Holiday rentals in Stock Island

A modern living area features a spacious layout with a comfortable seating arrangement and a large flat-screen TV mounted on the light green wall. Natural light floods in through expansive glass doors, revealing views of the outdoors. A stylish kitchen island with sleek countertops complements the space.

4.95 out of 5 average rating, 179 reviews

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

A charming entrance is framed by lush tropical plants and palm trees. The light green door complements the inviting beige exterior of the home. A cozy seating area is situated on the porch, and brick pathways lead through a landscaped yard filled with vibrant foliage.

4.96 out of 5 average rating, 70 reviews

Vacation Home Heron Hideaway

Welcome to our unique and charming Airbnb. This cozy retreat offers the perfect blend of comfort and style, featuring a private porch where you can relax and enjoy the island breeze. Take a dip in the refreshing pool or unwind in the private hot jacuzzi after a day of exploring. Enjoy cooking a delicious meal on the grill, and experience a peaceful stay in a one-of-a-kind space. Whether you're here to relax or explore, our home provides everything you need for an unforgettable Key West getaway!

The property is positioned near the shoreline, featuring a modern design with multiple balconies. Lush palm trees frame the exterior, while a landscaped garden adds greenery. The serene ocean can be seen in the background under a twilight sky.

4.86 out of 5 average rating, 7 reviews

Hyatt Windward Pointe! Great Location!

This Oceanside property has a two bedroom villa that features a master suite with king bed and adjoining bath with walk-in shower and jetted tub, guest bedroom with queen bed and full bath and a living room with a pull out sleeper sofa, TV and Wi-Fi internet access. The unit can accommodate up to 6 people. It features a full kitchen with granite countertops and appliances, including a full size fridge, stove-top burners, a microwave, a sink, a coffee maker, and a toaster. The unit also features

4.97 out of 5 average rating, 286 reviews

Home in Key West

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.

Aerial view showcasing a waterfront property bordered by vibrant green mangroves. The calm turquoise water reflects the blue sky dotted with white clouds. A marina with docked boats is visible nearby, creating a serene coastal landscape.

5 out of 5 average rating, 111 reviews

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.

Houseboat in Stock Island

A spacious sleeping area features a king bed dressed in soft linens and adorned with decorative pillows. Natural light enters through sliding glass doors that open to views of the marina. Warm wood flooring complements the modern design.

4.95 out of 5 average rating, 44 reviews

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.

Houseboat in Stock Island

The exterior of the houseboat is showcased, featuring a spacious upper sun deck with white railings. A staircase leads from the deck down to the dock. The houseboat is moored in calm waters, surrounded by sailboats and a clear blue sky adorned with scattered clouds.

4.87 out of 5 average rating, 30 reviews

Stella on Stock Island

Perched on the shimmering waters, this 1 bedroom, 1 bath houseboat epitomizes cozy waterfront living. Step inside and you'll find yourself welcomed into an inviting living space. The living area transitions into a kitchen complete with essential appliances. Down the hall from the living area lies the bedroom offering a peaceful haven for rest and relaxation after a day spent exploring. An elegantly appointed bathroom awaits, featuring modern fixtures and amenities. Queen Bed & Sofa Bed

Superhost

A spacious living area displays a blue sectional sofa, accented with patterned throw pillows. A wooden coffee table is positioned in front, featuring a small potted plant and a woven basket. The open-concept kitchen is visible in the background, equipped with modern appliances.

Flat in Stock Island

4.89 out of 5 average rating, 76 reviews

"Key Lime" 1 bedroom at Leo's

Our "Key Lime” one-bedroom apartment located in Stock Island is the perfect place for your Key West getaway. Located only two blocks from the entrance to Key West, you can easily ride a bicycle, scooter, or golf cart into town. This unit is located inside Leo’s RV Park, where guests can enjoy shared amenities including common-area tiki huts, outdoor ping pong, chess, billiards, and beautiful views of our nature preserve. For the comfort of all guests, pets are not allowed in this unit.

The living room features a spacious green sofa complemented by wicker armchairs. A glass dining table sits at the center, with light streaming through open shutters. The backdrop showcases ocean views, enhancing the connection to the balcony and natural surroundings.

4.86 out of 5 average rating, 59 reviews

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.

A spacious wooden deck features two light blue lounge chairs and a white umbrella, offering a relaxing spot to enjoy ocean views. The gentle waves of the Atlantic can be seen in the background, while the shore is lined with natural sand and small rocks.

4.97 out of 5 average rating, 111 reviews

Hidden Beach unit 1 The Perfect Place to stay

This place is extraordinary. There is nothing like it in Key West. Just 3 blocks from Duval Street, this property sits on Key West’s only natural beach. Hidden Beach is right on the Atlantic Ocean nestled between Key West’s best restaurant (Louie’s Backyard) and the beautiful, luxurious Reach Resort.Here, you can enjoy spectacular views and sunsets from one of the islands only private beaches or you can stroll through Old Town, an amazing architectural and botanical treasure.

A private balcony features a round table surrounded by four chairs, providing a comfortable space to enjoy the ocean view. Lush greenery and palm trees are visible in the background, with the tranquil ocean further enhancing the outdoor setting.

5 out of 5 average rating, 6 reviews

Oceanview condo w/pool, jacuzzi

Plan your next vacation at this peaceful, breathtaking, Ocean-view condo at La Brisa resort located across the street from largest beach on the island, Smathers Beach. Take advantage of the pool, tennis courts, hot tub, and sauna or just enjoy the Atlantic Ocean view from your private balcony. The condo is in a gated community with private parking and elevator access. Bring your family and lets enjoy your vacation in Key West 🌴☀️ No pets allowed !

A spacious living room is furnished with a soft blue sofa and matching armchair. Light wooden flooring complements the room's bright atmosphere, and a coffee table sits in the center. Large sliding glass doors lead to a patio area, allowing natural light to fill the space.

4.9 out of 5 average rating, 154 reviews

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.

Popular amenities for Stock Island holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Stock Island

5 out of 5 average rating, 10 reviews

Boat in Key West

Sentient Waters: 63’ Boat With Full Amenities

A lush garden expanse is depicted, featuring vibrant greenery and colorful flowers. Palm trees sway in the gentle breeze, while the ocean is visible in the background. A pool is nestled within the landscaped area, complemented by a shady outdoor dining space under a canopy.

5 out of 5 average rating, 3 reviews

Best Resort in Key West, 2BD/2BA

4.97 out of 5 average rating, 179 reviews

An aerial view showcases a coastal community with a spacious beach area, palm trees, and turquoise waters. The two-story unit features a large balcony above the entrance, with the surrounding buildings and lagoon clearly visible, highlighting the vibrant landscape of the area.

Home in Cudjoe Key

Cudjoe Key Home with a View

The interior of a studio room is displayed, featuring a comfortable sofa, a small dining area with two chairs, and a compact kitchen. A queen bed is positioned in the background, separated by light curtains. Natural light enters through a nearby window, enhancing the space.

4.62 out of 5 average rating, 297 reviews

Queen Studio

A bright living area is featured, with a comfortable grey sofa adorned with decorative pillows. Natural light filters through large sliding doors, leading to a balcony with seating. Vibrant yellow curtains frame the view, and wooden flooring enhances the space's warm ambiance.

4.51 out of 5 average rating, 239 reviews

2BR Suite | Pool | Hot Tub | Tennis | Dog Friendly

A spacious living room features two sofas, one of which is a fold-out bed, and a coffee table centered on a patterned area rug. Large windows with wooden blinds allow light to fill the room, highlighting the full kitchen area and breakfast bar in the background.

Houseboat in Key West

4.78 out of 5 average rating, 341 reviews

Key West Houseboat Paradise

A well-lit bedroom features wooden paneling and a spacious bed with a patterned blanket. Shelves filled with books are situated beside the bed. A sliding glass door leads to an outdoor area, while warm lighting enhances the cozy atmosphere.

4.89 out of 5 average rating, 45 reviews

Apartment at Safe Harbor Marina

A bright living area features a light blue sofa adorned with colorful throw pillows. Two accent tables with lamps flank the sofa. Natural light floods in through the open doors leading to an enclosed patio, while a decorative wall art piece adds a coastal touch.