Stock Island Rentals
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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 ...
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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 $2925 per night (USD)Expedia
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)Expedia
From $592 per night (USD)VRBO
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)VRBO
From $836 per night (USD)Expedia
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)Expedia
From $527 per night (USD)VRBO
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)VRBO
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)VRBO
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)VRBO
From $394 per night (USD)Expedia
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)Expedia
From $581 per night (USD)VRBO
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)VRBO
From $250 per night (USD)Expedia
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)Expedia
From $468 per night (USD)VRBO
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)VRBO
From $458 per night (USD)Expedia
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)Expedia
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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 ...
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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
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
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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 ...
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