Florida Keys Rentals
- From $221 per night (USD)
VRBO
Boot Key Harbor Comfy Condo 1bed 1bath
- 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 $221 per night (USD)VRBO
- From $481 per night (USD)
Expedia
Sweet Retreat! 4 bedroom 2.5 Baths Sombrero Beach w Pool Jacuzzi, 37` dock 2
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Plr2019-00281 Do you love the Tropical Waters of the Florida Keys? This vacation home is calling to you. Located on the ...
From $481 per night (USD)Expedia
- From $126 per night (USD)
VRBO
Tropical Oasis Home in Key Colony 3 bedrooms 2 Baths
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Rentals are Saturday – Saturday unless prior agent and guest agreement made or calendar matched to other reservations a ...
From $126 per night (USD)VRBO
- From $165 per night (USD)
Expedia
Castaway 2\/2 w\/ 50` Ft. Dock on the Atlantic
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
VACA-22-419 7-night minimum, NO Exceptions Max Occupancy: 5 (No Matter the age) Per the city of Marathon's rule. ***Ask ...
From $165 per night (USD)Expedia
- From $487 per night (USD)
VRBO
Palm Point 3bed\/2bath single family with brand new pool, dockage & stunning open
- 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 $487 per night (USD)VRBO
- From $800 per night (USD)
Expedia
Luxurious, Elegant Home, Waterfront\nWith Dockage
- Bedrooms:
- 3
- 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 $800 per night (USD)Expedia
- From $368 per night (USD)
VRBO
Waves of the Sea, Ocean View Home with Dock, Private Pool & Cabana Club Included
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
VACA-22-260 Booking Min age is 25 and must be present for the duration of the reservation. Max occupancy is 8 no matter ...
From $368 per night (USD)VRBO
- From $606 per night (USD)
Expedia
Mariners Club # 314 3 Bed 2.5 Bath Key Largo Beachfront Luxury Ocean views and
- Bedrooms:
- 3
- 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 $606 per night (USD)Expedia
- From $415 per night (USD)
VRBO
Ocean View Gem 3\/2.5 Home 70` Dock Cabana Club included, and Jacuzzi on Property
- Bedrooms:
- 3
- 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 $415 per night (USD)VRBO
- From $540 per night (USD)
Expedia
Shangri-La 3 Bedroom 3 Baths Gulf Front Estate
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
VACA-22-258 Rentals would be Saturday – Saturday unless prior agent and guest agreement made or calendar matched to othe ...
From $540 per night (USD)Expedia
- From $473 per night (USD)
VRBO
Coral Lagoon#8 3 Bed 2.5 bath 35` boat slip included MKB~Blanco
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
This Coral Lagoon Resort & Marina townhome in a quaint Key West village style atmosphere. 1450 sq ft and Built in 200 ...
From $473 per night (USD)VRBO
- From $435 per night (USD)
Expedia
A Pirates Great Escape ~ 3bed\/2baths Ocean View Boat Slip included
- 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 ...
From $435 per night (USD)Expedia
- From $774 per night (USD)
VRBO
Mahi Mahi House: Contemporary 3-Bed\/4-Bath Single-Family Oasis with Panoramic
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Mahi Mahi House, a stylish and contemporary single-family residence nestled in the desirable Coco Plum neighb ...
From $774 per night (USD)VRBO
- From $424 per night (USD)
Expedia
Beachy Keen House 3\/2 Water View Pool Home with Dock
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Vaca-21-258 Beachy Keen House! This home is just one house up from the white sands of Sombrero Beach. Three bedrooms, tw ...
From $424 per night (USD)Expedia
- From $165 per night (USD)
VRBO
Blue Marlin 2\/2 Pool home with 35` Dock Easy Access to Atlantic
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
VACA-21-25 7-night minimum, NO Exceptions Friday to Friday booking Only (for alternate dates message agent) We can do M ...
From $165 per night (USD)VRBO
- From $404 per night (USD)
VRBO
Keys Escape! Lovely Hammock View, Pools, Beach Access, Free Parking!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
We are about getting out there and having fun in the unmatched beauty of bayside Key Largo. Take an early morning swim i ...
From $404 per night (USD)VRBO
- From $267 per night (USD)
VRBO
Oceanview Condo 2bed 2bath second floor with elevator & ocean views!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Oceanview Condo is fully furnished and features two bedrooms, two bathrooms, a dining area, full kitchen, washer/dryer, ...
From $267 per night (USD)VRBO
- From $498 per night (USD)
Expedia
Yellowtail For Dinner 3bed 3bath updated single family home with private pool &
- 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 $498 per night (USD)Expedia
- From $856 per night (USD)
VRBO
Sunrise Paradise on Sombrero Brand New 4 bed 5 bath Pool Jacuzzi Kayaks
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 10
Plr2019-00051 Are you looking for an upscale, top-of-the-line, out of this world property? Then look no further than Sun ...
From $856 per night (USD)VRBO
- From $470 per night (USD)
Expedia
Casa De Tiki 4bed\/3bath half duplex with heated pool, dockage & more!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Casa De Tiki is a spacious 4-bedroom, 3-bathroom half duplex just up the road from the beautiful Sombrero Beach. Step in ...
From $470 per night (USD)Expedia
- From $268 per night (USD)
VRBO
🏝Waterfront 75’Dock POOL Kayaks Bikes SombreroBeach2mi OutdoorSpace WalkToStores
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
OUTDOORS @ LUNA BAY BREEZE We invite you to enjoy tropical tranquil breezes from the Atlantic Ocean side of Marathon an ...
From $268 per night (USD)VRBO
- From $425 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 $425 per night (USD)Expedia
- From $240 per night (USD)
VRBO
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 $240 per night (USD)VRBO
- From $173 per night (USD)
Expedia
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 $173 per night (USD)Expedia
- From $426 per night (USD)
VRBO
Oceanside home, dock,kayaks,bikes,pool,fishing,111
- 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 $426 per night (USD)VRBO
- From $430 per night (USD)
Expedia
Sea Breeze Cottage with 2 Large Decks in Beautiful 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. 3 bedro ...
From $430 per night (USD)Expedia
- From $194 per night (USD)
VRBO
Hip Studio in Old Town - Walk to the Beach!
- 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 $194 per night (USD)VRBO
- From $437 per night (USD)
Expedia
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 $437 per night (USD)Expedia
- From $800 per night (USD)
VRBO
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 $800 per night (USD)VRBO
- From $412 per night (USD)
Expedia
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 $412 per night (USD)Expedia
- From $430 per night (USD)
VRBO
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 $430 per night (USD)VRBO
- From $268 per night (USD)
Expedia
'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 Historic ...
From $268 per night (USD)Expedia
- From $146 per night (USD)
VRBO
Escape to Eden | 2 Bed, 1.5 Bath
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Newly renovated, tranquil half-duplex nestled among the natural beauty of Big Pine Key! Enjoy an immaculately clean spac ...
From $146 per night (USD)VRBO
- From $1156 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 $1156 per night (USD)VRBO
- From $367 per night (USD)
VRBO
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 $367 per night (USD)VRBO
- Click For Pricing
Expedia
Galleon Resort available. 2\/19\/21-2\/26\/21
- 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, ...
Click For PricingExpedia
- From $203 per night (USD)
VRBO
Key Largo Oasis.
- Bedrooms:
- 2
- 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 $203 per night (USD)VRBO
- From $254 per night (USD)
Expedia
**BANYAN ROSE @ BEACHSIDE** Modern Home & Pool + LAST KEY SERVICES…
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Nestled under ...
From $254 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 PricingVRBO
- From $420 per night (USD)
Expedia
COZY COTTAGE WITH PRIVATE DIPPING POOL OVERLOOKING BLUE WATER LAGOON
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
YOUR TROPICAL PARADISE AWAITS. TWO BEDROOM 2 1/2 BATH OVERLOOKING BLUE WATER LAGOON. SLEEPS 6 COMFORTABLY. GREAT FOR CO ...
From $420 per night (USD)Expedia
- From $677 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 $677 per night (USD)VRBO
- From $482 per night (USD)
Expedia
Marathon Keys Coral Lagoon Unit 2 Waterfront Villa
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to paradise! We are proud to offer you one of the nicest waterfront units in Coral Lagoon! Please Note: For you ...
From $482 per night (USD)Expedia
- From $265 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 $265 per night (USD)VRBO
- From $226 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 $226 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 PricingVRBO
- From $836 per night (USD)
Expedia
W08 - New Luxury Property! Stunning Canal Front Pool Home - Sleeps 14
- Bedrooms:
- 7
- 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 $836 per night (USD)Expedia
- From $235 per night (USD)
VRBO
Enjoy Insta-worthy Views and Ace Location for Ocean Adventures
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
AVAILABLE AS A 1 bedroom with sleeper sofa. This beautiful one bedroom unit has been completely renovated with beautif ...
From $235 per night (USD)VRBO
- From $601 per night (USD)
Expedia
Hidden Gem Sunset Views-Marlin Bay Resort & Marina
- Bedrooms:
- 4
- 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 $601 per night (USD)Expedia
- From $295 per night (USD)
VRBO
🌸Home #1: “ANCHORS ⚓ AWAY” (Ocean View Property-approximately 300 ft from beach entrance)- 🌸
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Home #1: “ANCHORS ⚓ AWAY” (Ocean View Property-approximately 300 ft from beach entrance)- 🌸 Totally Private😉- Turn-Key ...
From $295 per night (USD)VRBO
- From $395 per night (USD)
Expedia
Historic House, Gorgeous Porch, Great Location, See 5 Star Reviews
- Bedrooms:
- 4
- 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 $395 per night (USD)Expedia
- From $320 per night (USD)
VRBO
Happiness is the sand between your toes and the sunburn on your nose!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Nautical 2 bedroom & 2 bath inspired getaway in a gated and professionally managed community/resort with an abundance of ...
From $320 per night (USD)VRBO
- From $225 per night (USD)
Expedia
Fishing Till Sunset 1bed\/1bath Condo w\/Pool & dock
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Vaca-21-257 Located on Coco Plum at the Coco Plum Terraces. Shared Pool and private dock. The adorable one bedroom one ...
From $225 per night (USD)Expedia
- From $260 per night (USD)
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 ...
From $260 per night (USD)VRBO
- From $478 per night (USD)
Expedia
Coconut Palm by Brightwild | Island Home w\/ Pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: Coconut Palm is the perfect place for your beautiful tropical getaway in Key West. It is located just one block ...
From $478 per night (USD)Expedia
- Click For Pricing
VRBO
Lazy Lane at The Truman Annex - Pool & Parking
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Lazy Lane at the picturesque Shipyard Condominiums is just a few steps away from Fort Zachary Taylor Beach and ...
Click For PricingVRBO
- From $471 per night (USD)
Expedia
Casa Key West by Brightwild | Pool & Free Parking
- 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 $471 per night (USD)Expedia
- From $224 per night (USD)
VRBO
Sea Breeze by Brightwild | Off-Street Parking!
- 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 $224 per night (USD)VRBO
- From $215 per night (USD)
Expedia
Breeze On Inn: A Waterfront Retreat with 2 Bedrooms 2 bathrooms and Dockage
- 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 $215 per night (USD)Expedia
- From $342 per night (USD)
VRBO
Anglers Reef Islamorada home with ocean views, private marina, beach & pool
- Bedrooms:
- 3
- 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 $342 per night (USD)VRBO
- From $1017 per night (USD)
Expedia
Coastal Comfort; Waterfront Luxury Home with private pool!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Luxurious furnishings and spacious interiors centered around the expansive water views perfectly compliment the beautifu ...
From $1017 per night (USD)Expedia
- From $489 per night (USD)
VRBO
Top Floor Ocean Views from every window Newly Renovated
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
PROFESSIONAL CLEANING PER CDC GUIDELINES BEFORE & AFTER EACH STAY Key West Paradise Found hes been renovated for 2020 an ...
From $489 per night (USD)VRBO
- From $675 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 $675 per night (USD)Expedia
- From $293 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 $293 per night (USD)VRBO
- From $399 per night (USD)
Expedia
Penthouse Level Ocean Views- Live the Dream
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
PROFESSIONAL CLEANING PER CDC GUIDELINES BEFORE & AFTER EACH STAY You feel the excitement the moment you arrive. The war ...
From $399 per night (USD)Expedia
- From $1001 per night (USD)
VRBO
Havana Daydream; Spacious Waterfront 4 Bedroom Home With Private Heated Pool
- 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 $1001 per night (USD)VRBO
- From $499 per night (USD)
Expedia
Penthouse Level Ocean Views from every room Tropical Excellence
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
PROFESSIONAL CLEANING PER CDC GUIDELINES BEFORE & AFTER EACH STAY Ocean views from every room with floor to ceiling wind ...
From $499 per night (USD)Expedia
- From $568 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 $568 per night (USD)VRBO
- From $414 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 $414 per night (USD)Expedia
- From $727 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 $727 per night (USD)VRBO
- From $770 per night (USD)
Expedia
Banana Breeze: Oceanview 4-bedroom 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 $770 per night (USD)Expedia
- From $450 per night (USD)
VRBO
Hemingway Hideaway in the Truman Annex
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Perfectly positioned townhouse in Truman Annex At Historic Foundry building. Hemingway Hideaway in Truman Annex is a de ...
From $450 per night (USD)VRBO
- From $240 per night (USD)
Expedia
Meticulous End Unit Across From Pool - near local Diving, Fishing & Snorkeling
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Relax amongst the tropical sights and sounds in this charming, oceanfront, condo located in Ocean Pointe Suites Key Larg ...
From $240 per night (USD)Expedia
- From $125 per night (USD)
VRBO
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 $125 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 $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 $179 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 $179 per night (USD)Expedia
- From $531 per night (USD)
VRBO
UPSCALE KEY LARGO VILLA L1, MARINA, 2POOLS,SALTWATER LAGOON,TENNIS,BIKES,KAYAKS
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
IF YOUR DATES ARE NOT AVAILABLE, PLEASE SEE OUR OTHER PROPERTIES in Kawama by entering the following property numbers in ...
From $531 per night (USD)VRBO
- Click For Pricing
Expedia
Spacious condo, great location in paradise!
- Bedrooms:
- 3
- 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 $225 per night (USD)
VRBO
Conch Key Landing; three waterfront apartments on Florida Bay
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Boat Docking fee to be paid on site! One (1) Vehicle, Trailer and Boat Per Unit. Conch Key- An old-fashioned lobster ...
From $225 per night (USD)VRBO
- From $225 per night (USD)
Expedia
Beach House with Ocean View-No Contact Check-In
- 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 $225 per night (USD)Expedia
- From $575 per night (USD)
VRBO
Oceanfront two-bedroom gated condominium adjacent to marina and restaurant
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
**Perfect Getaway for Retirees** Imagine this: from the comfort of your bed, you wake up to a beautiful sun rising ove ...
From $575 per night (USD)VRBO
- From $242 per night (USD)
Expedia
Moon Bay Key Largo; Water View. Diver's Heaven Contactless check in!
- Bedrooms:
- 2
- 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 $242 per night (USD)Expedia
- From $294 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 $294 per night (USD)VRBO
- From $199 per night (USD)
Expedia
Canal Front Home in Big Pine Key
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This two bedroom two bath home open floor concept is very comfortable. Master bedroom has sliding doors to screened in ...
From $199 per night (USD)Expedia
- From $259 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 $259 per night (USD)VRBO
- From $218 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 $218 per night (USD)Expedia
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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 $320 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 $320 per night (USD)Expedia
- From $501 per night (USD)
VRBO
KEYS LIFE FOR ALL AGES, 🍹☀️🏊♂️⛱🎣
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
IF YOUR DATES ARE NOT AVAILABLE, PLEASE SEE OUR OTHER PROPERTIES in Kawama by entering the following property numbers in ...
From $501 per night (USD)VRBO
- From $270 per night (USD)
Expedia
Sunset Crush- Bayfront property for the perfect sunset, Tavernier
- Bedrooms:
- 3
- Bathrooms:
- 4
- 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 $270 per night (USD)Expedia
- From $251 per night (USD)
VRBO
Bahia Vista- Rare Bayfront townhouse at Moon Bay in Key Largo
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 25
Bahia Vista is a rare end unit within the Moon Bay community, boasting exquisite water bay views from nearly every room ...
From $251 per night (USD)VRBO
- From $275 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 $275 per night (USD)Expedia
- From $307 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 $307 per night (USD)VRBO
- From $307 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 $307 per night (USD)Expedia
- From $260 per night (USD)
VRBO
CONCH RETREAT Truman Annex Condo with 2 decks, Close to Beach, 2 Bikes
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
A TRUE CARIBBEAN PARADISE! Location! Location! Location! The Conch Retreat Condo is located in the prestigious Truman An ...
From $260 per night (USD)VRBO
- Click For Pricing
Expedia
Castaway Cove by Brightwild | Kayaks, Pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Just steps from mangrove tunnels and the breathtaking blue waters of the FL Keys, "Castaway Cove" is the perfec ...
Click For PricingExpedia
- From $319 per night (USD)
VRBO
**MIDTOWN MOSAIC @ MIDTOWN** Modern Private Home & Pool + LAST KEY SERVICES…
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Spanning an e ...
From $319 per night (USD)VRBO
- From $652 per night (USD)
Expedia
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 $652 per night (USD)Expedia
- Click For Pricing
VRBO
The Hammocks at Marathon Family, Fun, and Relaxation all Together in One Place!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The Hammocks at Marathon is located midway along the Florida Keys. Marathon is just before the famous Seven Mile Bridge ...
Click For PricingVRBO
- Click For Pricing
Expedia
ISLAND SPA at The Truman Annex in Key West
- 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 PricingExpedia