Condo vacation rentals in Key West

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

Superhost

4.82 out of 5 average rating, 114 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

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, 102 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 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

Time to relax! Bring your family & friends to this 1200 sqft Waterfront home - Stay spacious in Key West. Boat slips available on site with commercial ice machine, fish cleaning station and BBQ grills. Located in Downtown Key West. Walk/Bike everywhere less 1mi to Duval Street, Historic Seaport, Hemingway House, etc. On-site amenities: heated pool, tiki bar & grill, bike rentals, parking, secure keyless entry, & elevator. Large park adjacent with tennis courts. 10min from airport (EYW).

A spacious studio features a comfortable bed dressed in soft blue and white linens, complemented by decorative pillows. A cozy seating area with a light blue sofa and armchair stands nearby. Windows provide unobstructed ocean views, framed by tropical artwork and natural light.

4.92 out of 5 average rating, 251 reviews

Oceanfront Breeze, Stunning Views, Beach/Pool

Newly renovated ocean front condo with gorgeous, unobstructed views from every window. Beautiful studio condo on the 1st floor only steps away from the private beach and heated pool. Condo features a fresh, clean interior with brand furnishings, bathroom and kitchen stocked with everything (dishes, cookware, utensils, glassware, stove, oven, toaster, microwave, blender, fridge, etc). Guests enjoy the quiet private beach with lounge chairs, patio tables, tiki's and BBQ grills.

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, 256 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, 108 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.

The image captures a view of the Atlantic Ocean framed by lush palm trees. A pathway meanders alongside the vibrant green lawn, leading toward the beach. The clear blue sky is visible above, enhancing the calm and serene coastal atmosphere.

4.87 out of 5 average rating, 135 reviews

Beachside Unit 33-Private Tropical Beach Plus Pool

Unit 33 Details: Second Floor, Walk-in shower, Two Queen Beds, Maximum Occupancy 4 Guests, No elevator on site and Not Handicapped Accessible. A registration and liability waiver form signature will be required as part of your reservation. Our oceanfront property includes a private heated pool and private beach retreat on the Atlantic Ocean. Welcome to Continental Inn Condominiums in Key Colony Beach, Florida known as “The gem of the Florida Keys.”

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 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.

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!

Popular amenities for Key West condo rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Weekly condo rentals

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 balcony view captures a sunset over the water, with palm trees framing the scene. A small table and two wooden chairs overlook the harbor, providing a perfect setting for relaxation. The horizon is painted in warm hues, with boats visible in the distance.

4.69 out of 5 average rating, 16 reviews

Spacious 2BR Oceanfront | Balcony | Pool

A sandy beach transitions to calm waters, framed by palm trees and greenery. Sun loungers are arranged neatly along the shore. A private spiral staircase leads to the beach, while a wooden dock extends into the water, inviting leisurely excursions.

4.84 out of 5 average rating, 142 reviews

Ocean Front Suite with Direct Beach Access

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

Superhost

Condo in Marathon

4.83 out of 5 average rating, 6 reviews

P42 - Gulf Front condo with 3 bedrooms 2.5 baths,

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

A charming two-story corner property is framed by lush greenery and palm trees. A white picket fence surrounds the front yard, complementing the pastel-colored exterior. The entrance is marked by a circular window, while a small seating area is visible on the porch.

4.86 out of 5 average rating, 44 reviews

Corner Unit 2BR | Deck | Pool | W/D

Pet-friendly condo rentals

4.81 out of 5 average rating, 290 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.

4.87 out of 5 average rating, 38 reviews

Chagall’s Corner | Newly Remodeled!

Superhost

An open living area is highlighted by a vaulted wooden ceiling and features a combination of comfortable seating. A glass dining table is complemented by white chairs. Large windows provide views of the lagoon, while a staircase leads to an upper level.

Condo in Islamorada

180 Degrees of Ocean Views, Lagoon and Florida Bay

A spacious outdoor patio is viewed, featuring a dark wooden table and black wicker chairs. A decorative rope centerpiece is placed on the table. The horizon displays a vivid sunset with shades of orange, pink, and purple, casting a serene reflection over the calm water.

4.96 out of 5 average rating, 80 reviews

Oceanfront 3 bed condo Ocean Edge w/ optional slip

5 out of 5 average rating, 7 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 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

5 out of 5 average rating, 10 reviews

Condo in Marathon

Seashells Getaway - Boat Slip, Ramp, Pool

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

Condo rentals with a pool

A spacious bed is adorned with crisp white linens and a vibrant throw pillow featuring a fish design. Large windows frame the room, allowing natural light to illuminate the interior while offering views of the ocean and nearby palm trees.

4.96 out of 5 average rating, 220 reviews

Oceanfront Sunrise Condo Private Beach Heated Pool

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

A modern living area is displayed with light-colored walls and a wood-style floor. A comfortable sectional sofa and vibrant blue seating surround a circular table. A flat-screen television mounts on the wall, and natural light enters through two windows, enhancing the bright atmosphere.

4.97 out of 5 average rating, 252 reviews

Keys Breeze Ocean View Condo & Pool - Key Colony

A bright and airy bedroom features a spacious bed with crisp white bedding and decorative pillows. Nightstands with turquoise lamps flank the bed, and starfish art adorns the walls. Natural light filters through the shutters, creating a fresh and inviting atmosphere.

4.91 out of 5 average rating, 237 reviews

Poolside 2 Bdrm in Oceanfront Complex, Key Colony

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 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, 225 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 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.