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Florida Keys Rentals

From $483 per night (USD)
VRBO
Caribbean Conch 5 Minutes to Smathers Beach & 10 minute Bike Downtown - Value
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 Atlantic Start Date: May 2025-Estimated Completion: Spring 2026 ...
From $483 per night (USD)
VRBO
From $474 per night (USD)
Expedia
Key Largo Ocean Shore Villa 3 with pool & boat slip
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
This centrally located boater`s paradise is the perfect place to relax. Walk to restaurants, cook in kitchen or grill do ...
From $474 per night (USD)
Expedia
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VRBO
Close enough to Bike Ride to Mallory Square,far away to sleep during FantasyFest
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Coconut Mallory Resort and marina has multiple amenities including two pools, hot tubs, open air restaurant and bar, mar ...
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VRBO
From $494 per night (USD)
Expedia
Free Parking, Pool, & Pet Friendly - The Trinidad
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Welcome to Sunrise Suites, a peaceful community on Key West's southeast side. Just 1 mile from the beach and 10 ...
From $494 per night (USD)
Expedia
From $265 per night (USD)
VRBO
Coral Club Condo - Your Slice of Paradise in the Sombrero Beach Neighborhood
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Coral Club Condo is your tropical haven in the serene Sombrero Beach Neighborhood, just a brief 10-minute walk from the ...
From $265 per night (USD)
VRBO
From $298 per night (USD)
Expedia
P11 - Charming 2 bedroom 2 bath duplex with privat
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This lovely 2 bedroom, 2 bath home is located on the gulfside with immediate Gulf water access and near the Vaca Cut for ...
From $298 per night (USD)
Expedia
From $677 per night (USD)
VRBO
335 Mariners Club Key Largo | 3 Bed, 2.5 Bath
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Infinite horizons...from this third floor, luxury, three-bedroom, two and one-half bath villa! A peaceful, relaxing get ...
From $677 per night (USD)
VRBO
From $577 per night (USD)
Expedia
Beautiful Oceanside Mariner's 3 Bedroom Townhome
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Best vacation rental to explore the Florida keys. Marina Villa 210 (3b/3b) with Marina and ocean views. Escape to pa ...
From $577 per night (USD)
Expedia
From $1065 per night (USD)
VRBO
Waterfront, 100ft Dock, Kayaks, Bikes, Pool, Hot Tub, Basketball & Pickleball
Bedrooms:
5
Bathrooms:
4
Sleeps:
10
WELCOME TO COCO PLUM ON THE BAY - MARATHON, FLORIDA KEYS Welcome to Coco Plum on the Bay, your private waterfront retre ...
From $1065 per night (USD)
VRBO
From $300 per night (USD)
Expedia
RV Camper in the heart of Key Largo
Bedrooms:
1
Bathrooms:
2
Sleeps:
7
A beautiful RV camper right in the middle of paradise. A beautiful ambiance with such friendly neighbors. You wake up an ...
From $300 per night (USD)
Expedia
From $285 per night (USD)
VRBO
Rent a Piece of Paradise, Best Location on the Island!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Rent a piece of paradise right in the heart of beautiful Old Town Key West. Walking distance to all major attraction (r ...
From $285 per night (USD)
VRBO
From $704 per night (USD)
Expedia
W09 - New Luxury Property! Breathtaking 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 $417 per night (USD)
VRBO
**TIDEWATER VIEWS @ VENTURE OUT** 2BR/2BA Cottage + 35’ Private Slip | 80’ Pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! TIDEWATER VIE ...
From $417 per night (USD)
VRBO
From $267 per night (USD)
Expedia
Tropical Getaway in Paradise.
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
3 Nite Minimum Stay! ** 5 day minimum for Lobster Fest, July 22-Aug. 13. ** This bright, freshly decorated, modern 2 bed ...
From $267 per night (USD)
Expedia
From $662 per night (USD)
VRBO
Beautiful 4 Bedroom, 3 Bath, Spacious Pool/SPA Home with 200' wide Canal.
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Welcome to Casa del Cielo. Enjoy breathtaking views of the Gulf and Ocean from this beautiful canal front home. Bring y ...
From $662 per night (USD)
VRBO
From $390 per night (USD)
Expedia
Little Island Pearl
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Have you been dreaming of a get away in the Florida Keys in Key Colony Beach. A little piece of heaven with a brand ne ...
From $390 per night (USD)
Expedia
From $346 per night (USD)
VRBO
B-105 Moon Bay | 3 Bed, 2.5 Bath
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
6-night minimum stay requirement. Lovely bayside townhouse with 2 bedrooms, 1 1/2 baths on the main floor and a studio ...
From $346 per night (USD)
VRBO
From $563 per night (USD)
Expedia
Great Location , Great Vibes, Great Pool
Bedrooms:
6
Bathrooms:
6
Sleeps:
14
Quiet, secluded Keys house with a pool. Ideal for larger groups of friends and family's. Equal distance to Marathon an ...
From $563 per night (USD)
Expedia
From $499 per night (USD)
VRBO
The Palms...A beautiful space in the perfect place.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
The perfect space in the perfect place. A quiet oasis on the 2nd floor nestled amongst palm trees in the shipyard secti ...
From $499 per night (USD)
VRBO
From $384 per night (USD)
Expedia
Beautiful Family-Friendly, Dock, Marina, Heated Pool, near Key West, MM21.5
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
This beautiful home overlooking the Atlantic Ocean is part of the Sunrise Beach Resort, an exclusive gated community bui ...
From $384 per night (USD)
Expedia
From $525 per night (USD)
VRBO
Key Largo Ocean Shore Villa 1 with pool & boat slip
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Located in the heart of the Florida Keys, this one-of-a-kind vacation rental offers the perfect combination of luxury an ...
From $525 per night (USD)
VRBO
From $428 per night (USD)
Expedia
TA Beach, Pool, Marina, family friendly, Kitchen, Jacuzzi
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This listing is for a TROPICAL ISLAND villa, at Cocoplum Beach and Tennis Club and Marina, which is one of the 2 villas ...
From $428 per night (USD)
Expedia
From $325 per night (USD)
VRBO
Waterfront Fun: Pool, Marina, Tiki Bar & Beach!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
THE DAPPER DOLPHIN, an updated coastal-themed 1-bedroom, 1-bathroom condo, is the perfect getaway, accommodating up to 4 ...
From $325 per night (USD)
VRBO
From $520 per night (USD)
Expedia
**DANCE OF THE BUTTERFLIES @ SOUTHERNMOST** New Home & Pool + LAST KEY SERVICES.
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! For a month i ...
From $520 per night (USD)
Expedia
From $485 per night (USD)
VRBO
207 Mariners Club Key Largo | 3 Bed, 3 Bath
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Perfectly located along the picture perfect marina front overlooking the beautifully landscaped gardens of Mariners Club ...
From $485 per night (USD)
VRBO
From $687 per night (USD)
Expedia
611 Mariners Club Key Largo | 4 Bed, 4 Bath
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
This luxury Key Largo vacation townhome rental (Unit 611) is a 4 bedroom/4 bath unit. Ideal accommodations for the Flori ...
From $687 per night (USD)
Expedia
From $1238 per night (USD)
VRBO
**THE TOASTED COCONUT @ OLD TOWN** Fully Restored + Pool + LAST KEY SERVICES…
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Throughout Ke ...
From $1238 per night (USD)
VRBO
From $276 per night (USD)
Expedia
P63 - Beautiful, waterfront Key Colony Duplex. Short walk to the Cabana Beach...
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Beautiful duplex home in Key Colony Beach. Key Colony Beach is a small, friendly, walkable island with easy access to lo ...
From $276 per night (USD)
Expedia
From $507 per night (USD)
VRBO
M12 - Beautiful house in Key Colony offering 4 bed
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
This 4 bedroom, 3 bathroom home in the heart of the Florida Keys is located in the very desirable Key Colony Beach and w ...
From $507 per night (USD)
VRBO
From $267 per night (USD)
Expedia
M18 - Spacious 3 bedroom, 2 bath Gulf side condo!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Spacious 3 bedroom, 2 bathroom, second floor condo, with split floor plan. Large screened wrap around porc ...
From $267 per night (USD)
Expedia
From $221 per night (USD)
VRBO
M123 - Cabana Beach Duplex! Premier location across the street from Cabana...
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This comfy, cozy 2 bedroom, 2 bathroom duplex is ideally located in the heart of the Keys in Key Colony Beach. ...
From $221 per night (USD)
VRBO
From $626 per night (USD)
Expedia
Luxury and Lovely Water Front House
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
If you're looking for a low-key vacation, Big Pine Key is the place for you. In Big Pine Key, about 100 miles south of M ...
From $626 per night (USD)
Expedia
From $241 per night (USD)
VRBO
Florida keys Waterfront,Forever Summer
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
MINIMUM STAY OF 28 DAYS REQUIERED BY THE COUNTY.Booking from the 1st of the month. Waterfront house with heated pool. Lo ...
From $241 per night (USD)
VRBO
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Expedia
Fully Furnished Condo
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Large Living Room with water view. Park you boat at the private Boat Dock. Swim in the heated Pool. Grill you fresh cau ...
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Expedia
From $304 per night (USD)
VRBO
Boaters Delight [Ocean Pointe 5301]
Bedrooms:
2
Bathrooms:
1
Sleeps:
4
With thoughtful and creative touches both inside and out mixed with a keen attention to the smallest of details, this oc ...
From $304 per night (USD)
VRBO
From $504 per night (USD)
Expedia
Pool, Free Parking & Pet Friendly - The Barbados
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Welcome to the quiet Sunrise Suites community located on the southeast side of Key West. Just 1 mile from the b ...
From $504 per night (USD)
Expedia
From $320 per night (USD)
VRBO
Immaculate oceanfront townhouse with ocean view & private beach access
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Duck Key Retreat Villa #5105 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ...
From $320 per night (USD)
VRBO
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Expedia
Modern Key Largo Waterfront Bayside Home - Dock your boat!
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
WWW.MEETMEINKEYLARGO.COM Impeccable Waterfront Home in Key Largo on the bayside. This beautiful stilted home is new co ...
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Expedia
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VRBO
Affordable, Adorable home waiting for you in Cudjoe Key
Bedrooms:
3
Bathrooms:
2
Sleeps:
4
Adorable canal front 2 bed/2 bath home for rent in Cudjoe Key. This indoor/outdoor floor plan is complemented by 3 twelv ...
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VRBO
From $591 per night (USD)
Expedia
Waterfront luxury Villa (42) with sunset views and boat slip
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This spacious 3BD, 2.5BA Villa is the perfect blend of comfort and coastal charm. Each bedroom features its own televisi ...
From $591 per night (USD)
Expedia
From $393 per night (USD)
VRBO
The most setup home in BPK TIKI HUT,POOL ,GRILL ,CANAL FRONT, FREE UNLIMITED ICE
Bedrooms:
2
Bathrooms:
4
Sleeps:
12
This Private Canal front Pool/TIKI home with Dock, sits in Port Pine Heights BIG PINE KEY FL. See key deer every day wa ...
From $393 per night (USD)
VRBO
From $354 per night (USD)
Expedia
Waterfront Sunset View Aqua Villa at Sea Biscuit @ Mangrove Resort LLC
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
The Sea Biscuit houseboat has 1 Queen bed, 1 Queen sofa sleeper and 2 Twin beds in the loft. Each houseboat has flat-scr ...
From $354 per night (USD)
Expedia
From $809 per night (USD)
VRBO
Bright Key West House with Private Pool, Gas Grill, W/D, Central AC, & Free WiFi
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
Tropical Vibes Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $809 per night (USD)
VRBO
From $185 per night (USD)
Expedia
Atlantic Ocean Breezes Tropical Island Key West Sunrises
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 Atlantic Start Date: May 2025-Estimated Completion: Spring 2026 ...
From $185 per night (USD)
Expedia
From $300 per night (USD)
VRBO
Tropical 2BR Condo w/ Pool, Tennis, Near Beach & Downtown
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to our piece of paradise in Key West! Our beautifully maintained, fully tiled 2-bedroom condo is your perfect ho ...
From $300 per night (USD)
VRBO
From $594 per night (USD)
Expedia
409 Mariners Club Luxury Townhouse with Ocean Views
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Instantly feel the warmth of the island spirit as you enter this recently renovated and refreshed 3-bedroom, 3-bath, tri ...
From $594 per night (USD)
Expedia
From $223 per night (USD)
VRBO
Spacious Ocean View Suite with Private Kitchen & Balcony! Pool & Beach Access!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Surround yourself with a picturesque view of the ocean while enjoying your elegantly-curated suite, spacious and home-li ...
From $223 per night (USD)
VRBO
From $219 per night (USD)
Expedia
Condo in the Keys, Peaceful ocean view retreat!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Newly renovated ocean view condo in beautiful Tavernier, FL! Ideally situated in the Upper Keys, between Miami and Key W ...
From $219 per night (USD)
Expedia
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VRBO
Marathon 2BR Deluxe resort on the water w/ Resort Amenities
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Situated just off the historic Florida Keys Overseas Highway, The Hammocks at Marathon™ lets you and your family experie ...
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VRBO
From $2811 per night (USD)
Expedia
Private Parking & Pool, Near Duval - Contra House
Bedrooms:
4
Bathrooms:
4
Sleeps:
12
Summary: This captivating modern home with a striking exterior and vaulted ceilings makes for the perfect vacation home. ...
From $2811 per night (USD)
Expedia
From $582 per night (USD)
VRBO
Island Time Hideaway at Old Town Key West Historic Seaport - 3 Blocks to Duval
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Charming Historic Bungalow with Private Pool & Detached Cottage – Steps from Duval Street! Experience the best of Key W ...
From $582 per night (USD)
VRBO
From $474 per night (USD)
Expedia
Key West Cabana-Old Town Key West- Steps to Duval Street w/ Pool & Tiki Bar
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Experience the Best of Key West at Key West Cabana — Your Charming 2-Bedroom, 2-Bathroom Retreat in Old Town Welcome to ...
From $474 per night (USD)
Expedia
From $407 per night (USD)
VRBO
Fishermen's Paradise- Private Pool, Hot Tub, Quick Access To Ocean, 60 ft Dock
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
NO PETS. NO SMOKING. Vacation in Paradise in our spacious (approx 1,700 sq. ft living space 3 bedroom 2 bath ground l ...
From $407 per night (USD)
VRBO
From $418 per night (USD)
Expedia
Modern Nautical Townhome on Moonbay Key Largo
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Welcome to a piece of paradise! This is a beautiful two-story townhouse that has been newly furnished. Upstairs you will ...
From $418 per night (USD)
Expedia
From $471 per night (USD)
VRBO
🌸Home(#3) BIKINI👙 BOTTOM (Partial View Property-approximately 200 ft from private beach entrance🌸
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
#3: BIKINI BOTTOM 👙Totally Private😉- Turn-Key and fully Stocked- Single Family Home 4BR/3BA with your own Heated-Coole ...
From $471 per night (USD)
VRBO
From $212 per night (USD)
Expedia
Paradise Found – Oceanfront Condo w/ Pool Views & Private Beach in Key Colony!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Competently remodeled from quartz countertops in kitchen and both full bathrooms. New doors throughout the unit with up ...
From $212 per night (USD)
Expedia
From $354 per night (USD)
VRBO
Keep Summer Alive at Gulf side Gem! 45 ft. Dock, pool , hot tub and more
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Ease into Fall! Experience Late Summer Warm Water and Calm Water for Fishing! Great Getaway for couples and a group of f ...
From $354 per night (USD)
VRBO
From $398 per night (USD)
Expedia
DUPLEX IN DUCK KEY, 2 Bedroom /2 Bath w/40' Dock, Trailer Storage Incl.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Unit in Duck Key next to the biggest resort in the Florida Keys! Located near stores, restaurants, delicatessen, bait an ...
From $398 per night (USD)
Expedia
From $674 per night (USD)
VRBO
Waterfront Luxury Villa (62) with sunset views and boat slip
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
This renovated and spacious 3BD, 3.5BA Villa is the perfect blend of comfort and coastal charm. Each bedroom includes it ...
From $674 per night (USD)
VRBO
Click For Pricing
Expedia
Beautiful resort located just off the Florida Keys.
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Situated just off the historic Florida Keys Overseas Highway, The Hammocks at Marathon™ lets you and your family experie ...
Click For Pricing
Expedia
From $885 per night (USD)
VRBO
Beautiful Ocean Front View
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Oceanfront 2BD/2BA and separate 1BD/1BA pool-side overlooking the Atlantic* Enter your paradise dream home with stunni ...
From $885 per night (USD)
VRBO
From $458 per night (USD)
Expedia
Ocean view condo with balcony/marina view
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to the most visited resort in the beautiful Florida Keys. Ocean Pointe is one of the most luxurious resorts in ...
From $458 per night (USD)
Expedia
From $758 per night (USD)
VRBO
Venetian Shores Escape! Heated Pool, 3BR, 70ft Dock, Dog-Friendly!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Vacation Rental License No VR-001 WEEKLY RENTAL Located on the peaceful upper Keys, in Islamorada, this home is situat ...
From $758 per night (USD)
VRBO
From $457 per night (USD)
Expedia
Watch dolphins play in Shelter Cove while swimming in our oversized pool
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Forget Fall and experience warm late summer waters and calm ocean for fishing! Relax in the private pool with your fa ...
From $457 per night (USD)
Expedia
From $373 per night (USD)
VRBO
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 $373 per night (USD)
VRBO
From $581 per night (USD)
Expedia
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 $581 per night (USD)
Expedia
From $258 per night (USD)
VRBO
Canal front Fall 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 $258 per night (USD)
VRBO
Click For Pricing
Expedia
Key Largo Getaway
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Beautiful, 2-bedroom, 1 bathroom property located at the entrance to the Florida Keys. Property features full kitchen, 2 ...
Click For Pricing
Expedia
From $430 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
Totally Private😉- Turn-Key and fully Stocked- Single Family Home 4BR/3BA with your own Heated-Cooled Private Swimming P ...
From $430 per night (USD)
VRBO
From $430 per night (USD)
VRBO
2 Ocean View Units w/ Full Kitchens! Enjoy Outdoor Swimming Pool & Beach Access
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Adore the infinite ocean view from your room in this one-bedroom suite that welcomes you with its family-friendly amenit ...
From $430 per night (USD)
VRBO
From $389 per night (USD)
VRBO
Relax and Unwind! 2 Family-Friendly Suites To Stay w/ Swimming Pool Access
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Escape to a tropical paradise and experience the ultimate beachfront retreat! Nestled in the heart of Key Largo, this pr ...
From $389 per night (USD)
VRBO
From $295 per night (USD)
Expedia
El Tesoro a Beautiful 3 Bedroom 2 Bath Marathon Ho
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
VACA-23-40Welcome to El Tesoro: Your Perfect Florida Keys GetawayStep into paradise at *El Tesoro*a luxurious 3-bedroom, ...
From $295 per night (USD)
Expedia
From $470 per night (USD)
VRBO
Florida Keys Escape! Two Elegant Rooms for 8 Guests, Pool, FREE Breakfast
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Welcome to our family-friendly property! An unforgettable tropical vacation awaits you in the Middle Keys. Our room is p ...
From $470 per night (USD)
VRBO
From $319 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 $319 per night (USD)
Expedia
From $1634 per night (USD)
VRBO
Sublime Sunsets Waterfront Condo 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 $1634 per night (USD)
VRBO
From $416 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. Largest boat that can fit is 33 ft. Ask for availability. This villa b ...
From $416 per night (USD)
Expedia
From $161 per night (USD)
VRBO
Centrally located cottage apartment with patio - walk to beach & dining
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Bottoms Up Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $161 per night (USD)
VRBO
From $349 per night (USD)
Expedia
Waterfront home with 35-foot dock, Cabana Club membership with pool/beach access
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Dream in the Keys Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $349 per night (USD)
Expedia
From $336 per night (USD)
VRBO
Bonefish Bungalow: 3 BR, 3 BA Townhouse in MARATHON, Sleeps 8
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Bonefish Bungalow offers an idyllic vacation experience in the captivating Florida Keys, overlooking the picturesque Key ...
From $336 per night (USD)
VRBO
From $280 per night (USD)
Expedia
Private Tropical Beach • No Stairs • Pool • Fun Activities-Oceanside Restaurants
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Tropical Oceanfront Getaway | 2BR/2BA Condo w/ Private Beach, Pool & More Relax in tropical luxury just steps from your ...
From $280 per night (USD)
Expedia
From $227 per night (USD)
VRBO
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 $227 per night (USD)
VRBO
From $211 per night (USD)
Expedia
Gorgeous Home with Lush Patio & Private Pool - Two Blocks to Higgs Beach
Bedrooms:
3
Bathrooms:
3
Sleeps:
10
Sunshine Drive Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $211 per night (USD)
Expedia
From $395 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 $395 per night (USD)
VRBO
From $258 per night (USD)
Expedia
Winter Special - Beautiful Waterfront Pool Home
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
“A Little Slice of Heaven”- completely renovated and updated in December 2020 waterfront pool home in paradise. This is ...
From $258 per night (USD)
Expedia
From $722 per night (USD)
VRBO
Coastal Key 3 bed 2 bath with pool kayaks, bikes,
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Vaca-21-256Sombrero Beach area of Marathon. Beautifully decorated brand new home, located down the street from Sombrero ...
From $722 per night (USD)
VRBO
From $137 per night (USD)
Expedia
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 $137 per night (USD)
Expedia
From $281 per night (USD)
VRBO
A+ Location in Old Town Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
The house has beautiful vaulted high ceilings. Along with the en-suite there is also another bathroom on the 1st floor a ...
From $281 per night (USD)
VRBO
From $1124 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. License To Chill is back ...
From $1124 per night (USD)
Expedia
From $153 per night (USD)
VRBO
Fish Camp | Old Florida canalfront getaway close to Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Escape to this Old Florida-style cottage offering a quintessential retreat for fishing enthusiasts and nature lovers ali ...
From $153 per night (USD)
VRBO
From $688 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 $688 per night (USD)
Expedia
From $702 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 $702 per night (USD)
VRBO
Click For Pricing
Expedia
Studio in the heart of the Florida Keys, snowbird community
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
400 sq ft fully equipped studio,full bathroom & kitchenette. Chase sofa with sleeper. On wide private canal to the Ocea ...
Click For Pricing
Expedia
From $882 per night (USD)
VRBO
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 $882 per night (USD)
VRBO
From $398 per night (USD)
Expedia
Oceanfront, Snowbird-Friendly Home with High-Speed WiFi, Ocean Views, and Dock
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Humpty Dumpty Hacienda Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $398 per night (USD)
Expedia
From $194 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 $194 per night (USD)
VRBO
From $382 per night (USD)
VRBO
3BR/2BA Canalside Flamingo Island Home With Heated Pool, Jacuzzi, and 60' Boat Slip
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
License # VACA-23-219 - Discover paradise at this Flamingo Island retreat in Marathon boasting everything you'll need fo ...
From $382 per night (USD)
VRBO
From $351 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 $351 per night (USD)
VRBO
From $2357 per night (USD)
Expedia
**SWEET AMERICANA @ OLD TOWN** 8BR/8BA Compound + 2 Pools + LAST KEY SERVICES…
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 $2357 per night (USD)
Expedia
From $318 per night (USD)
VRBO
Dog-friendly home on a wide canal w/ WiFi & amazing water views
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Tarpon Cove Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
From $318 per night (USD)
VRBO
From $317 per night (USD)
Expedia
Airy Top Floor Blue Heron Suite [Ocean Pointe 3407]
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
With thoughtful and creative touches both inside and out mixed with a keen attention to the smallest of details, this oc ...
From $317 per night (USD)
Expedia

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