Condo holiday 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

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 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 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, 229 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 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.

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.

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.”

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 light-filled dining area features a round table surrounded by four wicker chairs, providing a cozy setting for meals. The kitchenette showcases white cabinetry and a full-sized fridge. The outdoor pool area is expansive, lined with lounge chairs and palm trees under a bright blue sky.

4.91 out of 5 average rating, 139 reviews

Waterfront Condo w/ Pool, Tiki Bar & Marina

Welcome to THE MAD MAHI – your ultimate waterfront getaway! This stunning 1-bedroom condo (sleeps 4) in Marathon is the perfect spot for a relaxing retreat. Enjoy the season while relaxing with a full kitchen, private balcony, resort pool, Tiki Bar, restaurant, & Marina with boat ramp, trailer parking, boat and slips. Located between Key Largo & Key West, with shops and dining just a walk or bike ride away.

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

Wi-Fi

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

5 out of 5 average rating, 3 reviews

Beach House Condo by AvantStay | Week-Long Stays

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

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 balcony view overlooking the Gulf of Mexico features a railing framing the scenic water below, where sunlight glimmers on the surface. Lush greenery is visible nearby, enhancing the serene coastal atmosphere.

4.94 out of 5 average rating, 47 reviews

2-story condo w/ panoramic bay views and balconies

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

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

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

An inviting outdoor space showcases a heated pool surrounded by a wooden deck and tropical landscaping. Two lounge chairs are positioned by the poolside, and a staircase leads to an upper balcony, adding vertical interest to the serene environment.

4.67 out of 5 average rating, 18 reviews

Salvador's Seclusion | Cozy Studio Retreat with a

5 out of 5 average rating, 10 reviews

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

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

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 spacious sleeping area includes a king-sized bed with crisp white bedding and decorative pillows. Metal fish sculptures adorn the wall, complemented by two bedside lamps. A dark sectional sofa is positioned nearby, creating a comfortable seating area for relaxation.

4.92 out of 5 average rating, 298 reviews

Key Colony Beach Luxury Condo, New Modern Interior

4.83 out of 5 average rating, 6 reviews

P42 - Gulf Front condo with 3 bedrooms 2.5 baths,

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 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.