
House holiday rentals in Stock Island
Find and book unique houses on Airbnb
Top-rated house rentals in Stock Island
Guests agree: These houses are highly rated for location, cleanliness and more.

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.

The Guest House - Sugarloaf Beach Key West
A truly one-of-a-kind beachfront retreat offering a private sandy beach and dock with boat dockage. This tropical escape delivers a relaxed, family-friendly atmosphere that makes you feel as if you’re on your own private island in the Florida Keys. Enjoy sweeping ocean views and direct access to a natural private beach—ideal for kayaking, paddleboarding, or simply unwinding beneath the swaying palm trees with a book in hand. Perfect for guests seeking both adventure and total relaxation.

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***

Near Duval: Hot Tub, Sleeps 6, Top Location
Just 30 seconds from vibrant Duval Street, this iconic conch home is your perfect Key West escape! With two bedrooms, one bathroom, a full kitchen, and private outdoor perks—like a hot tub, second-story sundeck, and outdoor shower—you’ll have everything you need to relax in paradise. Ideal for up to 6 guests, it’s a tropical haven steps from world-class dining, shopping, and beaches. Book now and soak up the island life! Don’t forget to click the ♥ to save it for later.

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 Anchor 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 Haven 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, March avail 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.

Gone Coastal 2
3 bedroom 2.5 bath home in Coral hammock townhome. Great location walking distance to great restaurants. 10 min Uber ride to Duval street. Community pool is 50 feet from the front door. Guests can use the pool if they arrive prior to 3.
Popular amenities for Stock Island house rentals
House rentals with a pool

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

Keys Island Villa - Venture Out Home 354

Secluded Waterfront home, Views, Dock, Amenities,

Gorgeous Romantic Private Villa, Steps from Duval!

Dolphin Daydreams at Venture Out

Blue Heaven Waterfront Home

Oceanside home 107,dock,kayaks,bikes,pool,fishing,

Paradise Place by AvantStay | Condo w/ Shared Pool
Weekly house rentals

Pelican's Roost, Waterfront comfort at Venture Out

Relaxing Home in the Keys

Ocean Front Home in Great Location

W10 - 4 Bedroom Sombrero Isle Beauty on Crystal Lake

Flamingo Palms-April availability

Waterfront Oasis3/2 Direct Ocean

Waterfront 2-bedroom Home w/Pool and Spa

Beautiful Beachfront Villa w/ Pool/Tiki/Dock
Private house rentals

Oceanfront 2BR in Venture Out - 35’ Dock + Pool

Sombrero Beach Getaway

Cudjoe Key Home with a View

106- Newly Renovated House with Oceanview and Pool

Starlight Serenity - Hideaway with Stunning Views

Waterfront Private Home w/Pool-Family&Pet Friendly

Marathon Paradise

MAY$Save BIG$ Oceanfront 4 BIKES/2Kayaks. KING bed
When is the best time to visit Stock Island?
| Month | Jan | Feb | Mar | Apr | May | June | July | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $700 AUD | $539 AUD | $694 AUD | $600 AUD | $679 AUD | $551 AUD | $485 AUD | $436 AUD | $361 AUD | $465 AUD | $543 AUD | $556 AUD |
| 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 |
Quick stats about house rentals in Stock Island

Total holiday rentals
Explore 30 holiday rentals in Stock Island

Nightly prices starting at
Stock Island holiday rentals start at $194 AUD per night before taxes and fees

Verified guest reviews
Over 2,320 verified reviews to help you choose

Family-friendly holiday rentals
30 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 10 rentals that welcome pets

Holiday 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 holiday 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!
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- Rentals with a kayak Stock Island
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- Rentals with pools Stock Island
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- Rentals with a washing machine and dryer Stock Island
- Rentals with a hot tub Stock Island
- Family-friendly rentals Stock Island
- Rentals with a patio Stock Island
- Fitness-friendly rentals Stock Island
- Waterfront rentals Stock Island
- Pet-friendly rentals Stock Island
- House rentals Monroe County
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- Sombrero Beach
- Smathers Beach
- Long Beach
- Bahia Honda State Park
- Fort Zachary Taylor Historic State Park
- Ernest Hemingway Home & Museum
- Sunset Park
- Seven Mile Bridge
- Key West Lighthouse Museum
- Florida Keys Aquarium Encounters
- The Turtle Hospital
- Key West Butterfly & Nature Conservatory
- Southernmost Point
- Boyd's Key West Campground
- Calusa Beach & Loggerhead Beach
- Boca Grande Key





