
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 514 per night before taxes and fees

Verified guest reviews
Over 2,320 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
20 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.

Gorgeous Romantic Private Villa, Steps from Duval!
Located 20 yards from historic Duval St in the heart of Old Town Key West w/ free ... first-come, first-serve PARKING in front (4 spots). Totally remodeled, beautiful spacious & private 2 story villa sleeps 4 comfortably. New furnishings, free hi-speed wifi, 65" smart tvs, ice machine, electric fireplace in large master suite, lush garden courtyard & shared plunge pool. We provide 2 coffee/tea stations. Walking distance to everything - convenience store, CVS, bars, restaurants & entertainment.

Duval Vibes • Pool • 10 Guests
Located only 30 seconds from Duval Street, this house will be your Key West headquarters for bachelor parties, family reunions, or any celebration that bring you to town. This 3 bedroom/ 2.5 bathroom home has a full kitchen, spacious outdoor living space, outdoor shower, private second story sundeck, and a pool. Your group of up to 10 will love being steps away from all KW has to offer- be Hemingway's neighbor! Add this listing to your wishlist by clicking the ♥ in the upper right hand corner.

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.

Tiki Time! Private Pool~Tiki Hut~Kayaks~Grill!
Tiki Time ~ your private paradise in beautiful Marathon, heart of the Florida Keys! This is the perfect place for a family vacation or relaxing getaway. Gorgeous 3BR home with your own private salt water pool, Tiki Hut, space to park a 30' boat/trailer, and ocean views from the balcony~Kayaks, grill, beach toys await you for your beautiful day in the Florida Keys! Less than 5 min to Sombrero Beach, Dining & Local Bars! Experience the Florida Keys like a local and book Tiki Time today!

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***

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.

Angler’s Terrace Conde Nast Traveler’s Best Airbnb
As published in Condé Nast Traveler, this is one of the best Airbnb's in Florida. Newly Built two story Tropical Oasis with pool has been thought-out meticulously. An open, very light & spacious floor plan, carefully appointed furnishings, and great location provide the perfect surroundings. Decorated with a Zen sensibility, It’s outdoor Patio deck and Rooftop Terrace extends your living space into the private quiet ocean setting with panoramic views

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!

Waterfront Cozy Modern Retreat w/Deep Canal
Welcome to our beautiful waterfront home in Marathon! Our smoke-free property is modern, clean and features a 37ft long concrete dock, perfect for boating and fishing enthusiasts. With easy access to the movie theater, Sombrero Beach, Turtle Hospital, Publix, Walgreens, and delicious restaurants, you'll have everything you need right at your fingertips. We can't wait for you to experience the peacefulness and convenience of our lovely home.

*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.

Spacious 3Br/3Ba, 70ft Dock, Beach VACA23-16
Enjoy the boutique decor of our large, spacious home. Our place is a short distance from Sombrero Beach, with bicycles available to ride there. Our property is on a wide and deep canal, with both ocean and gulf access. Our dock is 70 ft, so ideal place for large boats, or you can even bring 2 boats. Free parking, with space to park boat trailer. We include free passes to the Sea Turtle Hospital to guests.
Popular amenities for Stock Island house rentals
House rentals with a pool

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

Beach House in Marathon with Amazing Backyard!

July12-16,Waterfront/Pool/Golf cart/Bikes/muchmore

Florida Keys Resort-Style Home w/ Pool & Dock 5/3

Tropical Keys Retreat | Pool | Hot Tub | Cinema

Oceanside home 111, dock,kayaks,bikes,pool,fishing

Tiki Time in Cudjoe Key 136

Luxury Boating Paradise+Pool+Sailing Kayaks
Weekly house rentals

Luxe Super Snapper-Heated Pool, Tiki, Dock, Lanai

Flamingo Palms-JUNE Dates available at a discount!

Searenity Vacation Rental! Pool, Tiki Hut, Dockage

Oceanfront mermaid house pool and dock

Waterfront Oasis3/2 Direct Ocean

Blue Heaven Waterfront Home

Relaxing and Inviting home with 35' dock

Catherine House: A charming Old Town Key West
Private house rentals

Waterfront with Boat Lift/Kayaks and Hot Tub

Private Home,Hot Tub,BBQ.Boat & RV Parking FL Keys

Tiki Hut w/TV, Pool, Kayak, Paddleboards, Bikes!

Cudjoe Key Home with a View

Butterfly Cottage~ Enjoy hot tub, gourmet kitchen

Fisherman's Paradise Cudjoe Key

Casa Margarita - Steps to the historic seaport

Oceanview Marathon - Screened Porch, Theater & Bar
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 |
Destinations to explore
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- Boat rentals Stock Island
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- Rentals with a kayak Stock Island
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- Fitness-friendly rentals Stock Island
- Pet-friendly rentals Stock Island
- Villa rentals Stock Island
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- Rentals with a hot tub Stock Island
- Waterfront rentals Stock Island
- Beachfront rentals Stock Island
- Rentals with beach access Stock Island
- Hotel rooms Stock Island
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- Family-friendly rentals Stock Island
- Rentals with a fire pit Stock Island
- House rentals Monroe County
- House rentals Florida
- House rentals United States
- Sombrero Beach
- Smathers Beach
- Ernest Hemingway Home & Museum
- Bahia Honda State Park
- Seven Mile Bridge
- The Turtle Hospital
- Florida Keys Aquarium Encounters
- Fort Zachary Taylor Historic State Park
- Key West Butterfly & Nature Conservatory
- Southernmost Point
- Key West Lighthouse Museum
- Boca Grande Key
- Mel Fisher Maritime Museum
- Curry Hammock State Park
- Key West Aquarium
- Truman Little White House





