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  • 4 bed 2.5 bath home w\/ ocean views, private pool oasis on Gulfview
    From $298 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 $298 per night (USD)

    VRBO

    Details
  • Royal Palm in Key West
    From $480 per night (USD)

    Expedia

    Royal Palm in Key West

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    5

    There's no better way to experience island time - that slow shifting of hours that makes Key West such an ideal vacation ...

    From $480 per night (USD)

    Expedia

    Details
  • Mariners Club Townhouse, Unit 603, Epic Amenities, Tennis & Indoor Pickleball
    From $658 per night (USD)

    VRBO

    Mariners Club Townhouse, Unit 603, 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 $658 per night (USD)

    VRBO

    Details
  • Gulf-front pool home in the heart of the Keys! Close to the beach! Guest house!
    From $1779 per night (USD)

    Expedia

    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 $1779 per night (USD)

    Expedia

    Details
  • Cozy Houseboat
    From $431 per night (USD)

    VRBO

    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 $431 per night (USD)

    VRBO

    Details
  • Key West Home on Golf Course w\/ Patio & Grill!
    From $245 per night (USD)

    Expedia

    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 $245 per night (USD)

    Expedia

    Details
  • Key West Escape
    Click For Pricing

    VRBO

    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

    VRBO

    Details
  • Mermaid House - Venture Out Lot 089
    From $413 per night (USD)

    Expedia

    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 $413 per night (USD)

    Expedia

    Details
  • Cudjoe Cottage - Venture Out Lot 268
    From $400 per night (USD)

    VRBO

    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 $400 per night (USD)

    VRBO

    Details
  • Pelicans View - Venture Out Lot 318
    From $319 per night (USD)

    Expedia

    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 $319 per night (USD)

    Expedia

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

    VRBO

    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)

    VRBO

    Details
  •   Extremely Rare Private White Sand Beach Front Unit on the Ocean
    From $580 per night (USD)

    Expedia

    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 $580 per night (USD)

    Expedia

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

    VRBO

    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)

    VRBO

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

    Expedia

    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)

    Expedia

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

    VRBO

    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)

    VRBO

    Details
  • A Gulfview Paradise in Key West - Call for more information!
    From $509 per night (USD)

    Expedia

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

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    8

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

    From $509 per night (USD)

    Expedia

    Details
  • Dog-friendly waterfront retreat with dock, private pool, washer\/dryer, patio
    From $482 per night (USD)

    VRBO

    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 $482 per night (USD)

    VRBO

    Details
  • Oceanside 5\/4 Home with Heated Pool and Big Dock.  Easy access to Ocean and Bay
    From $693 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 $693 per night (USD)

    VRBO

    Details
  • Gorgeous Beach Bungalow Just Steps from Private Sandy Beach!
    From $245 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 $245 per night (USD)

    VRBO

    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

    Expedia

    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

    Expedia

    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

    Expedia

    Details
  • Private Parking & Pool - The Delaney House
    From $2126 per night (USD)

    VRBO

    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 $2126 per night (USD)

    VRBO

    Details
  • Nauti Hideaway Ocean Pointe 2314
    From $273 per night (USD)

    Expedia

    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 $273 per night (USD)

    Expedia

    Details
  • Aqua Vista Ocean Pointe 3307
    From $278 per night (USD)

    VRBO

    Aqua Vista Ocean Pointe 3307

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    5

    Summary: Privately Owned - Oceanfront escape with pool, hot tub, marina & beach Enjoy this recently renovated suite with ...

    From $278 per night (USD)

    VRBO

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

    Expedia

    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)

    Expedia

    Details
  • Blue Heaven in Cudjoe Key #99
    From $530 per night (USD)

    VRBO

    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 $530 per night (USD)

    VRBO

    Details
  • Fun in the Sun in Cudjoe Key! #51
    From $522 per night (USD)

    Expedia

    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 $522 per night (USD)

    Expedia

    Details
  • Tiki Time in Cudjoe Key 136
    From $638 per night (USD)

    VRBO

    Tiki Time in Cudjoe Key 136

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

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

    From $638 per night (USD)

    VRBO

    Details
  • Paradise Palms in Cudjoe Key #635
    From $396 per night (USD)

    Expedia

    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 $396 per night (USD)

    Expedia

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

    VRBO

    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)

    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
  • Private Beach Bayside 6 Bedroom Resort Home with Pool, Dock, & Garage
    From $1724 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 $1724 per night (USD)

    VRBO

    Details
  • New Large Luxury Rental - Sombrero Palms
    From $1307 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 $1307 per night (USD)

    Expedia

    Details
  • Sunkissed Bungalow-B205
    From $187 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 $187 per night (USD)

    VRBO

    Details
  • Welcome to Kokomo Cottage-A311
    From $208 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 $208 per night (USD)

    Expedia

    Details
  • Sandy Toes Retreat-A310
    From $222 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 $222 per night (USD)

    VRBO

    Details
  • Florida Keys Condo with Pool, Beach Access, Marina, Pickleball & More
    From $277 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 $277 per night (USD)

    Expedia

    Details
  • Take it Keysie, Waterfront House
    From $397 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 $397 per night (USD)

    VRBO

    Details
  • Coral House in Key Colony 3 Bed, 2 Bath, Pet Friendly, Dockage & Cabana Club!
    From $807 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 $807 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 3bedroom Retreat with WiFi & AC in Stunning Key Largo Paradise Pet-friendly
    From $689 per night (USD)

    VRBO

    Cozy 3bedroom Retreat with WiFi & AC in Stunning Key Largo Paradise Pet-friendly

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    10

    Escape to paradise in this charming 3-bedroom Key Largo retreat, perfectly located to give you easy access to the vibran ...

    From $689 per night (USD)

    VRBO

    Details
  • Tropical cottage with private pool, two blocks from Duval - near Hemingway House
    From $227 per night (USD)

    VRBO

    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 $227 per night (USD)

    VRBO

    Details
  • Island Comfort at Cudjoe Key
    From $294 per night (USD)

    Expedia

    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 $294 per night (USD)

    Expedia

    Details
  • Beachside Bliss~ Luxury Private Beachfront Home w Pool
    From $695 per night (USD)

    VRBO

    Beachside Bliss~ Luxury Private Beachfront Home w Pool

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    10

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

    From $695 per night (USD)

    VRBO

    Details
  • When Paradise is Key: Tropical Oceanfront Condo
    From $421 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 $421 per night (USD)

    Expedia

    Details
  • Boomerang Boathouse in Key West
    From $438 per night (USD)

    VRBO

    Boomerang Boathouse in Key West

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Richley individual yet classic Key West are phrases that echo from Boomerang Boathouse, a 4 bedroom, 2.5 bath home with ...

    From $438 per night (USD)

    VRBO

    Details
  • Double Queen with Balcony, Ocean View, Isla Bella, Beach & Pool, Spa Wellness
    From $703 per night (USD)

    VRBO

    Double Queen with Balcony, Ocean View, Isla Bella, Beach & Pool, Spa Wellness

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Welcome to your ultimate oceanfront escape, perfectly located in the heart of the Florida Keys. Here, you are in the pri ...

    From $703 per night (USD)

    VRBO

    Details
  • Oceanfront Veranda King Suite, Beach Access, Isla Bella, Right Off Florida Keys
    From $809 per night (USD)

    VRBO

    Oceanfront Veranda King Suite, Beach Access, Isla Bella, Right Off Florida Keys

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Welcome to your ultimate oceanfront escape, perfectly located in the heart of the Florida Keys. Here, you are in the pri ...

    From $809 per night (USD)

    VRBO

    Details
  • Right in the Middle of Florida Keys | Relaxing Private Beach & Outdoor Pools
    From $528 per night (USD)

    VRBO

    Right in the Middle of Florida Keys | Relaxing Private Beach & Outdoor Pools

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Welcome to your ultimate oceanfront escape, perfectly located in the heart of the Florida Keys. Here, you are in the pri ...

    From $528 per night (USD)

    VRBO

    Details
  • Oceanfront Accommodation | Enjoy Breakfast with a Scenic View on Your Veranda
    From $647 per night (USD)

    VRBO

    Oceanfront Accommodation | Enjoy Breakfast with a Scenic View on Your Veranda

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Welcome to your ultimate oceanfront escape, perfectly located in the heart of the Florida Keys. Here, you are in the pri ...

    From $647 per night (USD)

    VRBO

    Details
  • 2 Units | Double Queen Oceanfront w\/ Balcony, Scenic Cycling, Isla Bella
    From $885 per night (USD)

    VRBO

    2 Units | Double Queen Oceanfront w\/ Balcony, Scenic Cycling, Isla Bella

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Welcome to your ultimate oceanfront escape, perfectly located in the heart of the Florida Keys. Here, you are in the pri ...

    From $885 per night (USD)

    VRBO

    Details
  • Scenic Veranda Double Queen, Isla Bella, Private Beach, Near Seven Miles Bridge
    From $665 per night (USD)

    VRBO

    Scenic Veranda Double Queen, Isla Bella, Private Beach, Near Seven Miles Bridge

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Welcome to your ultimate oceanfront escape, perfectly located in the heart of the Florida Keys. Here, you are in the pri ...

    From $665 per night (USD)

    VRBO

    Details
  • 2 Oceant Front Room w\/ Own Balcony | Short Drive to Seven Mile Bridge
    From $885 per night (USD)

    VRBO

    2 Oceant Front Room w\/ Own Balcony | Short Drive to Seven Mile Bridge

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Welcome to your ultimate oceanfront escape, perfectly located in the heart of the Florida Keys. Here, you are in the pri ...

    From $885 per night (USD)

    VRBO

    Details
  • Relaxing Beachside Resort w\/ 5 Outdoor Pools | Near Famous Seven Mile Bridge
    From $701 per night (USD)

    VRBO

    Relaxing Beachside Resort w\/ 5 Outdoor Pools | Near Famous Seven Mile Bridge

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Welcome to your ultimate oceanfront escape, perfectly located in the heart of the Florida Keys. Here, you are in the pri ...

    From $701 per night (USD)

    VRBO

    Details
  • Gorgeous Beach Front Resort | Short Drive from Iconic Seven Mile Bridge
    From $885 per night (USD)

    VRBO

    Gorgeous Beach Front Resort | Short Drive from Iconic Seven Mile Bridge

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Welcome to your ultimate oceanfront escape, perfectly located in the heart of the Florida Keys. Here, you are in the pri ...

    From $885 per night (USD)

    VRBO

    Details
  • King Balcony Suite, Beachfront Experience, Isla Bella Beach, Florida Keys
    From $884 per night (USD)

    VRBO

    King Balcony Suite, Beachfront Experience, Isla Bella Beach, Florida Keys

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Welcome to your ultimate oceanfront escape, perfectly located in the heart of the Florida Keys. Here, you are in the pri ...

    From $884 per night (USD)

    VRBO

    Details
  • New Mariners Club Listing, Preferred Partner, Great Location, Epic Amenities
    From $400 per night (USD)

    Expedia

    New Mariners Club Listing, Preferred Partner, Great Location, Epic Amenities

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

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

    From $400 per night (USD)

    Expedia

    Details
  • Casa Margarita Islamorada, Paradise awaits!!
    From $332 per night (USD)

    VRBO

    Casa Margarita Islamorada, Paradise awaits!!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Experience Islamorada like a local in this 3-bedroom 3-bath pool home. This beautiful recently remodeled 3 bed 3 bath po ...

    From $332 per night (USD)

    VRBO

    Details
  • Atlantis House's Banyan Suite-voted top 25 in USA
    From $653 per night (USD)

    Expedia

    Atlantis House's Banyan Suite-voted top 25 in USA

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    The Banyan Suite is a stunning vacation rental property located in the heart of Key West. This luxurious suite is situat ...

    From $653 per night (USD)

    Expedia

    Details
  • Atlantis House's Palm Suite-voted top 25 in USA
    From $617 per night (USD)

    VRBO

    Atlantis House's Palm Suite-voted top 25 in USA

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    The Palm Suite is a stunning vacation rental property located in the heart of Key West. This luxurious suite is situated ...

    From $617 per night (USD)

    VRBO

    Details
  • Key West King Escape, Fairfield Inn, Outdoor Swimming Pool | Near Mallory Square
    From $255 per night (USD)

    VRBO

    Key West King Escape, Fairfield Inn, Outdoor Swimming Pool | Near Mallory Square

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Explore Key West with us! Enjoy proximity to Historic Old Town, known for its rich history, vibrant culture, and stunnin ...

    From $255 per night (USD)

    VRBO

    Details
  • Key West Stay Ideal For Couple Close to Mallory Square | Outdoor Swimming Pool
    From $255 per night (USD)

    VRBO

    Key West Stay Ideal For Couple Close to Mallory Square | Outdoor Swimming Pool

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Explore Key West with us! Enjoy proximity to Historic Old Town, known for its rich history, vibrant culture, and stunnin ...

    From $255 per night (USD)

    VRBO

    Details
  • Family 2BR w\/ Ocean Views, Pool & Beach Access
    From $324 per night (USD)

    Expedia

    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 $324 per night (USD)

    Expedia

    Details
  • 2BR Condo w\/ Partial Ocean Views, Pool & Beach
    From $316 per night (USD)

    VRBO

    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 $316 per night (USD)

    VRBO

    Details
  • 2BR Condo w\/ Ocean Views, Pool & Private Beach
    From $322 per night (USD)

    Expedia

    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 $322 per night (USD)

    Expedia

    Details
  • 1BR w\/ Partial Ocean View, Pool & Beach
    From $306 per night (USD)

    VRBO

    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 $306 per night (USD)

    VRBO

    Details
  • Key Largo 2BR - Ocean View, Pool & Near Bird Sanctuary
    From $395 per night (USD)

    Expedia

    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 $395 per night (USD)

    Expedia

    Details
  • Key Largo 2BR w\/ Partial Ocean Views & Pool
    From $316 per night (USD)

    VRBO

    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 $316 per night (USD)

    VRBO

    Details
  • Escape to the Keys, Ocean View 2BR - Pool, Beach
    From $385 per night (USD)

    Expedia

    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 $385 per night (USD)

    Expedia

    Details
  • Ocean View 2 Bedroom Condo – Pool, Beach, & More
    From $395 per night (USD)

    VRBO

    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 $395 per night (USD)

    VRBO

    Details
  • 2BR Condo w\/ Ocean View, Pool & Tropical Setting
    From $372 per night (USD)

    Expedia

    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 $372 per night (USD)

    Expedia

    Details
  • Key Largo 2 BR Condo - Ocean Views, Pool, Beach
    From $451 per night (USD)

    VRBO

    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 $451 per night (USD)

    VRBO

    Details
  • Family-Friendly 2BR w\/ Views, Pool, & Beach
    From $316 per night (USD)

    Expedia

    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 $316 per night (USD)

    Expedia

    Details
  • Couples 2BR w\/ Ocean View, Pool & Tropical Setting
    From $372 per night (USD)

    VRBO

    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 $372 per night (USD)

    VRBO

    Details
  • Family 2BR w\/ Ocean View, Pool & Tropical Landscaping
    From $395 per night (USD)

    Expedia

    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 $395 per night (USD)

    Expedia

    Details
  • Key Largo Getaway 2BR - Ocean View, Pool
    From $388 per night (USD)

    VRBO

    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 $388 per night (USD)

    VRBO

    Details
  • Ocean View 2BR - Pool, Beach – Relax. Unwind.
    From $388 per night (USD)

    Expedia

    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 $388 per night (USD)

    Expedia

    Details
  • 2BR w\/ Ocean Views, Pool, Beach, Near Pennekamp Park
    From $351 per night (USD)

    VRBO

    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 $351 per night (USD)

    VRBO

    Details
  • Couples' Getaway 2BR w\/ Ocean View, Pool & Beach
    From $372 per night (USD)

    Expedia

    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 $372 per night (USD)

    Expedia

    Details
  • 2BR Ocean View Condo, Pool, Near Marine Park
    From $455 per night (USD)

    VRBO

    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 $455 per night (USD)

    VRBO

    Details
  • 2BR Condo w\/ Ocean Views, Tropical Landscaping, Pool
    From $351 per night (USD)

    Expedia

    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 $351 per night (USD)

    Expedia

    Details
  • Couples' Retreat 2BR w\/ Ocean Views, Pool & Beach
    From $438 per night (USD)

    VRBO

    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 $438 per night (USD)

    VRBO

    Details
  • Ocean View 2BR - Pool & Near Bird Sanctuary
    From $395 per night (USD)

    Expedia

    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 $395 per night (USD)

    Expedia

    Details
  • Family 2BR w\/ Ocean View, Pool & Near Marine Park
    From $351 per night (USD)

    VRBO

    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 $351 per night (USD)

    VRBO

    Details
  • 2BR Condo w\/ Ocean Views, Private Beach & Pool
    From $395 per night (USD)

    Expedia

    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 $395 per night (USD)

    Expedia

    Details
  • Ocean View 2BR - Pool, Beach & Sanctuary
    From $376 per night (USD)

    VRBO

    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 $376 per night (USD)

    VRBO

    Details
  • 2BR w\/ Ocean View, Pool, Beach, Near Coral Reef Park
    From $395 per night (USD)

    Expedia

    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 $395 per night (USD)

    Expedia

    Details
  • Family-Friendly 2BR w\/ Ocean View, Pool, Beach
    From $388 per night (USD)

    VRBO

    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 $388 per night (USD)

    VRBO

    Details
  • Family-Friendly 2BR w\/ Ocean Views, Pool & Beach
    From $371 per night (USD)

    Expedia

    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 $371 per night (USD)

    Expedia

    Details
  • Ocean View 2BR - Pool, Beach & Tropical Landscaping
    From $391 per night (USD)

    VRBO

    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 $391 per night (USD)

    VRBO

    Details
  • Cozy 2BR Condo w\/ Ocean Views, Pool & Beach
    From $324 per night (USD)

    Expedia

    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 $324 per night (USD)

    Expedia

    Details
  • Relaxing 2BR w\/ Ocean View, Pool & Private Beach
    From $360 per night (USD)

    VRBO

    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 $360 per night (USD)

    VRBO

    Details
  • 2BR - Ocean View, Pool & Near Founders Park
    From $391 per night (USD)

    Expedia

    2BR - Ocean View, Pool & Near Founders 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 $391 per night (USD)

    Expedia

    Details
  • Friends' Getaway 2BR w\/ Ocean View, Pool & Beach
    From $395 per night (USD)

    VRBO

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

    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 $395 per night (USD)

    VRBO

    Details
  • Key Largo 2BR Condo - Ocean View, Pool, and Beach
    From $384 per night (USD)

    Expedia

    Key Largo 2BR Condo - Ocean View, Pool, and 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 $384 per night (USD)

    Expedia

    Details
  • Secluded and Private Monthly Tropical Modern Oasis with a Large Pool
    From $1061 per night (USD)

    VRBO

    Secluded and Private Monthly Tropical Modern Oasis with a Large Pool

    Bedrooms:
    4
    Bathrooms:
    3
    Sleeps:
    8

    Experience Key West like a local in this 4-bedroom house with a large saltwater pool. Step into your own private tropic ...

    From $1061 per night (USD)

    VRBO

    Details
  • 4-bedroom house in Islamorada, The Sportfishing Capital of the World
    From $694 per night (USD)

    Expedia

    4-bedroom house in Islamorada, The Sportfishing Capital of the World

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    12

    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
  • The Perfect Catch: Family Fun and Boater's Bliss in the Keys!
    From $488 per night (USD)

    VRBO

    The Perfect Catch: Family Fun and Boater's Bliss in the Keys!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

    THE PERFECT CATCH! Escape to paradise in our private stunning Summerland Key Home! This beautifully remodeled residence ...

    From $488 per night (USD)

    VRBO

    Details
  • Hideaway in Key Largo 2BR Condo - Ocean View, Pool
    From $401 per night (USD)

    Expedia

    Hideaway in Key Largo 2BR Condo - Ocean View, 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 $401 per night (USD)

    Expedia

    Details