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From $573 per night (USD)
VRBO
Watch dolphins play in Shelter Cove while swimming in our oversized pool!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Jump into Summer and experience warm Florida Keys weather and calm ocean for fishing! Relax in the private pool with ...
From $573 per night (USD)
VRBO
From $416 per night (USD)
Expedia
Stunning Panoramic rooftop views from this gulf side Tuscan style Villa!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
3 Bedroom 3 Bathroom Freestanding villa located in Bougainvillea, a Gated Community, with a pool exclusive to Bougain ...
From $416 per night (USD)
Expedia
From $625 per night (USD)
VRBO
Happy’s Houseboat Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
This beautiful houseboat is the best way to stay in Key West. Recently Featured in Old Dominion‘s music video “I was on ...
From $625 per night (USD)
VRBO
From $398 per night (USD)
Expedia
Canal View Summer Escape With Dock, Hot Tub and Cabana Club Access
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Welcome to Orchid House, a lushly landscaped canal front home located on the beautiful island of Key Colony Beach. Th ...
From $398 per night (USD)
Expedia
From $491 per night (USD)
VRBO
🌸Home #2: THE REEL WORLD (Off Water Property-approximately 250 ft from Private beach entrance)- 🌸
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
🌸Home #2: THE REEL WORLD (Off Water Property-approximately 250 ft from Private beach entrance)- 🌸Totally Private😉- Tu ...
From $491 per night (USD)
VRBO
From $281 per night (USD)
Expedia
Private Paradise with Heated Waterfall Pool
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Time to sit back and relax! Paradise found in this completely redone home in Key West. Private outdoor heated pool, show ...
From $281 per night (USD)
Expedia
From $1460 per night (USD)
VRBO
Sublime Sunsets at the Truman Annex in Key West
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Breathtaking waterfront view from this 4 bedroom, 4.5 bath condominium in Harbour Place in the Truman Annex is ready to ...
From $1460 per night (USD)
VRBO
From $500 per night (USD)
Expedia
Villa 5027 on Duck Key Boat Slip Available - 2BD 2.5BA
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Boat slip available for additional $100 a night. Ask for availability. This villa boasts breathtaking sunsets, close to ...
From $500 per night (USD)
Expedia
From $315 per night (USD)
VRBO
Bonefish Bungalow
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Summary: You can’t beat the views in this open-harbor townhouse that overlooks the Key Colony Beach channel out to the ...
From $315 per night (USD)
VRBO
From $272 per night (USD)
Expedia
Beautiful vacation mobile home at the Florida keys.
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
You can enjoy a spacious terrace with built in kitchen/bbq, TV and Bluetooth speakers, in a campground resort with plent ...
From $272 per night (USD)
Expedia
From $392 per night (USD)
VRBO
Long Key florida,Beachfront Paradise, two bedroom ,3.5 bath, on Ocean, with Pool
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Booking for August & September are at a discounted rate of 30%!!! Do not miss out....NEW LISTING. 30-day Minimum Stay. ...
From $392 per night (USD)
VRBO
From $540 per night (USD)
Expedia
Coastal Key 3 bed 2 bath with pool kayaks, bikes, paddlebooards and dock
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Vaca-21-256 Coastal Key is located in the Sombrero Beach area of Marathon. Beautifully decorated, brand-new home, locat ...
From $540 per night (USD)
Expedia
From $164 per night (USD)
VRBO
Rent a place in Paradise.
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
A private, Charming 1 bed 1 bath Condo with a full kitchen, heated pool, and spectacular views of the Sunset right from ...
From $164 per night (USD)
VRBO
From $954 per night (USD)
Expedia
Affordable luxury yacht charters.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This is a private yacht charter. Only your family and friends aboard along with your captains. Please ask about current ...
From $954 per night (USD)
Expedia
From $151 per night (USD)
VRBO
Fish Camp | Old Florida canalfront getaway
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: Old Florida canalfront getaway close to Key West The Space: Escape to this Old Florida-style cottage offer ...
From $151 per night (USD)
VRBO
From $607 per night (USD)
Expedia
Casa Cay West Beautiful Tropical 3 bedrooms 2 KING suites - 2 miles to beach
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
This house is a 3 bedroom stand alone unit with 2 king bedrooms upstairs with balconies and own bathrooms and the bedroo ...
From $607 per night (USD)
Expedia
From $607 per night (USD)
VRBO
Casa Capri Beautiful Tropical with 3 King Suites - 2 miles to beach
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
This house is a 3 bedroom stand alone unit with 2 king bedrooms upstairs with balconies and own bathrooms and the b ...
From $607 per night (USD)
VRBO
From $626 per night (USD)
Expedia
Afternoon Delight at The Truman Annex in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This amazing 2 bedroom/2 bath condo has one of the best views in Key West. Located in the historic Mills Place in Truman ...
From $626 per night (USD)
Expedia
From $209 per night (USD)
VRBO
3BR/3BA Duck Key Island Retreat With Private Pool
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
In the Heart of the Florida Keys, this three bedroom and three bath Duck Key retreat is located within just minutes of t ...
From $209 per night (USD)
VRBO
From $485 per night (USD)
VRBO
3BR/2BA Canalside Sombrero Beach Home with Heated Pool, Jacuzzi, and 60' Dock
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
License # VACA-23-219 - Discover paradise at this Flamingo Island retreat in Marathon, boasting everything you'll need f ...
From $485 per night (USD)
VRBO
From $339 per night (USD)
VRBO
2BR/1BA Serene Cozy Cottage of Shady Palms in Islamorada With Heated Pool
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Enjoy a unique and secluded vacation experience in the heart of Islamorada at Shady Palms! Our charming cottage features ...
From $339 per night (USD)
VRBO
From $2349 per night (USD)
Expedia
**SWEET AMERICANA** 8BR/8BA Compound & 2 Pools + Last Key White Glove Service...
Bedrooms:
9
Bathrooms:
8
Sleeps:
20
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! It doesn't ge ...
From $2349 per night (USD)
Expedia
From $327 per night (USD)
VRBO
Airy Top Floor Blue Heron Suite; Ocean Pointe 3407
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Escape to this charming oceanfront condominium in Tavernier for the perfect Florida Keys getaway. Whether you ...
From $327 per night (USD)
VRBO
From $1123 per night (USD)
Expedia
**GOOD VIBRATIONS @ OLD TOWN** Villa & Pool + Last Key White Glove Service...
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 $1123 per night (USD)
Expedia
From $3099 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 histor ...
From $3099 per night (USD)
VRBO
From $345 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 $345 per night (USD)
Expedia
From $496 per night (USD)
VRBO
Spectacular Ocean Front Home In Beautiful Islamorada!Slip,Com Pool, & Prv Bch
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
VRL# 26-0132 We are one of Islamorada’s limited number of licensed weekly vacation homes. This magnificent home with di ...
From $496 per night (USD)
VRBO
From $537 per night (USD)
Expedia
New Key Largo Escape• 2 Kings • Marina• Pickleball
Bedrooms:
2
Bathrooms:
2
Sleeps:
7
TAKE A VIRTUAL TOUR OF THE ENTIRE UNIT BEFORE BOOKING http:www.youtube.com/@Keylargotravels This property is managed b ...
From $537 per night (USD)
Expedia
From $635 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 $635 per night (USD)
VRBO
From $256 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 $256 per night (USD)
Expedia
From $231 per night (USD)
VRBO
**DRIFTWOOD DREAMS** Beachside Condo & Pool + Last Key White Glove Service...
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! This freshly ...
From $231 per night (USD)
VRBO
From $459 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 $459 per night (USD)
VRBO
From $486 per night (USD)
VRBO
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. Ask for availability. This villa boasts breathtaking sunsets, close to ...
From $486 per night (USD)
VRBO
From $710 per night (USD)
Expedia
403 Mariners Club - Oceanfront 3 bedroom Townhome with stunning views
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 wis ...
From $710 per night (USD)
Expedia
From $946 per night (USD)
VRBO
Poolside Paradise - Heated Pool & Steps to Duval St
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 ...
From $946 per night (USD)
VRBO
From $385 per night (USD)
Expedia
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 ...
From $385 per night (USD)
Expedia
From $515 per night (USD)
VRBO
Lou & Mary`s Getaway ~ 2 bed 2 Bath home W/Dock, Inch Beach & Cabana Club
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- ...
From $515 per night (USD)
VRBO
From $501 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 $501 per night (USD)
VRBO
From $390 per night (USD)
VRBO
Comfy Condo 1bed/1bath nightly condo with pool
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 $390 per night (USD)
VRBO
From $467 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 $467 per night (USD)
Expedia
From $1058 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 $1058 per night (USD)
VRBO
From $469 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 $469 per night (USD)
Expedia
From $333 per night (USD)
VRBO
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 $333 per night (USD)
VRBO
From $427 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 $427 per night (USD)
Expedia
From $1007 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 $1007 per night (USD)
VRBO
From $407 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 $407 per night (USD)
Expedia
From $479 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 $479 per night (USD)
VRBO
From $520 per night (USD)
Expedia
STEPS TO DUVAL, OLD TOWN! 'LA DOLCE VITA' SLEEPS 2-4, 3 BLKS TO STH BCH
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
STEPS TO DUVAL! WALK EVERYWHERE...TO ALL THE SHOPS, RESTAURANTS AND BARS OF OLD TOWN! You don’t need a car with ...
From $520 per night (USD)
Expedia
From $442 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 $442 per night (USD)
VRBO
From $332 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 $332 per night (USD)
VRBO
From $250 per night (USD)
VRBO
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 $250 per night (USD)
VRBO
From $267 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 $267 per night (USD)
Expedia
From $452 per night (USD)
VRBO
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 $452 per night (USD)
VRBO
From $955 per night (USD)
Expedia
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 $955 per night (USD)
Expedia
From $762 per night (USD)
VRBO
Marathon Keys Coral Lagoon Unit 2 Waterfront Villa
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Coral Lagoon #2 Welcome to paradise! We are proud to offer you one of the nicest waterfront units in Coral Lagoon! The ...
From $762 per night (USD)
VRBO
From $1007 per night (USD)
Expedia
W08 - 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 includ ...
From $1007 per night (USD)
Expedia
From $646 per night (USD)
VRBO
Spectacular Sunsets, a Hidden Gem – Marlin Bay
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 $646 per night (USD)
VRBO
From $487 per night (USD)
Expedia
🌸Home #1: “ANCHORS ⚓ AWAY” (Off Water-approximately 300 ft from our private 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 $487 per night (USD)
Expedia
From $260 per night (USD)
VRBO
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 $260 per night (USD)
VRBO
From $338 per night (USD)
Expedia
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 $338 per night (USD)
Expedia
From $218 per night (USD)
VRBO
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 $218 per night (USD)
VRBO
From $903 per night (USD)
Expedia
Coconut Palm - Steps from Duval with Private Pool
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 ...
From $903 per night (USD)
Expedia
From $910 per night (USD)
VRBO
Parking & Shared Pool - Casa Key West
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Summary: - Please note the pool will be closed for renovations 9/8-9/9. - Located on the south end of Duval Street st ...
From $910 per night (USD)
VRBO
From $539 per night (USD)
Expedia
Sea Breeze - One Block from Duval Street
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 o ...
From $539 per night (USD)
Expedia
From $387 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 $387 per night (USD)
VRBO
From $753 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 $753 per night (USD)
Expedia
From $267 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 $267 per night (USD)
VRBO
From $880 per night (USD)
Expedia
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 $880 per night (USD)
Expedia
$🌸Home #7 \BEACHY🏖KEEN\ Full Oceanfront View Property!🌸$
From $858 per night (USD)
VRBO
🌸Home #7 \"BEACHY🏖KEEN\" Full Oceanfront View Property!🌸
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
🌸Home #7 "BEACHY🏖KEEN" Full OCEANFRONT View over the docks and beach and Ocean!🌸 Totally Private😉- Turn-Key and full ...
From $858 per night (USD)
VRBO
From $399 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! The hom ...
From $399 per night (USD)
Expedia
$🌸Home #8 \DEJA⛵BLUE\ Premium WATERFRONT 🌸$
From $893 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 $893 per night (USD)
VRBO
From $843 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 $843 per night (USD)
Expedia
From $575 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 $575 per night (USD)
VRBO
From $379 per night (USD)
Expedia
2 BR End Suite w/ Vast Views+Pool, Beach & Bar
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Discover your perfect Florida Keys sanctuary in this spacious 2 bedroom condo at Ocean Pointe Suites. Surround ...
From $379 per night (USD)
Expedia
From $149 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 $149 per night (USD)
VRBO
From $338 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 $338 per night (USD)
Expedia
From $235 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 $235 per night (USD)
VRBO
From $569 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 $569 per night (USD)
Expedia
From $274 per night (USD)
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 ...
From $274 per night (USD)
VRBO
From $500 per night (USD)
Expedia
ConchKeyLanding https://www.conchkeylandingflkeys.com/
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
https://www.conchkeylandingflkeys.com/ Boat Docking fee to be paid on site! One (1) Vehicle, Trailer and Boat Per Uni ...
From $500 per night (USD)
Expedia
From $302 per night (USD)
VRBO
Beach House- Ocean & Beach View-Upgraded-Over 146 Five Star Reviews
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
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 $302 per night (USD)
VRBO
From $733 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* Awaken each morning to breathtaking sunrises stret ...
From $733 per night (USD)
Expedia
From $202 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 (5th floor). Incredible views o ...
From $202 per night (USD)
VRBO
From $258 per night (USD)
Expedia
Loved By Guests! Oceanfront Condo On The Beach With A Pool!!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Time to get away! This renovated condo with an outstanding high-end, kitchen and updated bathrooms (see pictures) is so ...
From $258 per night (USD)
Expedia
From $345 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 $345 per night (USD)
VRBO
From $334 per night (USD)
Expedia
OCEANVIEW / OCEANFRONT APARTMENT WITH RESORT AMENITIES, 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 $334 per night (USD)
Expedia
From $246 per night (USD)
VRBO
See the Reviews! Oceanfront Condo on the Beach with a swimming pool!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Create a memory that will last a lifetime! Rent this 2 bedroom, 2 bath condo with an outstanding View of the beach, pa ...
From $246 per night (USD)
VRBO
From $457 per night (USD)
Expedia
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 $457 per night (USD)
Expedia
From $586 per night (USD)
VRBO
Sunset Crush- Bayfront property for the perfect sunset, Tavernier
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Welcome to Sunset Crush, a beautifully restored bayfront conch house where some of the most breathtaking sunsets in the ...
From $586 per night (USD)
VRBO
From $322 per night (USD)
Expedia
Rare Bayfront End Unit Moon Bay 2BR w/ Boat Slip, Pool, Beach & Sunset Views
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to Bahia Vista at Moon Bay, a rare bayfront end-unit condo offering panoramic Florida Bay views, resort amenitie ...
From $322 per night (USD)
Expedia
From $270 per night (USD)
VRBO
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 $270 per night (USD)
VRBO
From $247 per night (USD)
Expedia
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 $247 per night (USD)
Expedia
From $314 per night (USD)
VRBO
Another Three Hour Tour at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to your slice of paradise in the Shipyard at Truman Annex. This charming first‑floor 2BR/1BA condo captures the ...
From $314 per night (USD)
VRBO
From $557 per night (USD)
Expedia
**MIDTOWN MOSAIC @ MIDTOWN** Home & Pool + Last Key White Glove Service...
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Spanning an e ...
From $557 per night (USD)
Expedia
From $863 per night (USD)
VRBO
Luxury 4B/3B, Private Canal, Kayaks, 13 ft Hot Tub, 4 H Mini-Golf & Pedal Boat.
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
The whole family will enjoy this luxury tranquil, waterfront getaway in Tavernier with a 13 foot Hydrotherapy Swim Spa a ...
From $863 per night (USD)
VRBO
From $412 per night (USD)
Expedia
Quiet Conch House in Historic District
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
Discover a piece of paradise with a beautiful conch home located in the historic district of Key West. 4-bedrooms, 2 ba ...
From $412 per night (USD)
Expedia
From $222 per night (USD)
VRBO
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 $222 per night (USD)
VRBO
From $211 per night (USD)
Expedia
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 $211 per night (USD)
Expedia
From $363 per night (USD)
VRBO
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 $363 per night (USD)
VRBO
From $282 per night (USD)
Expedia
Oyster's Pearl at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Live steps from everything that makes Key West unforgettable. This first‑floor Shipyard condo blends comfort with island ...
From $282 per night (USD)
Expedia

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