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Florida Keys Rentals

From $293 per night (USD)
VRBO
Julia's Secret
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Best location in Key West! Just steps from the world class shops and restaurants of world famous Duval Street. There are ...
From $293 per night (USD)
VRBO
From $1411 per night (USD)
Expedia
**GOOD VIBRATIONS @ OLD TOWN** Unique Villa & Pool + LAST KEY SERVICES…
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Key West has ...
From $1411 per night (USD)
Expedia
From $3258 per night (USD)
VRBO
1 Block to Duval St | Banana's Foster Guesthouse
Bedrooms:
7
Bathrooms:
7
Sleeps:
19
Summary: Palm trees, sunsets, and the blissful pace of island time will all be yours when you stay at this large histori ...
From $3258 per night (USD)
VRBO
From $603 per night (USD)
Expedia
Fully renovated Condo with Private Balcony, Shared Pool, Hot Tub and Parking
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
*Brand New Listing* Welcome to Captains Choice The NICEST Unit at Sunrise Suites Resort in Key West- Unit 302. Tropical ...
From $603 per night (USD)
Expedia
From $453 per night (USD)
VRBO
Spectacular Ocean Front Home In Beautiful Islamorada!Slip,Com Pool, & Prv Bch
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
VRL# 25-0132 we are one of Islamorada’s limited number of licensed weekly vacation homes. This magnificent home with di ...
From $453 per night (USD)
VRBO
From $470 per night (USD)
Expedia
Villa Valbuena Gem Key Largo- Marina 2 Kings, Pickleball
Bedrooms:
2
Bathrooms:
2
Sleeps:
7
<p>This property is managed by KEYLARGOTRAVELS We own several remodeled high-end units in Key Largo. Please check out al ...
From $470 per night (USD)
Expedia
From $585 per night (USD)
VRBO
Luxury Key Largo Home w/ Guest House & Pool!
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
Total relaxation awaits you at this Key Largo vacation rental. Located in prestigious Buccaneer Point, this 3-bedroom, 4 ...
From $585 per night (USD)
VRBO
From $276 per night (USD)
Expedia
Upscale end unit home @ Truman Annex close to Duval St
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Now more than ever it is important it is important to choose a home that is thoroughly cleaned and well maintained. We ...
From $276 per night (USD)
Expedia
From $342 per night (USD)
VRBO
**DRIFTWOOD DREAMS @ 1800 ATLANTIC** Beachside Condo & Pool + LAST KEY SERVICES.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE - 25% off!!! - 25% off any stay through summer 2026 due to construction at the complex! 25% discount ...
From $342 per night (USD)
VRBO
From $420 per night (USD)
VRBO
Breezy Beach Waterfront home in Port Antigua
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Relax in this beautiful and comfortably updated bayside home in Port Antigua. Port Antigua is the Lower Keys best kept ...
From $420 per night (USD)
VRBO
From $300 per night (USD)
VRBO
Waterfront 75’Dock POOL Kayaks Bikes SombreroBeach2mi OutdoorSpace WalkToStores
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
PARADISE AWAITS AT LUNA BAY BREEZE Experience the perfect Florida Keys getaway at this waterfront oasis where Atlantic ...
From $300 per night (USD)
VRBO
From $339 per night (USD)
Expedia
Villa 5053 on Duck Key Boat Slip Available - 2BD 2.5BA
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Boat slip available for additional $100 a night. Largest boat that can fit is 33 ft. Ask for availability. This villa b ...
From $339 per night (USD)
Expedia
From $568 per night (USD)
VRBO
403 Mariners Club | 3 Bed, 3 Bath
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Starlight star bright...first star I see tonight...I wish I may I wish I might have the wish I wish tonight… And I wish ...
From $568 per night (USD)
VRBO
From $1529 per night (USD)
Expedia
Heated Pool, Steps to Duval St - Poolside Paradise
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Summary: This 3 bed 2 bath home with an amazing HEATED pool is located right off the quieter end of Duval St. The home c ...
From $1529 per night (USD)
Expedia
From $368 per night (USD)
VRBO
Shared Heated Pool, Near Duval - Poolside Retreat
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: Poolside Retreat is the PERFECT vacation home for a couple or small group of friends looking for a fun-filled g ...
From $368 per night (USD)
VRBO
From $198 per night (USD)
Expedia
Lou & Mary`s Getaway ~ 2 bed 2 Bath home W/Dock, I
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Welcome to Your Perfect Florida Keys Retreat!Relax, fish, and enjoy the laid-back island lifestyle in this charming 2-be ...
From $198 per night (USD)
Expedia
From $644 per night (USD)
VRBO
Reel Sunset 3/2 with Pool and Canalfront in Duck K
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Beautiful 3 bedroom 2.5 bath canal front home with private pool. Seaside decor and casual elegance define this comfortab ...
From $644 per night (USD)
VRBO
From $440 per night (USD)
VRBO
Keys Escape! Lovely Hammock View, Pools, Beach Access, Pets Allowed!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Oceanfront family-friendly property with direct beach access and pool This listing is for a room within a hotel. ✦ You ...
From $440 per night (USD)
VRBO
From $305 per night (USD)
VRBO
Oceanview Condo in Key Colony Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Oceanview Condo is fully furnished and features two bedrooms, two bathrooms, a dining area, full kitchen, washer/dryer, ...
From $305 per night (USD)
VRBO
From $469 per night (USD)
Expedia
Yellowtail for Dinner
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Yellowtail For Dinner is a stunning 3bed/3bath that is it is only one house away from the mouth of a deep-water canal th ...
From $469 per night (USD)
Expedia
From $940 per night (USD)
VRBO
Sunrise Paradise on Sombrero Brand New 4 bed 5 bat
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Are you looking for an upscale, top-of-the-line, out of this world property? Then look no further than Sunrise Paradise. ...
From $940 per night (USD)
VRBO
From $405 per night (USD)
Expedia
Casa De Tiki in Marathon
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Casa De Tiki is a spacious 4-bedroom, 3-bathroom half duplex located just minutes from the stunning Sombrero Beach. Insi ...
From $405 per night (USD)
Expedia
From $290 per night (USD)
VRBO
Comfy Condo in Marathon
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This updated one-bedroom condo, centrally located in Marathon, offers convenient access to historical sites such as Cran ...
From $290 per night (USD)
VRBO
From $754 per night (USD)
Expedia
Sweet Retreat! 4 bedroom 2.5 Baths Sombrero Beach
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Do you love the Tropical Waters of the Florida Keys? This vacation home is calling to you. Located on the water in the e ...
From $754 per night (USD)
Expedia
From $198 per night (USD)
VRBO
Tropical Oasis Home in Key Colony 3 bedrooms 2
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Rentals are Saturday Saturdayunless prior agent and guest agreement made or calendar matched to other reservations alre ...
From $198 per night (USD)
VRBO
From $215 per night (USD)
Expedia
Castaway 2/2 w/ 50` Ft. Dock on the Atlantic
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
VACA-22-4197-night minimum, NO ExceptionsMax Occupancy: 5 (No Matter the age) Per the city of Marathon's rule.**Castaway ...
From $215 per night (USD)
Expedia
From $527 per night (USD)
VRBO
Palm Point in Marathon
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Palm Point presents a breathtaking 3-bedroom, 2-bathroom single-family residence located in Marathon on the gulf side of ...
From $527 per night (USD)
VRBO
$Luxurious, Elegant Home, Waterfront\nWith Dockage$
From $1016 per night (USD)
Expedia
Luxurious, Elegant Home, Waterfront\nWith Dockage
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Oasis getaway, 3 bedroom, 3 bath, including chefs kitchen. This home has all the amenities on the water, located in a q ...
From $1016 per night (USD)
Expedia
From $445 per night (USD)
VRBO
Waves of the Sea, Ocean View Home with Dock, Priva
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
VACA-22-260Booking Min age is 25 and must be present for the duration of the reservation. Max occupancy is 8 no matter a ...
From $445 per night (USD)
VRBO
From $759 per night (USD)
Expedia
Mariners Club # 314 3 Bed 2.5 Bath Key Largo Beac
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Every one will love this luxurious and spacious 3 bedroom and 2.5 bathroom condo in the exclusive Mariner's Club gated c ...
From $759 per night (USD)
Expedia
From $645 per night (USD)
VRBO
Ocean View Gem 3/2.5 Home 70` Dock Cabana Club inc
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Easy Breezy Oceanside home on the Atlantic Ocean, just one house in from open water, with easy deep water access by boat ...
From $645 per night (USD)
VRBO
From $759 per night (USD)
Expedia
Shangri-La 3 Bedroom 3 Baths Gulf Front Estate
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
VACA-22-258Rentals would be Saturday Saturdayunless prior agent and guest agreement made or calendar matched to other r ...
From $759 per night (USD)
Expedia
From $441 per night (USD)
VRBO
A Pirates Great Escape ~ 3bed/2baths Ocean View B
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Oceanfront Penthouse Condo with a Private Boat slip. Small Gated Community on the southern tip of Islamorada.The condo h ...
From $441 per night (USD)
VRBO
From $602 per night (USD)
Expedia
Beachy Keen House 3/2 Water View Pool Home with Do
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Vaca-21-258Beachy Keen House! This home is just one house up from the white sands of Sombrero Beach. Three bedrooms, two ...
From $602 per night (USD)
Expedia
From $277 per night (USD)
VRBO
Blue Marlin 2/2 Pool home with 35` Dock Easy Acces
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
VACA-21-257-night minimum, NO Exceptions Friday to Friday booking Only (for alternate dates message agent) We can do Mon ...
From $277 per night (USD)
VRBO
From $506 per night (USD)
Expedia
Compelling Canal Home with Pool & Large Dock on each side-Cabana Club Included
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
DUPLEX, THIS LISTING NUMBER IS 561552 OTHER SIDE LISTING IS 1275459. EACH SIDE HAS 4 BEDROOMS 3 BATHS, YOUR OWN POOL AND ...
From $506 per night (USD)
Expedia
From $1534 per night (USD)
VRBO
Old Town Retreat near Upper Duval St
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Casa Caribe! When you think of the Caribbean, you think of tranquil blue green waters and a fun vibe. That's the feel wh ...
From $1534 per night (USD)
VRBO
From $188 per night (USD)
Expedia
Canal-front condo with amazing views & convenient location
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Sombrero Siesta Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $188 per night (USD)
Expedia
From $340 per night (USD)
VRBO
Dog-friendly condo with pool & hot tub - walk or bike to beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Sunrise Suites - Paradise Escape 407 Our calendar is updated in real-time & our nightly rates are accurately displayed. ...
From $340 per night (USD)
VRBO
From $541 per night (USD)
Expedia
Oceanside home, dock,kayaks,bikes,pool,fishing,111
Bedrooms:
4
Bathrooms:
2
Sleeps:
6
This luxurious home overlooking the Atlantic Ocean is part of Sunrise Beach Resort, an exclusive gated community built i ...
From $541 per night (USD)
Expedia
From $503 per night (USD)
VRBO
Sea Breeze Cottage 2 Large Decks, pool, free parking/wifi in Truman Annex
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Sea Breeze Cottage Cottage is a private, tropical, stand alone cottage located in the prestigious Truman Annex. This is ...
From $503 per night (USD)
VRBO
From $445 per night (USD)
Expedia
Charming Studio in Historic Key West, 5-Min Bike Ride to Beach & Bikes Included!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Location, location, location! Situated in the heart of the Cuban district, steps from arguably the best 'con leche' in ...
From $445 per night (USD)
Expedia
From $489 per night (USD)
VRBO
Oceanside home, dock,kayaks,bikes,pool,fishing,109
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
This luxurious home overlooking the Atlantic Ocean is part of Sunrise Beach Resort, an exclusive gated community built i ...
From $489 per night (USD)
VRBO
From $975 per night (USD)
Expedia
3 bedroom 2 bath Ocean front condo on marina with opt boat slip.
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
3 bedroom 2 bathroom Ocean front condo. Full service marina on site. Restaurant/bar on site. Pool and spa Optional 50 ...
From $975 per night (USD)
Expedia
From $468 per night (USD)
VRBO
Oceanside home, dock,kayaks,bikes,pool,fishing,107
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
This luxurious home overlooking the Atlantic Ocean is part of Sunrise Beach Resort, an exclusive gated community built i ...
From $468 per night (USD)
VRBO
From $503 per night (USD)
Expedia
Ocean Front Modern Home
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
This luxurious cozy and comfortable, three-story home, overlooks the blue Atlantic, punctuated by small tropical islands ...
From $503 per night (USD)
Expedia
From $375 per night (USD)
VRBO
'LA DOLCE VITA' OLD TOWN! STEPS TO DUVAL! SLEEPS 2-4, 3 BLOCKS TO SOUTH BEACH!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
La Dolce Vita is located in the heart of Old Town Key West and just steps to Duval Street in the heart of the Hist ...
From $375 per night (USD)
VRBO
From $585 per night (USD)
Expedia
Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Here in Key West we believe in One Human Family where everyone is welcome and treated like family. Key West! .....it’s ...
From $585 per night (USD)
Expedia
From $390 per night (USD)
VRBO
Galleon Resort efficiency
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This unit has a queen size bed. Updated ceramic stand up shower. The unit is an efficiency.It has a small refrigerator, ...
From $390 per night (USD)
VRBO
From $181 per night (USD)
Expedia
Key Largo Oasis.
Bedrooms:
1
Bathrooms:
3
Sleeps:
4
Relax with the whole family at this peaceful place to stay. The upstairs of the home features 3 bedrooms, 1 and half bat ...
From $181 per night (USD)
Expedia
From $304 per night (USD)
VRBO
Beautiful Key Largo awaits
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Enjoy this lavishly decorated 2 bedroom 2 bathroom ground floor unit in beautiful Buttonwood Bay. Unit is a smoke free, ...
From $304 per night (USD)
VRBO
From $249 per night (USD)
Expedia
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Cottage #14 - Quaint, clean, comfortable cottage just 20 miles from Key West. Bring the family. Located on a compound wi ...
From $249 per night (USD)
Expedia
Click For Pricing
VRBO
3 blocks from waterfront and 1 block off Duval in heart of Old Town Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Want to “ Get away from it all” but still be in the heart of Olde Town Key West with everything you need right there? Th ...
Click For Pricing
VRBO
From $418 per night (USD)
Expedia
PLUNGE POOL VILLA ON BLUE WATER LAGOON DUCK Key/MARATHON, FL
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
In Duck Key/Marathon, Florida's sun-kissed beaches, you can find total relaxation at our beautiful two-bedroom house. Ne ...
From $418 per night (USD)
Expedia
From $1089 per night (USD)
VRBO
Seaside Retreat: Waterfront Home with private heated pool & lush landscaping
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Luxurious furnishings and spacious interiors centered around the expansive water views perfectly compliment the beautifu ...
From $1089 per night (USD)
VRBO
From $612 per night (USD)
Expedia
Marathon Keys Coral Lagoon Unit 2 Waterfront Villa
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
***A quick update regarding the property. The community has scheduled construction to begin on the seawall in our backya ...
From $612 per night (USD)
Expedia
Click For Pricing
VRBO
3 blocks from waterfront and 1 block off Duval in Old Town Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Want to “ Get Away from it all” but still in the heart of Old Town Key West with everything you need within walking dist ...
Click For Pricing
VRBO
From $704 per night (USD)
Expedia
W08 - New Luxury Property! Stunning Canal Front Pool Home - Sleeps 14
Bedrooms:
6
Bathrooms:
6
Sleeps:
14
Welcome to paradise! Escape to this luxurious 6 bedroom/6.5 bathroom home designed for VIP guests. Each bedroom i ...
From $704 per night (USD)
Expedia
From $318 per night (USD)
VRBO
Key Largo Getaway [ Ocean Pointe 1316 ]
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
In beautiful Tavernier, you'll find our impressive 2-bedroom condo waiting for your escape. Nestled just a short 19-minu ...
From $318 per night (USD)
VRBO
From $894 per night (USD)
Expedia
Hidden Gem Sunset Views-Marlin Bay Resort & Marina
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Marlin Bay Resort & Marina is a hidden gem located in the heart of The Keys! It is a newly launched boutique resort fea ...
From $894 per night (USD)
Expedia
From $465 per night (USD)
VRBO
🌸Home #1: “ANCHORS ⚓ AWAY” (Off Water-approximately 300 ft from beach entrance)- 🌸
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Home #1: “ANCHORS ⚓ AWAY” (Off Water-approximately 300 ft from beach entrance)- 🌸 Totally Private😉- Turn-Key and fully ...
From $465 per night (USD)
VRBO
From $408 per night (USD)
Expedia
Historic House, Gorgeous Porch, Great Location, See 5 Star Reviews
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Treat yourself, your family and friends to a grand Key West home ideal for an extended stay on the island. This wonderfu ...
From $408 per night (USD)
Expedia
From $302 per night (USD)
VRBO
Chic Coastal Retreat with Pool, Marina, Beach Access & Resort-Style Amenities
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Nautical-inspired 2-bedroom, 2-bath getaway located in a secure, professionally managed resort community offering abunda ...
From $302 per night (USD)
VRBO
From $273 per night (USD)
Expedia
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 $273 per night (USD)
Expedia
Click For Pricing
VRBO
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 Pricing
VRBO
From $1231 per night (USD)
Expedia
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 $1231 per night (USD)
Expedia
From $746 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 $746 per night (USD)
VRBO
From $265 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 $265 per night (USD)
Expedia
From $393 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 $393 per night (USD)
VRBO
From $976 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 $976 per night (USD)
Expedia
From $560 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 $560 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 $554 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 $554 per night (USD)
Expedia
From $1248 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 $1248 per night (USD)
VRBO
From $815 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 $815 per night (USD)
Expedia
$🌸Home #7 \BEACHY🏖KEEN\ Full WATERFRONT View Property!🌸$
From $811 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 $811 per night (USD)
VRBO
From $357 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 $357 per night (USD)
Expedia
$🌸Home #8 \DEJA⛵BLUE\ Premium WATERFRONT 🌸$
From $881 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 $881 per night (USD)
VRBO
From $1113 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 $1113 per night (USD)
Expedia
From $659 per night (USD)
VRBO
Hemingway Hideaway in the Truman Annex
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Hemingway Hideaway – Charming Townhouse in Truman Annex at Historic Foundry Building Discover your perfect Key West ret ...
From $659 per night (USD)
VRBO
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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 ...
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Expedia
From $291 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 $291 per night (USD)
VRBO
From $287 per night (USD)
Expedia
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 $287 per night (USD)
Expedia
From $237 per night (USD)
VRBO
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)
VRBO
From $599 per night (USD)
Expedia
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 $599 per night (USD)
Expedia
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VRBO
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 ...
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VRBO
From $371 per night (USD)
Expedia
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 $371 per night (USD)
Expedia
From $703 per night (USD)
VRBO
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 each morning to breathtaking sunrises stre ...
From $703 per night (USD)
VRBO
From $381 per night (USD)
Expedia
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 $381 per night (USD)
Expedia
From $282 per night (USD)
VRBO
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)
VRBO
From $318 per night (USD)
Expedia
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)
Expedia
From $271 per night (USD)
VRBO
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 $271 per night (USD)
VRBO
Click For Pricing
Expedia
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 ...
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Expedia
From $282 per night (USD)
VRBO
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)
VRBO
From $662 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 $662 per night (USD)
Expedia
From $235 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 $235 per night (USD)
VRBO
From $317 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 $317 per night (USD)
Expedia
From $456 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 $456 per night (USD)
VRBO
From $401 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 $401 per night (USD)
Expedia

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