Condo vacation 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

4.82 out of 5 average rating, 115 reviews

A Cuban Club Suite by Rent Key West Vacations

Built in 1917 as a “club” for Cuban cigar makers and their families as their home-away-from-home, this building soon became the center of social and community life for the Cuban population in Key West. After the original Cuban Club burned down in 1983, it was restored and converted to luxurious and spacious suites. The Cuban Club Suite stands as an award-winning historical landmark converted to a gorgeous two-bedroom suite filled with all the amenities needed for comfortable living. Climb the

A balcony view reveals the expansive Atlantic Ocean, featuring a peir extending into the water. Palm trees are visible, adding a tropical ambiance. The serene blue waters and clear sky harmonize in the background, enhancing the coastal experience.

4.9 out of 5 average rating, 94 reviews

Ocean Front Studio private Sandy Beach in Key West

Studio unit with fridge, microwave, settings for 2 and a king sized bed. Doors that open to a balcony overlooking the Atlantic Ocean. There is pool, hot tub, and a private sandy beach on the Atlantic ocean. 5 minutes walk to Duval street. The resort is located between the prestigious Casa Marina and the top restaurant on the island Louise Back Yard. There is free garage parking with the room. Washer, dryers and ice maker are available for guests. Powerful, but sometimes noisy air conditioning.

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, 112 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.

A spacious balcony overlooks the harbor, featuring a dining table and wooden chairs. Lush palm trees are visible nearby, with the serene water reflecting the blue sky. The scene is perfect for outdoor relaxation and enjoying the coastal ambiance.

4.88 out of 5 average rating, 113 reviews

Key West Andros 2BR•Waterfront, Pool, Dock&Pet OK

Time to relax and unwind in this spacious 1,350 sq ft waterfront corner condo in historic Downtown Key West. Walk or bike everywhere—less than 1 mile to Duval Street, the Historic Seaport, and the Hemingway House. Enjoy a heated pool, tiki bar, BBQ grills, building elevator, and secure keyless entry. Please note: The condominium dock will be under construction beginning April 27, 2026 for approximately 30 days; dock access will be unavailable and daytime construction noise is expected.

A private balcony is shown, featuring colorful patio chairs and vibrant tropical plants. The space is framed by white railings and light blue shutters, creating a fresh and inviting setting for relaxation.

4.89 out of 5 average rating, 269 reviews

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.

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 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, 155 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.

An open-concept living area offers a view of comfortable seating arrangements and natural light. The kitchen features a marble countertop and modern appliances. A balcony is visible through sliding glass doors, surrounding greenery enhancing the serene environment.

4.91 out of 5 average rating, 43 reviews

Key Lime Paradise Condo with Pool Near Beach

Escape to Key Lime Paradise, a bright 2 bedroom 2 bath Key West condo with a king suite, queen room, and a queen sleeper sofa. Relax or work with high speed WiFi and smart TVs offering more than 150 channels including HBO Max. Enjoy an open living area, balcony, kitchen, workspace, beach gear, safe, and smart lock. Dive into resort vibes with a large pool, hot tub, gym, courts, and a BBQ area

4.91 out of 5 average rating, 116 reviews

Vacation home Island Suite 16

The Island Suite is part of a historic Key West property built around 1889. Suite #16 is located on the first floor at the rear of the 411 William Street building. The Island Suite has one of the premiere locations in Old Town, Key West with lively Duval Street just 3 blocks away and the neighborhood boasting some of the finest older homes in Key West.

A cozy room features mid-century style furnishings, including two blue velvet chairs adjacent to a small dining table. A queen murphy bed is visible in the background, alongside a television mounted on the wall. Natural light enters through the window, highlighting the vibrant yellow walls.

4.92 out of 5 average rating, 103 reviews

Duval Street Suites on Duval Free Parking and heat

Cuban Club Suite is a one bedroom (queen) 1 bath suite with a queen murphy bed 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.

An Olympic size pool is highlighted in the image, surrounded by palm trees and lounge chairs. The building in the background offers several balconies, and a well-maintained garden area is visible, enhancing the outdoor setting next to the beach.

4.78 out of 5 average rating, 305 reviews

Affordable Beachfront Luxury Condo Sleeps 6

My place sits on Smather's beach! Close to downtown and the airport. You’ll love the condo because of the location, the large indoor space, it's quiet, the pool, and has all the comforts of home. My condo is good for couples, solo adventurers, business travelers, families (with kids), and big groups. It’s spacious - and very clean!

Popular amenities for Stock Island condo rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Weekly condo rentals

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

A private balcony features a round table set with soft blue plates and glasses of juice. Comfortable chairs surround the table, with a bowl of fresh fruit placed in the center. Lush greenery and partial ocean views contribute to a serene outdoor setting.

4.85 out of 5 average rating, 160 reviews

Anchor Drop modern elegance upgrades throughout vi

4.9 out of 5 average rating, 113 reviews

Prime Downtown Key West Spot - Walk Everywhere!

An Olympic-sized swimming pool is surrounded by a sun deck, featuring lounge chairs and palm trees. The pool’s clear water reflects the sky, creating a serene atmosphere. The ocean and well-maintained tropical garden can be seen in the background.

4.81 out of 5 average rating, 26 reviews

Oceanfront Key West Condo

A spacious balcony view reveals a heated pool surrounded by lounge chairs. Tiki huts are visible nearby, alongside the boat slips and palm trees, set against a clear blue sky, showcasing a relaxing outdoor space for guests.

4.87 out of 5 average rating, 179 reviews

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

A living area features a gray sectional sofa, vibrant wall art, and a colorful bean bag. Large sliding glass doors open to a private balcony, with views of the ocean and palm trees. A dining area with wooden chairs is visible in the background.

4.69 out of 5 average rating, 29 reviews

205e la brisa-2br 2ba beachfront condo w/parking,

The living area features plush brown sofas arranged around a wooden coffee table, with a flat-screen TV mounted on a cabinet. Light-colored walls and large windows allow natural light to fill the space, complemented by light curtains. A ceiling fan provides added comfort.

4.81 out of 5 average rating, 26 reviews

Set Sail at Coconut Mallory

An oceanfront view captures the sunset over the water, with silhouettes of palm trees framing the scene. The gently rippling waves reflect warm hues of orange and pink in the sky. Sailboats can be seen in the distance, contributing to the serene atmosphere.

5 out of 5 average rating, 3 reviews

Seaport Serenity-Beach-Pool-King-BBQ-ExtraEntrance

Pet-friendly condo rentals

4.81 out of 5 average rating, 297 reviews

La Dolce Vita, Old Town Steps to Duval! 3 blks bch

A cozy sleeping area features a spacious bed with crisp white linens, framed by warm wooden walls. Light streams in through multiple windows with plantation shutters. A wall-mounted TV and a small shelf are positioned across from the bed, and a ceiling fan provides ventilation.

4.81 out of 5 average rating, 43 reviews

Chagall’s Corner | Newly Remodeled!

5 out of 5 average rating, 10 reviews

An aerial view showcases the resort's central pool surrounded by palm trees and landscaped gardens. The inviting pool area is complemented by a spacious pavilion with a metal roof, providing a gathering space. The background features the resort's accommodations and the lush natural environment.

Condo in Summerland Key

Family Suite at Sugarloaf Key Hotel (Pet Friendly)

A refreshing outdoor pool area is surrounded by palm trees under a bright blue sky. A poolside cabana with a green roof provides shade. The well-maintained pool deck offers ample space for relaxation and sunbathing.

4.67 out of 5 average rating, 103 reviews

The Trinidad at Sunrise Suites - Shared Pool

A bright living area features a comfortable blue sofa and armchair arranged around a glass coffee table. Natural light enters through the windows and reflects off the light-colored walls. A wooden console holds a television, while decorative art pieces enhance the homey atmosphere.

4.77 out of 5 average rating, 154 reviews

Dog Friendly 1BR | Pool | Easy Beach Access

4.85 out of 5 average rating, 262 reviews

Curaçao Key West 2BR Condo w/ Pool&Waterfront Dock

A bright and airy living space features a large sectional sofa, a dining area with a light-colored table and chairs, and large glass doors leading to a balcony with water views. Light wood paneling and artwork enhance the overall ambiance.

4.88 out of 5 average rating, 239 reviews

Florida | Waterfront 2BR/2BA w/ Pool + Dock Access

The living area features a light, airy ambiance with natural wood tones and comfortable furnishings. A spacious sofa is complemented by two armchairs, all arranged around a central coffee table on a textured area rug. Natural light filters through the woven shades of the windows, enhancing the serene atmosphere.

4.83 out of 5 average rating, 42 reviews

La Maisonnette~ Gated Condominium 1 Block to Duval

Condo rentals with a pool

An open-concept living area features a spacious seating arrangement with plush sofas and decorative cushions. A television is mounted on a sleek entertainment unit. A dining table with chairs is visible, surrounded by soft lighting and cheerful wall decor, complementing the overall ambiance.

4.69 out of 5 average rating, 87 reviews

Paradise Found Key West

A bright living area features a comfortable couch with decorative pillows and a large flat-screen TV. Natural light floods the space through sliding glass doors, which lead to an outdoor area. A patterned area rug adds warmth, while tropical plants enhance the decor.

4.79 out of 5 average rating, 24 reviews

Duval Square Retreat: A beautiful condo

A spacious living area features a comfortable leather couch and armchair set, complemented by a coffee table and vibrant area rug. Large sliding glass doors provide views of the outdoors and access to a private balcony with seating. A flat-screen TV sits atop a wooden console.

4.86 out of 5 average rating, 35 reviews

Rum Cay at Sunrise Suites

The view from the balcony captures the sparkling blue Atlantic Ocean and the surrounding lush greenery. The pool area can be seen below, along with neighboring buildings that blend into the landscape. Soft clouds float in the bright sky, enhancing the serene atmosphere.

4.86 out of 5 average rating, 28 reviews

Top floor amazing view Toms Chicken Coop awaits yo

A large outdoor pool area is surrounded by lounge chairs with cushioned blue fabric. Lush palm trees and greenery create a relaxed atmosphere. The pool is clear and inviting, under a bright blue sky, with a shallow section and a diving area visible.

4.93 out of 5 average rating, 14 reviews

Coconut Mallory. Waterfront & Key West charm.

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

A charming building features a white exterior with decorative balconies, surrounded by lush greenery and large Banyan trees. A sign for The Banyan Resort is visible, nestled among vibrant plants. The scene reflects a blend of nature and architecture in a tranquil setting.

Best location Key West, Florida

The brightly lit living space features comfortable seating with teal upholstery and a large glass-top coffee table. Mirrored walls enhance the room's spaciousness, while art pieces add a pop of color. An open layout connects to the kitchen and dining area.