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Stock Island Rentals

From $287 per night (USD)
VRBO
All-Day Fun in Key West |Lawn Games, Pools & Cabanas, Karaoke Fun, Free Shuttle
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Experience the lively atmosphere of Blue Flamingo Resort, complete with poolside bars and daily entertainment. This room ...
From $287 per night (USD)
VRBO
From $328 per night (USD)
VRBO
Spacious Double Queen Room with Contemporary Touches
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 $328 per night (USD)
VRBO
From $1376 per night (USD)
VRBO
Blue Flamingo Resort l 4 Rooms, Pool, Cabanas, Karaoke & Old Town Shuttle
Bedrooms:
4
Bathrooms:
4
Sleeps:
16
Blue Flamingo Resort offers a vibrant stay at Key West's entrance, with easy access to beaches, dining, and entertainmen ...
From $1376 per night (USD)
VRBO
From $658 per night (USD)
VRBO
Three Rooms w/ 2 Queen beds at Blue Flamingo Resort Key West l 2 Pools & Shuttle
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Stay at Blue Flamingo Resort Key West, featuring comfortable two queen beds and convenient access to South Roosevelt Bou ...
From $658 per night (USD)
VRBO
From $320 per night (USD)
VRBO
Sun, Sip, & Socialize | Island Stay with 2 Pools & Lawn Games
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Situated on a higher floor, this room at Blue Flamingo Resort offers panoramic views of Key West's charming landscape. F ...
From $320 per night (USD)
VRBO
From $270 per night (USD)
VRBO
Tropical Playground | Relaxed Key West Stay w/ Pool, Karaoke Nights & Tiki Bar
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 $424 per night (USD)
VRBO
Your Happy Place in Key West | 2 Pools, Fire Pits, Food Trucks & Free Shuttle
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Indulge in the ultimate Key West experience in this one-bedroom suite at Blue Flamingo Resort, boasting direct ocean vie ...
From $424 per night (USD)
VRBO
From $296 per night (USD)
VRBO
Key West Poolside Paradise w/ Cabanas, Lawn Games & Tiki Bar
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Enjoy the tropical ambiance of Blue Flamingo Resort, featuring lush gardens and vibrant poolside activities. This room p ...
From $296 per night (USD)
VRBO
From $296 per night (USD)
VRBO
Island Charm & Retro Fun | Pools, Comfort Eats, Shuttle & Fire Pits
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Enjoy the tropical ambiance of Blue Flamingo Resort, featuring lush gardens and vibrant poolside activities. This room p ...
From $296 per night (USD)
VRBO
From $409 per night (USD)
VRBO
Shuttle to Town, Stay for the Party, Poolside Fun | Key West’s New Hot Spot
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Key West’s newest island escape offers breezy rooms, poolside cabanas, and nonstop fun. Lounge by the pool, enjoy tiki c ...
From $409 per night (USD)
VRBO
From $316 per night (USD)
VRBO
Poolside Paradise in Key West | Renovated Room, 2 Pools, Games & Live Music
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Blue Flamingo Resort's oceanfront location offers guests breathtaking sea views and easy beach access. This room feature ...
From $316 per night (USD)
VRBO
From $316 per night (USD)
VRBO
Key West Cool | Chill Days, Fun Nights, Poolside Drinks & Lawn Games
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Perched above the vibrant streets of Key West, this room provides sweeping island vistas. With two queen beds and contem ...
From $316 per night (USD)
VRBO
From $334 per night (USD)
VRBO
Live the Island Life | Pool, Lawn Games, Cabanas & Karaoke Nights
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 $316 per night (USD)
VRBO
Poolside Paradise l Fire Pits, Lawn Games, Live Music & Endless Fun
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Perched above the vibrant streets of Key West, this room provides sweeping island vistas. With two queen beds and contem ...
From $316 per night (USD)
VRBO
From $982 per night (USD)
VRBO
Three Rooms w/ 2 Queen beds at Blue Flamingo Resort Key West l 2 Pools & Shuttle
Bedrooms:
3
Bathrooms:
3
Sleeps:
12
Blue Flamingo Resort offers a vibrant stay at Key West's entrance, with easy access to beaches, dining, and entertainmen ...
From $982 per night (USD)
VRBO
From $320 per night (USD)
VRBO
Relax & Play in Key West | Shuttle, Lawn Games & Poolside Dining
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Situated on a higher floor, this room at Blue Flamingo Resort offers panoramic views of Key West's charming landscape. F ...
From $320 per night (USD)
VRBO
From $632 per night (USD)
VRBO
Where Fun Meets Chill | 2 Island View Rooms in Blue Flamingo Resort Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Perched above the vibrant streets of Key West, this room provides sweeping island vistas. With two queen beds and contem ...
From $632 per night (USD)
VRBO
From $1264 per night (USD)
VRBO
Island Views & Comfort | 4 Rooms at Blue Flamingo Key West l Pools & Cabanas
Bedrooms:
4
Bathrooms:
4
Sleeps:
16
Perched above the vibrant streets of Key West, this room provides sweeping island vistas. With two queen beds and contem ...
From $1264 per night (USD)
VRBO
From $424 per night (USD)
VRBO
Carefree Key West Days | 2 Pools, Karaoke Nights, Tiki Drinks & Games
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Indulge in the ultimate Key West experience in this one-bedroom suite at Blue Flamingo Resort, boasting direct ocean vie ...
From $424 per night (USD)
VRBO
From $237 per night (USD)
VRBO
Colorful Key West Escape | Pools, Food Trucks, Karaoke Night & Free Shuttle
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 $327 per night (USD)
VRBO
Laid-Back Luxe | Pools, Comfort Foods, Lawn Games & Shuttle to Fun
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Wake up to the soothing sounds of the ocean in this spacious room at Blue Flamingo Resort. With two queen beds and panor ...
From $327 per night (USD)
VRBO
From $286 per night (USD)
VRBO
Key West Fun Zone: Pools, Lawn Games, Fire Pits, Tiki Cocktails & More
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Experience the lively atmosphere of Blue Flamingo Resort, complete with poolside bars and daily entertainment. This room ...
From $286 per night (USD)
VRBO
From $327 per night (USD)
VRBO
Relax & Have Fun | Key West Poolside Stay w/ Pools, Games & Comfort Eats
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Wake up to the soothing sounds of the ocean in this spacious room at Blue Flamingo Resort. With two queen beds and panor ...
From $327 per night (USD)
VRBO
From $948 per night (USD)
VRBO
Blue Flamingo Key West | Three Island View Rooms w/ 2 Queen Beds
Bedrooms:
3
Bathrooms:
3
Sleeps:
12
Perched above the vibrant streets of Key West, this room provides sweeping island vistas. With two queen beds and contem ...
From $948 per night (USD)
VRBO
From $316 per night (USD)
VRBO
Key West Resort Room | Fun Dining, Pools, Music Nights & Free Shuttle to Town
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Blue Flamingo Resort's oceanfront location offers guests breathtaking sea views and easy beach access. This room feature ...
From $316 per night (USD)
VRBO
From $410 per night (USD)
VRBO
Breezy Key West Stay | Renovated Rooms, Pool, Bar & Nightly Fun
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Enjoy the vibrant energy of Blue Flamingo Resort from this one-bedroom suite overlooking the pool. Featuring a separate ...
From $410 per night (USD)
VRBO
From $1310 per night (USD)
VRBO
Group Getaway in 3 Ocean-View Rooms | Blue Flamingo Resort Key West with Pools
Bedrooms:
4
Bathrooms:
4
Sleeps:
16
Wake up to the soothing sounds of the ocean in this spacious room at Blue Flamingo Resort. With two queen beds and panor ...
From $1310 per night (USD)
VRBO
From $224 per night (USD)
Expedia
Super-cozy boat in 5 Star Key West Marina.
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Escape to paradise on a fully renovated 3 bed 34ft cabin cruiser at a 5-star Key West yacht club for JUST $199/NIGHT! Th ...
From $224 per night (USD)
Expedia
From $133 per night (USD)
VRBO
Charming 1-bedroom/Sleeps 5/kitchenette in the Heart of Key West- , shared pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover the beauty of Key West from this adorable one-bedroom cottage. The cozy space features a queen bed, queen pull- ...
From $133 per night (USD)
VRBO
Click For Pricing
Expedia
Stay Together, Stay Afloat - 4 Bed & 4 Bath - Catamaran in Key West
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Make your Key West getaway unforgettable aboard this stunning 4-bedroom, 4-bath luxury catamaran, docked at a private ma ...
Click For Pricing
Expedia
From $512 per night (USD)
VRBO
Charming 1-Bedroom, 1-Beth Sailboat in wonderful Key West
Bedrooms:
0
Bathrooms:
1
Sleeps:
2
A Unique Key West Getaway! Welcome aboard Sparhawk! This beautiful 30-foot Baba double-ender sailboat offers a cozy and ...
From $512 per night (USD)
VRBO
From $1583 per night (USD)
Expedia
Luxurious 4-Bedroom Catamaran, sleeps up to 8 in delightful Key West
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 $1583 per night (USD)
Expedia
From $2281 per night (USD)
VRBO
The Dreamside House at Lunara Bay
Bedrooms:
8
Bathrooms:
8
Sleeps:
16
Summary: Discover a luxurious new build featuring waterfront views, eight spacious bedrooms and a private pool. This stu ...
From $2281 per night (USD)
VRBO
From $816 per night (USD)
Expedia
FREE TIME 50’ 2 Cabin Yacht Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
All aboard your 50-foot luxury motor yacht in stunning Key West—your adventure starts here! Experience the best of life ...
From $816 per night (USD)
Expedia
From $2925 per night (USD)
VRBO
Modern 46' Yacht 2BR + Salon Bed and 2Bath ~ Key West / Dry Tortugas
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Experience Key West from the water in elevated style aboard this 46’ Sea Ray—your floating luxury suite docked at one of ...
From $2925 per night (USD)
VRBO
From $592 per night (USD)
Expedia
2BR/2BA Beachfront Resort Villa @ Windward Pointe along Atlantic Ocean
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Enjoy a two-bedroom residential-style villa with a fully equipped kitchen, private patio or balcony, washer and dryer, a ...
From $592 per night (USD)
Expedia
From $836 per night (USD)
VRBO
Gorgeous Condo at Hyatt Beach House fantastic amenities
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Situated in the NE corner of Key West, the lushly landscaped Beach House represents island living at its best. Your home ...
From $836 per night (USD)
VRBO
From $527 per night (USD)
Expedia
Docked in Paradise
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Experience the best of Key West from your own private houseboat docked at The Perry Hotel & Marina. Enjoy stunning water ...
From $527 per night (USD)
Expedia
From $1141 per night (USD)
VRBO
Fantasy Fest FUN in Key West! 2-bdrms, 2 baths, Kitchen, Laundry, pool, balcony
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Your Fantasy Fest getaway awaits in Key West. With 2 bedrooms, 2 bathrooms and a fully equiped kitchen, escape to a Flor ...
From $1141 per night (USD)
VRBO
From $880 per night (USD)
Expedia
SERENITY ON SUNRISE ~ 5 BR/5.5 Bath New Town Home w/ Pool & Dockage!
Bedrooms:
5
Bathrooms:
5
Sleeps:
12
MASTERPIECE CANAL ESTATE ON ELEGANT LANE... Located on Key West's only canal system in quiet New Town, this expansive sa ...
From $880 per night (USD)
Expedia
From $394 per night (USD)
VRBO
Rare Beach Front Resort in Key West, Florida- 2 Bedroom/2 Bathroom!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Relax with the whole family at this peaceful place to stay! As our guest, you will have exclusive access to our luxurio ...
From $394 per night (USD)
VRBO
From $581 per night (USD)
Expedia
Accommodates 8 Guests 50% Discount! 3 bedroom boat with AC in amazing Key West
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Discover the charm of “Old Key West” aboard Vita Felice, a Luxurious Vintage Yacht and a piece of American History. Thi ...
From $581 per night (USD)
Expedia
From $250 per night (USD)
VRBO
Glamorous 3BDR/2BA Home in Key West
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Swarovski Sanctuary, a luxurious 3-bedroom, 2-bathroom retreat nestled in a lush tropical garden vibrant. Thi ...
From $250 per night (USD)
VRBO
From $468 per night (USD)
Expedia
Party Like A Local in Key West, 1 bedroom 1 bath yacht at marina.
Bedrooms:
1
Bathrooms:
1
Sleeps:
8
Located in Key West, enjoy what this 1 bedroom house boat has to offer. This delightful property features 1 queen bed, a ...
From $468 per night (USD)
Expedia
From $458 per night (USD)
VRBO
Sentient Waters: 63' Boat With Full Amenities & Sun Deck
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome aboard Sentient, your own private 63’ boat in Key West! We're thrilled to have you & hope you enjoy every moment ...
From $458 per night (USD)
VRBO
From $261 per night (USD)
Expedia
1-bedroom boat at the Perry with AC, fitness room and 2 swimming pools
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Located in Key West, enjoy what this delightful 1-bedroom boat has to offer. With a cozy living room featuring a queen b ...
From $261 per night (USD)
Expedia
Click For Pricing
VRBO
Charming villa in enchanting Key West with AC, fitness room
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Your cozy getaway awaits in Key West at this phenomenal villa. With 2 bathrooms featuring a jetted bathtub and hair drye ...
Click For Pricing
VRBO
From $516 per night (USD)
Expedia
3-bedroom boat in beautiful Key West Sleeps 10 People 50% Off
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Discover the charm of “Old Key West” aboard Vita Felice, a Luxurious Vintage Yacht and a piece of American History. Thi ...
From $516 per night (USD)
Expedia
From $478 per night (USD)
VRBO
Hyatt Windward Pointe, Key West 2-Bdrm Condo Oct 23-26, 2025 Fantasy Fest
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Celebrate Fantasy Fest in beautiful Key West. Enjoy the last full weekend of Fantasy Fest in this 2 bedroom condo that ...
From $478 per night (USD)
VRBO
$Close To Perfect \nTropical Elegance in the Heart of Key West Golf Club w/Pool$
From $194 per night (USD)
Expedia
Close To Perfect \nTropical Elegance in the Heart of Key West Golf Club w/Pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to your private oasis in paradise! This beautifully furnished 2-bedroom, 2.5-bath townhouse is nestled in the l ...
From $194 per night (USD)
Expedia
From $481 per night (USD)
VRBO
RISE AND SHINE ~ Canal Front 3 BR/3Ba Home w/ Heated Pool!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
WONDERFUL WATERFRONT HOME ON GORGEOUS LOT... You have discovered a prime canal sanctuary second to none in the peaceful ...
From $481 per night (USD)
VRBO
From $4490 per night (USD)
Expedia
The Joyrise House at Solaire Lunara Bay
Bedrooms:
6
Bathrooms:
6
Sleeps:
12
Summary: Discover a luxurious new build featuring six spacious bedrooms and a private pool. This stunning home offers ex ...
From $4490 per night (USD)
Expedia
From $3270 per night (USD)
VRBO
The Greenmoor House at Lunara Bay
Bedrooms:
6
Bathrooms:
6
Sleeps:
14
Summary: Discover a luxurious new build featuring six spacious bedrooms and a private pool. This stunning home offers ex ...
From $3270 per night (USD)
VRBO
From $3618 per night (USD)
Expedia
The Fairhaven House at Solaire Lunara Bay
Bedrooms:
8
Bathrooms:
8
Sleeps:
16
Summary: Explore a luxurious new build featuring eight spacious bedrooms and a private pool. This stunning home offers t ...
From $3618 per night (USD)
Expedia
From $256 per night (USD)
VRBO
43' Classic Trawler 5 Star Resort Pools, Views, Dining Free Shuttle to Downtown
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This memorable boat is the perfect home base for your trip to Key West. With 2 pleasant bedrooms featuring queen beds an ...
From $256 per night (USD)
VRBO
From $1164 per night (USD)
Expedia
Luxury on the Sea! 47' Motor Yacht in Beautiful 5-Star Resort!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
You and your guests will have exclusive use of this 47 ft yacht all to yourselves. The yacht stays docked, the entire re ...
From $1164 per night (USD)
Expedia
From $1192 per night (USD)
VRBO
Luxury 2BR Condo • Oceans Edge Resort, Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Enjoy breathtaking ocean views from this 2BR/2BA condo at Oceans Edge Resort in Key West. The master suite features a ki ...
From $1192 per night (USD)
VRBO
From $316 per night (USD)
Expedia
Super-Cozy boat in Key West!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Welcome aboard your Key West getaway! This charming one-bedroom boat is anchored in a peaceful, protected channel with b ...
From $316 per night (USD)
Expedia
$Spacious Fountaine-Pajot S/V \Devine Sailing\ at The Perry Hotel Marina & Resort$
Click For Pricing
VRBO
Spacious Fountaine-Pajot S/V \"Devine Sailing\" at The Perry Hotel Marina & Resort
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
Set sail for a delightful stay on this 5-bedroom boat in Key West. Each room features a cozy queen bed, ensuring a restf ...
Click For Pricing
VRBO

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Stock Island Rentals

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Results: 459 Rentals