Apartment 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, 185 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.

4.98 out of 5 average rating, 118 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, 121 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.

Apartment in Summerland Key

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.

5 out of 5 average rating, 18 reviews

Family Suite at Sugarloaf Key Hotel (Pet Friendly)

Discover the perfect blend of comfort, relaxation and adventure at the Sugarloaf Key Hotel, nestled within the Sugarloaf Key / Key West KOA Resort campground. Newly built in 2023, this beautiful 6-person pet-friendly vacation suite offers everything you need for a great stay. Nestled amongst gorgeous tropical scenery, this resort includes robust amenities including resort-style pool and hot tub with an adjacent pub, quaint sand beach, marina, water rentals, café, camp store and more!

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, 275 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 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, 161 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 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, 106 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.

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, 64 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, 307 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!

4.9 out of 5 average rating, 124 reviews

Prime Downtown Key West Spot - Walk Everywhere!

Welcome to The Cozy Little Cottage! A REAL ISLAND GETAWAY IN KEY WEST!!! Nestled in the heart of Key West, The Cozy Little Cottage, welcomes you to a sanctuary of comfort and convenience. As your host, we're delighted to extend our warmest greetings and ensure your stay is nothing short of exceptional.

4.87 out of 5 average rating, 135 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.

A serene beach scene is captured at sunset, showcasing gentle waves lapping against the shore. Silhouettes of palm trees frame the view, while smooth rocks line the beach. The sky transitions from soft hues of orange to blue, providing a tranquil backdrop over the calm water.

4.89 out of 5 average rating, 38 reviews

Poolside Breeze Retreat

Spacious two bedroom two bath 1st floor condominium, great location close to the pool. Ideal family unit with a king, queen and a queen sleeper sofa.Enjoy the tranquility that this location has to offer. Brand new Kitchen in 2018. Totally renovated.

Popular amenities for Stock Island apartment rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Weekly apartment rentals

Oceanfront Oasis Smathers Beach Condo Sunrise view

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.

4.7 out of 5 average rating, 90 reviews

Paradise Found Cayo Hueso

A serene beachfront scene features swaying palm trees against a bright blue sky. Two blue umbrellas are positioned on the sand, providing shade near rows of lounge chairs that face the tranquil water. The ocean's gentle waves lap against the shore, creating a calm atmosphere.

4.69 out of 5 average rating, 62 reviews

Caribbean Conch 5 Minutes to Smathers Beach & 10 m

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.

4.85 out of 5 average rating, 34 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, 160 reviews

Anchor Drop modern elegance upgrades throughout vi

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.

4.95 out of 5 average rating, 79 reviews

Vacation Home Heron Hideaway

5 out of 5 average rating, 6 reviews

The Grand Cayman | Beautifully Remodeled Key West!

A lush outdoor area is surrounded by tropical greenery and illuminated by soft lighting. Several colorful lounge chairs are positioned along the path, with shaded tables and umbrellas inviting relaxation. The space offers a serene setting for gatherings in nature.

5 out of 5 average rating, 7 reviews

2 Bedroom Townhouse Style Condo

Pet-friendly apartment rentals

4.81 out of 5 average rating, 298 reviews

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

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.

4.68 out of 5 average rating, 105 reviews

The Trinidad at Sunrise Suites - Shared Pool

4.86 out of 5 average rating, 268 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, 247 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.

4.8 out of 5 average rating, 44 reviews

La Maisonnette~ Gated Condominium 1 Block to Duval

4.62 out of 5 average rating, 101 reviews

Sunrise Suites Condo with Balcony - Shared Pool

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.

4.86 out of 5 average rating, 184 reviews

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

A serene waterfront scene is captured at sunset, featuring palm trees, boat docks, and a gently reflecting harbor. A large boat is tied up alongside the dock, with colorful lights and silhouettes of the surrounding structures visible in the background.

4.9 out of 5 average rating, 252 reviews

"Abaco" Key West • 2/2 End Unit Waterfront+Dockage

Apartment rentals with a pool

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.

4.91 out of 5 average rating, 95 reviews

Ocean Front Studio private Sandy Beach in Key West

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 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, 37 reviews

Rum Cay at Sunrise Suites

A scenic view from the balcony showcases palm trees swaying gently near a sandy beach. The turquoise ocean blends into the blue sky, with wispy clouds visible. Sunlight reflects off the water, enhancing the tranquil atmosphere of the coastal landscape.

4.86 out of 5 average rating, 66 reviews

Somewhere on the beach

A welcoming living area features a blue sofa and armchair, complemented by a coffee table. Large sliding glass doors open to a private balcony, offering expansive views of the surrounding landscape. Soft blue curtains frame the windows, creating a relaxed atmosphere.

4.71 out of 5 average rating, 7 reviews

The Andros | Incredible Views w/ Shared Pool

4.62 out of 5 average rating, 13 reviews

3-Bedroom 3-Bath Condo at Bayfront Suites & Marina

A bright living area features a coral-colored sofa, rattan seating, and a flat-screen TV. Natural light floods the space through large sliding glass doors leading to a private balcony with outdoor seating. The adjoining bedroom is visible through an open doorway.

4.89 out of 5 average rating, 9 reviews

The Samana Cay | Tropical, Airy Retreat w/ Pool

The bedroom features a spacious bed with light blue bedding against a red accent wall. A standing lamp provides soft lighting beside a dresser. A mirror reflects the bathroom area, showing a sink and light cabinetry with a contrasting black-and-white tiled floor.