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Villa vacation rentals in Stock Island

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Top-rated villa rentals in Stock Island

Guests agree: these villas are highly rated for location, cleanliness, and more.

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Guest favorite
A spacious dining area features a long wooden table paired with matching benches. Bright artwork adorns the white walls, while a chandelier hangs above. Large glass doors open to a view of the outdoor space, allowing natural light to fill the room.
Villa in Marathon
5 out of 5 average rating, 12 reviews

Harbor hideaway 50’dock 3Br/2Ba All amenities

VACA-23-42 is a charming villa that perfectly serves as your cozy retreat, featuring a private saltwater pool right by the water’s edge. There’s ample space available for your boat, trailer, and several vehicles. Enjoy our bicycles and kayaks during your stay. The property also boasts a tiki hut equipped with a commercial ice machine, grill, and a fish freezer for all your fishing needs. This unique getaway is conveniently situated near all local attractions, making your trip planning a breeze.

Guest favorite
A coastal-style home features a light green exterior with a covered porch and white railings. Colorful chairs are arranged on the lower deck, while stairs lead up to the entrance. The property is adjacent to a calm waterway, enhancing its scenic appeal.
Villa in Cudjoe Key
4.96 out of 5 average rating, 26 reviews

Howard House on the Sea

Oceanfront coastal elegant 10.5 feet from door to ocean with an extraordinary, unobstructed view of sunrises. Dock your 30’ boat here. Designed to make you feel like it’s your home from the minute you walk in the door. Fresh,clean and fabulously landscaped. Gourmet kitchen. Kayaks. Pool. Hot tub, tennis/pickle ball courts, washer/dryer, high speed internet and smart TV. Only 20 minutes north of key west. Fish off the dock! $100 gift card to Square Grouper or Broils for 7 or more night stay

Guest favorite
A serene scene features palm trees silhouetted against a vibrant sunset sky. Warm hues reflect on the water's surface, while string lights hang delicately, adding a soft glow to the beachfront area. A sandy space below invites relaxation and enjoyment of the coastal view.
Villa in Marathon
4.86 out of 5 average rating, 44 reviews

(#4)Beautiful 4 Bed 3 Bath Pool Home w Free Dock

#4: A WAVE💦 FROM IT ALL (Partial Ocean View Property-approximately 150 ft from beach entrance)🌸 Totally Private😉- Turn-Key and fully Stocked- Single Family Home 4BR/3BA with your own Heated-Cooled Private Swimming Pool 🤿and BBQ Patio. Includes Private Guest Beach🏖 with Kayaks and Paddle boards and Private powered ⛵Boat Dock right on the Gulf of Mexico! 🌅🥂 Kick back and completely🍷 relax in our Beautiful and 🍹comfortable home! Perfect for 🍻Adults and kids of all Ages!

Villa in Cudjoe Key
New place to stay

Eco Friendly Secluded OceanView Pool near Key West

Bring the whole family to this great place with lots of room for fun Private Secluded Ocean View & Pool Near Key West This beautiful Eco-friendly Ocean view home is away from the hustle-bustle of Key West. Welcome to this luxury deluxe vacation home that can comfortably accommodate for a large family. Come to Beautiful Key West and stay in this immaculate, beautifully furnished Home in the beautiful 2-acres green lush tropical Estates.

Superhost
The shared community pool is surrounded by tropical palm trees and lush landscaping. Lounge chairs are arranged around the pool area, and a thatched-roof hut provides shade. The pool features a curved shape with clear blue water reflecting the sky.
Villa in Key West
4.66 out of 5 average rating, 53 reviews

Coral Villa by AvantStay| Close 2 DT Key West!

- Minutes from Key West's restaurants & bar - Back patio and balcony off of the bedroom and living area - Shared community pool and clubhouse - Close to Downtown

Superhost
A shared pool area is surrounded by lush tropical landscaping, featuring palm trees and vibrant greenery. Lounge chairs are arranged around the pool, which reflects the bright blue sky and fluffy white clouds, creating a relaxed atmosphere for guests.
Villa in Key West
4.9 out of 5 average rating, 39 reviews

Coral Palm by AvantStay | Mins From DT Key West

- Shared Pool - Located in the private gated community - >5 miles from downtown Key West - Private porch & outdoor dining space

Popular amenities for Stock Island villa rentals

Kitchen
Wifi
Pool
Free parking on premises
Air conditioning

Private villa rentals

Guest favorite
A serene scene features palm trees silhouetted against a vibrant sunset sky. Warm hues reflect on the water's surface, while string lights hang delicately, adding a soft glow to the beachfront area. A sandy space below invites relaxation and enjoyment of the coastal view.
Villa in Marathon
4.86 out of 5 average rating, 44 reviews

(#4)Beautiful 4 Bed 3 Bath Pool Home w Free Dock

Superhost
The shared community pool is surrounded by tropical palm trees and lush landscaping. Lounge chairs are arranged around the pool area, and a thatched-roof hut provides shade. The pool features a curved shape with clear blue water reflecting the sky.
Villa in Key West
4.66 out of 5 average rating, 53 reviews

Coral Villa by AvantStay| Close 2 DT Key West!

Guest favorite
A spacious dining area features a long wooden table paired with matching benches. Bright artwork adorns the white walls, while a chandelier hangs above. Large glass doors open to a view of the outdoor space, allowing natural light to fill the room.
Villa in Marathon
5 out of 5 average rating, 12 reviews

Harbor hideaway 50’dock 3Br/2Ba All amenities

Guest favorite
A coastal-style home features a light green exterior with a covered porch and white railings. Colorful chairs are arranged on the lower deck, while stairs lead up to the entrance. The property is adjacent to a calm waterway, enhancing its scenic appeal.
Villa in Cudjoe Key
4.96 out of 5 average rating, 26 reviews

Howard House on the Sea

Superhost
A shared pool area is surrounded by lush tropical landscaping, featuring palm trees and vibrant greenery. Lounge chairs are arranged around the pool, which reflects the bright blue sky and fluffy white clouds, creating a relaxed atmosphere for guests.
Villa in Key West
4.9 out of 5 average rating, 39 reviews

Coral Palm by AvantStay | Mins From DT Key West

Villa in Cudjoe Key
New place to stay

Eco Friendly Secluded OceanView Pool near Key West

Villa rentals with a pool

Guest favorite
A serene scene features palm trees silhouetted against a vibrant sunset sky. Warm hues reflect on the water's surface, while string lights hang delicately, adding a soft glow to the beachfront area. A sandy space below invites relaxation and enjoyment of the coastal view.
Villa in Marathon
4.86 out of 5 average rating, 44 reviews

(#4)Beautiful 4 Bed 3 Bath Pool Home w Free Dock

Superhost
The shared community pool is surrounded by tropical palm trees and lush landscaping. Lounge chairs are arranged around the pool area, and a thatched-roof hut provides shade. The pool features a curved shape with clear blue water reflecting the sky.
Villa in Key West
4.66 out of 5 average rating, 53 reviews

Coral Villa by AvantStay| Close 2 DT Key West!

Guest favorite
A spacious dining area features a long wooden table paired with matching benches. Bright artwork adorns the white walls, while a chandelier hangs above. Large glass doors open to a view of the outdoor space, allowing natural light to fill the room.
Villa in Marathon
5 out of 5 average rating, 12 reviews

Harbor hideaway 50’dock 3Br/2Ba All amenities

Guest favorite
A coastal-style home features a light green exterior with a covered porch and white railings. Colorful chairs are arranged on the lower deck, while stairs lead up to the entrance. The property is adjacent to a calm waterway, enhancing its scenic appeal.
Villa in Cudjoe Key
4.96 out of 5 average rating, 26 reviews

Howard House on the Sea

Superhost
A shared pool area is surrounded by lush tropical landscaping, featuring palm trees and vibrant greenery. Lounge chairs are arranged around the pool, which reflects the bright blue sky and fluffy white clouds, creating a relaxed atmosphere for guests.
Villa in Key West
4.9 out of 5 average rating, 39 reviews

Coral Palm by AvantStay | Mins From DT Key West

Villa in Cudjoe Key
New place to stay

Eco Friendly Secluded OceanView Pool near Key West

Family-friendly villa rentals

A sparkling pool is set against a backdrop of lush greenery and calm water. A hammock is suspended between palm trees, inviting relaxation. Surrounding the pool, well-maintained landscaping features vibrant plants and manicured grass, enhancing the serene outdoor space.
Villa in Marathon
4.75 out of 5 average rating, 4 reviews

Villa Sombrero

Guest favorite
Villa in Marathon
4.96 out of 5 average rating, 28 reviews

Discount to Jan 31! Outdoor TV! Lots of Amenities!

The canal front property features a two-story home with a spacious patio and a private pool surrounded by lounge chairs. A covered dock extends along the water's edge, providing access for boating. Lush greenery and palms enhance the scenic view of the outdoor space.
Villa in Marathon
4.76 out of 5 average rating, 37 reviews

Discount Available-Pool/Dock/Bikes/Local Beach

Top guest favorite
A private heated pool is surrounded by a spacious patio with laid brick flooring. Palm trees frame the scene, while a vibrant sunset casts warm colors across the sky. Lounge chairs are positioned by the pool, inviting relaxation by the serene water view.
Villa in Marathon
4.95 out of 5 average rating, 146 reviews

Private 4/3 Pool Heater/Dock/Kayaks/Bikes,etc

Guest favorite
A shaded Tiki Hut features comfortable seating arranged around a small pool. A television is mounted on the bamboo ceiling, with a view of vibrant kayaks resting nearby. Sun loungers align along the poolside, surrounded by lush greenery and a white fence.
Villa in Marathon
4.9 out of 5 average rating, 39 reviews

5% Off Thru January - 4Bed 3Bath! Tiki Hut w/ TV!

Superhost
A two-story house is set against a clear blue sky, featuring balconies and a light blue exterior. A wooden dock extends into tranquil water, with paddleboards and kayaks visible. A heated pool is surrounded by palms, offering a relaxing outdoor space.
Villa in Marathon
5 out of 5 average rating, 4 reviews

Marathon Villa w/ Priv Pool/Dock

Guest favorite
A Tiki Hut is seen with a thatched roof and an inviting seating area featuring plush cushions. A large grill is positioned nearby, and a flat-screen TV is mounted above. The backdrop includes a large private pool surrounded by green foliage, creating a relaxed outdoor space.
Villa in Marathon
5 out of 5 average rating, 9 reviews

Discount to Jan 31! Private Pool, Fun Amenities!

Quick stats about villa rentals in Stock Island

  • Nightly prices starting at

    Stock Island vacation rentals start at € 266 per night before taxes and fees

  • Verified guest reviews

    Over 90 verified reviews to help you choose

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Stock Island rentals

  • 4.9 Average rating

    Stock Island stays are highly rated by guests—averaging 4.9 out of 5!

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