Holiday rentals in Key West

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Top-rated holiday rentals in Key West

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
Home in Key West
4.97 out of 5 average rating, 297 reviews

Harrison's Hideaway-Sleeps up to 4, K & F Sl Sofa!

Historic Harrison's Hideaway is in an 1880's Cigar Maker's cottage renovated in 2010. It features a K size Pottery Barn memory foam bed, custom made full sleeper sofa, renovated kitchen with granite counter tops, 2 burner stove, under counter fridge/freezer, dishwasher, microwave, air fryer/oven tumbled marble 2 person shower, private front deck with seating for 4, 2 person Solana spa. Perfect for a couple or a family with children. Freshly painted a Caribbean blue with plantation shutters.

Guest favourite
A motorboat is anchored on calm waters, featuring a spacious front deck. Two individuals are seated comfortably, enjoying the view. The boat's sleek design is complemented by a canopy overhead and small steps leading into the water, creating a relaxed atmosphere.
Boat in Key West
4.9 out of 5 average rating, 230 reviews

Stay on Roxie - free transport & snacks, BYOB.

Read our reviews and relax with last minute weather cancellation! 🌞 Shower, toilet and power to recharge phones, full cellular. Enjoy a peaceful night or two on the water! Free parking and one free round trip transport to/from Roxie per night stay! Roxie is anchored in ~3ft lagoon. We live on a boat a half-mile away if you need anything at all! Roxie has a Keurig, coffee pods, bread, peanut butter-jelly, and bottled waters. No cooking but you may bring to-go food, beer/booze/wine. 🛥️🌴🎣

Guest favourite
A spacious living area features a comfortable futon adorned with a decorative pillow. Large windows provide views of the tranquil water, allowing natural light to brighten the space. The walls are designed in a soft, neutral tone, enhancing the overall welcoming feel.
Houseboat in Key West
4.94 out of 5 average rating, 167 reviews

Amazing houseboat with 2nd floor observation deck

Escape to our one-of-a-kind houseboat “Wild One,” anchored minutes from Soencers boat yard Key West. Surrounded by turquoise waters, enjoy one complimentary round trip per day, with times arranged around our charters. Evening rides may be available on request, last ride 10 PM. Extra charge after 8 PM Special Promotion: End your day with a private Sunset Eco Trip (6–7 PM) as your nightly ride to the houseboat—watch the sky ignite before settling in for a peaceful night afloat.

Top guest favourite
A wooden deck overlooks the ocean, featuring two light blue lounge chairs positioned under a large umbrella. A sandy area is visible nearby, and a wooden pier extends into the water, with people engaged in activities in the distance.
Apartment in Key West
4.99 out of 5 average rating, 104 reviews

Hidden Beach Duplex, Best Place in Key West

Go to sleep and wake up smiling listening to the waves. 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. This is an extraordinary condo on an extraordinary property. This is nicest unit of 3 for rent at Hidden Beach. If you are discerning, this really is best place place to stay in Key West.

Guest favourite
A private outdoor area features a hot tub surrounded by tropical foliage. A dining table with chairs is situated nearby on a wooden deck, offering shade from the overhead structure and a relaxing atmosphere for outdoor meals.
Home in Key West
4.87 out of 5 average rating, 107 reviews

Near Duval: Hot Tub, Sleeps 6, Top Location

Just 30 seconds from vibrant Duval Street, this iconic conch home is your perfect Key West escape! With two bedrooms, one bathroom, a full kitchen, and private outdoor perks—like a hot tub, second-story sundeck, and outdoor shower—you’ll have everything you need to relax in paradise. Ideal for up to 6 guests, it’s a tropical haven steps from world-class dining, shopping, and beaches. Book now and soak up the island life! Don’t forget to click the ♥ to save it for later.

Top guest favourite
Flat in Key West
4.98 out of 5 average rating, 542 reviews

Bella Vita: 1B/1B Condo for 2 Just Steps off Duval

1B/1B condo located in Old Town less than 1/2 block from Duval St. & a couple blocks from the Southernmost Point, Hemingway House & many other Key West attractions. Bella Vita accommodates 2 adults only and features a large porch with chairs & table, living room with leather sofa, galley kitchen with bar seating, king-size bed with Tempurpedic mattress, desk area, bathroom with large walk-in shower, wi-fi, sound machine, 2 Smart TVs & DVD players.

Top guest favourite
Boat in Key West
5 out of 5 average rating, 30 reviews

Key West • 2 Cabin • Yacht by Luxury Sea Charters

Skip the hotel room—own the horizon. Step aboard FREE TIME, your 50-foot floating suite in Key West. Two ensuite staterooms, a sun-soaked salon, and a private deck made for sunrise coffee or champagne sunsets. Docked in a premier marina with resort-style perks, this yacht redefines luxury travel—it’s not a stay, it’s a story you’ll tell for years.

Top guest favourite
A well-appointed bedroom features a spacious bed adorned with crisp white linens and blue accent pillows. The vibrant lime-patterned wallpaper creates a lively atmosphere. A mounted television is present, and natural light filters through two sets of blinds on the windows, offering a bright yet relaxing space.
Flat in Key West
4.91 out of 5 average rating, 129 reviews

Duval Street Suites full kitchen Old Town with hea

The Key Lime Suite is a one bedroom (king) 1 bath suite with a sleeper sofa (queen) and kitchen. Overlooking the pool in historic Old Town, Key West. Located in the middle of everything yet quiet and away from it all. This space is truly unique and sure to please all ages.

Superhost
A vibrant outdoor space is surrounded by lush tropical plants and trees. A pathway leads to a light green door, with seating visible underneath a bright red umbrella. The area offers a welcoming atmosphere perfect for relaxation.
Townhouse in Key West
4.77 out of 5 average rating, 184 reviews

Nassau Suite just steps to Duval Tropical oasis q

Nassau Suite is a one bedroom Townhouse with a very spacious bedroom upstairs a king bed, TV. Downstairs queen sleeper in the living area and full kitchen. Parking is on street. Pool for the compound. 921 Center Street #12. Key West FL 33040. 3 NIGHT MIN

Guest favourite
Apartment in Key West
5 out of 5 average rating, 22 reviews

Palm Garden retreat with Hot Tub & Prime Key West

Welcome to the Poolside Hide-Away @ Palm Gardens. A lovely one bedroom, one bath historic condo on the edge of Old Town just blocks to Duval St and the Historic Seaport. Private hot tub and community pool for your enjoyment.

Top guest favourite
A serene pool area is visible in the foreground, bordered by lush greenery and ocean views. Tall palm trees sway gently along the shoreline, where the calm water reflects the sky. A distant pier can be seen, enhancing the coastal atmosphere.
Apartment in Key West
4.94 out of 5 average rating, 173 reviews

Beach Club Ocean Front 2BR Condo

Come fall in love with Key West in our luxurious ocean front condo. The Key West Beach Club is located directly on the Atlantic in a quiet residential secured building. It is a 2BR, 2 1/2 Bath located in Mid-Town.

Guest favourite
A warm-toned room features wood-paneled walls accented by natural light from two windows. A spacious bed with an orange bedspread is positioned alongside a cozy seating area comprising two cream-colored couches facing a small round table.
Flat in Key West
4.84 out of 5 average rating, 863 reviews

Duval Balcony - Street Suite

Located in the heart of Duval St, this unique property offers a central location to the Key West landmarks and sights. Enjoy all Key West has to offer from a historic building with a balcony overlooking Duval St.

Popular amenities for Key West holiday rentals

When is the best time to visit Key West?

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Avg. price$498 SGD$556 SGD$527 SGD$450 SGD$405 SGD$368 SGD$377 SGD$343 SGD$316 SGD$390 SGD$442 SGD$494 SGD
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Frequently Asked Questions

  • What are the best places to stay in Key West?

    Key West has inviting neighborhoods like Old Town, known for historic homes, and Mallory Square, which is close to lively waterfront activities. Staying near Duval Street places you close to dining and entertainment, while quieter areas like Truman Annex often attract those seeking a relaxed atmosphere.

  • What are the best things to do in Key West with kids?

    Families often explore the Key West Butterfly and Nature Conservatory, visit the Key West Aquarium, and play on sandy beaches. Interactive museums, pirate-themed tours, and dolphin-watching excursions are frequently suggested for children.

  • What are some of the best things to do in Key West?

    You can explore Ernest Hemingway Home and Museum, stroll lively Duval Street, or watch the sunset at Mallory Square. Visitors frequently snorkel in clear waters, discover art galleries, and tour historic sites around the island.

  • How is the weather in Key West?

    Key West has warm weather year-round, with winter temperatures around 65–76°F (19–24°C) and summer highs reaching 91°F (33°C). Rainfall tends to be higher from June through October, while breezes help make coastal areas pleasant.

  • What are the best places to visit in Key West?

    Mallory Square draws crowds for daily sunset gatherings, and the Southernmost Point is popular for photos. The Ernest Hemingway Home and Museum and Key West Lighthouse highlight the island’s historic character.

  • What are some hiking trails in Key West?

    Key West has shorter walking paths, like the nature trails at Key West Tropical Forest & Botanical Garden and scenic shoreline walks around Fort Zachary Taylor Historic State Park. These areas combine greenery with views of the water.

  • What are some family activities we can do in Key West?

    Families can explore interactive exhibits at the Key West Shipwreck Museum, watch sea life at the Key West Aquarium, or join mangrove kayak tours. Sandy beaches and creative workshops are frequently suggested, especially for children.

  • What are some of the best day trip ideas from Key West?

    Day trips often include exploring the islands and marine life in Dry Tortugas National Park, visiting nearby wildlife refuges, or snorkeling from local boat tours. Historic landmarks and island nature preserves are also frequently suggested.

  • Are there any pet friendly accommodations available in Key West?

    Key West has pet-friendly vacation rentals in several neighborhoods, including Old Town and New Town. Many hosts welcome pets, and local parks make it easy to enjoy island walks with your dog.

  • What are some local tips for visiting Key West?

    Locals recommend wearing reef-safe sunscreen, exploring by bike or foot, and trying fresh seafood at casual spots. Sunset gatherings in Mallory Square and early morning walks along quiet streets offer unique island perspectives.

  • What is Key West known for?

    Key West is known for its lively Duval Street, colorful sunsets, and waterfront celebrations in Mallory Square. The city has a rich literary history, historic architecture, and active arts and water sports communities.

  • What are the best hidden gems to explore in Key West?

    Smaller museums like the Key West Firehouse Museum and Secret Garden, tucked-away art studios, and secluded beaches are frequently suggested by locals. Exploring side streets often reveals tucked-away architecture and murals.

  • What are the best foods to try in Key West?

    Key lime pie is frequently suggested, alongside fresh grouper sandwiches, conch fritters, and tropical fruit salads. Coastal restaurants highlight Caribbean-influenced seafood and Cuban flavors in many dishes.

  • What should I bring for a trip to Key West?

    Pack light clothing, sun protection, swimwear, sturdy sandals, and a reusable water bottle for outdoor activities. A wide-brimmed hat and rain jacket can be useful, especially from late spring through early fall.

  • What is the nightlife in Key West like?

    Duval Street is known for lively bars, music venues, and late-night gatherings, while waterfront lounges around Mallory Square attract sunset crowds. Explore dance floors, drag shows, and laid-back patios throughout the area for varied experiences.

  • What are the most popular events or festivals in Key West?

    Fantasy Fest draws creative costumes and parades each fall, and Hemingway Days celebrates the author's legacy in summer. The Conch Republic Days highlight local history, while waterfront sunset celebrations are daily traditions.

  • Are there family friendly vacation rentals in Key West?

    Key West has family-friendly vacation rentals in neighborhoods such as Old Town, Truman Annex, and Bahama Village. Many hosts provide amenities suitable for children, with easy access to beaches and parks.

  • When is the best time to visit Key West?

    Late winter through spring is often recommended for milder temperatures, less rainfall, and lively events. The island buzzes with festivals, water activities, and vibrant sunsets during these months.

Quick stats about holiday rentals in Key West

  • Total holiday rentals

    Explore 2,130 holiday rentals in Key West

  • Nightly prices starting at

    Key West holiday rentals start at $13 SGD per night before taxes and fees

  • Verified guest reviews

    Over 69,260 verified reviews to help you choose

  • Family-friendly holiday rentals

    1,280 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 680 rentals that welcome pets

  • Holiday rentals with a pool

    1,650 properties feature pools

  • Rentals with dedicated workspaces

    1,010 properties have a dedicated workspace

  • Wifi availability

    2,050 of Key West holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Self check-in, Free parking on premises and Monthly stays across Key West rentals

  • 4.8 Average rating

    Key West stays are highly rated by guests – averaging 4.8 out of 5!

Destinations to explore

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