Stock Island, Florida Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Stock Island, Florida on RentalSaver.com!

Stock Island Rentals

From $452 per night (USD)
VRBO
Ocean View Balcony King Room at Oceans Edge, Panoramic Water Views, Pets Welcome
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This listing is for a room within a hotel. ✦ Your room is 380 sq. ft, equipped with complimentary toiletries, high defi ...
From $452 per night (USD)
VRBO
From $303 per night (USD)
VRBO
Serene Retreat w/ Waterfront Balcony & Easy Access to Paddleboarding
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This listing is for a room within a hotel. ✦ Your room is 570 sq. ft, equipped with complimentary toiletries, high defi ...
From $303 per night (USD)
VRBO
From $365 per night (USD)
VRBO
Room in Coastal Resort w/ Oceanview - Six Pools & Pvt Oceanview Balcony
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
This listing is for a room within a hotel. ✦ Your room is 570 sq. ft, equipped with complimentary toiletries, high defi ...
From $365 per night (USD)
VRBO
From $382 per night (USD)
VRBO
Elegant Resort Room w/ Paddleboards, Kayaks & Breathtaking Oceanviews
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This listing is for a room within a hotel. ✦ Your room is 380 sq. ft, equipped with complimentary toiletries, high defi ...
From $382 per night (USD)
VRBO
From $729 per night (USD)
VRBO
2 Suites 2 Queen w/ Oceanview at Oceans Edge Resort, Kayak Rentals, 6 Pools
Bedrooms:
2
Bathrooms:
2
Sleeps:
12
This listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms. ✦ Each room is ...
From $729 per night (USD)
VRBO
From $382 per night (USD)
VRBO
Oceanview Balcony 2 Queen Room at Oceans Edge Resort, Six Saltwater Pools
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This listing is for a room within a hotel. ✦ Your room is 380 sq. ft, equipped with complimentary toiletries, high defi ...
From $382 per night (USD)
VRBO
From $767 per night (USD)
VRBO
2 Cozy Resort Rooms Perfect for Family Vacations, Enjoy Pools & Water Activities
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
This listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms. ✦ Each room is ...
From $767 per night (USD)
VRBO
From $767 per night (USD)
VRBO
Ocean View Balcony 2 Queen at Oceans Edge Key West, Saltwater Pools - 2 Units
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
This listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms. ✦ Each room is ...
From $767 per night (USD)
VRBO
From $729 per night (USD)
VRBO
2 Charming Oceanfront Rooms w/ Full-Service Marina & Bike Rentals - Pets Welcome
Bedrooms:
2
Bathrooms:
2
Sleeps:
12
This listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms. ✦ Each room is ...
From $729 per night (USD)
VRBO
From $452 per night (USD)
VRBO
Comfortable Family Resort Room w/ Ocean Views, Kayak Rentals & Six Pools
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This listing is for a room within a hotel. ✦ Your room is 380 sq. ft, equipped with complimentary toiletries, high defi ...
From $452 per night (USD)
VRBO
From $1367 per night (USD)
VRBO
Skip the Hotel - Stay on the Water aboard a 46 foot Yacht in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
All aboard this 48 foot motor yacht in Key West. Get ready to live your best life on this yacht, featuring a luxurious p ...
From $1367 per night (USD)
VRBO
From $1900 per night (USD)
Expedia
Catchlight House at Lunara Bay
Bedrooms:
6
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 $1900 per night (USD)
Expedia
From $365 per night (USD)
VRBO
Ocean View Balcony 2 Queen Suite at Oceans Edge Resort, Marina Access, 6 Pools
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
This listing is for a room within a hotel. ✦ Your room is 570 sq. ft, equipped with complimentary toiletries, high defi ...
From $365 per night (USD)
VRBO
From $2218 per night (USD)
Expedia
Larkshine House at Lunara Bay
Bedrooms:
8
Bathrooms:
8
Sleeps:
18
Summary: Welcome to Larkshine House in Lunara Bay, Key West—a perfect retreat for families and large groups! This 8-bedr ...
From $2218 per night (USD)
Expedia
From $230 per night (USD)
VRBO
Island Oasis-2 Bedroom Townhouse in the Gated Community of the Key West Golf Club
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Step into our Island Oasis! A very spacious 2-bedroom, 1 1/2 -bathroom home, perfect for your island getaway, in the cov ...
From $230 per night (USD)
VRBO
From $370 per night (USD)
VRBO
2 Bedroom Townhome in the Key West Golf Club
Bedrooms:
2
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 $370 per night (USD)
VRBO
From $900 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 $900 per night (USD)
VRBO
From $2736 per night (USD)
Expedia
Floralee House at Lunara Bay
Bedrooms:
6
Bathrooms:
6
Sleeps:
16
Summary: Welcome to your dream Key West escape! This stunning 6-bedroom, 6.5-bath home offers luxury and island charm ju ...
From $2736 per night (USD)
Expedia
From $2249 per night (USD)
VRBO
Palmgale Estate at Lunara Bay
Bedrooms:
6
Bathrooms:
6
Sleeps:
16
Summary: Discover your perfect Key West getaway! This luxurious 6-bedroom, 6.5-bath home combines sophistication with is ...
From $2249 per night (USD)
VRBO
From $245 per night (USD)
Expedia
PAINTED SKY~2 BR/2 Ba Waterfront Condo at Sunset Marina w/ Pool & Boat Slip!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
ISLAND MASTERPIECE... In the private gated community of Sunset Marina, this exquisite waterfront condo's view is awash i ...
From $245 per night (USD)
Expedia
From $624 per night (USD)
VRBO
Mermaid's Retreat at Coral Hammock Key West Island living at its best
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Welcome to Mermaids Retreat Escape to the tropical charm of Mermaids Retreat, where comfort meets convenience in a sere ...
From $624 per night (USD)
VRBO
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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, ...
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Expedia
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VRBO
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 ...
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VRBO
From $795 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 $795 per night (USD)
VRBO
From $351 per night (USD)
VRBO
NEW monthly LISTING: 3000+ SQUARE FOOT HOME 0N OVER 1/4 ACRE POOL SPA AND GARDEN
Bedrooms:
4
Bathrooms:
3
Sleeps:
7
BEDAZZLING COMPOUND... This wonderful home is situated on a tremendously landscaped and walled double lot in New Town. ...
From $351 per night (USD)
VRBO
From $217 per night (USD)
Expedia
Cabana at the Golf Club-Monthly Rental Charming 2-Bedroom Golf Course Retreat
Bedrooms:
1
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 $217 per night (USD)
Expedia
From $833 per night (USD)
VRBO
Waterfront 5 Bedroom Mansion with Pool&Dock
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
Escape to a luxurious waterfront oasis located at Key Haven, just a stone's throw from Key West. Bring your boat up to 3 ...
From $833 per night (USD)
VRBO
From $533 per night (USD)
Expedia
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 $533 per night (USD)
Expedia
Click For Pricing
VRBO
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 ...
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VRBO
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Expedia
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 ...
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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
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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 ...
Click For Pricing
Expedia
From $157 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 $157 per night (USD)
VRBO
From $587 per night (USD)
Expedia
The Salt Cay | Updated! Stunning Sunset View, Pool!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The Salt Cay | Updated! Stunning Sunset View, Pool! Escape to The Salt Cay, a serene, beautifully updated, and well-app ...
From $587 per night (USD)
Expedia
From $563 per night (USD)
VRBO
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 $563 per night (USD)
VRBO
From $635 per night (USD)
Expedia
**OCEANFRONT OASIS @ KEY HAVEN** Private Home & Pool + LAST KEY SERVICES…
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! OCEANFRONT OA ...
From $635 per night (USD)
Expedia
From $768 per night (USD)
VRBO
New Listing! Key Lime Paradise/Condo
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Come find your slice of paradise in this 2 bed 2 full bath newly renovated condo. This listing is perfect for those want ...
From $768 per night (USD)
VRBO
From $838 per night (USD)
Expedia
Oceanfront Resort, RWO Championship Boat Races, Pool, Hot Tub, Sleeps 6, Hyatt
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Have I mentioned that this listing is for Race World Offshore Power Boat World Championship Races in sunny Key West, FL? ...
From $838 per night (USD)
Expedia
From $381 per night (USD)
VRBO
Charming 4-bedroom Yacht with AC, Pool, fitness room in fantastic Key West
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Discover the charm of “Old Key West” aboard Vita Felice, a Luxurious Vintage Yacht and a piece of American History. Thi ...
From $381 per night (USD)
VRBO
From $838 per night (USD)
Expedia
Waterfront Resort, RWO Championship Boat Races, Pool, Hot Tub, Sleeps 6, Hyatt
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Have I mentioned that this listing is for Race World Offshore Power Boat World Championship Races in sunny Key West, FL? ...
From $838 per night (USD)
Expedia
From $979 per night (USD)
VRBO
Waterfront Resort, Fantasy Fest, Private Beach, Boat Docks, Sleeps 6, Pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Have I mentioned that this listing is for celebrating Fantasy Fest in sunny Key West, FL? You will be staying at the Hya ...
From $979 per night (USD)
VRBO
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Expedia
Brand new VRBO exclusive offer! 50 foot motor yacht in Key West!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
You and your guests will have exclusive use of this 50 ft yacht all to yourselves. The yacht stays docked, the entire re ...
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Expedia
From $894 per night (USD)
VRBO
Oceanfront Resort, Thanksgiving Week, Infinity Pool, Hot Tub, Sleeps 6, Hyatt
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Enjoy your Thanksgiving vacation get-away at the Hyatt Windward Pointe in sunny Key West, FL; 7 nights; fully furnished ...
From $894 per night (USD)
VRBO
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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 ...
Click For Pricing
Expedia
From $403 per night (USD)
VRBO
Charming catamaran sailboat with AC, pool in stock island yacht club, Key West.
Bedrooms:
0
Bathrooms:
2
Sleeps:
3
**Escape to Paradise on a Floating Retreat in Key West!** Welcome to your unforgettable getaway aboard this gemini sa ...
From $403 per night (USD)
VRBO
From $894 per night (USD)
Expedia
Oceanfront Resort, Fantasy Fest, Infinity Pool, Hot Tub, Sleeps 6 7 Nites, Hyatt
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Have I mentioned that this listing is for celebrating Fantasy Fest in sunny Key West, FL? You will be staying at the Hya ...
From $894 per night (USD)
Expedia
From $572 per night (USD)
VRBO
Waterfront Boater's Paradise on deep water canal, boat dock, ocean access
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Tropical WATERFRONT getaway. A Boater's Paradise. This charming 4 bedroom (1 King, 3 Queens), 2 bath house is located on ...
From $572 per night (USD)
VRBO
From $373 per night (USD)
Expedia
Cat Island Suite | Beautifully Renovated w/ Pool!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Cat Island Suite | Updated! Stunning Sunset View, Pool! Escape to Cat Island Suite, a serene, beautifully updated, and ...
From $373 per night (USD)
Expedia
From $598 per night (USD)
VRBO
Butterfly Nest | Newly Updated w/ Shared Pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Butterfly Nest | Newly Updated w/ Shared Pool Escape to Butterfly Nest, a serene, beautifully designed 2-bedroom condo ...
From $598 per night (USD)
VRBO
From $701 per night (USD)
Expedia
The Andros | Incredible Views w/ Shared Pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The Andros | Incredible Views w/ Shared Pool Escape to The Andros, a serene, beautifully designed 2-bedroom, 2-bath con ...
From $701 per night (USD)
Expedia
From $159 per night (USD)
VRBO
Key West Happy Hideaway! Beautifully Renovated! 2 BDR/1.5 BA, GOLF, POOL, GYM
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Key West Happy Hideaway is exactly that! Your perfect little hideaway nestled in the beautiful and lush landscaping of t ...
From $159 per night (USD)
VRBO
From $828 per night (USD)
VRBO
Key West Paradise 3-bedroom townhome w/large shared pool
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Perfect for family getaways or group trips, this spacious townhome offers plenty of room for everyone to enjoy. It featu ...
From $828 per night (USD)
VRBO
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VRBO
Key West 2 BR Villa with full kitchen, ocean view with Infinity pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Located in Key West just minutes from beautiful sunsets at Mallory Square or renowned dining and nightlife of Duval Stre ...
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VRBO
From $683 per night (USD)
Expedia
Coral Oasis – Spacious 3BR Retreat, Shared Pool, Dog Friendly, Parking, Minutes to Downtown Key West
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Welcome to Coral Oasis, a charming 3-bedroom townhouse nestled in a gated community just over Cow Key Bridge from Key We ...
From $683 per night (USD)
Expedia
From $291 per night (USD)
VRBO
8th Hole Golf Retreat
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Luxury Two-Bedroom Condo with Resort-Style Amenities for Rent in Key West Golf Club Community. ...
From $291 per night (USD)
VRBO
From $405 per night (USD)
Expedia
The Samana Cay | Tropical, Airy Retreat w/ Private Balcony & Pool!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The Samana Cay | Tropial, Airy Retreat w/ Private Balcony & Pool! Escape to The Samana Cay, a bright and inviting 2-bed ...
From $405 per night (USD)
Expedia
From $1350 per night (USD)
VRBO
Charming 2-bedroom resort with WiFi, fitness room in phenomenal Key West.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Discover this enchanting 2-bedroom gem in Key West. This charming resort boasts a cozy atmosphere with 1 king bed and 2 ...
From $1350 per night (USD)
VRBO
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Expedia
Stunning 2-Bedroom Villa in Key West - Desirable Location - Hyatt Beach House!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Get ready to relax in this 2-bedroom villa in Key West. Hyatt Beach House Resort features over seventy luxurious two-be ...
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Expedia
From $649 per night (USD)
VRBO
3-bedroom ocean view condo in delightful Key West with WiFi, AC
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Discover this delightful 3-bedroom gem in Key West. This charming condo features 1 king bed, 1 queen bed, and 2 twin bed ...
From $649 per night (USD)
VRBO
From $334 per night (USD)
Expedia
Poolside Suite with Direct Pool Access
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: Experience luxury at Beachside Resort, set on seven acres of property overlooking the Gulf of Mexico. Unwind in ...
From $334 per night (USD)
Expedia
From $374 per night (USD)
VRBO
Poolside Suite with Direct Pool Access
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: Experience luxury at Beachside Resort, set on seven acres of property overlooking the Gulf of Mexico. Unwind in ...
From $374 per night (USD)
VRBO
From $496 per night (USD)
Expedia
Poolside Suite with Direct Pool Access
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: Experience luxury at Beachside Resort, set on seven acres of property overlooking the Gulf of Mexico. Unwind in ...
From $496 per night (USD)
Expedia
From $521 per night (USD)
VRBO
Poolside Suite with Direct Pool Access
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: Experience luxury at Beachside Resort, set on seven acres of property overlooking the Gulf of Mexico. Unwind in ...
From $521 per night (USD)
VRBO
From $415 per night (USD)
Expedia
Sunrise Condo at Seaside - KEY WEST!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Now through September: Reduced Rates + 2-Night Minimum! The owners of Sunrise Condo have made thoughtful upgrades based ...
From $415 per night (USD)
Expedia
From $1085 per night (USD)
VRBO
Your Luxurious Key West Escape Awaits – A Boater’s Dream Retreat!
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Your Luxurious Key West Escape Awaits – A Boater’s Dream Retreat... Nestled in the exclusive Key Haven neighborhood, ju ...
From $1085 per night (USD)
VRBO
From $412 per night (USD)
Expedia
Charming Key West Town Home Beach/Pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Home of Famous Ernest Hemingway and Jimmy Buffet. Enjoy the downtown area on Duval Street where Sloppy Joe's and Captain ...
From $412 per night (USD)
Expedia
From $362 per night (USD)
VRBO
Key Haven Coastal Retreat - Canal front with pool
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Key Haven Coastal Retreat – Your Private Waterfront Paradise Discover luxury island living at Key Haven Coas ...
From $362 per night (USD)
VRBO
From $571 per night (USD)
VRBO
Cozy 1 Bedroom Green Flash Houseboat @ the Perry Marina with WiFi, AC
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Escape to our unique and Cozy houseboat, where tranquility meets adventure! Enjoy a spacious living room and a fully equ ...
From $571 per night (USD)
VRBO
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VRBO
Fantasy Fest Week 2-bedroom condo in lovely Key West with WiFi, AC
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Fantasy Fest Week . Nestled in Key West, this delightful condo offers a superb retreat for guests. With 2 bedrooms featu ...
Click For Pricing
VRBO
From $491 per night (USD)
VRBO
Cozy Modern Casa Azul Houseboat Experience & Scenic Views @ The Perry
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Welcome to the Casa Azul Houseboat! Experience tranquility on the water at Perry Marina. This stylish floating haven boa ...
From $491 per night (USD)
VRBO
From $571 per night (USD)
VRBO
Glamorous Houseboat Stay - Enchantress Experience @ The Perry
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Welcome to the Enchantress. This modern houseboat has been handcrafted to provide a warm and wholehearted True Key West ...
From $571 per night (USD)
VRBO
From $712 per night (USD)
Expedia
Spacious 52 ft Catamaran for Dockside Stay
Bedrooms:
6
Bathrooms:
6
Sleeps:
12
Summary: Welcome aboard S/V SeaLab, a 52-foot Lagoon sailing catamaran docked at the premier Perry Marina in Key West, F ...
From $712 per night (USD)
Expedia
From $730 per night (USD)
VRBO
NEW VRBO Listing! Elegant 40' Yacht in 5-Star Resort
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
You and your guests will have exclusive use of this 40ft yacht all to yourselves. The yacht stays docked, the entire res ...
From $730 per night (USD)
VRBO
From $270 per night (USD)
Expedia
Tropical Tee-Time: 2BR Townhome in Key West Golf Club with Two Shared Pools, Fitness Center, Dogs OK
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
County zoning requires a minimum rental period of 28 nights, and no exceptions can be made. Please review additional pol ...
From $270 per night (USD)
Expedia
From $1180 per night (USD)
VRBO
SPECIAL OFFER! 50 Foot Luxury Sailing Catamaran in Five Star Resort, Key West!
Bedrooms:
6
Bathrooms:
6
Sleeps:
12
This yacht is new to our fleet and VRBO! Boasting 6 staterooms with each having its own private bath and shower, sleepin ...
From $1180 per night (USD)
VRBO
From $168 per night (USD)
VRBO
Quiet 2-bedroom plus office townhome on the Key West golf course!
Bedrooms:
3
Bathrooms:
2
Sleeps:
5
Just a short walk from the Resort style pool and fitness center, our townhome, situated on the 1st fairway of the Key We ...
From $168 per night (USD)
VRBO
From $2281 per night (USD)
VRBO
The Starboard House at Solaire Lunara Bay
Bedrooms:
8
Bathrooms:
8
Sleeps:
20
Summary: Explore a stunning new build with eight generous bedrooms and a private pool. This exceptional home offers top- ...
From $2281 per night (USD)
VRBO
From $444 per night (USD)
VRBO
Antique trawler 2-bedroom boat in phenomenal Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Experience Key West like a local in this adorable 2-bedroom antique trawler 37' yacht located at The Perry Marina. This ...
From $444 per night (USD)
VRBO
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VRBO
Hyatt Windward Pointe Resort is one of the finest Resorts in all of Key West.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Hyatt Windward Pointe offers an ideal respite from reality. Ocean view. Located on the southeast end of Key West, this S ...
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VRBO
From $315 per night (USD)
VRBO
Oceanfront 2-bedroom Villa at a Resort in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This memorable resort is the perfect home base for your trip to Key West. With 2 bedrooms and 2 bathrooms featuring a je ...
From $315 per night (USD)
VRBO
From $1096 per night (USD)
VRBO
51' Luxury Yacht in Key West
Bedrooms:
4
Bathrooms:
4
Sleeps:
9
Introducing Andiamo our 51' power catamaran. You and your guests will have exclusive use of this amazing boat to yourse ...
From $1096 per night (USD)
VRBO
$Luxurious \Atlantia\ 2020 6-bedrooms 64ft yacht with full time crew$
From $7602 per night (USD)
Expedia
Luxurious \"Atlantia\" 2020 6-bedrooms 64ft yacht with full time crew
Bedrooms:
6
Bathrooms:
6
Sleeps:
12
Stay comfortably in Key West at this amazing 6-bedroom yacht. With 5 queen beds and 1 single bed, this luxury yacht off ...
From $7602 per night (USD)
Expedia
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VRBO
Hyatt Vacation Club at Windward Point Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Hotel Description Be sure to enjoy recreational amenities, including an outdoor pool, a spa tub, and bicycles to rent. T ...
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VRBO
From $3991 per night (USD)
Expedia
The Sunray Home at Lunara Bay
Bedrooms:
8
Bathrooms:
8
Sleeps:
16
Summary: Discover a luxurious new build featuring waterfront views, a private dock, eight spacious bedrooms and a privat ...
From $3991 per night (USD)
Expedia
From $3613 per night (USD)
VRBO
Tidelands House at Lunara Bay
Bedrooms:
8
Bathrooms:
8
Sleeps:
16
Summary: Discover a luxurious new build featuring waterfront views, boat docking, eight spacious bedrooms and a private ...
From $3613 per night (USD)
VRBO
From $332 per night (USD)
Expedia
A Sunset Celebration at the Key West Golf Club - Photos Coming Soon!
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
This lovely, fully furnished, townhouse has three bedrooms that sleeps up to 6 and two full baths . The spacious upstair ...
From $332 per night (USD)
Expedia
$\nHyatt Vacation Club at Beach House, Key West$
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VRBO
\nHyatt Vacation Club at Beach House, Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Lush tropical beauty welcomes you to a spacious residential-style villa featuring a primary bedroom with a king-size bed ...
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VRBO
From $595 per night (USD)
Expedia
Hyatt Vacation Club at Windward Pointe Resort. 2 Bedroom/2 Bath Villa
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Relax in a tropical retreat overlooking the Atlantic Ocean, Windward Pointe captures the essence of Key West. The resort ...
From $595 per night (USD)
Expedia
From $557 per night (USD)
VRBO
Best Resort in Key West! 2-bedroom/2 Bath condo with WiFi, AC in lovely Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Your Key West adventure begins at this lovely 2-bedroom condo. With a king bed, a queen bed, and a cozy living room with ...
From $557 per night (USD)
VRBO
From $400 per night (USD)
VRBO
Superb waterfront Coconut Mallory 2 BR, 2 bath condo, 2 pools, incredible views
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
No matter where you stay on the Key West island, you'll be able to get to whatever historical site, beach, restaurant, b ...
From $400 per night (USD)
VRBO
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VRBO
Your 2025 Labor Day Week Getaway in Paradise ..... Coconut Mallory, Key West.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This is a ONE-WEEK opportunity to enjoy Paradise! Our week can be yours in September 2025. This wonderful 2-bd con ...
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VRBO
From $591 per night (USD)
VRBO
Your Island Base | 3 Pool View Rooms at Fun & Breezy Blue Flamingo Resort
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Enjoy the tropical ambiance of Blue Flamingo Resort, featuring lush gardens and vibrant poolside activities. This room p ...
From $591 per night (USD)
VRBO
From $886 per night (USD)
VRBO
Kick Back in 3 Pool-View Rooms at Key West’s Blue Flamingo Resort
Bedrooms:
3
Bathrooms:
3
Sleeps:
12
Enjoy the tropical ambiance of Blue Flamingo Resort, featuring lush gardens and vibrant poolside activities. This room p ...
From $886 per night (USD)
VRBO
From $1181 per night (USD)
VRBO
4 Pool-view Rooms with 2 Queen Beds l Island Vibes Await in Blue Flamingo Resort
Bedrooms:
4
Bathrooms:
4
Sleeps:
16
Key West’s newest island escape offers breezy rooms, poolside cabanas, and nonstop fun. Lounge by the pool, enjoy tiki c ...
From $1181 per night (USD)
VRBO
From $270 per night (USD)
VRBO
Colorful Stay at Blue Flamingo | Poolside Bar, Lawn Games, Music & Fire Pits
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Perched at the gateway to Key West, Blue Flamingo Resort immerses guests in island vibes with tiki cocktails, poolside c ...
From $270 per night (USD)
VRBO
From $982 per night (USD)
VRBO
Group Getaway in 3 Ocean-View Rooms | Blue Flamingo Resort Key West with Pools
Bedrooms:
3
Bathrooms:
3
Sleeps:
12
Wake up to the soothing sounds of the ocean in this spacious room at Blue Flamingo Resort. With two queen beds and panor ...
From $982 per night (USD)
VRBO
From $334 per night (USD)
VRBO
Chill & Play in Key West | Pools, Tiki Bar, Games, Fire Pits & Island Eats
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Experience luxury and space in this studio suite at Blue Flamingo Resort, offering uninterrupted ocean vistas. The suite ...
From $334 per night (USD)
VRBO
From $237 per night (USD)
VRBO
Sun, Sip, & Socialize | Island Stay w/ 2 Pools & Backyard Bash
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Located at the entrance to Key West, Blue Flamingo Resort offers a tropical escape with easy access to Duval Street, Mal ...
From $237 per night (USD)
VRBO
From $655 per night (USD)
VRBO
Blue Flamingo Resort Key West | 2 Relaxing Ocean View Rooms for Your Stay
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Wake up to the soothing sounds of the ocean in this spacious room at Blue Flamingo Resort. With two queen beds and panor ...
From $655 per night (USD)
VRBO
From $327 per night (USD)
VRBO
Family-Friendly Two Queen Beds Room Near Key West Hotspots
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Blue Flamingo Resort offers a vibrant stay at Key West's entrance, with easy access to beaches, dining, and entertainmen ...
From $327 per night (USD)
VRBO

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