Condo 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, 173 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, 105 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, 262 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 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.

4.91 out of 5 average rating, 235 reviews

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

Time to fish & relax! Bring your family & friends to this 1350 sqft waterfront corner condo home. Boat slip available on-site with commercial ice machine and fish cleaning station. Located in historic Downtown Key West. Walk/Bike everywhere less 1mi to Duval Street, Seaport, Hemingway House, etc. On-site amenities: heated pool, boat slip, tiki bar & grills, parking, secure keyless entry, & building elevator. Large Park adjacent with tennis courts. 10min from airport (EYW).

A serene waterfront view reveals gentle waves lapping against a sandy shoreline. Beach chairs are arranged near the water, providing a relaxing spot to enjoy the scenery. Lush palm trees frame the tranquil setting, enhancing the sense of peacefulness.

4.95 out of 5 average rating, 42 reviews

Condo de Paradise/Salt Water Pool/Boat Dock

This is one of the best kept secret locations. Can be a very romantic escape. This is a good place for honeymooners, guys or gals getaway, fishermen/fisherwomen weekend get away or family time. A private unit in paradise in a gated community. Only 10 miles to Duval Street and all that Key West has to offer. There is a dock that can be used to dock up to a 26 foot boat that can be launched at Geiger Key, a mile down the road and they will store your trailer.

4.93 out of 5 average rating, 104 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, 151 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.

4.9 out of 5 average rating, 39 reviews

Key Lime Paradise 2BR w/ Pool, HotTub, 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

A clear, inviting outdoor pool is surrounded by lush tropical landscaping. Palm trees are scattered around, softening the edges of the pool area. A multi-story building with a light-colored exterior provides a backdrop, featuring several balconies with white railings.

5 out of 5 average rating, 10 reviews

Hyatt Beach House-Quiet Key West Spot!

Located 2.7 miles from Smathers Beach and 3.8 miles from the Ernest Hemingway Home & Museum, this quiet piece of Key West is the best location for relaxation. The property is on a corner of the island featuring its own private beach and water access. Other activities in the area include scuba diving, snorkeling, parasailing, fishing, dolphin watching, and boating.

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, 45 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, 301 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, 103 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.

Popular amenities for Stock Island condo rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Weekly condo rentals

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.

4.87 out of 5 average rating, 109 reviews

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

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, 60 reviews

Vacation Home Heron Hideaway

4.86 out of 5 average rating, 22 reviews

Condo in Marathon

Cozy apartment in Marathon Key

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.

4.82 out of 5 average rating, 49 reviews

Casa Arosa

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, 233 reviews

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

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.

4.79 out of 5 average rating, 24 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, 172 reviews

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

Pet-friendly condo rentals

4.81 out of 5 average rating, 293 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.

4.86 out of 5 average rating, 42 reviews

Chagall’s Corner | Newly Remodeled!

5 out of 5 average rating, 8 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, 98 reviews

The Trinidad at Sunrise Suites - Shared Pool

5 out of 5 average rating, 14 reviews

Modern 2BR Condo Old Town/Balcony & Pool

4.85 out of 5 average rating, 258 reviews

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

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.

4.5 out of 5 average rating, 234 reviews

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

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.

4.85 out of 5 average rating, 39 reviews

La Maisonnette~ Gated Condominium 1 Block to Duval

Condo rentals with a pool

The entrance showcases a decorative door framed by vibrant greenery and tropical plants. A stone pathway leads to the door, providing a welcoming access point to the townhome. The exterior features light wood siding, contributing to a relaxed coastal ambiance.

4.8 out of 5 average rating, 20 reviews

Villa Serena @ Duval Square - A peaceful retreat

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.

4.85 out of 5 average rating, 34 reviews

Rum Cay at Sunrise Suites

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.

4.92 out of 5 average rating, 13 reviews

Coconut Mallory. Waterfront & Key West charm.

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, 29 reviews

Key West's Crown Jewel

A charming two-story building with light pastel-colored siding and white railings is shown. The entrance features a circular window and a welcoming porch with comfortable seating. Lush greenery and a white picket fence frame the entrance, enhancing the inviting exterior.

4.9 out of 5 average rating, 186 reviews

A Perfect Getaway

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, 104 reviews

Orchid Suite @ the Old Town Villas, steps from

A spacious living room features cream leather seating arranged around a coffee table. Tropical plants accentuate the space, complemented by decorative lamps. Large windows with sheer curtains allow natural light, while a television is positioned against one wall, offering entertainment options.

4.85 out of 5 average rating, 39 reviews

Henry's Piece of Paradise On The Ocean In Key West

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.