
Florida Keys National Marine Sanctuary Rentals

- From $197 per night (USD)
VRBO
Fishing Till Sunset 1bed/1bath Condo w/Pool & dock
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Vaca-21-257Located on Coco Plum at the Coco Plum Terraces. Shared Pool and private dock. The adorable one bedroom one ba ...
From $197 per night (USD)VRBO
- Click For Pricing
Expedia
Key Largo Paradise Home in Calusa Campground
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Fully furnished, 2 bedroom/1 bath mobile home featuring 2 bedrooms with bunk beds Full over Full. The property has an o ...
Click For PricingExpedia
- From $1092 per night (USD)
VRBO
Steps from Duval with Private Pool – Coconut Palm
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: Step into the heart of Key West at Coconut Palm! Just one block from Duval Street, this tropical gem features a ...
From $1092 per night (USD)VRBO
- From $1017 per night (USD)
Expedia
Parking & Shared Pool - Casa Key West
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: - Located on the south end of Duval Street steps from the Southernmost Point! - Large open-concept condo with p ...
From $1017 per night (USD)Expedia
- From $586 per night (USD)
VRBO
Private Parking & Near Downtown - Sea Breeze
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Sea Breeze is the perfect location for your tropical getaway. This two bedroom condo is located in the heart of ...
From $586 per night (USD)VRBO
- From $258 per night (USD)
Expedia
Breeze On Inn in Marathon
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This 2-bedroom, 2-bath mobile home is located on Grassy Key, in the Florida Keys, on the Gulf side. It sits on a canal, ...
From $258 per night (USD)Expedia
- From $388 per night (USD)
VRBO
Anglers Reef Islamorada home with ocean views, private marina, beach & pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Angler's Retreat is a 2 bedroom, 2.5 bathroom single-family home with picturesque ocean views, privacy, and space. The p ...
From $388 per night (USD)VRBO
- From $879 per night (USD)
Expedia
Waterfront Luxury Home with private pool!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Luxurious furnishings and spacious interiors centered around the expansive water views perfectly compliment the beautifu ...
From $879 per night (USD)Expedia
- From $613 per night (USD)
VRBO
Panoramic Ocean: Beach from every window
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
CONSTRUCTION NOTICE - There will be concrete restoration project happening at 1800 Atlantic Starting in May 2025 through ...
From $613 per night (USD)VRBO
- From $801 per night (USD)
Expedia
Luxury waterfront Islamorada Retreat w/private pool, hot tub, lanai bar& firepit
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to "Casa de Karma", your own private, resort style paradise! Enjoy your large heated pool (with sun shelf and s ...
From $801 per night (USD)Expedia
- From $339 per night (USD)
VRBO
Another Day in Paradise! PRIVATE POOL! Blocks from Duval, 2BR/2BA in Old Town!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
*** Located in the Old Town neighborhood. This exclusive residential area of Old Town Key West is really an extension of ...
From $339 per night (USD)VRBO
- From $569 per night (USD)
Expedia
Penthouse Beach Ocean Views- Live the Dream
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
CONSTRUCTION NOTICE - There will be concrete restoration project happening at 1800 Atlantic Starting in May 2025 through ...
From $569 per night (USD)Expedia
- From $748 per night (USD)
VRBO
Spacious Waterfront 4 Bedroom Home
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
If you’re looking for an upscale escape by the sea, Havana Daydream is your Key West hidden gem. Enjoy the island life i ...
From $748 per night (USD)VRBO
- From $854 per night (USD)
Expedia
Beach Penthouse: Ocean Views from every room Tropical Excellence
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
CONSTRUCTION NOTICE - There will be concrete restoration project happening at 1800 Atlantic Starting in May 2025 throug ...
From $854 per night (USD)Expedia
- From $744 per night (USD)
VRBO
🌸Home #7 \"BEACHY🏖KEEN\" Full WATERFRONT View Property!🌸
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
🌸Home #7 "BEACHY🏖KEEN" Full WATERFRONT View over the docks and beach and Ocean!🌸 Totally Private😉- Turn-Key and full ...
From $744 per night (USD)VRBO
- From $391 per night (USD)
Expedia
P55 - Beautiful 3 bedroom, 3 bath home with private pool and hot tub.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
This fabulous 3 bedroom, 3 bath, Gulf side home has been remodeled inside and out and the results are perfect! ...
From $391 per night (USD)Expedia
- From $700 per night (USD)
VRBO
🌸Home #8 \"DEJA⛵BLUE\" Premium WATERFRONT 🌸
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
🌸Home #8 "DEJA⛵BLUE" Full Premium WATERFRONT view of Beach, Docks and Ocean🌸 Totally Private😉- Turn-Key and fully Sto ...
From $700 per night (USD)VRBO
- From $901 per night (USD)
Expedia
Oceanview home with private pool & lush landscaping!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
"Banana Breeze" is an upscale escape by the sea, and considered by some to be a hidden gem. Tucked away in your own oasi ...
From $901 per night (USD)Expedia
- From $635 per night (USD)
VRBO
Hemingway Hideaway in the Truman Annex
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Perfectly positioned townhouse in Truman Annex At Historic Foundry building. Hemingway Hideaway in Truman Annex is a de ...
From $635 per night (USD)VRBO
- Click For Pricing
Expedia
NEW LISTING - Cudjoe Key - Canal with Quick Ocean Access
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Home is located in a very quiet and nice neighborhood! Home is minutes away from Key West or Big Pine for quick access t ...
Click For PricingExpedia
- From $264 per night (USD)
VRBO
Meticulous End Unit Across From Pool - near Local Diving, Fishing & Snorkeling
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Come unwind at our tastefully decorated 2 bedroom, 2 bathroom, condo in Ocean Pointe Suites. Located directly on the Atl ...
From $264 per night (USD)VRBO
- From $144 per night (USD)
Expedia
Key Largo - Sexton Cove (BaySide)
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to "Casa del Agua"!! The property is a Bay-Side Trailer located in the community of Sexton Cove on Mile Marker ...
From $144 per night (USD)Expedia
- From $307 per night (USD)
VRBO
P73 - Charming 4 bedroom duplex with deep water dockage and Cabana Club access.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Beautiful 4 Bedroom, 2 bathroom duplex in Key Colony Beach. Key Colony Beach is a small, friendly, walkable island with ...
From $307 per night (USD)VRBO
- From $237 per night (USD)
Expedia
Oceanside, pet friendly, smart home with plenty of paddle equipment
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
We are offering a nice discount in May of 2023 because we are putting in a new dock. Wonderful, pet-friendly, and beaut ...
From $237 per night (USD)Expedia
- From $528 per night (USD)
VRBO
Key Largo Kawama Villa L1, 3/3
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Welcome to paradise! This beautiful and modern unit is located in the highly sought-after Kawama Yacht Club in the heart ...
From $528 per night (USD)VRBO
- Click For Pricing
Expedia
Spacious condo, great location in paradise!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Looking for a tropical getaway that’s easy to get to? This is it! This Condo offers spacious (yes SPACIOUS!) rooms. Newl ...
Click For PricingExpedia
- From $237 per night (USD)
VRBO
Beach House- Ocean & Beach View-Upgraded-Over 146 Five Star Reviews
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
If you are looking to stay in accommodations of high standards. This is the one for you! As you enter this large one bed ...
From $237 per night (USD)VRBO
- From $703 per night (USD)
Expedia
OCEAN MEMORIES CONDO- 2 Bedroom, 2 Bath Oceanfront w/ Pool & Hot Tub
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
*Oceanfront Escape with Breathtaking Views – Steps from the Marina* Wake up to unforgettable sunrises over the Atlanti ...
From $703 per night (USD)Expedia
- From $278 per night (USD)
VRBO
Water View. Diver's Heaven. Fishing. Paradise Key Largo, Moonbay
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Our rental is contactless from start to finish. Magnificent top floor end unit suite. Incredible views of the bay/oc ...
From $278 per night (USD)VRBO
- From $282 per night (USD)
Expedia
Outstanding Oceanfront Condo On The Beach With A Pool!!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Time to get away! Rent our newest addition! This newly renovated condo with a brand new, high-end, kitchen and updated b ...
From $282 per night (USD)Expedia
- From $318 per night (USD)
VRBO
Beautiful Key Largo Town Home Fully Renovated Top to Bottom
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Are you looking for a peaceful island vacation with hints of luxury? Look no further. Casa Key Largo is the place for ...
From $318 per night (USD)VRBO
- From $267 per night (USD)
Expedia
OCEANFRONT 2 BDRM, 2 BATH APT, KEY LARGO, TAVERNIER
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This is one of the finest destinations in the Florida Keys. Recently renovated property! Our unit is Oceanfront with a ...
From $267 per night (USD)Expedia
- Click For Pricing
VRBO
Old Town Island House Near a grocery store, beach, bike rental shop, Restaurants
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Two Story Apartment in central Old Town Key West location. Only a 5 min bike ride to Duval. 1 King size bed on 3rd flo ...
Click For PricingVRBO
- From $282 per night (USD)
Expedia
Amazing Ocean View Condo on the Beach!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Create a memory that will last a lifetime! Rent this 2 bedroom, 2 bath condo with an outstanding View of the beach, pa ...
From $282 per night (USD)Expedia
- From $489 per night (USD)
VRBO
Key Largo Kawama villa K1, 3/3
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Experience the charm and relaxation of the Florida Keys at Kawama Yacht Club. Our private community located in the hear ...
From $489 per night (USD)VRBO
- From $620 per night (USD)
Expedia
Sunset Crush- Bayfront property for the perfect sunset, Tavernier
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Do you love sunsets and all things ocean? Sunset Crush is aptly named and will have you crushing HARD over one of the m ...
From $620 per night (USD)Expedia
- From $265 per night (USD)
VRBO
Rare Bayfront End Unit in Moon Bay, Unmatched Sunsets, Boat Slip, Pool, Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 25
Looking for the perfect Key Largo vacation rental? Welcome to Bahia Vista, a rare end unit condo located in the desirabl ...
From $265 per night (USD)VRBO
- From $292 per night (USD)
Expedia
Beautiful House on Canal - minutes to the Atlantic, no bridges
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
The 3 bed/3 bath canal front home provides quick access to the Atlantic and Looe Key with no bridges. 60' of canal fr ...
From $292 per night (USD)Expedia
- From $373 per night (USD)
VRBO
GREEN SPOT at The Truman Annex in Key West
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to our comfortable and delightful 2nd floor condo in the Shipyard section of Truman Annex. Unit #258 is a tastef ...
From $373 per night (USD)VRBO
- From $380 per night (USD)
Expedia
ANOTHER THREE HOUR TOUR 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 $380 per night (USD)Expedia
- From $285 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 $285 per night (USD)VRBO
- From $440 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 $440 per night (USD)Expedia
- From $446 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 $446 per night (USD)VRBO
- From $1369 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 $1369 per night (USD)Expedia
- From $307 per night (USD)
VRBO
Quiet Conch House in Historic District
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Discover a piece of paradise with a beautiful conch home located in the historic district of Key West. 4-bedrooms, 2 ba ...
From $307 per night (USD)VRBO
- From $295 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 $295 per night (USD)Expedia
- Click For Pricing
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 PricingVRBO
- 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 ...
Click For PricingExpedia
- From $351 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 $351 per night (USD)VRBO
- From $306 per night (USD)
Expedia
P46 - Beautiful updated home on the Gulf side with pool and dock!
- 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 $306 per night (USD)Expedia
- From $415 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 $415 per night (USD)VRBO
- From $410 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 $410 per night (USD)Expedia
- From $1898 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 $1898 per night (USD)VRBO
- From $193 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 $193 per night (USD)Expedia
- From $645 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 $645 per night (USD)VRBO
- From $597 per night (USD)
Expedia
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 $597 per night (USD)Expedia
- From $2451 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 $2451 per night (USD)VRBO
- From $673 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 Be ...
From $673 per night (USD)Expedia
- From $311 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 s ...
From $311 per night (USD)VRBO
- Click For Pricing
Expedia
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 ...
Click For PricingExpedia
- From $581 per night (USD)
VRBO
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 $581 per night (USD)VRBO
- From $470 per night (USD)
Expedia
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 $470 per night (USD)Expedia
- From $560 per night (USD)
VRBO
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 $560 per night (USD)VRBO
- From $969 per night (USD)
Expedia
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 $969 per night (USD)Expedia
- From $472 per night (USD)
VRBO
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 $472 per night (USD)VRBO
- From $457 per night (USD)
Expedia
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 $457 per night (USD)Expedia
- From $307 per night (USD)
VRBO
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 $307 per night (USD)VRBO
- From $477 per night (USD)
Expedia
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 $477 per night (USD)Expedia
- From $688 per night (USD)
VRBO
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)VRBO
- From $325 per night (USD)
Expedia
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 $325 per night (USD)Expedia
- From $458 per night (USD)
VRBO
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 $458 per night (USD)VRBO
- From $587 per night (USD)
Expedia
*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)Expedia
- From $655 per night (USD)
VRBO
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 $655 per night (USD)VRBO
- From $547 per night (USD)
Expedia
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 $547 per night (USD)Expedia
- From $209 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 $209 per night (USD)VRBO
- From $493 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 $493 per night (USD)Expedia
- 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 $1272 per night (USD)
Expedia
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 $1272 per night (USD)Expedia
- From $2845 per night (USD)
VRBO
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 $2845 per night (USD)VRBO
- From $1410 per night (USD)
Expedia
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 $1410 per night (USD)Expedia
- From $469 per night (USD)
VRBO
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 $469 per night (USD)VRBO
- From $306 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 $306 per night (USD)Expedia
- From $236 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 $236 per night (USD)VRBO
- From $270 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 $270 per night (USD)Expedia
- From $302 per night (USD)
VRBO
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 $302 per night (USD)VRBO
- From $919 per night (USD)
Expedia
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 $919 per night (USD)Expedia
- From $244 per night (USD)
VRBO
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 $244 per night (USD)VRBO
- From $489 per night (USD)
Expedia
Peachy Keen Private Heated Pool, Cabana, & Prime Location Truman Annex!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 7
This beautiful home has 3 bedrooms and 3 baths in the main house with a bonus cabana. There is a private and heated po ...
From $489 per night (USD)Expedia
- From $305 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 $305 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 $261 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 $261 per night (USD)VRBO
- From $664 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 $664 per night (USD)Expedia
- From $196 per night (USD)
VRBO
RESERVE QUICKLY! YOU’LL LOVE IT! EVERYONE DOES!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Huge terrace! Right on the water with unobstructed views! Accessible from every room! Spacious and clean. Peaceful and a ...
From $196 per night (USD)VRBO
- From $950 per night (USD)
Expedia
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 $950 per night (USD)Expedia
- From $255 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 $255 per night (USD)VRBO
- From $1236 per night (USD)
Expedia
**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 $1236 per night (USD)Expedia
- From $389 per night (USD)
VRBO
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 $389 per night (USD)VRBO
- From $430 per night (USD)
Expedia
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 $430 per night (USD)Expedia
- From $195 per night (USD)
VRBO
Cayman Cottage | 3 bed/2 bath boating home on Ramrod Key
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Escape to Cayman Cottage, a charming three-bedroom, two-bathroom monthly vacation rental in Breezeswept Beach Estates on ...
From $195 per night (USD)VRBO
- From $217 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 $217 per night (USD)Expedia