Condo vacation rentals in Key West

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Top-rated condo rentals in Key West

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Superhost

Condo in Key West

4.83 out of 5 average rating, 275 reviews

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

La Dolce Vita is a one bedroom, one bath condo with granite galley kitchen, living room, newer a/c, flooring, located in the heart of the Historic District in Old Town and is walking distance to all the shops, restaurants, bars and just steps to Duval Street! You will not need a car with this location. Large wraparound balcony with sitting chairs & table. Community Pool is 1 block away. Southernmost Beach is just 3 short blocks away. Southernmost Point, Hemingway House, Butterfly World.

Guest favorite

A modern kitchen countertop features a sleek, white Keurig coffee maker next to a wooden cutting board engraved with 'Captain's Choice.' A green ceramic mug sits prominently on the surface, surrounded by a carousel of coffee pods, showcasing an organized and inviting coffee station.

Condo in Key West

4.95 out of 5 average rating, 151 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

A row of charming buildings is visible along the street, showcasing multiple stories with balconies and colorful facades. A mix of shops and outdoor seating is featured on the ground level, while palm trees and bright skies add to the vibrant atmosphere.

Condo in Key West

4.81 out of 5 average rating, 110 reviews

The 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

Guest favorite

Condo in Tavernier

4.9 out of 5 average rating, 285 reviews

SPECTACULAR VIEWS OCEAN FRONT MODERN BEACH CONDO!

Enjoy a Top Floor condo with stunning ocean views from your living room and balcony. This condo features a King bed in the bedroom, updated kitchen, a queen pull out sofa and a new washer and dryer. Enjoy the wonderful amenities the property offers to include a Large pool/ spa area or relax on the private beach with lounge chairs provided. There are lighted tennis courts, areas to grill out and a small playground. This property sits on 68 acres and one side is surrounded by a nature preserve.

Guest favorite

A sandy beach area is lined with turquoise lounge chairs, oriented towards sparkling waters. Tall palm trees provide shade in parts, while a wooden pier extends into the ocean on the right. The bright sun adds warmth to the tranquil scene.

Condo in Tavernier

4.94 out of 5 average rating, 146 reviews

Key Largo Coastal Condo-Ocean View ~ Pool ~ Beach

Welcome to our remodeled costal 1BR 1 Bath condo nestled in the premier oceanfront complex in Tavernier, FL. Escape to paradise and enjoy the wonderful Ocean views from the private balcony while just a few steps away from the sunny private beach, marina, minutes away from restaurants, shops, and attractions. ✔ Comfortable Queen BR ✔ Open Design Living ✔ Fully Equipped Kitchen ✔ Balcony ✔ Smart TVs/WI FI ✔ Complex Amenities (Pool, Hot Tub, Marina, BBQ, Sports, Free Parking) Learn more below!

Guest favorite

A covered deck features two lounge chairs with blue cushions, accompanied by a small round table. Lush green palm trees and tropical plants surround the area, while soft natural light filters in, creating a serene outdoor space for relaxation.

Condo in Key West

4.93 out of 5 average rating, 111 reviews

WALK TO BEACH, MALLORY SQUARE, DUVAL STREET

Key West a little piece of the Caribbean, always warm with lovely turquoise waters. It's a short walk to Mallory Square, Hemingway's Home, the Truman White House, Duval Street. You're just a walk away from Zachary Taylor Park (where you can do yoga on the beach, swim, snorkel, or hang hammocks between the palms). We’re near numerous shops, restaurants, and museums. Enjoy coffee in the morning, wine at night on our oversized deck. THE ADJACENT UNIT MAY BE AVAILABLE FOR ADDITIONAL SPACE.

Guest favorite

A panoramic view of the oceanfront reveals clear turquoise waters meeting the sandy beach. Palm trees gently sway, and tiki huts are scattered across the shoreline. Lounge chairs are positioned for relaxing under the sun, inviting guests to enjoy the serene coastal atmosphere.

Condo in Key Colony Beach

4.92 out of 5 average rating, 237 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.

Guest favorite

An inviting pathway is flanked by charming wooden structures, featuring pale green shutters. Lush greenery and tropical plants complement the brick walkway, leading toward the lush landscape beyond. The setting conveys a sense of tranquility and a connection to the vibrant surroundings.

Condo in Key West

4.89 out of 5 average rating, 236 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.

Guest favorite

A thatched-roof tiki hut is positioned on a sandy beach, framed by palm trees. Sunlight glistens on the ocean, creating a serene backdrop. Beach chairs are arranged nearby, inviting relaxation by the water's edge.

Condo in Key Colony Beach

4.81 out of 5 average rating, 135 reviews

Beachside Unit 28 - Private Beach, Pool & Paradise

Unit 28 Details: First Floor Unit, Walk-in Shower, King Bed, Maximum Occupancy 2 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.”

Guest favorite

The bathroom features a clean and modern design with a sink, mirrored cabinet, and a shower. A stacked washer and dryer unit is conveniently located near the entrance, providing accessible laundry facilities. Soft lighting enhances the neutral color palette throughout the space.

Condo in Key West

4.9 out of 5 average rating, 141 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.

Guest favorite

A modern kitchen area features gray cabinetry and white countertops, with stainless steel appliances visible. To the left, a seating area with a large turquoise couch and dining table overlooks the waterfront through floor-to-ceiling windows.

Condo in Key West

4.87 out of 5 average rating, 201 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!

Guest favorite

A detailed floor plan outlines the layout of the condo, featuring a master bedroom with a balcony, a second bedroom, and bathrooms. The living/dining area is noted for its wide dimensions, connected to the kitchen area, showcasing spatial relationships within the home.

Condo in Key West

4.78 out of 5 average rating, 299 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!