
House vacation rentals in Stock Island
Find and book unique houses on Airbnb
Quick stats about house rentals in Stock Island

Total vacation rentals
Explore 30 vacation rentals in Stock Island

Nightly prices starting at
Stock Island vacation rentals start at ﺩ.ﺇ 477 per night before taxes and fees

Verified guest reviews
Over 2,570 verified reviews to help you choose

Family-friendly vacation rentals
30 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Vacation rentals with a pool
30 properties feature pools

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
30 of Stock Island vacation rentals include wi-fi access

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!
Top-rated house rentals in Stock Island
Guests agree: these houses are highly rated for location, cleanliness, and more.

Sea Glass Cottage in Historic Key West
Spend time in beautiful Key West and live like a local in a Conch Home! The Sea Glass Cottage is perfect for groups with 4-6 guests & a furry friend! A fully-renovated 2 bedroom, 2 bath home on the second floor with a queen pull-out sofa. Located in an historic neighborhood in downtown KW near beaches, and parks. Enjoy beautiful foliage on your private porch with seating/ grill. Reserve its sister cottage, the Coral Cottage, to accommodate parties of 8-10 in separate units within the same home.

Harrison's Hideaway-Sleeps up to 4, K & F Sl Sofa!
Historic Harrison's Hideaway is in an 1880's Cigar Maker's cottage renovated in 2010. It features a K size Pottery Barn memory foam bed, custom made full sleeper sofa, renovated kitchen with granite counter tops, 2 burner stove, under counter fridge/freezer, dishwasher, microwave, air fryer/oven tumbled marble 2 person shower, private front deck with seating for 4, 2 person Solana spa. Perfect for a couple or a family with children. Freshly painted a Caribbean blue with plantation shutters.

Luxury Home- Parking, Bikes, WI-FI, Big Pool.
Very clean and spacious, including parking, bikes, wifi, pool and close to many restaurants Luxury 2 /2 1/2 condo sleeping 6 *1100 sq. ft *FREE Covered Parking *7 Bikes FREE - included *Queen bed each room with private bath *FREE wifi *All linens/bath/beach towels included *Huge heated pool *Clubhouse/fitness ctr *Queen sleeper sofa with 5" thick memory foam mattress (very comfortable) *AC *Near many eateries *Coolers *Gas Grill *42" SONY TV -Fire Stick- no cable Maximum 6 person occupancy

Casa Calypso 3bed3bath sleeps 8 beautiful decorate
Bring the whole family to this great place with lots of room for fun. Very clean, organized stand alone house with everything you will need to have a great stay! Fully stocked kitchen with a kuerig and drip coffee pot. Can have twin beds downstairs or convert into a king. Two king bedrooms upstairs. Each bedroom has its own bath! A queen sleeper couch in living room with a screen divider for privacy if needed. Steps away from the large heated community pool. Several nice restaurants around.

Starlight Serenity - Hideaway with Stunning Views
Escape to paradise at this serene 1-bedroom, 1-bath home in beautiful Sugarloaf Key sleeping up to four guests. Enjoy breathtaking views from the expansive wrap-around balcony, perfect for sunrise coffee or sunset cocktails. The spacious outdoor area is ideal for dining, lounging, and soaking in the tropical ambiance. Whether you're relaxing indoors or savoring the outdoors, this home offers the perfect blend of comfort and tranquility. Book your next getaway for 3 nights or more!

Waterfront Sanctuary in the Keys!
Your WATERFRONT Keys getaway!! Updated appliances & fixtures, this 2BR/2BA elevated property won’t disappoint! Fully stocked kitchen/bathrooms. Never ending activities for your group at the Venture Out Resort- a gated community with oversized pool, hot tub, pickle ball/tennis/basketball courts, fishing, lobstering, biking, kayaking, boating! Launch your boat from the private ramp and tie it up on our 35’ seawall! Situated between Key West & Marathon, this property is THE PLACE!

Spanish Queen @Venture Out
Experience the beautiful Florida Keys and stay at the popular Venture Out Private Community at Cudjoe Key. Newly furnished two-bedroom, 2 bath stilt home checks all the boxes for the ultimate Florida Keys Vacation. Sun- filled open floor plan allows family to spend the their precious time together cooking and entertaining. Two-2 person kayaks and 4 bikes included *** Please note that guests must pay a resort entry fee of $125 directly to security upon entry into the park***

Cudjoe Key Home with a View
We are so excited to share our little piece of paradise with you! Our unit is located a short walk away from all the amenities the Venture Out community has to offer such as a pool, hot tub, lagoon, bocce ball, tennis courts, playground and boat marina. On the property we have a 2-person hybrid kayak for your enjoyment. We also provide table games (we love a game night) as well as the equipment to play bocce ball and darts which can be played in the recreation center.

Palm Breezes! Room for Everyone on the Ocean.
This 5 bedroom 3 bath house with pool on Ocean front property on Highway 1.. This lovely home has its own huge pool area with full lounge chairs all the way around pool area, the pool is heated. Grill, Jacuzzi. Full WiFi. TVs in every bedroom! Travel down our private dock way to the beautiful Cudjoe Bay, hop one of the many kayaks and take a healthy paddle with your friends/family or just enjoy the breathtaking ocean view while you sit on the porch.

Waterfront Haven House with Boat Basin & Ramp!
Welcome to Paradise! Stay in the amazing Keys and beautiful waterfront home with boat basin and ramp for your boat. The property lot is almost an acre with another rental home and still very spacious (search for Anchor House to reserve both homes if available). Stunning panoramic water views, sunrise and sunset. Steps away from ocean water. Bring or rent fishing and snorkel gear nearby to fish right off the point and enjoy the underwater scenery!

Hemingway - Beach Houses Key West
If you’re reading this, you’re already on the path to paradise! Thank you for considering us for your dream vacation—we can’t wait to host you. Off the beaten path you will find a unique location and a beach front bungalow with endless unobstructed views of the ocean from every bedroom. Featuring an open family area, full kitchen, deck and its own tiki, excellent for grilling, having a cold drink or just gazing at the ocean.

*Emerald Seas*-Florida Keys Ocean Front Paradise!
Welcome to our Florida Keys Ocean Paradise, Emerald Seas! Truly a special place to get away and relax. Enjoy the crystal-clear waters and amazing views. Bring or rent a boat, look for sea turtles, manatees, dolphins, lobster & tropical fish right from your patio or dock. Take in a glorious sunrise or moonlit night over the water. The amazing, 180 degree panoramic ocean views will take your breath away every moment you are there.
Popular amenities for Stock Island house rentals
House rentals with a pool

Keys Island Villa - Venture Out Home 354

Key West Paradise

Mermaid's Retreat at Coral Hammock Spacious 3BR Ne

KW CanalFront 3BR: Htd Pool, Boat Tie-Up, Pet OK

Gorgeous Romantic Private Villa, Steps from Duval!

Tiki Time in Cudjoe Key 136

White House - Receive $400 towards a Boat Rental!

JULY/AUG. Save$ Oceanfront 4 BIKE/2 Kayak KING Bed
Weekly house rentals

Pelican's Roost, Waterfront comfort at Venture Out

Aug. Discount, Waterfront Retreat/Pool/golf cart

Ocean~View w/ Dock, Pool, Kayaks, King Bed

Blue Heaven Waterfront Home

Oceanfront Cottage with Open Water Views

Waterfront 2BR w/ Dock & Pool Access

Beachfront Condo w/ Pool & Hot Tub | Papaya Place

Atlantis House Suites
Private house rentals

Waterfront, Dock, Pool, Pickleball, near Key West!

Relaxing Cottage in Cudjoe

106- Newly Renovated House with Oceanview and Pool

Cozy 2 br/2 bath home in Cudjoe

Ocean Breeze Retreat w/ Dock| Keys Escape

Relaxing and Inviting home with 35' Private Dock

Island Villas Rentals

Fisherman's Paradise Cudjoe Key
When is the best time to visit Stock Island?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ 1,638 | ﺩ.ﺇ 1,737 | ﺩ.ﺇ 2,027 | ﺩ.ﺇ 1,587 | ﺩ.ﺇ 1,796 | ﺩ.ﺇ 1,458 | ﺩ.ﺇ 1,282 | ﺩ.ﺇ 1,153 | ﺩ.ﺇ 955 | ﺩ.ﺇ 1,230 | ﺩ.ﺇ 1,436 | ﺩ.ﺇ 1,469 |
| Avg. temp | 21°C | 22°C | 24°C | 25°C | 27°C | 29°C | 30°C | 30°C | 29°C | 27°C | 25°C | 23°C |
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- Rentals with a hot tub Stock Island
- Rentals with a washer and dryer Stock Island
- Rentals with pools Stock Island
- Fitness-friendly rentals Stock Island
- Pet-friendly rentals Stock Island
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- Boat rentals Stock Island
- Rentals with outdoor seating Stock Island
- Rentals with a patio Stock Island
- Family-friendly rentals Stock Island
- Beachfront rentals Stock Island
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- Rentals with a kayak Stock Island
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