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Florida Keys Rentals

From $526 per night (USD)
VRBO
Quiet canal-front 3/3 Single-Family Home with Private Pool & Cabana Club Access
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Welcome to Blue Heron House. Enjoy and relax in our ground-level 3 bedroom / 3 bathroom private, single-family home whi ...
From $526 per night (USD)
VRBO
From $262 per night (USD)
Expedia
Easy Ocean Access House 30' Dock & Pool at Cabana Club
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to our Beach House in the prestigious Key Colony Beach. 30 FT dock house in a 90 FT canal with easy access to th ...
From $262 per night (USD)
Expedia
From $671 per night (USD)
VRBO
Amazing Views in Florida Keys Bayside BAY BREEZES, SUNSETS, SAILBOATS n SEAGULLS
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Make memories lasting a lifetime at Anchors Aweigh - experience Bay Breezes, Sunsets, Sailboats n Seagulls with this per ...
From $671 per night (USD)
VRBO
From $269 per night (USD)
Expedia
Tropical oasis near all the action with central AC & balcony
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Harbor Villa 7103 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $269 per night (USD)
Expedia
From $580 per night (USD)
VRBO
Parking, Pool, Near Duval St - Poolside Suite
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Summary: Poolside Suite is the PERFECT vacation home for family and friends looking for a fun-filled getaway in the hear ...
From $580 per night (USD)
VRBO
From $362 per night (USD)
Expedia
Cozy Home!!!!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Newly renovated half duplex on a quiet street in Marathon. Conveniently located in the heart of Marathon, on a canal jus ...
From $362 per night (USD)
Expedia
From $433 per night (USD)
VRBO
AWAY FROM IT ALL @ The Truman Annex
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 $433 per night (USD)
VRBO
From $539 per night (USD)
Expedia
Coral Lagoon #13: Pool, Water Views, off Vaca Cut with Gulf & Atlantic Access
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Coral Lagoon #13: Pool, Water Views, Located just off Vaca Cut with easy Gulf & Atlantic Access. ****Please note that t ...
From $539 per night (USD)
Expedia
From $619 per night (USD)
VRBO
Galleon Resort beach hotel luxury in Old Town Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
5
This is a large (1245 SF) 1BR/1BA condo on the 6th floor of the Galleon Resort & Marina.....and is a one of a kind. It ...
From $619 per night (USD)
VRBO
From $354 per night (USD)
Expedia
Waterfront Sunset View Aqua Villa at Conch Shell @ Mangrove Resort LLC
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
The Conch Shell 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 $429 per night (USD)
VRBO
Villa Valbuena Azul Escape Key Largo 2 Kings, Pickleball
Bedrooms:
3
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 $429 per night (USD)
VRBO
From $580 per night (USD)
Expedia
P18 - Spectacular 4 bedroom home with dockage and
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
This lovely 4 bedroom, 4 bath home is located in the highly desirable area of Key Colony Beach. - Maximum ...
From $580 per night (USD)
Expedia
From $2070 per night (USD)
VRBO
NEW PRICING: DRIVE TO YOUR GETAWAY - BIG Pool, Steps to Beach & Free Parking
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
Seaside Place welcomes guests from all states and follows all cleanliness and safety guidelines. Your safety and comfor ...
From $2070 per night (USD)
VRBO
From $478 per night (USD)
Expedia
Gorgeous 3/2 plus loft Islamorada next to Marina, Pool, Dock & Beach
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
Townhome with all extras. Keys style with beautiful new furnishings, newly remodeled with three bedrooms plus oversized ...
From $478 per night (USD)
Expedia
From $169 per night (USD)
VRBO
Enjoy this relaxing beachy house on a canal flowing into sexton cove bay.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Enjoy this cozy home with a beautiful water front terrace. Conveniently located close to grocery stores, great restaura ...
From $169 per night (USD)
VRBO
From $485 per night (USD)
Expedia
P82 - Sombrero Beach - 4 bedroom pool home with do
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Sombrero Beach Sea-clusion awaits our guests! Get ready to create great vacation memories! This spacious 4- ...
From $485 per night (USD)
Expedia
From $701 per night (USD)
VRBO
3bed vacation ocean side townhome 2pools,marina,lagoon,golf cart,bikes,kayaks
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Family and Friends vacation in mind - beautiful Key Largo townhouse with 2 separate living rooms which that offers a un ...
From $701 per night (USD)
VRBO
From $833 per night (USD)
Expedia
**THE ZESTY LIME @ OLD TOWN** Beautifully Restored Home + 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! Key West is k ...
From $833 per night (USD)
Expedia
From $419 per night (USD)
VRBO
Sunsets on the bay at Villa Mia
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Come and enjoy sunsets on the bay at Villa Mia! We created a peaceful retreat for our family and friends to enjoy. It is ...
From $419 per night (USD)
VRBO
From $515 per night (USD)
Expedia
Pet Friendly, Pool, Free Parking - The Grand Turk
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 $515 per night (USD)
Expedia
From $414 per night (USD)
VRBO
The Salty Sailfish: Live the Keys Life, Stunning Canal Front Home, Pool, Dock & Dog-Friendly Bliss!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
County zoning requires a minimum rental period of 28 nights, and no exceptions can be made. Please review additional pol ...
From $414 per night (USD)
VRBO
From $348 per night (USD)
Expedia
Reel Paradise 1 in Marathon
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This two bedroom two bath half duplex is recently remodeled and updated with brand new everything! The kitchen & living ...
From $348 per night (USD)
Expedia
From $625 per night (USD)
VRBO
P87 - New Construction house. 4 bedrooms, open wat
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Stunning views with premier Sombrero Beach location sets this home apart from all others! This ocean front home is spect ...
From $625 per night (USD)
VRBO
From $111 per night (USD)
Expedia
Beautiful, sunlit home with pool, tennis court & beach access - near the marina
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Executive Bay Club Condo M-1 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ...
From $111 per night (USD)
Expedia
From $1270 per night (USD)
VRBO
5 bedrooms, pool/spa heated, bikes, kayaks, game room, elevator, deep 75' dock.
Bedrooms:
7
Bathrooms:
5
Sleeps:
12
Mediterranean-Style Paradise Retreat in Key Colony Beach Escape to luxury at this stunning Mediterranean-style waterfron ...
From $1270 per night (USD)
VRBO
From $354 per night (USD)
Expedia
Waterfront Community in Key Largo, Florida - Moon Bay Condo A210 Sunsets
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to Moon Bay, a piece of paradise! It is located on Blackwater Sound in Key Largo, Florida. Unit A210 is an end ...
From $354 per night (USD)
Expedia
From $561 per night (USD)
VRBO
Duval Street Suites full kitchen Old Town with heated pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: The Key Lime Suite is a one bedroom (king) 1 bath suite with a sleeper sofa (queen) and full kitchen complete w ...
From $561 per night (USD)
VRBO
From $569 per night (USD)
Expedia
Oceanside Kawama Villa R5
Bedrooms:
3
Bathrooms:
3
Sleeps:
10
Come experience ultimate relaxation and comfort in this stunning three-story vacation home. On the first floor, you will ...
From $569 per night (USD)
Expedia
From $3199 per night (USD)
VRBO
BEAUTIFUL SANCTUARY PRIVATE ISLAND CONNECTED BY BRIDGE TO KEY WEST
Bedrooms:
8
Bathrooms:
9
Sleeps:
20
A Castle on an Island On A Privately Owned Key West Island Private Bridge for Cars and Trucks connected to Key West Fr ...
From $3199 per night (USD)
VRBO
From $233 per night (USD)
Expedia
Relax in Paradise! Enjoy a tropical lifestyle.
Bedrooms:
1
Bathrooms:
1
Sleeps:
1
Impeccable 42' Luxury RV: One bedroom, loft with 3 beds,1 Bath stylish kitchen and living areas. Welcoming and spacious ...
From $233 per night (USD)
Expedia
From $852 per night (USD)
VRBO
Luxurious waterfront home with panoramic views, pool, spa, & dock
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Plein Air Point Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $852 per night (USD)
VRBO
From $172 per night (USD)
Expedia
Keys Life Cottage ~ Downtown Islamorada Cottage with Pool Access!
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Welcome to the Keys Life Cottage! This coastal inspired two-bedroom, one-bath home is tucked away on a large landscaped ...
From $172 per night (USD)
Expedia
From $666 per night (USD)
VRBO
Ocean Hideaway a Key West Nature retreat close to Smathers & 15 to Duval
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 Atlantic Start Date: May 2025-Estimated Completion: Spring 2026 ...
From $666 per night (USD)
VRBO
From $483 per night (USD)
Expedia
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)
Expedia
From $474 per night (USD)
VRBO
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)
VRBO
Click For Pricing
Expedia
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 ...
Click For Pricing
Expedia
From $494 per night (USD)
VRBO
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)
VRBO
From $265 per night (USD)
Expedia
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)
Expedia
From $298 per night (USD)
VRBO
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)
VRBO
From $677 per night (USD)
Expedia
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)
Expedia
From $577 per night (USD)
VRBO
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)
VRBO
From $1065 per night (USD)
Expedia
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)
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 $276 per night (USD)
VRBO
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)
VRBO
From $507 per night (USD)
Expedia
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)
Expedia
From $267 per night (USD)
VRBO
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)
VRBO
From $221 per night (USD)
Expedia
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)
Expedia
From $626 per night (USD)
VRBO
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)
VRBO
From $241 per night (USD)
Expedia
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)
Expedia
Click For Pricing
VRBO
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 ...
Click For Pricing
VRBO
From $304 per night (USD)
Expedia
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)
Expedia
From $504 per night (USD)
VRBO
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)
VRBO
From $320 per night (USD)
Expedia
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)
Expedia
Click For Pricing
VRBO
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 ...
Click For Pricing
VRBO
Click For Pricing
Expedia
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 ...
Click For Pricing
Expedia
From $591 per night (USD)
VRBO
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)
VRBO
From $393 per night (USD)
Expedia
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)
Expedia
From $354 per night (USD)
VRBO
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)
VRBO
From $809 per night (USD)
Expedia
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)
Expedia
From $185 per night (USD)
VRBO
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)
VRBO
From $300 per night (USD)
Expedia
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)
Expedia
From $594 per night (USD)
VRBO
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)
VRBO
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)
VRBO
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)
VRBO
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Expedia
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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Expedia
From $2811 per night (USD)
VRBO
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)
VRBO
From $582 per night (USD)
Expedia
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)
Expedia
From $474 per night (USD)
VRBO
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)
VRBO
From $407 per night (USD)
Expedia
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)
Expedia
From $418 per night (USD)
VRBO
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)
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
Click For Pricing
VRBO
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 ...
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VRBO
From $885 per night (USD)
Expedia
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)
Expedia
From $458 per night (USD)
VRBO
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)
VRBO
From $758 per night (USD)
Expedia
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)
Expedia
From $457 per night (USD)
VRBO
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)
VRBO
From $373 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 $373 per night (USD)
Expedia
From $581 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 $581 per night (USD)
VRBO
From $258 per night (USD)
Expedia
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)
Expedia
Click For Pricing
VRBO
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 ...
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VRBO
From $430 per night (USD)
Expedia
🌸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)
Expedia
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

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