Stock Island Rentals
From $2415 per night (USD)VRBO
Prestigious | Hyatt | Hot Tub | Pool | Concierge
- 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 $2415 per night (USD)VRBO
From $2371 per night (USD)VRBO
Sleeps 6 | Hyatt | Lux Resort | Concierge | Pool | Spa
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Set along the stunning Atlantic Ocean, Hyatt Windward Pointe Resort seamlessly blends Key West’s laid-back vibe with mod ...
From $2371 per night (USD)VRBO
From $2334 per night (USD)VRBO
Sleeps 6 | Hyatt | Beachfront | Lux Resort | Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Set along the stunning Atlantic Ocean, Hyatt Windward Pointe Resort seamlessly blends Key West’s laid-back vibe with mod ...
From $2334 per night (USD)VRBO
From $1396 per night (USD)VRBO
Prestigious | Gym | Pool | Marina | Concierge
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Oceans Edge Key West Hotel & Marina is a luxurious resort located on the serene Stock Island, just minutes from the vibr ...
From $1396 per night (USD)VRBO
From $2537 per night (USD)VRBO
Sleeps 6 | Lux Resort | Hot Tub | Pool | Concierge
- 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 $2537 per night (USD)VRBO
From $2352 per night (USD)VRBO
Top Class | Hyatt | Beachfront | Pool | Lux Resort
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Set along the stunning Atlantic Ocean, Hyatt Windward Pointe Resort seamlessly blends Key West’s laid-back vibe with mod ...
From $2352 per night (USD)VRBO
From $481 per night (USD)VRBO
Changes In Latitude
- Bedrooms:
- 6
- Bathrooms:
- 4
- Sleeps:
- 8
Escape to coastal perfection at this upscale waterfront retreat in Key Haven, just minutes from Old Town Key West and Du ...
From $481 per night (USD)VRBO
From $3388 per night (USD)Expedia
VRBO NEW OFFER!! LUXURIOUS 63 ft. Yacht in an amazing resort! Jet Ski & more.
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 12
This colossal yacht is new to our fleet and VRBO! Colossal indeed, boasting 6 staterooms with each having its own privat ...
From $3388 per night (USD)Expedia
From $402 per night (USD)VRBO
Island Oasis-2 Bedroom Townhouse in the Gated Community of the Key West Golf Club
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Step into this spacious 2-bedroom, 1 1/2 -bathroom home, perfect for your island getaway, in the gated community of the ...
From $402 per night (USD)VRBO
From $368 per night (USD)VRBO
2 Bedroom Townhome in the Key West Golf Club
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 5
**Beautiful 2-Bedroom Townhome in Key West Golf Club** Welcome to this charming 2-bedroom, 2.5-bathroom townhome locate ...
From $368 per night (USD)VRBO
From $300 per night (USD)VRBO
Nautical Nights in Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Set sail into a unique and unforgettable stay aboard our luxurious boat, docked in the vibrant heart of Key West. Offeri ...
From $300 per night (USD)VRBO
From $258 per night (USD)VRBO
Coconut Mallory Resort - Charming 2 bedroom Key West, Florida
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Coconut Mallory Marina and Resort located in Key West. Relax at one of two pools or the hot tub located onsi ...
From $258 per night (USD)VRBO
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Hyatt Vacation Club at Beach House, Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Spend your days relaxing by the zero-entry pool or at our on-site beach. Set on the northeastern corner of Key West, whe ...
Click For PricingVRBO
From $987 per night (USD)Expedia
NEW Special Offer! 60 ft. Yacht with Jet Ski! Located in a Beautiful Resort!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
This luxurious yacht is new to our fleet and VRBO! She is elegant in every way, Italian made, to host an amazing experie ...
From $987 per night (USD)Expedia
From $660 per night (USD)VRBO
3-bedroom townhome in Key West with fitness room, WiFi
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Your cozy getaway awaits in Key West at this lovely townhome. With 3 bedrooms including 2 king beds and 2 queen beds, th ...
From $660 per night (USD)VRBO
From $2022 per night (USD)Expedia
NEW! Private Pool & Docking - Floralee House
- Bedrooms:
- 7
- Bathrooms:
- 6
- Sleeps:
- 16
Summary: Welcome to your dream escape in Key West! This exquisite 6-bedroom, 6.5-bath residence combines luxury, eleganc ...
From $2022 per night (USD)Expedia
From $2002 per night (USD)VRBO
Brand New & Private Pool - Palmgale House
- Bedrooms:
- 7
- Bathrooms:
- 6
- Sleeps:
- 16
Summary: Discover your perfect getaway in Key West! This stunning 6-bedroom, 6.5-bath home effortlessly blends luxury, s ...
From $2002 per night (USD)VRBO
From $268 per night (USD)Expedia
PAINTED SKY ~ 2 BR\/2 Ba Waterfront Condo at Sunset Marina w\/ Community Pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
STOCK ISLAND MASTERPIECE... In the private gated community of Sunset Marina, this exquisite waterfront condo's view is a ...
From $268 per night (USD)Expedia
From $903 per night (USD)VRBO
Mermaid's Retreat at Coral Hammock Key West Island living at its best
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Mermaids Retreat features a full-sized kitchen and a comfortable dining area, along with front and back porches for rela ...
From $903 per night (USD)VRBO
- Click For Pricing
Expedia
Charming 2-bedroom resort with WiFi, AC in gorgeous Key West. Quiet & relaxing
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Your home away from home in Key West with 2 bedrooms. This enchanting resort offers a cozy living room with a sofa bed, ...
Click For PricingExpedia
From $274 per night (USD)VRBO
Key West Golf Club 2 Bedroom Spa Home in the sanctuary
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Escape to your own private retreat at this stunning standalone townhouse in the Sanctuary of the Key West Golf Course. T ...
From $274 per night (USD)VRBO
From $946 per night (USD)VRBO
2| Coconut Mallory | Lux Stay | Pool | Hot Tub
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Coconut Mallory Marina & Resort is a perfect blend of Key West’s laid-back charm and modern resort luxury. Nestled near ...
From $946 per night (USD)VRBO
From $899 per night (USD)VRBO
3-bedroom condo in Key West with 180 degree Ocean View\/Marina View Cold AC, WiFi
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Key West is waiting for you at this 3-bedroom Condo. Spectacular 180 degree view of the Ocean and Yachts in the Marina. ...
From $899 per night (USD)VRBO
From $255 per night (USD)Expedia
Florida Keys Living: Your Charming Houseboat Getaway in the Florida Keys!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Come and experience living the FLORIDA KEYS dream. As seen on the TV show “ My Floating Home”. This charming tiny float ...
From $255 per night (USD)Expedia
From $825 per night (USD)VRBO
Funky Chicken Cottage with shared pool, 3 bed 3 bath minutes from Key West
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Discover this 3-bedroom gem in Key West. This tranquil townhome offers a wonderful escape for guests. With 1 king bed an ...
From $825 per night (USD)VRBO
From $566 per night (USD)VRBO
NEW monthly LISTING: 3000+ SQUARE FOOT HOME 0N OVER 1\/4 ACRE POOL SPA AND GARDEN
- Bedrooms:
- 5
- Bathrooms:
- 3
- Sleeps:
- 8
BEDAZZLING COMPOUND... This wonderful home is situated on a tremendously landscaped and walled double lot in New Town. ...
From $566 per night (USD)VRBO
From $299 per night (USD)VRBO
A slice of paradise in the Florida Keys
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
About this space As seen on My Tiny Home (reality tv) this is the pefect getaway for a romantic night in Key West. The s ...
From $299 per night (USD)VRBO
From $268 per night (USD)Expedia
Cabana at the Golf Club-Monthly Rental Charming 2-Bedroom Golf Course Retreat
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Charming 2-Bedroom Retreat with Golf Course Views | Key West Golf Club Community Nestled in the picturesque Key West Go ...
From $268 per night (USD)Expedia
From $958 per night (USD)VRBO
Waterfront 5 Bedroom Mansion with Pool&Dock
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 10
Escape to a luxurious waterfront oasis located at Key Haven, just a stone's throw from Key West. Nring your boat up to 4 ...
From $958 per night (USD)VRBO
From $309 per night (USD)VRBO
Hyatt Windward Pointe, 2 bedroom Waterfront Condo, 2 Night Stay in December
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Whether you choose to spend your days simply relaxing by the infinity pool or setting off on a dive adventure, Key West ...
From $309 per night (USD)VRBO
From $198 per night (USD)VRBO
Salt Pond Hideaway | Comfortable Condo with Pool, Hot Tub, Close to Beach!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Salt Pond Hideaway | Comfortable Condo with Pool, Hot Tub, and Close to Beach! Salt Pond Hideaway is your ideal retreat ...
From $198 per night (USD)VRBO
From $894 per night (USD)Expedia
Waterfront Resort, New Year’s Eve, 7 Nights, Sleeps 6, Pool, Hot Tub, Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Have I mentioned that this listing is for celebrating New Year’s Eve in sunny Key West, FL? You will be staying at the H ...
From $894 per night (USD)Expedia
From $669 per night (USD)VRBO
Waterfront Resort, Private Beach, Boat Docks, Sleeps 6, Pool, Hot Tub, Hyatt
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Enjoy your vacation get-away at the Hyatt Beach House in sunny Key West, FL; 7 nights; fully furnished condo style resid ...
From $669 per night (USD)VRBO
From $669 per night (USD)Expedia
Oceanfront Resort, Infinity Pool, Hot Tub, Courtyard, Sleeps 6, 7 Nights, Hyatt
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Enjoy your vacation get-away at the Hyatt Windward Pointe in sunny Key West, FL; 7 nights; fully furnished condo style r ...
From $669 per night (USD)Expedia
From $669 per night (USD)VRBO
Oceanfront Resort, Infinity Pool, Hot Tub, Courtyard, Sleeps 6, 7 Nights, Hyatt
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Enjoy your vacation get-away at the Hyatt Windward Pointe in sunny Key West, FL; 7 nights; fully furnished condo style r ...
From $669 per night (USD)VRBO
From $394 per night (USD)Expedia
Charming 2-bedroom resort with WiFi, AC in lovely Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Discover this 2-bedroom gem in Key West. This gorgeous resort features 1 king bed and 1 queen bed, perfect for a wonderf ...
From $394 per night (USD)Expedia
From $468 per night (USD)VRBO
NEW LISTING - CHARMING 2-BEDROOM CONDO IN BEAUTIFUL KEY WEST
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
We just purchased our 2-bedroom, 2-bathroom property at the beautifully landscaped Las Salinas Condominiums in Key West. ...
From $468 per night (USD)VRBO
From $428 per night (USD)Expedia
Heron House | Canal Front 3-Bedroom Home w\/ Private Boat Docking in Key Haven
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Heron House | Canal Front 3-Bedroom Home with Private Boat Docking in Key Haven Located in the serene and sought-after ...
From $428 per night (USD)Expedia