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Results: 538 Rentals

  • Resort View Three Bedroom Residence
    From $969 per night (USD)

    VRBO

    Resort View Three Bedroom Residence

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Summary: Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residenc ...

    From $969 per night (USD)

    VRBO

    Details
  • Resort View Three Bedroom Residence
    From $969 per night (USD)

    Expedia

    Resort View Three Bedroom Residence

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Summary: Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residenc ...

    From $969 per night (USD)

    Expedia

    Details
  • Ocean Front Presidential Suite | Beachside Resort
    From $1057 per night (USD)

    VRBO

    Ocean Front Presidential Suite | Beachside Resort

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Summary: Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residenc ...

    From $1057 per night (USD)

    VRBO

    Details
  • Ocean Front Presidential Suite | Beachside Resort
    From $1057 per night (USD)

    Expedia

    Ocean Front Presidential Suite | Beachside Resort

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Summary: Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residenc ...

    From $1057 per night (USD)

    Expedia

    Details
  • Ocean Front Presidential Suite | Beachside Resort
    From $1057 per night (USD)

    VRBO

    Ocean Front Presidential Suite | Beachside Resort

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Summary: Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residenc ...

    From $1057 per night (USD)

    VRBO

    Details
  • Resort View Three Bedroom Residence
    From $969 per night (USD)

    Expedia

    Resort View Three Bedroom Residence

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Summary: Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residenc ...

    From $969 per night (USD)

    Expedia

    Details
  • Ocean Front Presidential Suite | Beachside Resort
    From $1057 per night (USD)

    VRBO

    Ocean Front Presidential Suite | Beachside Resort

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Summary: Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residenc ...

    From $1057 per night (USD)

    VRBO

    Details
  • Resort View Three Bedroom Residence
    From $969 per night (USD)

    Expedia

    Resort View Three Bedroom Residence

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Summary: Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residenc ...

    From $969 per night (USD)

    Expedia

    Details
  • Resort View Three Bedroom Residence
    From $969 per night (USD)

    VRBO

    Resort View Three Bedroom Residence

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Summary: Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residenc ...

    From $969 per night (USD)

    VRBO

    Details
  • Ocean Front Presidential Suite | Beachside Resort
    From $1057 per night (USD)

    Expedia

    Ocean Front Presidential Suite | Beachside Resort

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Summary: Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residenc ...

    From $1057 per night (USD)

    Expedia

    Details
  • Two Bedroom Residence
    From $651 per night (USD)

    VRBO

    Two Bedroom Residence

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Summary: Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residenc ...

    From $651 per night (USD)

    VRBO

    Details
  • Two Bedroom Residence
    From $651 per night (USD)

    Expedia

    Two Bedroom Residence

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Summary: Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residenc ...

    From $651 per night (USD)

    Expedia

    Details
  • Two Bedroom Residence
    From $651 per night (USD)

    VRBO

    Two Bedroom Residence

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Summary: Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residenc ...

    From $651 per night (USD)

    VRBO

    Details
  • Two Bedroom Residence
    From $651 per night (USD)

    Expedia

    Two Bedroom Residence

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Summary: Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residenc ...

    From $651 per night (USD)

    Expedia

    Details
  • Two Bedroom Residence
    From $651 per night (USD)

    VRBO

    Two Bedroom Residence

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Summary: Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residenc ...

    From $651 per night (USD)

    VRBO

    Details
  • Two Bedroom Residence
    From $651 per night (USD)

    Expedia

    Two Bedroom Residence

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Summary: Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residenc ...

    From $651 per night (USD)

    Expedia

    Details
  • Two Bedroom Residence
    From $651 per night (USD)

    VRBO

    Two Bedroom Residence

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Summary: Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residenc ...

    From $651 per night (USD)

    VRBO

    Details
  • Two Bedroom Residence
    From $651 per night (USD)

    Expedia

    Two Bedroom Residence

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Summary: Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residenc ...

    From $651 per night (USD)

    Expedia

    Details
  • Resort View Three Bedroom Residence
    From $969 per night (USD)

    VRBO

    Resort View Three Bedroom Residence

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Summary: Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residenc ...

    From $969 per night (USD)

    VRBO

    Details
  • Ocean Front Presidential Suite | Beachside Resort
    From $1057 per night (USD)

    Expedia

    Ocean Front Presidential Suite | Beachside Resort

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Summary: Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residenc ...

    From $1057 per night (USD)

    Expedia

    Details
  • Ocean Front Presidential Suite | Beachside Resort
    From $1057 per night (USD)

    VRBO

    Ocean Front Presidential Suite | Beachside Resort

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Summary: Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residenc ...

    From $1057 per night (USD)

    VRBO

    Details
  • Sunrise 307-2BR\/2BA condo near beaches with pool, parking, balcony
    From $431 per night (USD)

    Expedia

    Sunrise 307-2BR\/2BA condo near beaches with pool, parking, balcony

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

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

    From $431 per night (USD)

    Expedia

    Details
  • Reduced Rate! 46’ Yacht in Beautiful Resort!
    From $810 per night (USD)

    VRBO

    Reduced Rate! 46’ Yacht in Beautiful Resort!

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    9

    New Listing on VRBO! You and your guests will have exclusive use of this 46 ft yacht all to yourselves. The yacht stays ...

    From $810 per night (USD)

    VRBO

    Details
  • Triple Crown Villa- Boaters Paradise with Pool
    From $716 per night (USD)

    Expedia

    Triple Crown Villa- Boaters Paradise with Pool

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    If you're looking for a luxurious and unforgettable waterfront vacation experience, look no further than this stunning v ...

    From $716 per night (USD)

    Expedia

    Details
  • Spacious Luxury Super Yacht
    From $2831 per night (USD)

    VRBO

    Spacious Luxury Super Yacht

    Bedrooms:
    5
    Bathrooms:
    4
    Sleeps:
    8

    Take your vacation to the next level by staying dockside on this115 foot private, luxury yacht. Hot Tub, hammocks, & BBQ ...

    From $2831 per night (USD)

    VRBO

    Details
  • Heron House  | Luxury Waterfront Home
    From $570 per night (USD)

    Expedia

    Heron House | Luxury Waterfront Home

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    9

    Summary: Beautifully renovated canal home located just outside Key West in an exclusive Key Haven neighborhood. This 28- ...

    From $570 per night (USD)

    Expedia

    Details
  • NEW! Haven House | Waterfront Home, Amazing Views!
    From $629 per night (USD)

    VRBO

    NEW! Haven House | Waterfront Home, Amazing Views!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Summary: The Haven House is truly heavenly on the quiet residential canals in Key Haven. This home boasts a modern water ...

    From $629 per night (USD)

    VRBO

    Details
  • Awai's Floating Villa - Luxury Houseboat
    From $769 per night (USD)

    Expedia

    Awai's Floating Villa - Luxury Houseboat

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Summary: Experience Key West in a new way: aboard a luxury houseboat! From watching sunrise on the dock to watching suns ...

    From $769 per night (USD)

    Expedia

    Details
  • Memories of a Lifetime! A one of a Kind Sailboat!\n
    From $462 per night (USD)

    VRBO

    Memories of a Lifetime! A one of a Kind Sailboat!\n

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Based in the incredible Perry Marina and Resort, your vacation aboard this stunning historical sailboat will be a treasu ...

    From $462 per night (USD)

    VRBO

    Details
  • Amazing 4 Bdrm, 4 Bath Catamaran - Purpus\n
    From $1090 per night (USD)

    Expedia

    Amazing 4 Bdrm, 4 Bath Catamaran - Purpus\n

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    Enjoy all the comforts of home including 4 luxurious staterooms with queen sized beds each with its own private bathroom ...

    From $1090 per night (USD)

    Expedia

    Details
  • Last Mango Beach Retreat
    From $271 per night (USD)

    VRBO

    Last Mango Beach Retreat

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Experience the allure of La Brisa Penthouse! Step into this captivating two-bedroom, two-bathroom condo nestled within t ...

    From $271 per night (USD)

    VRBO

    Details
  • Key Haven 3bedroom 2bath canal front home w\/boat dock, private pool, parking
    From $355 per night (USD)

    Expedia

    Key Haven 3bedroom 2bath canal front home w\/boat dock, private pool, parking

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

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

    From $355 per night (USD)

    Expedia

    Details
  • Escape to \Oasis on 18th\ w\/ PRIVATE HEATED Pool in the KW Golf Club Sanctuary
    From $571 per night (USD)

    VRBO

    Escape to \"Oasis on 18th\" w\/ PRIVATE HEATED Pool in the KW Golf Club Sanctuary

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Escape to your own private paradise at "Oasis on 18th," a luxurious three-bedroom, three-bathroom haven nestled within t ...

    From $571 per night (USD)

    VRBO

    Details
  • Escape to the Keys! Modern Pet-friendly Unit! EV Charger and Parking! Pool
    From $691 per night (USD)

    VRBO

    Escape to the Keys! Modern Pet-friendly Unit! EV Charger and Parking! Pool

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...

    From $691 per night (USD)

    VRBO

    Details
  • Tropical Dream! Pool, Restaurant, Bar, Gym, Bike Rental, Parking!
    From $524 per night (USD)

    VRBO

    Tropical Dream! Pool, Restaurant, Bar, Gym, Bike Rental, Parking!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...

    From $524 per night (USD)

    VRBO

    Details
  • VRBO Elite 72' Luxury Motor Yacht
    From $2854 per night (USD)

    Expedia

    VRBO Elite 72' Luxury Motor Yacht

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    New VRBO listing! Be one of the first guests aboard this beautiful, one of kind yacht. You and your guests will have exc ...

    From $2854 per night (USD)

    Expedia

    Details
  • Beautiful Coral Hammock Key West Condo
    From $465 per night (USD)

    VRBO

    Beautiful Coral Hammock Key West Condo

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    7

    Two Bedroom and 2 and Half Bath beautiful condo in great private Coral Hammock community, close to Golf Course and short ...

    From $465 per night (USD)

    VRBO

    Details
  • Seaside Serenity-2BD 2BA condo w\/ pool, parking, tennis courts, near beaches
    From $250 per night (USD)

    Expedia

    Seaside Serenity-2BD 2BA condo w\/ pool, parking, tennis courts, near beaches

    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 $250 per night (USD)

    Expedia

    Details
  • Dog-friendly duplex with a furnished patio & fast WiFi - near beaches
    From $315 per night (USD)

    VRBO

    Dog-friendly duplex with a furnished patio & fast WiFi - near beaches

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Tropical Treat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...

    From $315 per night (USD)

    VRBO

    Details
  • Hyatt Windward Point, Beach!
    From $1238 per night (USD)

    VRBO

    Hyatt Windward Point, Beach!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Set along the Atlantic Ocean, Hyatt Windward Pointe Resort blends the laid-back Key West style with a modern, upscale re ...

    From $1238 per night (USD)

    VRBO

    Details
  • Hyatt Windward Pointe 2BR in Key West 6\/22\/2024 to 6\/29\/2024 for 7 nights
    Click For Pricing

    VRBO

    Hyatt Windward Pointe 2BR in Key West 6\/22\/2024 to 6\/29\/2024 for 7 nights

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    This listing is for 7 nights from Saturday 6/22/2024 to Saturday 6/29/2024 only (Dates cannot be changed.). Hyatt Wind ...

    Click For Pricing

    VRBO

    Details
  • Oceans Edge Key West Resort, Hotel & Marina!
    From $945 per night (USD)

    VRBO

    Oceans Edge Key West Resort, Hotel & Marina!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    This stylish place to stay is perfect for group trips. This smoke-free hotel features a marina, 6 outdoor pools, and a r ...

    From $945 per night (USD)

    VRBO

    Details
  • Windward Point Beachfront Resort, Hot Tub, Pool
    From $1591 per night (USD)

    VRBO

    Windward Point Beachfront Resort, Hot Tub, Pool

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Set along the Atlantic Ocean, Hyatt Windward Pointe Resort blends the laid-back Key West style with a modern, upscale re ...

    From $1591 per night (USD)

    VRBO

    Details
  • Windward Point Beachfront Resort, Hot Tub, Pool
    From $1573 per night (USD)

    VRBO

    Windward Point Beachfront Resort, Hot Tub, Pool

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Enjoy the glamour of this stylish, upscale place. Set along the Atlantic Ocean, Hyatt Windward Pointe Resort blends the ...

    From $1573 per night (USD)

    VRBO

    Details
  • Mallory Resort, Beach, Hot Tub, Pool, BBQ, Marina
    From $1629 per night (USD)

    VRBO

    Mallory Resort, Beach, Hot Tub, Pool, BBQ, Marina

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Let your spirit rejuvenate and your soul relax in lush tropical surroundings at the Coconut Mallory Marina & Resort! Loc ...

    From $1629 per night (USD)

    VRBO

    Details
  • Oceans Edge Key West Resort, Hotel & Marina!
    From $1474 per night (USD)

    VRBO

    Oceans Edge Key West Resort, Hotel & Marina!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Stay in an upscale place that's near everything you want to visit. Located in Key West, Oceans Edge Key West Resort, Hot ...

    From $1474 per night (USD)

    VRBO

    Details
  • Hyatt Beach House Residences! Keys, Hot Tub, Pool
    From $1520 per night (USD)

    VRBO

    Hyatt Beach House Residences! Keys, Hot Tub, Pool

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Welcome to your own private sanctuary among the lush landscape of Key West - envision old-fashioned screen-enclosed porc ...

    From $1520 per night (USD)

    VRBO

    Details
  • Windward Point Beachfront Resort, Hot Tub, Pool
    From $1584 per night (USD)

    VRBO

    Windward Point Beachfront Resort, Hot Tub, Pool

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Enjoy the glamour of this stylish, upscale place. Set along the Atlantic Ocean, Hyatt Windward Pointe Resort blends the ...

    From $1584 per night (USD)

    VRBO

    Details
  • Hyatt Beach House Residences! Keys, Hot Tub, Pool
    From $1621 per night (USD)

    VRBO

    Hyatt Beach House Residences! Keys, Hot Tub, Pool

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Enjoy the glamour of this stylish, upscale place. Welcome to your own private sanctuary among the lush landscape of Key ...

    From $1621 per night (USD)

    VRBO

    Details
  • You Found the One!!! Approx 4 miles from Duval St. 2 BDRM 2BATH CONDO. SLEEPS 6
    Click For Pricing

    Expedia

    You Found the One!!! Approx 4 miles from Duval St. 2 BDRM 2BATH CONDO. SLEEPS 6

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Sleeps up to 6 guests Lush tropical beauty welcomes you to a spacious residential-style condominium featuring a primary ...

    Click For Pricing

    Expedia

    Details
  • Mariner's Oasis at Sunset Marina- 2bed 2 bath condo w\/boat slip for rent
    From $266 per night (USD)

    VRBO

    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 $266 per night (USD)

    VRBO

    Details
  • Gorgeous 53’ Hatteras yacht on Safe Harbor Channel.
    Click For Pricing

    Expedia

    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 ...

    Click For Pricing

    Expedia

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

    VRBO

    Details
  • Key West Home on Golf Course w\/ Patio & Grill!
    From $254 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 $254 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
  • Stay at SUNRISE SUITES 203!
    From $428 per night (USD)

    Expedia

    Stay at SUNRISE SUITES 203!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Sunrise Suite 203 is a quiet alternative to the bustling noise of downtown Key West. Located just a 10-minute drive from ...

    From $428 per night (USD)

    Expedia

    Details
  • Retreat to RUM CAY @ Sunrise Suites
    From $457 per night (USD)

    VRBO

    Retreat to RUM CAY @ Sunrise Suites

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Rum Cay offers a quiet alternative to the downtown area of Key West. This modern condo is located a short 10-minute ride ...

    From $457 per night (USD)

    VRBO

    Details
  • New! Butterfly Nest- Newly Decorated & Shared Pool
    From $530 per night (USD)

    Expedia

    New! Butterfly Nest- Newly Decorated & Shared Pool

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Summary: - Welcome to the quiet Sunrise Suites community located on the southeast side of Key West. - Just 1 mile from t ...

    From $530 per night (USD)

    Expedia

    Details
  • Cozy 1BR, Spacious Felix Boat Experience in Key West, Perry Marina - Wifi & AC
    From $431 per night (USD)

    VRBO

    Cozy 1BR, Spacious Felix Boat Experience in Key West, Perry Marina - Wifi & AC

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Welcome aboard our newly renovated houseboat nestled in the Perry Marina! Uniquely crafted by legendary artist, immerse ...

    From $431 per night (USD)

    VRBO

    Details
  • Key West King Escape, Fairfield Inn, Outdoor Swimming Pool | Near Mallory Square
    From $434 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 $434 per night (USD)

    VRBO

    Details
  • Key West Stay Ideal For Couple Close to Mallory Square | Outdoor Swimming Pool
    From $483 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 $483 per night (USD)

    VRBO

    Details
  • Newly Renovated Hotel w\/ Outdoor Pool | Short Drive to Historic Old Town
    From $510 per night (USD)

    VRBO

    Newly Renovated Hotel w\/ Outdoor Pool | Short Drive to Historic Old Town

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

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

    From $510 per night (USD)

    VRBO

    Details
  • Relaxing Double Queen, Fairfield Inn, Breakfast Included, Near Downtown Key West
    From $510 per night (USD)

    VRBO

    Relaxing Double Queen, Fairfield Inn, Breakfast Included, Near Downtown Key West

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

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

    From $510 per night (USD)

    VRBO

    Details
  • Modern Houseboat Oasis, 1BD, WiFi & AC - Writer’s Block in Key West
    From $527 per night (USD)

    VRBO

    Modern Houseboat Oasis, 1BD, WiFi & AC - Writer’s Block in Key West

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Welcome aboard the Writer's Block! A Houseboat, where the gentle lull of the waves inspires creativity and ignites the i ...

    From $527 per night (USD)

    VRBO

    Details
  • The SeaRay Experience boat with 2 bedrooms and WiFi, AC in Perry Marina Key West
    From $449 per night (USD)

    VRBO

    The SeaRay Experience boat with 2 bedrooms and WiFi, AC in Perry Marina Key West

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Welcome aboard the Cozy Sea Ray Experience! This cozy yacht boasts a stylish interior with two staterooms, one half bath ...

    From $449 per night (USD)

    VRBO

    Details
  • Dockside 2BD Monte Carlo in enchanting Key West, Perry Marina with WiFi & Gym
    From $350 per night (USD)

    VRBO

    Dockside 2BD Monte Carlo in enchanting Key West, Perry Marina with WiFi & Gym

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Experience the ultimate getaway on the water with our stunning Wellcraft Monte Carlo boat! This stylish and vessel offer ...

    From $350 per night (USD)

    VRBO

    Details
  • Luxury Houseboat, 1BD WiFi & AC Oasis @ The Perry, Key West
    From $522 per night (USD)

    VRBO

    Luxury Houseboat, 1BD WiFi & AC Oasis @ The Perry, Key West

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Welcome to the Enchantress. This modern houseboat has been handcrafted to provide a warm and wholehearted True Key West ...

    From $522 per night (USD)

    VRBO

    Details
  • New Property!  An Island Siesta
    From $310 per night (USD)

    Expedia

    New Property! An Island Siesta

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    This lovely, fully furnished, townhouse has two bedrooms that sleeps up to 6 and two full baths . The spacious upstairs ...

    From $310 per night (USD)

    Expedia

    Details
  • Ocean Front Lower Keys on Stock Island, 3\/2 luxury condo at the Ocean's Edge!
    From $562 per night (USD)

    VRBO

    Ocean Front Lower Keys on Stock Island, 3\/2 luxury condo at the Ocean's Edge!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    This ocean front 3/2 condominium is fully equipped with all the amenities you will need for a relaxing stay. The gated c ...

    From $562 per night (USD)

    VRBO

    Details
  • Keys to Paradise by AvantStay | Balcony, Pool, Golf
    From $343 per night (USD)

    Expedia

    Keys to Paradise by AvantStay | Balcony, Pool, Golf

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    This home is available for stays of 28 nights or longer. Welcome to Keys to Paradise, your Key West sanctuary nestled r ...

    From $343 per night (USD)

    Expedia

    Details
  • Hyatt 2-bedroom resort in delightful Key West with WiFi, AC
    From $5625 per night (USD)

    VRBO

    Hyatt 2-bedroom resort in delightful Key West with WiFi, AC

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Nestled along the Atlantic Ocean, Hyatt Windward Pointe Resort seamlessly combines the relaxed Key West vibe with a mode ...

    From $5625 per night (USD)

    VRBO

    Details
  • Hyatt Beach House Resort Key West 2-bedroom with WiFi, AC
    From $5625 per night (USD)

    VRBO

    Hyatt Beach House Resort Key West 2-bedroom with WiFi, AC

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Welcome to your private sanctuary in the lush landscape of Key West. Imagine old-fashioned screen-enclosed porches, gard ...

    From $5625 per night (USD)

    VRBO

    Details
  • Key West Oasis-1Br\/2Ba  Loft Town Home in a Resort
    From $313 per night (USD)

    VRBO

    Key West Oasis-1Br\/2Ba Loft Town Home in a Resort

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

    Experience the perfect balance of excitement and tranquility in this charming loft town home. Minutes from downtown, ye ...

    From $313 per night (USD)

    VRBO

    Details
  • Charming 3-bedroom townhome with WiFi, AC in fantastic Key West Golf Course
    From $262 per night (USD)

    Expedia

    Charming 3-bedroom townhome with WiFi, AC in fantastic Key West Golf Course

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    5

    Your home away from home in Key West with 3 bedrooms. This adorable townhome features a cozy sofa bed, a comfortable que ...

    From $262 per night (USD)

    Expedia

    Details
  • 𝐅𝐒𝐧𝐝𝐒𝐧𝐠 𝐌𝐞𝐒π₯𝐒 Dream Getaway at the Beach House Resort+Amenities. 2BR
    From $1046 per night (USD)

    VRBO

    𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢 Dream Getaway at the Beach House Resort+Amenities. 2BR

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Welcome to 𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢🌴 Experience Key West Paradise at the Beach House Resort Retreat! 🏖️ Additional $ ...

    From $1046 per night (USD)

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    Details
  • Luxurious 40' Sailing Yacht located in a beautiful resort! VRBO NEW OFFER!
    From $668 per night (USD)

    Expedia

    Luxurious 40' Sailing Yacht located in a beautiful resort! VRBO NEW OFFER!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    5

    You and your guests will have exclusive use of this 40ft yacht all to yourselves. The yacht stays docked, the entire res ...

    From $668 per night (USD)

    Expedia

    Details
  • 2BR Apt in Oceanview Resort w\/ Sunset Cruises & Poolside Relaxation
    From $1390 per night (USD)

    VRBO

    2BR Apt in Oceanview Resort w\/ Sunset Cruises & Poolside Relaxation

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    Located in Stock Island, a tropical paradise inside Key West. Enjoy fine dining w/ outstanding landscaping just around t ...

    From $1390 per night (USD)

    VRBO

    Details
  • 2 Suites Oceanview Balcony King at Oceans Edge Key West, Full Service Marina
    From $1158 per night (USD)

    VRBO

    2 Suites Oceanview Balcony King at Oceans Edge Key West, Full Service Marina

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    Located in Stock Island, a tropical paradise inside Key West. Enjoy fine dining w/ outstanding landscaping just around t ...

    From $1158 per night (USD)

    VRBO

    Details
  • Oceanview Balcony King Suite at Oceans Edge Key West, Sunset Cruises
    From $567 per night (USD)

    VRBO

    Oceanview Balcony King Suite at Oceans Edge Key West, Sunset Cruises

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Located in Stock Island, a tropical paradise inside Key West. Enjoy fine dining w/ outstanding landscaping just around t ...

    From $567 per night (USD)

    VRBO

    Details
  • Ocean View Balcony King Room at Oceans Edge, Panoramic Water Views, Pets Welcome
    From $532 per night (USD)

    VRBO

    Ocean View Balcony King Room at Oceans Edge, Panoramic Water Views, Pets Welcome

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Located in Stock Island, a tropical paradise inside Key West. Enjoy fine dining w/ outstanding landscaping just around t ...

    From $532 per night (USD)

    VRBO

    Details
  • Serene Retreat w\/ Waterfront Balcony & Easy Access to Paddleboarding
    From $678 per night (USD)

    VRBO

    Serene Retreat w\/ Waterfront Balcony & Easy Access to Paddleboarding

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Located in Stock Island, a tropical paradise inside Key West. Enjoy fine dining w/ outstanding landscaping just around t ...

    From $678 per night (USD)

    VRBO

    Details
  • Room in Coastal Resort w\/ Oceanview - Six Pools & Pvt Oceanview Balcony
    From $570 per night (USD)

    VRBO

    Room in Coastal Resort w\/ Oceanview - Six Pools & Pvt Oceanview Balcony

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    6

    Located in Stock Island, a tropical paradise inside Key West. Enjoy fine dining w/ outstanding landscaping just around t ...

    From $570 per night (USD)

    VRBO

    Details
  • Elegant Resort Room w\/ Paddleboards, Kayaks & Breathtaking Oceanviews
    From $539 per night (USD)

    VRBO

    Elegant Resort Room w\/ Paddleboards, Kayaks & Breathtaking Oceanviews

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Located in Stock Island, a tropical paradise inside Key West. Enjoy fine dining w/ outstanding landscaping just around t ...

    From $539 per night (USD)

    VRBO

    Details
  • 2 Suites 2 Queen w\/ Oceanview at Oceans Edge Resort, Kayak Rentals, 6 Pools
    From $1141 per night (USD)

    VRBO

    2 Suites 2 Queen w\/ Oceanview at Oceans Edge Resort, Kayak Rentals, 6 Pools

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    12

    Located in Stock Island, a tropical paradise inside Key West. Enjoy fine dining w/ outstanding landscaping just around t ...

    From $1141 per night (USD)

    VRBO

    Details
  • Oceanview Balcony 2 Queen Room at Oceans Edge Resort, Six Saltwater Pools
    From $514 per night (USD)

    VRBO

    Oceanview Balcony 2 Queen Room at Oceans Edge Resort, Six Saltwater Pools

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Located in Stock Island, a tropical paradise inside Key West. Enjoy fine dining w/ outstanding landscaping just around t ...

    From $514 per night (USD)

    VRBO

    Details
  • 2 Cozy Resort Rooms Perfect for Family Vacations, Enjoy Pools & Water Activities
    From $1077 per night (USD)

    VRBO

    2 Cozy Resort Rooms Perfect for Family Vacations, Enjoy Pools & Water Activities

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    Located in Stock Island, a tropical paradise inside Key West. Enjoy fine dining w/ outstanding landscaping just around t ...

    From $1077 per night (USD)

    VRBO

    Details
  • Ocean View Balcony 2 Queen at Oceans Edge Key West, Saltwater Pools - 2 Units
    From $1041 per night (USD)

    VRBO

    Ocean View Balcony 2 Queen at Oceans Edge Key West, Saltwater Pools - 2 Units

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    Located in Stock Island, a tropical paradise inside Key West. Enjoy fine dining w/ outstanding landscaping just around t ...

    From $1041 per night (USD)

    VRBO

    Details
  • 2 Charming Oceanfront Rooms w\/ Full-Service Marina & Bike Rentals - Pets Welcome
    From $1369 per night (USD)

    VRBO

    2 Charming Oceanfront Rooms w\/ Full-Service Marina & Bike Rentals - Pets Welcome

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    12

    Located in Stock Island, a tropical paradise inside Key West. Enjoy fine dining w/ outstanding landscaping just around t ...

    From $1369 per night (USD)

    VRBO

    Details
  • Comfortable Family Resort Room w\/ Ocean Views, Kayak Rentals & Six Pools
    From $562 per night (USD)

    VRBO

    Comfortable Family Resort Room w\/ Ocean Views, Kayak Rentals & Six Pools

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Located in Stock Island, a tropical paradise inside Key West. Enjoy fine dining w/ outstanding landscaping just around t ...

    From $562 per night (USD)

    VRBO

    Details
  • Ocean Oasis at Sunset Marina-2 bed 2 bath oceanfront condo w\/boat slip rental
    From $260 per night (USD)

    Expedia

    Ocean Oasis at Sunset Marina-2 bed 2 bath oceanfront condo w\/boat slip rental

    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 $260 per night (USD)

    Expedia

    Details
  • Yacht Primary Guest Quarters - Key West Resort
    From $325 per night (USD)

    VRBO

    Yacht Primary Guest Quarters - Key West Resort

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    This 1-bedroom Primary Guest Suite in Key West is perfect for your escape. The bright bedroom features a nice queen bed, ...

    From $325 per night (USD)

    VRBO

    Details
  • Tropical Tee Time Villa
    From $219 per night (USD)

    Expedia

    Tropical Tee Time Villa

    Bedrooms:
    4
    Bathrooms:
    2
    Sleeps:
    4

    Escape to a stunning vacation rental in Key West, nestled on a picturesque golf course within an amazing resort. This pr ...

    From $219 per night (USD)

    Expedia

    Details
  • Casa Del Mar in Beautiful Key west. Amazing open water view!
    From $263 per night (USD)

    VRBO

    Casa Del Mar in Beautiful Key west. Amazing open water view!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    Experience Key West like a local in this charming 4-bedroom house. With 1 king bed, 2 queen beds, and 1 twin bed, guests ...

    From $263 per night (USD)

    VRBO

    Details
  • Brand New! Catchlight House with Private Pool!
    From $2587 per night (USD)

    Expedia

    Brand New! Catchlight House with Private Pool!

    Bedrooms:
    7
    Bathrooms:
    6
    Sleeps:
    16

    Summary: Welcome to your ultimate Key West getaway! This stunning 6-bed, 6.5-bath home perfectly blends comfort, style, ...

    From $2587 per night (USD)

    Expedia

    Details
  • Ocean View Balcony 2 Queen Suite at Oceans Edge Resort, Marina Access, 6 Pools
    From $802 per night (USD)

    VRBO

    Ocean View Balcony 2 Queen Suite at Oceans Edge Resort, Marina Access, 6 Pools

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    6

    Located in Stock Island, a tropical paradise inside Key West. Enjoy fine dining w/ outstanding landscaping just around t ...

    From $802 per night (USD)

    VRBO

    Details
  • Brand New Build! Larkshine House - Pool
    From $2058 per night (USD)

    Expedia

    Brand New Build! Larkshine House - Pool

    Bedrooms:
    9
    Bathrooms:
    8
    Sleeps:
    18

    Summary: Welcome to Larkshine House in Key Haven Estates, Key West—a perfect retreat for families and large groups! This ...

    From $2058 per night (USD)

    Expedia

    Details
  • New Years in Key West! 2 bedroom Sleeps 6
    From $501 per night (USD)

    VRBO

    New Years in Key West! 2 bedroom Sleeps 6

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Spread out with the whole family in this spacious two-bedroom suite. Stunning waters and pristine beach greet you in Key ...

    From $501 per night (USD)

    VRBO

    Details
  • Ocean's Edge | Lux Resort | Concierge | Marina
    From $1407 per night (USD)

    VRBO

    Ocean's Edge | Lux Resort | Concierge | Marina

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    10

    Oceans Edge Key West Hotel & Marina is a luxurious resort located on the serene Stock Island, just minutes from the vibr ...

    From $1407 per night (USD)

    VRBO

    Details
  • Hyatt Beach | Concierge | Spa | Pool | Hot Tub
    From $1918 per night (USD)

    VRBO

    Hyatt Beach | Concierge | Spa | Pool | Hot Tub

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Welcome to your private sanctuary at Hyatt Beach House Resort, where the lush landscapes of Key West meet unparalleled l ...

    From $1918 per night (USD)

    VRBO

    Details
  • Sleeps 6 | Lux Resort | Pool | Hot Tub | Concierge
    From $1556 per night (USD)

    VRBO

    Sleeps 6 | Lux Resort | Pool | Hot Tub | Concierge

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Oceans Edge Key West Hotel & Marina is a luxurious resort located on the serene Stock Island, just minutes from the vibr ...

    From $1556 per night (USD)

    VRBO

    Details