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, 166 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

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, 101 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 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, 254 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, 107 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.

4.94 out of 5 average rating, 102 reviews

The image showcases a vibrant living space within the Dapper Dolphin condo, featuring a stylish kitchen with granite countertops, a cozy dining area, and a comfortable bedroom with a king-sized bed. The outdoor area displays a large pool surrounded by lounge chairs, highlighting the resort's inviting atmosphere.

Condo in Marathon

Canal View Condo w/ Pool, Balcony & Bar

Celebrate the season in paradise at THE DAPPER DOLPHIN, an updated coastal-themed 1-bedroom, 1-bathroom condo, accommodating up to 4 guests. Featuring a complete kitchen, balcony, and access to resort amenities including a pool, Tiki Bar, restaurant, Marina, and more! Situated in the heart of Marathon, it offers proximity to the beach, restaurants, activities, and all the essentials for an unforgettable vacation experience right on-site!

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.

4.89 out of 5 average rating, 147 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.

A scenic view of the waterfront reveals a calm harbor lined with boat slips. The vibrant blue water reflects the sky, while a tiki hut and chaise lounge chairs surround a heated pool in the foreground, enhancing the coastal ambiance.

4.88 out of 5 average rating, 224 reviews

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

Bring friends and family to this updated 1,350 sqft waterfront corner condo in historic downtown Key West! Just 1 mile to Duval St, the Seaport, and Hemingway House. Enjoy on-site boat slips, heated pool, tiki bar, BBQ grills, parking, elevator, and secure keyless entry. Fish cleaning station and commercial ice machine available. Large park with tennis courts next door. Walk or bike everywhere—only 10 minutes from EYW airport!

A spacious bedroom features a dark wooden bed framed by warm lamps on either side. A gray blanket covers the bed, complemented by decorative pillows. Natural light fills the room through a large window with sheer drapes, enhancing the soft, neutral tones of the walls and flooring.

4.91 out of 5 average rating, 109 reviews

The Island Suite @ KW vacation

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 light-filled living area features a comfortable sofa paired with accent tables. Soft blue walls create a calming backdrop, while stylish decor elements, such as framed artwork and lamps, add character. A mirror reflects the space, enhancing its openness and inviting ambiance.

5 out of 5 average rating, 41 reviews

EYW Getaway

Relax with the whole family at this peaceful place to stay. Our two-bedroom two-bathroom condo with complete kitchen is located at Sunrise Suites Resort. Amenities include shared heated pool, hot tub, tennis court and a basic gym. Our condo is located 1mile from the airport, 1.5 miles from the beach and 3.5 miles from downtown Duval St.

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, 300 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!

4.89 out of 5 average rating, 36 reviews

Key Lime Paradise 2BR w/ Pool, HotTub, Near Beach!

Escape to Key Lime Paradise, a modern 2BR/2BA condo just 3 minutes to Smathers Beach and 10–15 minutes to Duval Street. Enjoy a bright coastal vibe, full kitchen, pool, hot tub, and pickleball courts. Each bedroom has its own full bath for privacy. Close to beaches, yet peaceful and relaxing — your perfect Key West retreat!

4.87 out of 5 average rating, 134 reviews

Moonlight Paradise Upgraded Family oasis Tropical

Moonlight is a totally renovated condo that is located at 1800 Atlantic Blvd on the beach, with sunset views right from your own private balcony. Beautiful tropical decor. No attention to detail has been spared. Stainless Appliances & luxurious finishes.

Popular amenities for Stock Island condo rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Weekly condo rentals

A view of a marina shows several boats docked along wooden piers, with palm trees dotting the shoreline. The surrounding buildings display a tropical architecture style, under a sky filled with scattered clouds.

Condo in Marathon

4.62 out of 5 average rating, 13 reviews

The Reef at Marathon private villa/ Marina incl

A spacious patio area features a lounge chair and a grill, surrounded by a white picket fence. Large glass doors lead into the condo, allowing natural light to enhance the space. Shadows from nearby trees create a pattern on the decking.

4.96 out of 5 average rating, 76 reviews

Key West Paradise Poolside

A clear view of a swimming pool is framed by palm trees and greenery. Lounge chairs are positioned alongside the pool, and the ocean can be seen in the distance. The scene conveys a relaxed outdoor atmosphere, inviting guests to enjoy the coastal surroundings.

5 out of 5 average rating, 4 reviews

Key West 2 BR Deluxe, Beach Front, sleeps: 6

A shared heated pool is surrounded by lush tropical greenery, providing a peaceful atmosphere. Comfortable lounge chairs are positioned nearby, inviting relaxation. The pool features a blue tile border and a gentle slope, enhancing accessibility and enjoyment for all guests.

4.83 out of 5 average rating, 23 reviews

Palm Isle: 2nd-Floor Unit, Shared Heated Pool

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, 159 reviews

Anchor Drop modern elegance upgrades throughout vi

The exterior of a two-story corner property is showcased, featuring light-colored siding and a white picket fence. Lush tropical landscaping surrounds the building, with palm trees and flowering shrubs adding greenery. Two porches are seen, inviting relaxation in a serene setting.

4.93 out of 5 average rating, 72 reviews

Bright Condo in Paradise

The entrance of a resort is captured, featuring tall palm trees swaying gently in the breeze. A clear sky with soft sunlight peeks through the trees, illuminating the path lined with greenery. A white picket fence borders the area, adding to the welcoming ambiance.

4.81 out of 5 average rating, 47 reviews

Casa Arosa

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, 163 reviews

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

Pet-friendly condo rentals

4.81 out of 5 average rating, 290 reviews

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

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

5 out of 5 average rating, 6 reviews

Family Suite at Sugarloaf Key Hotel (Pet Friendly)

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, 151 reviews

Dog Friendly 1BR | Pool | Easy Beach Access

A spacious living area is depicted, featuring a light blue couch, a decorative armchair, and a coffee table made of reclaimed wood. Large glass doors open to a balcony with waterfront views, allowing natural light to brighten the room. A ceiling fan is visible above, enhancing comfort.

4.85 out of 5 average rating, 250 reviews

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

A cozy studio space features a Queen bed dressed in soft linens, positioned beside a wooden dresser. A wall-mounted TV is visible across from the bed, and natural light enters through a nearby window. A ceiling fan adds comfort to the room.

4.79 out of 5 average rating, 24 reviews

Andy’s Attic | Budget-Friendly!

A private balcony offers a view of the pool surrounded by lush palm trees and tropical landscaping. A glass-top table and two chairs are set up for outdoor seating, allowing for enjoying the pleasant surroundings and fresh air.

4.82 out of 5 average rating, 172 reviews

Newly Renovated Condo - St. Martin Suite

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, 35 reviews

La Maisonnette~ Gated Condominium 1 Block to Duval

An inviting entrance features a bright blue door labeled 'Orchid Suite'. Two white wicker chairs are positioned on a covered porch, flanked by lush greenery, creating a serene and welcoming atmosphere. Natural light filters through the surrounding plants.

4.75 out of 5 average rating, 102 reviews

Orchid Suite @ the Old Town Villas, steps from

Condo rentals with a pool

The living area features a white sofa adorned with decorative pillows, a wooden coffee table, and wall art in multiple frames. A flat-screen TV is mounted on the wall, while lush tropical views are offered through double French doors leading to the balcony.

4.95 out of 5 average rating, 20 reviews

La Petite Penthouse at The Annex

A well-lit living area features a large sectional sofa and a comfortable accent chair, both offering seating options for relaxation. Natural light floods in through multiple windows, while a Smart TV and ceiling fan provide modern conveniences. Tropical artwork adds a touch of coastal living.

5 out of 5 average rating, 4 reviews

Old Town Oasis at The Annex

A balcony is seen featuring a dining table set for four, with place settings and seaside views. Two chaise lounges are positioned nearby, ideal for relaxing. Lush greenery and ocean views are visible beyond the railing, creating a serene outdoor space.

4.74 out of 5 average rating, 46 reviews

Shang-Ri-La at The Beach

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, 105 reviews

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

The living room is characterized by wood-beamed ceilings and spacious glass doors framing ocean views. Comfortable seating arrangements include a sofa adorned with colorful cushions. Natural light fills the space, enhancing the warm wood tones and elegant decor throughout.

4.93 out of 5 average rating, 28 reviews

Key West's Crown Jewel

A wrap-around balcony features a dining table set for four, surrounded by lush greenery. Two lounging chairs are positioned nearby, with a view of the tranquil Atlantic Ocean. The gentle waves reflect the soft sunlight, creating a serene seaside atmosphere.

4.89 out of 5 average rating, 27 reviews

Neptune's Penthouse at The Beach

The living area features comfortable leather sofas with accent pillows, arranged around a glass coffee table. A large flat-screen TV is mounted on the wall, and natural light enters through sliding glass doors. Decorative elements, like a wall-mounted fish, add character to the space.

4.93 out of 5 average rating, 40 reviews

Coastline Comfort at Coconut Mallory

A community pool is surrounded by palm trees and lounge chairs, with a shaded cabana in the background. The clear water reflects the blue sky, creating a serene setting for relaxation. Poolside features include a pathway leading to the water and two ladders for easy access.