
Holiday rentals with a pool in Stock Island
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Top-rated rentals with a pool in Stock Island
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

Fully renovated 2/2 bath condo w/ shared pool!
**Brand New Listing** Welcome to Captains Choice - The NICEST Unit at Sunrise Suites Key West, unit 302. Tropical winds, sunset views and Key West charm await when you book your stay in this gorgeous completely renovated two bedroom, two bathroom condo "Captain's Choice". Highlights include: Smart TVs in each room Keurig New stainless Kitchen/appliances In-unit, full size washer/dryer Located near restaurants, a convenience store, & Smathers Beach End unit One parking space, free of charge

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.

Historic Cigar House. 3rd floor Suite W/Kitchen
This unit is located in the historic "Cigar House" of the Island City House Hotel. Unit 12 is on the 3rd floor and is one of the most requested units in the entire hotel. Your private balcony overlooks the pool. Only 3 blocks from Duval street so close everything, yet quiet enough for a good nights sleep. You will have your own private entrance and use of all the hotel amenities. The space is a private 1BR with a kitchen and NEW sleeper sofa (12/23). In Old Town, walk to everything.

Gorgeous Ocean View in Paradise, Close to Key West
This is paradise! Wake up to a gentle breeze and birds singing just outside your balcony. Watch the sunrise over the ocean and mangroves from your private balcony. Enjoy your privacy as you start your day, then venture out to explore all that Key West has to offer: water sports, quaint shops, delicious food, history all around you, and so much more! On property features: Pool, Hot Tub, Yellowfin Bar & Kitchen and Parking. Beach supplies included: Coolers, Snorkel Gear and Beach Towels.

The Writer's Block- Key West
Discover tranquility aboard this unique floating haven. It's a sleek modern retreat for those who crave space to read, write or find inspiration far from the stresses of the modern world --yet it's steps away from upscale restaurants, two fabulous pools, a gym and so much more. From a king bed to a full-sized shower and kitchenette, you'll enjoy the comforts of home while living directly on the water. Features a large private deck with panoramic views of the marina and its glorious sunsets.

Ocean front 1BR/1BA Suite w/ kitchen & living rm
1BR 1BA ocean front suite with a living room, kitchen and one bedroom. Doors that open to a balcony overlooking the Atlantic Ocean. Heated pool, hot tub, sun deck and a private sandy beach on the Atlantic ocean. 5 minutes walk to Duval street and the most Southern Point. Located between the prestigious Casa Marina and the top restaurant on the island Louise Back Yard. Free garage parking. Washer, dryers and ice maker are available for guests. Powerful, but sometimes noisy central a/c.

The Lighthouse - Beach Houses Key West
If you’re reading this, you’re already one step closer to paradise. Thank you for considering us for your getaway. Our charming Lighthouse Bungalow is a 2-bedroom, 1-bath loft-style retreat located just steps from our private beach. The master bedroom loft, accessed by a spiral staircase, offers a stunning bird’s-eye view of the Atlantic Ocean. The nautical-inspired living area opens to an exterior deck overlooking the beach—an ideal spot for peaceful mornings and ocean breezes.

Tropical Old Town Bungalow
Great Location, Close to Duval & Beach Welcome to paradise! This Tropical Old Town Bungalow is located perfectly between Key West’s best beaches and the best restaurants and nightlife! The rental unit sits right between the White Street Art Gallery District and the Historic District, which features some of Key West’s most historic homes and properties. Whether you are walking, riding bikes or grabbing a quick cab, no destination is too far from this conveniently located rental.

Poolside Cottage #412
Welcome! This beautiful cottage is located in the Coconut Mallory Resort & Marina on the eastern end of KW. This secluded, waterfront oasis includes outdoor pools, hot tub, on-site marina and dock. There's also a new bar & grill, Gumbo's, in the resort. When you want to get out and explore KW, you're only minutes from beaches, the seaport and world famous Duval Street! Bikes, golf carts, kayaks, stand-up paddleboards and other watercraft can all be rented locally!

Tropical Escape at Sunrise
We thoroughly sanitize upon check-out. This luxurious condo features a wonderful tropical interior design. It includes 2 spacious BR's: king bed/ full bath, queen bed/ full bath). Our living room sofa bed accommodates 1 guest. A fully equipped kitchen. Patio overlooks pool. WiFi, basic cable, 3 TV's, A/C, washer-dryer, workout center, BBQ, tennis court, elevator, parking. Accommodates no more than 5 guests. Must be 25 and older.

The simple life on Seaplicity!
Come stay on our beautiful & Super Comfy 38 ft Hunter Sailboat at the Perry Hotel & Marina! Start your morning with a fresh cup of coffee on board & "SIMPLIFY" your vacation with unrestricted access to all resort amenities! Two heated salt water pools, gym, laundry, and bathrooms and try one of the great restaurants onsite. Shuttle service takes you to old town Key West, leaving every hour from the hotel lobby.

Duval Street Suites with full kitchen heated pool,
Mile Zero Suite is a one bedroom (queen) 1 bath suite with a sleeper sofa (queen) and kitchen. Overlooking Duval street in historic Old Town, Key West. Free parking available and the pool is privately located behind the building . Located in the middle of everything yet quiet and away from it all. This space is truly unique and sure to please all ages.
Popular amenities for Stock Island rentals with a pool
House rentals with a pool

Key West Paradise

Keys Island Villa - Venture Out Home 354

Cancellation Deal: March 21 thru March 28

Cozy 2 br/2 bath home in Cudjoe

Gorgeous Romantic Private Villa, Steps from Duval!

Coral Hammock Poolside Home 3 bdrm 3 bath10 minute

Jan. Save $!$ Oceanfront 4 Bikes/2Kayaks. KING bed

Angler’s Terrace Conde Nast Traveler’s Best Airbnb
Condo rentals with a pool

Canal View Condo w/ Pool, Balcony & Bar

Family Suite at Sugarloaf Key Hotel (Pet Friendly)

Magical Sunrises on the Atlantic, Upgraded Condo &

Affordable Beachfront Luxury Condo Sleeps 6

A Perfect Getaway

Downtown Key West 2BR/2BA•Pool, Dock, Pet "Aruba"

Superb 2 BR 2 bath condo in waterfront resort

Coral Palms 1BR/King/Queen, Pool, block to Duval
Other holiday rentals with a pool

Castaway Cove: Pet-friendly 2/2 condo near beach!

Coral Garden by AvantStay | Gated Community w/Pool

Secluded Waterfront home, Views, Dock, Amenities,

Key West Condo 2B/2B with Pool & Boat FREE Slip

Blue Heaven Waterfront Home

Rise And Shine On The Water

Key West • 2 Cabin • Yacht by Luxury Sea Charters

Beautiful Cottage & Amenities in Gated Community
When is the best time to visit Stock Island?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $588 AUD | $632 AUD | $579 AUD | $546 AUD | $486 AUD | $457 AUD | $443 AUD | $415 AUD | $360 AUD | $455 AUD | $477 AUD | $549 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 holiday rentals with a pool in Stock Island

Total holiday rentals
Explore 330 holiday rentals in Stock Island

Nightly prices starting at
Stock Island holiday rentals start at $178 AUD per night before taxes and fees

Verified guest reviews
Over 11,970 verified reviews to help you choose

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

Pet-friendly accommodation
Find 90 rentals that welcome pets

Rentals with dedicated workspaces
180 properties have a dedicated workspace

Wi-Fi availability
300 of Stock Island holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Stock Island rentals

4.7 Average rating
Stock Island stays receive an average rating of 4.7 out of 5 from guests
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- Key West Lighthouse Museum
- Ernest Hemingway Home & Museum
- Sombrero Beach
- Smathers Beach
- The Turtle Hospital
- Calusa Beach & Loggerhead Beach
- Long Beach
- Bahia Honda State Park
- Fort Zachary Taylor Historic State Park
- Sunset Park
- Florida Keys Aquarium Encounters
- Seven Mile Bridge
- Key West Butterfly & Nature Conservatory
- Southernmost Point
- Boyd's Key West Campground




