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  • Ocean View Room Barnacle bed and breakfast
    From $536 per night (USD)

    VRBO

    Ocean View Room Barnacle bed and breakfast

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Summary: Welcome to Barnacle Bed and Breakfast, your seaside sanctuary where luxury, comfort and adventure combine seaml ...

    From $536 per night (USD)

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    Details
  • Ocean Depth Room Barnacle bed and breakfast Suite
    From $478 per night (USD)

    Expedia

    Ocean Depth Room Barnacle bed and breakfast Suite

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Summary: Welcome to Barnacle Bed and Breakfast, your oceanfront sanctuary where comfort, luxury, and adventure blend per ...

    From $478 per night (USD)

    Expedia

    Details
  • Star Room Barnacle Bed And Breakfast, Big Pine Key
    From $349 per night (USD)

    VRBO

    Star Room Barnacle Bed And Breakfast, Big Pine Key

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Summary: Welcome to Barnacle, your beachfront haven where comfort, luxury, and adventure merge effortlessly. Enjoy plush ...

    From $349 per night (USD)

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    Details
  • Gulf front home with 3 bedrooms, pool, hot tub and Dock seconds to open water.
    From $587 per night (USD)

    VRBO

    Gulf front home with 3 bedrooms, pool, hot tub and Dock seconds to open water.

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    This three-bedroom, two-bath home has a 45-foot dock with ample room for your boat. It is only one house away from the m ...

    From $587 per night (USD)

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    Details
  • Amazing Yacht With Resort Amenities In The Heart Of Key Largo
    From $416 per night (USD)

    VRBO

    Amazing Yacht With Resort Amenities In The Heart Of Key Largo

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Live the real Keys lifestyle with a beautiful 50 foot yacht while having all the benefits of a resort. All hotel ameniti ...

    From $416 per night (USD)

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    Details
  • MANGROVE HIDEAWAY,  KEY LARGO\nCome Enjoy our Piece of Paradise .\n
    From $193 per night (USD)

    Expedia

    MANGROVE HIDEAWAY, KEY LARGO\nCome Enjoy our Piece of Paradise .\n

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Welcome to our Piece of Paradise. This home Features tranquility inside and out with a cozy coastal vibe that you will l ...

    From $193 per night (USD)

    Expedia

    Details
  • Waterfront Resort House + Private boat dock!
    From $1907 per night (USD)

    VRBO

    Waterfront Resort House + Private boat dock!

    Bedrooms:
    5
    Bathrooms:
    4
    Sleeps:
    12

    Hosted by a Hilton Hotel General Manager, behold, the most incredible home in all of Key Largo. A private dock attached ...

    From $1907 per night (USD)

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  • Lofted 1 bedroom suite right off Duval St
    From $498 per night (USD)

    VRBO

    Lofted 1 bedroom suite right off Duval St

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Welcome to sweet paradise! Located on Petronia Street, the Orange Blossom Suite is in close proximity to all the fun-fil ...

    From $498 per night (USD)

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    Details
  • Seabreeze Escape WF RV Lot 489
    From $210 per night (USD)

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    Seabreeze Escape WF RV Lot 489

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    6

    Seabreeze Escape WF RV Lot 489 Open Water Views! 35' Dockage with Tropical Landscaping!! Fish and swim right from your ...

    From $210 per night (USD)

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    Details
  • Relax at The Reef - Pool\/Boat slip\/Kayaks\/Bikes
    From $284 per night (USD)

    Expedia

    Relax at The Reef - Pool\/Boat slip\/Kayaks\/Bikes

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

    Summary: Relax At the Reef in this classic Florida Keys style first floor hotel condo. Relax At The Reef is situated rig ...

    From $284 per night (USD)

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    Details
  • The Finn in the Keys
    From $319 per night (USD)

    VRBO

    The Finn in the Keys

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    The Finn houseboat has 1 Queen bed. This houseboat has 2 SMART flat-screen TVs and complimentary Wi-Fi. The kitchen feat ...

    From $319 per night (USD)

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    Details
  • Secluded Tropical Retreat: 60' Dock,Expansive Pool,World-Class Fishing & Lobster
    From $417 per night (USD)

    Expedia

    Secluded Tropical Retreat: 60' Dock,Expansive Pool,World-Class Fishing & Lobster

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Welcome to Finding Remo—a premier, private, luxury retreat nestled within the Great Heron and Key Deer National Wildlife ...

    From $417 per night (USD)

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    Details
  • COZY HOUSE ON THE WATER, BRING YOUR OWN BOAT.
    From $141 per night (USD)

    VRBO

    COZY HOUSE ON THE WATER, BRING YOUR OWN BOAT.

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    DINING IN FRONT OF THE WATER AND RELAXING FROM STRESSFULL LIFE HAVE TO BE A HABIT. BRING YOUR OWN BOAT UP TO 28 FEET. TH ...

    From $141 per night (USD)

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    Details
  • Mariner's Oasis at Sunset Marina- 2bed 2 bath condo w\/boat slip for rent
    From $353 per night (USD)

    Expedia

    Mariner's Oasis at Sunset Marina- 2bed 2 bath condo w\/boat slip for rent

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    AGE REQUIREMENT: Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their ...

    From $353 per night (USD)

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    Details
  • Tut's Cay: 4  BR, 5.5  BA House in Tavernier, Sleeps 10
    From $784 per night (USD)

    VRBO

    Tut's Cay: 4 BR, 5.5 BA House in Tavernier, Sleeps 10

    Bedrooms:
    6
    Bathrooms:
    4
    Sleeps:
    10

    Welcome to Tut’s Cay, an opulent 4-bedroom, 5.5-bathroom sanctuary nestled in the heart of Islamorada within the captiva ...

    From $784 per night (USD)

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    Details
  • Custom canal-front home with private pool, palapa hut, & outdoor kitchen
    From $1058 per night (USD)

    Expedia

    Custom canal-front home with private pool, palapa hut, & outdoor kitchen

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Keys Free & Easy Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...

    From $1058 per night (USD)

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    Details
  • Gorgeous 53’ Hatteras yacht on Safe Harbor Channel.
    From $570 per night (USD)

    VRBO

    Gorgeous 53’ Hatteras yacht on Safe Harbor Channel.

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    4

    Stay on this gorgeous 53’ Hatteras yacht with cherry wood throughout and a huge salon with everything you need to relax ...

    From $570 per night (USD)

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    Details
  • Truly sitting right on the ocean. Ocean's Edge has forever ocean views.
    From $409 per night (USD)

    Expedia

    Truly sitting right on the ocean. Ocean's Edge has forever ocean views.

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Don’t be fooled by canal front listings. Lose yourself in the ever changing beauty of the Atlantic Ocean in this charmin ...

    From $409 per night (USD)

    Expedia

    Details
  • 4 bed 2.5 bath home w\/ ocean views, private pool oasis on Gulfview
    From $314 per night (USD)

    VRBO

    4 bed 2.5 bath home w\/ ocean views, private pool oasis on Gulfview

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    6

    AGE REQUIREMENT: Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their ...

    From $314 per night (USD)

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    Details
  • Royal Palm in Key West
    From $674 per night (USD)

    Expedia

    Royal Palm in Key West

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    5

    Season 2025 just made available!There's no better way to experience island time - that slow shifting of hours that makes ...

    From $674 per night (USD)

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    Details
  • Mariners Club Townhouse, Epic Amenities, Tennis & Indoor Pickleball
    From $730 per night (USD)

    VRBO

    Mariners Club Townhouse, Epic Amenities, Tennis & Indoor Pickleball

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    10

    The Florida Keys are located off the southern coast of Florida. They are a string of tropical islands stretching about 1 ...

    From $730 per night (USD)

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    Details
  • Gulf-front pool home in the heart of the Keys! Close to the beach! Guest house!
    From $1697 per night (USD)

    VRBO

    Gulf-front pool home in the heart of the Keys! Close to the beach! Guest house!

    Bedrooms:
    5
    Bathrooms:
    5
    Sleeps:
    12

    Escape to the tranquil waterways of Serene Sunset Paradise, where aqua waters meet a pristine shoreline and gentle Gulf ...

    From $1697 per night (USD)

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    Details
  • Caribbean Cabana: Your Perfect 3BR Oceanfront Retreat with Dockage, Pool and Breathtaking Views!
    From $407 per night (USD)

    VRBO

    Caribbean Cabana: Your Perfect 3BR Oceanfront Retreat with Dockage, Pool and Breathtaking Views!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Experience the ultimate in waterfront luxury at Caribbean Cabana, where every moment is a postcard-perfect memory waitin ...

    From $407 per night (USD)

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    Details
  • Cozy Houseboat
    From $439 per night (USD)

    Expedia

    Cozy Houseboat

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Perched on the shimmering waters, this 1 bedroom, 1 bath houseboat epitomizes cozy waterfront living. Step inside and y ...

    From $439 per night (USD)

    Expedia

    Details
  • Key West Home on Golf Course w\/ Patio & Grill!
    From $246 per night (USD)

    VRBO

    Key West Home on Golf Course w\/ Patio & Grill!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    4

    Play a round of golf, snorkel the crystal-clear waters, and explore Key West’s bustling downtown when you stay at this l ...

    From $246 per night (USD)

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  • Key West Escape
    Click For Pricing

    Expedia

    Key West Escape

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    Luxurious accommodations, recreational amenities include an outdoor pool, a spa tub, and bicycles to rent. This hotel a ...

    Click For Pricing

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    Details
  • Mermaid House - Venture Out Lot 089
    From $435 per night (USD)

    VRBO

    Mermaid House - Venture Out Lot 089

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Mermaid House - VO089 Ocean Views 35' Dockage 2Bd/2Ba Midrise Covered Porch This vacation home is located right off the ...

    From $435 per night (USD)

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    Details
  • Cudjoe Cottage - Venture Out Lot 268
    From $402 per night (USD)

    Expedia

    Cudjoe Cottage - Venture Out Lot 268

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Cudjoe Cottage - VO lot 268 This sparkling clean 2 Bedroom 2 full bathroom vacation home is located only 3 lots in from ...

    From $402 per night (USD)

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    Details
  • Pelicans View - Venture Out Lot 318
    From $305 per night (USD)

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    Pelicans View - Venture Out Lot 318

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Pelicans View - VO318 Island Gem-Walk to POOL & Marina! Gorgeous Open Water Views! This beautifully remodeled midrise ...

    From $305 per night (USD)

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    Details
  • Sunset Peninsula—a multi-family, original,  Florida Keys waterfront retreat!
    From $520 per night (USD)

    Expedia

    Sunset Peninsula—a multi-family, original, Florida Keys waterfront retreat!

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    12

    Welcome to the Sunset Peninsula! This gated, multi-family compound is perfect for those traveling in larger groups with ...

    From $520 per night (USD)

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    Details
  •   Extremely Rare Private White Sand Beach Front Unit on the Ocean
    From $557 per night (USD)

    VRBO

    Extremely Rare Private White Sand Beach Front Unit on the Ocean

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    This professionally decorated ocean front unit has everything that you need. 2+2 laundry in unit, upgraded kitchen full ...

    From $557 per night (USD)

    VRBO

    Details
  • PARADISE SHORES
    From $694 per night (USD)

    Expedia

    PARADISE SHORES

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    11

    You won't be disappointed once you arrive at Paradise Shores. This completely remodeled Venetian Shores 4 BD / 3 BA cana ...

    From $694 per night (USD)

    Expedia

    Details
  • Islamorada's Premier Boating Neighborhood; Venetian Shores. A boaters paradise.
    From $432 per night (USD)

    VRBO

    Islamorada's Premier Boating Neighborhood; Venetian Shores. A boaters paradise.

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Nestled within the serene surroundings of Islamorada, Florida, awaits a charming oasis at 116 Stromboli Drive. This sing ...

    From $432 per night (USD)

    VRBO

    Details
  • Islamorada Slice of Paradise with private beach and glorious sunsets!
    From $241 per night (USD)

    Expedia

    Islamorada Slice of Paradise with private beach and glorious sunsets!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Beautifully decorated townhome community located right next door to Founder’s Park in Islamorada. This community offer ...

    From $241 per night (USD)

    Expedia

    Details
  • A Gulfview Paradise in Key West - Call for more information!
    From $686 per night (USD)

    VRBO

    A Gulfview Paradise in Key West - Call for more information!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Welcome to your dream vacation rental in Gulfview Pointe, Key West! This stunning property offers breathtaking waterfron ...

    From $686 per night (USD)

    VRBO

    Details
  • Dog-friendly waterfront retreat with dock, private pool, washer\/dryer, patio
    From $531 per night (USD)

    Expedia

    Dog-friendly waterfront retreat with dock, private pool, washer\/dryer, patio

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Casa Mariner Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...

    From $531 per night (USD)

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    Details
  • Oceanside 5\/4 Home with Heated Pool and Big Dock.  Easy access to Ocean and Bay
    From $617 per night (USD)

    VRBO

    Oceanside 5\/4 Home with Heated Pool and Big Dock. Easy access to Ocean and Bay

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    12

    Welcome to paradise and everything under the sun! This charming 5/4 has been fully updated. Upstairs is a spacious all ...

    From $617 per night (USD)

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    Details
  • Gorgeous Beach Bungalow Just Steps from Private Sandy Beach!
    From $238 per night (USD)

    VRBO

    Gorgeous Beach Bungalow Just Steps from Private Sandy Beach!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    You have found a sandy beach paradise in the Florida Keys! Located just 4 houses from a secret, sandy beach, Little Pea ...

    From $238 per night (USD)

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  • Located on a private beach along the shore, Casa Marina Key West ...
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    VRBO

    Located on a private beach along the shore, Casa Marina Key West ...

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    2

    Located on a private beach along the shore, Casa Marina Key West, Curio Collection by Hilton is a historic 1920s resort ...

    Click For Pricing

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    Details
  • Located on a private beach along the shore, Casa Marina Key West ...
    Click For Pricing

    Expedia

    Located on a private beach along the shore, Casa Marina Key West ...

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    2

    Located on a private beach along the shore, Casa Marina Key West, Curio Collection by Hilton is a historic 1920s resort ...

    Click For Pricing

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    Details
  • Located on a private beach along the shore, Casa Marina Key West ...
    Click For Pricing

    VRBO

    Located on a private beach along the shore, Casa Marina Key West ...

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    2

    Located on a private beach along the shore, Casa Marina Key West, Curio Collection by Hilton is a historic 1920s resort ...

    Click For Pricing

    VRBO

    Details
  • Private Parking & Pool - The Delaney House
    From $2925 per night (USD)

    Expedia

    Private Parking & Pool - The Delaney House

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    Summary: Step into the classic conch cottage known as the Delaney House, situated just half a block from Duval Street. ...

    From $2925 per night (USD)

    Expedia

    Details
  • Relax and Recharge! 2 Premium Units, Pet-friendly, Beach Access, Onsite Pool!
    From $2332 per night (USD)

    VRBO

    Relax and Recharge! 2 Premium Units, Pet-friendly, Beach Access, Onsite Pool!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    We are about getting out there and having fun in the unmatched beauty of bayside Key Largo. Take an early morning swim i ...

    From $2332 per night (USD)

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    Details
  • Key Largo Village - 89 Tarpon
    From $124 per night (USD)

    Expedia

    Key Largo Village - 89 Tarpon

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Located in Key Largo, enjoy what this 2-bedroom has to offer. With 2 nice queen beds, AC, WiFi, a washing machine, and ...

    From $124 per night (USD)

    Expedia

    Details
  • Nauti Hideaway | Ocean Pointe 2314
    From $456 per night (USD)

    VRBO

    Nauti Hideaway | Ocean Pointe 2314

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    5

    Summary: New listing at Ocean Pointe - this bright and modern condo is ready to help you create life long memories. This ...

    From $456 per night (USD)

    VRBO

    Details
  • Aqua Vista Ocean Pointe 3307
    From $504 per night (USD)

    Expedia

    Aqua Vista Ocean Pointe 3307

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    5

    Summary: New Listing at Ocean Pointe - Oceanfront escape with pool, hot tub, marina & beach Enjoy this recently renovate ...

    From $504 per night (USD)

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    Details
  • Southern Exposure in Cudjoe Key #49
    From $464 per night (USD)

    VRBO

    Southern Exposure in Cudjoe Key #49

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    This 2 bedroom, 1 bathroom home has Panoramic Ocean Views, Southern Exposure, direct oceanfront access with a 45-foot co ...

    From $464 per night (USD)

    VRBO

    Details
  • Blue Heaven in Cudjoe Key #99
    From $522 per night (USD)

    Expedia

    Blue Heaven in Cudjoe Key #99

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Spectacular water views from this beautifully maintained 2-bedroom, 2 full bathroom waterfront home located only 4 lots ...

    From $522 per night (USD)

    Expedia

    Details
  • Fun in the Sun in Cudjoe Key! #51
    From $534 per night (USD)

    VRBO

    Fun in the Sun in Cudjoe Key! #51

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Panoramic Ocean Views! 35' Concrete Seawall to Dock your Boat! This beautifully updated and well-maintained stilt home o ...

    From $534 per night (USD)

    VRBO

    Details
  • Tiki Time in Cudjoe Key 136
    From $649 per night (USD)

    Expedia

    Tiki Time in Cudjoe Key 136

    Bedrooms:
    4
    Bathrooms:
    2
    Sleeps:
    4

    Upscale Oceanfront Retreat! This waterfront gem offers amazing views of the Atlantic Ocean and is the perfect getaway fo ...

    From $649 per night (USD)

    Expedia

    Details
  • Paradise Palms in Cudjoe Key #635
    From $405 per night (USD)

    VRBO

    Paradise Palms in Cudjoe Key #635

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    This tropical 2-bedroom, 2 full bathroom home has something for everyone! The kitchen boats new stainless-steel applianc ...

    From $405 per night (USD)

    VRBO

    Details
  • Key Largo Waterfront Paradise w\/Kayaks, Private Dock & BBQ
    From $236 per night (USD)

    Expedia

    Key Largo Waterfront Paradise w\/Kayaks, Private Dock & BBQ

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Imagine yourself "Paradise Living" at this Tiki Stay! Enjoy the beautiful Florida Keys in the relaxing community of Mana ...

    From $236 per night (USD)

    Expedia

    Details
  • Private Beach Bayside 6 Bedroom Resort Home with Pool, Dock, & Garage
    From $2075 per night (USD)

    VRBO

    Private Beach Bayside 6 Bedroom Resort Home with Pool, Dock, & Garage

    Bedrooms:
    8
    Bathrooms:
    6
    Sleeps:
    12

    Owner managed property. We would love to welcome you to our oceanfront retreat, please note we take great care of our pr ...

    From $2075 per night (USD)

    VRBO

    Details
  • 4-bedroom airport community house in Tavernier
    From $405 per night (USD)

    Expedia

    4-bedroom airport community house in Tavernier

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

    *MORE PHOTOS TO COME AFTER RENOVATIONS* Experience Tavernier like a local in this 4-bedroom house. Step into a wonderful ...

    From $405 per night (USD)

    Expedia

    Details
  • Charming 3-bedroom house in Islamorada with Marina access.
    From $279 per night (USD)

    VRBO

    Charming 3-bedroom house in Islamorada with Marina access.

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    This Islamorada house boasts 3 inviting bedrooms. Bedrooms are furnished with 1 king bed and 2 full beds, ensuring a com ...

    From $279 per night (USD)

    VRBO

    Details
  • New Large Luxury Rental - Sombrero Palms
    From $1569 per night (USD)

    Expedia

    New Large Luxury Rental - Sombrero Palms

    Bedrooms:
    4
    Bathrooms:
    6
    Sleeps:
    14

    Sombrero Palms, a captivating retreat just a stone's throw away from the shores of Sombrero Beach. This charming rental ...

    From $1569 per night (USD)

    Expedia

    Details
  • Sunkissed Bungalow-B205
    From $208 per night (USD)

    VRBO

    Sunkissed Bungalow-B205

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    A perfect beach getaway in Key West! See the Sunset and stroll the sidewalks at this fabulous location away from the cr ...

    From $208 per night (USD)

    VRBO

    Details
  • Welcome to Kokomo Cottage-A311
    From $212 per night (USD)

    Expedia

    Welcome to Kokomo Cottage-A311

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    This beautifully renovated 3 bedroom, 2 bathroom beach getaway is waiting for your perfect escape. See the Sunset and s ...

    From $212 per night (USD)

    Expedia

    Details
  • Sandy Toes Retreat-A310
    From $207 per night (USD)

    VRBO

    Sandy Toes Retreat-A310

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    This beautifully renovated 3 bedroom, 2 bathroom beach getaway is waiting for your perfect escape. See the Sunset and s ...

    From $207 per night (USD)

    VRBO

    Details
  • Florida Keys Condo with Pool, Beach Access, Marina, Pickleball & More
    From $415 per night (USD)

    Expedia

    Florida Keys Condo with Pool, Beach Access, Marina, Pickleball & More

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Welcome to Tarpon Cove at Ocean Pointe Resort! Experience a high-quality resort that combines the comforts of a first-cl ...

    From $415 per night (USD)

    Expedia

    Details
  • Take it Keysie, Waterfront House
    From $409 per night (USD)

    VRBO

    Take it Keysie, Waterfront House

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Welcome to “Take it Keysie” your tropical/waterfront retreat in Marathon, Florida! Located in the heart of the Florida ...

    From $409 per night (USD)

    VRBO

    Details
  • Coral House in Key Colony 3 Bed, 2 Bath, Pet Friendly, Dockage & Cabana Club!
    From $780 per night (USD)

    VRBO

    Coral House in Key Colony 3 Bed, 2 Bath, Pet Friendly, Dockage & Cabana Club!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    10

    Please Note *this home is on a Saturday-to-Saturday reservation schedule* The legendary Coral House available to rent f ...

    From $780 per night (USD)

    VRBO

    Details
  • Green Turtle Cottage KW 1 Block from Mile Marker 0 in Gated Truman Annex
    From $592 per night (USD)

    VRBO

    Green Turtle Cottage KW 1 Block from Mile Marker 0 in Gated Truman Annex

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    6

    This 2 bedroom 2.5 bath private home in a secluded section of the gated community of Truman Annex quietly sits among pre ...

    From $592 per night (USD)

    VRBO

    Details
  • Charming 3-bedroom house with Amazing Gulf Views!
    From $442 per night (USD)

    VRBO

    Charming 3-bedroom house with Amazing Gulf Views!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Have a truly blissful vacation at this charming, Gulf Front home that sits on one acre of pristine property on exclusive ...

    From $442 per night (USD)

    VRBO

    Details
  • Cozy 3-bedroom house with WiFi, AC in gorgeous Key Largo
    From $712 per night (USD)

    VRBO

    Cozy 3-bedroom house with WiFi, AC in gorgeous Key Largo

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    2

    This 3-bedroom house is perfect for your escape to Key Largo. With its brilliant location, you'll be just moments away f ...

    From $712 per night (USD)

    VRBO

    Details
  • Tropical cottage with private pool, two blocks from Duval - near Hemingway House
    From $311 per night (USD)

    Expedia

    Tropical cottage with private pool, two blocks from Duval - near Hemingway House

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    5

    The Conch-Out Cottage Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter y ...

    From $311 per night (USD)

    Expedia

    Details
  • Island Comfort at Cudjoe Key
    From $244 per night (USD)

    VRBO

    Island Comfort at Cudjoe Key

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Your Keys Getaway! Escape to paradise with this charming 3-bd, 2-ba canal-front home, perfect for those looking to unwin ...

    From $244 per night (USD)

    VRBO

    Details
  • NEW CONSTRUCTION-4-Bedroom- 3.5 Bathroom - Cudjoe Key- Canal Front W\/ Pool
    From $501 per night (USD)

    Expedia

    NEW CONSTRUCTION-4-Bedroom- 3.5 Bathroom - Cudjoe Key- Canal Front W\/ Pool

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    Unwind at the Artist House on Tarpon Lane on Cudjoe Key! This perfect new construction waterfront home checks all the ...

    From $501 per night (USD)

    Expedia

    Details
  • Beachside Bliss ~ Private Beach and Pool Home!
    From $952 per night (USD)

    VRBO

    Beachside Bliss ~ Private Beach and Pool Home!

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    10

    Beachside Bliss Step into your coastal sanctuary! Immerse yourself in the Southeast Exposure, letting the sun's rays em ...

    From $952 per night (USD)

    VRBO

    Details
  • When Paradise is Key: Tropical Oceanfront Condo
    From $563 per night (USD)

    Expedia

    When Paradise is Key: Tropical Oceanfront Condo

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    ☀️ Discover the ultimate beachfront getaway in our newly renovated two-bedroom, two-bathroom condo, perfectly designed t ...

    From $563 per night (USD)

    Expedia

    Details
  • Family 2BR w\/ Ocean Views, Pool & Beach Access
    From $400 per night (USD)

    VRBO

    Family 2BR w\/ Ocean Views, Pool & Beach Access

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    4

    Oceanfront resort with private sandy beach, marina, Jr. Olympic pool, hot tub, tennis, and more Located near Key Largo a ...

    From $400 per night (USD)

    VRBO

    Details
  • 2BR Condo w\/ Partial Ocean Views, Pool & Beach
    From $397 per night (USD)

    Expedia

    2BR Condo w\/ Partial Ocean Views, Pool & Beach

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Oceanfront resort with private sandy beach, marina, Jr. Olympic pool, hot tub, tennis, and more Located near Key Largo a ...

    From $397 per night (USD)

    Expedia

    Details
  • 2BR Condo w\/ Ocean Views, Pool & Private Beach
    From $406 per night (USD)

    VRBO

    2BR Condo w\/ Ocean Views, Pool & Private Beach

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Oceanfront resort with private sandy beach, marina, Jr. Olympic pool, hot tub, tennis, and more Located near Key Largo a ...

    From $406 per night (USD)

    VRBO

    Details
  • 1BR w\/ Partial Ocean View, Pool & Beach
    From $274 per night (USD)

    Expedia

    1BR w\/ Partial Ocean View, Pool & Beach

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Oceanfront resort with private sandy beach, marina, Jr. Olympic pool, hot tub, tennis, and more Located near Key Largo a ...

    From $274 per night (USD)

    Expedia

    Details
  • Key Largo 2BR - Ocean View, Pool & Near Bird Sanctuary
    From $391 per night (USD)

    VRBO

    Key Largo 2BR - Ocean View, Pool & Near Bird Sanctuary

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    4

    Oceanfront resort with private sandy beach, marina, Jr. Olympic pool, hot tub, tennis, and more Located near Key Largo a ...

    From $391 per night (USD)

    VRBO

    Details
  • Key Largo 2BR w\/ Partial Ocean Views & Pool
    From $397 per night (USD)

    Expedia

    Key Largo 2BR w\/ Partial Ocean Views & Pool

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    4

    Oceanfront resort with private sandy beach, marina, Jr. Olympic pool, hot tub, tennis, and more Located near Key Largo a ...

    From $397 per night (USD)

    Expedia

    Details
  • Escape to the Keys, Ocean View 2BR - Pool, Beach
    From $440 per night (USD)

    VRBO

    Escape to the Keys, Ocean View 2BR - Pool, Beach

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Oceanfront resort with private sandy beach, marina, Jr. Olympic pool, hot tub, tennis, and more Located near Key Largo a ...

    From $440 per night (USD)

    VRBO

    Details
  • Ocean View 2 Bedroom Condo – Pool, Beach, & More
    From $441 per night (USD)

    Expedia

    Ocean View 2 Bedroom Condo – Pool, Beach, & More

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    4

    Oceanfront resort with private sandy beach, marina, Jr. Olympic pool, hot tub, tennis, and more Located near Key Largo a ...

    From $441 per night (USD)

    Expedia

    Details
  • 2BR Condo w\/ Ocean View, Pool & Tropical Setting
    From $435 per night (USD)

    VRBO

    2BR Condo w\/ Ocean View, Pool & Tropical Setting

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Oceanfront resort with private sandy beach, marina, Jr. Olympic pool, hot tub, tennis, and more Located near Key Largo a ...

    From $435 per night (USD)

    VRBO

    Details
  • Key Largo 2 BR Condo - Ocean Views, Pool, Beach
    From $416 per night (USD)

    Expedia

    Key Largo 2 BR Condo - Ocean Views, Pool, Beach

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Oceanfront resort with private sandy beach, marina, Jr. Olympic pool, hot tub, tennis, and more Located near Key Largo a ...

    From $416 per night (USD)

    Expedia

    Details
  • Family-Friendly 2BR w\/ Views, Pool, & Beach
    From $397 per night (USD)

    VRBO

    Family-Friendly 2BR w\/ Views, Pool, & Beach

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Oceanfront resort with private sandy beach, marina, Jr. Olympic pool, hot tub, tennis, and more Located near Key Largo a ...

    From $397 per night (USD)

    VRBO

    Details
  • Couples 2BR w\/ Ocean View, Pool & Tropical Setting
    From $416 per night (USD)

    Expedia

    Couples 2BR w\/ Ocean View, Pool & Tropical Setting

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Oceanfront resort with private sandy beach, marina, Jr. Olympic pool, hot tub, tennis, and more Located near Key Largo a ...

    From $416 per night (USD)

    Expedia

    Details
  • Family 2BR w\/ Ocean View, Pool & Tropical Landscaping
    From $416 per night (USD)

    VRBO

    Family 2BR w\/ Ocean View, Pool & Tropical Landscaping

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Oceanfront resort with private sandy beach, marina, Jr. Olympic pool, hot tub, tennis, and more Located near Key Largo a ...

    From $416 per night (USD)

    VRBO

    Details
  • Key Largo Getaway 2BR - Ocean View, Pool
    From $422 per night (USD)

    Expedia

    Key Largo Getaway 2BR - Ocean View, Pool

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    4

    Oceanfront resort with private sandy beach, marina, Jr. Olympic pool, hot tub, tennis, and more Located near Key Largo a ...

    From $422 per night (USD)

    Expedia

    Details
  • Ocean View 2BR - Pool, Beach – Relax. Unwind.
    From $416 per night (USD)

    VRBO

    Ocean View 2BR - Pool, Beach – Relax. Unwind.

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Oceanfront resort with private sandy beach, marina, Jr. Olympic pool, hot tub, tennis, and more Located near Key Largo a ...

    From $416 per night (USD)

    VRBO

    Details
  • 2BR w\/ Ocean Views, Pool, Beach, Near Pennekamp Park
    From $376 per night (USD)

    Expedia

    2BR w\/ Ocean Views, Pool, Beach, Near Pennekamp Park

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Oceanfront resort with private sandy beach, marina, Jr. Olympic pool, hot tub, tennis, and more Located near Key Largo a ...

    From $376 per night (USD)

    Expedia

    Details
  • Couples' Getaway 2BR w\/ Ocean View, Pool & Beach
    From $394 per night (USD)

    VRBO

    Couples' Getaway 2BR w\/ Ocean View, Pool & Beach

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Oceanfront resort with private sandy beach, marina, Jr. Olympic pool, hot tub, tennis, and more Located near Key Largo a ...

    From $394 per night (USD)

    VRBO

    Details
  • 2BR Ocean View Condo, Pool, Near Marine Park
    From $419 per night (USD)

    Expedia

    2BR Ocean View Condo, Pool, Near Marine Park

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Oceanfront resort with private sandy beach, marina, Jr. Olympic pool, hot tub, tennis, and more Located near Key Largo a ...

    From $419 per night (USD)

    Expedia

    Details
  • 2BR Condo w\/ Ocean Views, Tropical Landscaping, Pool
    From $391 per night (USD)

    VRBO

    2BR Condo w\/ Ocean Views, Tropical Landscaping, Pool

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    4

    Oceanfront resort with private sandy beach, marina, Jr. Olympic pool, hot tub, tennis, and more Located near Key Largo a ...

    From $391 per night (USD)

    VRBO

    Details
  • Couples' Retreat 2BR w\/ Ocean Views, Pool & Beach
    From $392 per night (USD)

    Expedia

    Couples' Retreat 2BR w\/ Ocean Views, Pool & Beach

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Oceanfront resort with private sandy beach, marina, Jr. Olympic pool, hot tub, tennis, and more Located near Key Largo a ...

    From $392 per night (USD)

    Expedia

    Details
  • Ocean View 2BR - Pool & Near Bird Sanctuary
    From $416 per night (USD)

    VRBO

    Ocean View 2BR - Pool & Near Bird Sanctuary

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Oceanfront resort with private sandy beach, marina, Jr. Olympic pool, hot tub, tennis, and more Located near Key Largo a ...

    From $416 per night (USD)

    VRBO

    Details
  • Family 2BR w\/ Ocean View, Pool & Near Marine Park
    From $259 per night (USD)

    Expedia

    Family 2BR w\/ Ocean View, Pool & Near Marine Park

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    4

    Oceanfront resort with private sandy beach, marina, Jr. Olympic pool, hot tub, tennis, and more Located near Key Largo a ...

    From $259 per night (USD)

    Expedia

    Details
  • 2BR Condo w\/ Ocean Views, Private Beach & Pool
    From $416 per night (USD)

    VRBO

    2BR Condo w\/ Ocean Views, Private Beach & Pool

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Oceanfront resort with private sandy beach, marina, Jr. Olympic pool, hot tub, tennis, and more Located near Key Largo a ...

    From $416 per night (USD)

    VRBO

    Details
  • Ocean View 2BR - Pool, Beach & Sanctuary
    From $406 per night (USD)

    Expedia

    Ocean View 2BR - Pool, Beach & Sanctuary

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Oceanfront resort with private sandy beach, marina, Jr. Olympic pool, hot tub, tennis, and more Located near Key Largo a ...

    From $406 per night (USD)

    Expedia

    Details
  • 2BR w\/ Ocean View, Pool, Beach, Near Coral Reef Park
    From $429 per night (USD)

    VRBO

    2BR w\/ Ocean View, Pool, Beach, Near Coral Reef Park

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Oceanfront resort with private sandy beach, marina, Jr. Olympic pool, hot tub, tennis, and more Located near Key Largo a ...

    From $429 per night (USD)

    VRBO

    Details
  • Family-Friendly 2BR w\/ Ocean View, Pool, Beach
    From $420 per night (USD)

    Expedia

    Family-Friendly 2BR w\/ Ocean View, Pool, Beach

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Oceanfront resort with private sandy beach, marina, Jr. Olympic pool, hot tub, tennis, and more Located near Key Largo a ...

    From $420 per night (USD)

    Expedia

    Details
  • Family-Friendly 2BR w\/ Ocean Views, Pool & Beach
    From $416 per night (USD)

    VRBO

    Family-Friendly 2BR w\/ Ocean Views, Pool & Beach

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Oceanfront resort with private sandy beach, marina, Jr. Olympic pool, hot tub, tennis, and more Located near Key Largo a ...

    From $416 per night (USD)

    VRBO

    Details
  • Ocean View 2BR - Pool, Beach & Tropical Landscaping
    From $418 per night (USD)

    Expedia

    Ocean View 2BR - Pool, Beach & Tropical Landscaping

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Oceanfront resort with private sandy beach, marina, Jr. Olympic pool, hot tub, tennis, and more Located near Key Largo a ...

    From $418 per night (USD)

    Expedia

    Details
  • Cozy 2BR Condo w\/ Ocean Views, Pool & Beach
    From $349 per night (USD)

    VRBO

    Cozy 2BR Condo w\/ Ocean Views, Pool & Beach

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Oceanfront resort with private sandy beach, marina, Jr. Olympic pool, hot tub, tennis, and more Located near Key Largo a ...

    From $349 per night (USD)

    VRBO

    Details
  • Relaxing 2BR w\/ Ocean View, Pool & Private Beach
    From $424 per night (USD)

    Expedia

    Relaxing 2BR w\/ Ocean View, Pool & Private Beach

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Oceanfront resort with private sandy beach, marina, Jr. Olympic pool, hot tub, tennis, and more Located near Key Largo a ...

    From $424 per night (USD)

    Expedia

    Details