marina Cafe now open. Deluxe, upgraded 1-bedroom 1 full bath (sleeps four with sofabed) loca ...
From $277 per night (USD)
Expedia
From $507 per night (USD)
VRBO
P13 - Loggerhead House 3 Bedroom Home with Private Pool
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
The Loggerhead House A beautiful home in a premier location! This stunning 3-bedroom, 2-bathroom canal-front retreat of ...
From $507 per night (USD)
VRBO
From $301 per night (USD)
Expedia
Key Largo Sunset - Bayside open water - Tropical inspired 3 bed/2 bath
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
This three bedroom, two bathroom bayside retreat provides ideal coastal living with stunning views of the Florida Bay. T ...
From $301 per night (USD)
Expedia

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