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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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Superhost
Home in Key Colony Beach
5 out of 5 average rating, 4 reviews

P08 - Beautiful 4 bedroom, 3 bath with Cabana Club

Now offering Cabana Club Membership! This lovely two-story half duplex in Key Colony Beach offers 4 bedrooms, 3 bathrooms and abundant living space on both levels. The upper level offers 2 bedrooms, 2 bathrooms, a kitchen with oversized breakfast bar and abundant living space. The lower level offers 2 bedrooms, 1 bathroom, a kitchenette and den. Key Colony Beach offers a par 3, nine-hole golf course, public pickle ball courts, Sunset Park, several restaurants, clothing boutiques ...

Superhost
Three modern Aqua Lodges are positioned on water, featuring white exteriors and blue roofs. Each lodge has a furnished deck with chairs, providing relaxed seating options. A smooth, concrete path runs alongside the lodges, leading to a marina setting with sailboats in the background.
Villa in Marathon
4.89 out of 5 average rating, 518 reviews

New Aqua Lodge 2Beds 1 Bath with Full Kitchens

This hip spot is the new thing in lodging. Aqua Lodge is all the modern amenities while being on the water. Full kitchens, flat screen tv's, wi-fi , pool, bikes, sunset beach. We have it all right at your finger tips. You can sleep up to 5 people comfortably. We have great air conditioning and big showers. The deck is furnished with a dining table for those romantic outdoor dinners in the moonlight. We also have a sunset beach area for the best sunsets in the Florida keys!

Top guest favourite
An open walkway features white railings and is bordered by palm trees and greenery. Directly visible are multiple buildings in the background, contributing to the relaxed atmosphere. The bright blue sky and scattered clouds enhance the sense of space and light.
Flat in Marathon
5 out of 5 average rating, 14 reviews

Steps to the Ocean & Heated Pool

Escape to paradise in a new 1 bed/2 bath centrally located in Marathon. Our condo is steps away from open ocean views, where you can fish off the docks, lounge under one of the many Tiki huts, or cool off in the vast elevated swimming pool that overlooks the Atlantic. Fully air conditioned clubhouse on property is equipped with a commercial ice machine. Convenient grilling stations located next to the clubhouse, to cook your fresh catch. Come enjoy paradise. VACA-23-312

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.

Guest favourite
Aerial view of a waterfront property featuring a semi-circle dock leading to a small island. Brightly colored chairs in green and turquoise sit on sandy areas, surrounded by clear blue water and lush tropical vegetation. Nearby, additional properties can be seen amidst palm trees.
Home in Summerland Key
4.92 out of 5 average rating, 112 reviews

Waterfront Haven House with Boat Basin & Ramp!

Welcome to Paradise! Stay in the amazing Keys and beautiful waterfront home with boat basin and ramp for your boat. The property lot is almost an acre with another rental home and still very spacious (search for Anchor House to reserve both homes if available). Stunning panoramic water views, sunrise and sunset. Steps away from ocean water. Bring or rent fishing and snorkel gear nearby to fish right off the point and enjoy the underwater scenery!

Top guest favourite
Apartment in Key Colony Beach
4.96 out of 5 average rating, 273 reviews

Amazing Ocean Front Views Key Colony Beach

Newly renovated studio condo in Key Colony Beach, Florida Keys. Unit #40 offers two queen beds, a full equipped kitchen with full-size appliances and essentials, reliable WiFi, and a SmartTV for a comfortable stay. Enjoy the heated pool and private sandy beach just steps away. Sunset Park is next door-perfect for catching a beautiful Florida Keys Sunset.

Guest favourite
Apartment in Key West
4.92 out of 5 average rating, 122 reviews

Vacation home Island Suite 16

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.

Guest favourite
The modern building is designed with balconies overlooking a serene pool area. A turquoise pool is bordered by lounge chairs and palm trees, creating a refreshing outdoor space. The backdrop features a clear sky and a sandy waterfront, enhancing the tranquil ambiance.
Flat in Key West
4.92 out of 5 average rating, 38 reviews

Oceanfront Condo in Key West, FL

Key West Beach Club is a serene waterfront oasis located in an upscale gated community within walking or biking distance to the local’s finest spots, including restaurants, beaches, shopping centers, bars and the infamous Duval Street. This complex prides itself for being one of the very few on the island that sits directly on the water.

Guest favourite
A cozy bedroom features a spacious bed dressed in white linens and decorative pillows. Natural light filters through a window adorned with wooden blinds. A mirror and wicker accents complement the tropical wall decor, while dark hardwood flooring adds warmth to the space.
Flat in Key West
4.96 out of 5 average rating, 126 reviews

Duval Street Suites full kitchen, free parking, he

Paradise Suite is a one bedroom (king) 1 bath suite with a sleeper sofa (queen) and kitchen. In historic Old Town, Key West. Free parking available and the pool is privately located behind the building . Located in the middle of everything yet quiet and away from it all. This space is truly unique and sure to please all ages.

Guest favourite
A shared pool area is showcased overlooking Garrison Bight Marina. Lounge chairs are arranged around the pool, with a thatched gazebo providing shaded seating. The marina is visible in the background, featuring moored boats and palm trees against a clear sky.
Flat in Key West
4.92 out of 5 average rating, 104 reviews

Waterfront Condo FREE Slip & Pool 2B2B in Key West

🌴 Key West Waterfront Paradise – FREE Dockage Included! Wake up to breathtaking marina views, unwind in the heated pool, and walk or bike to Duval Street in minutes. Enjoy a spacious condo with a private balcony, exclusive boat slip, and all the comforts you need for an unforgettable stay in the heart of Key West.

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.

Guest favourite
Flat in Key West
4.82 out of 5 average rating, 11 reviews

Jerry's Escape - Truman @ Duval | Cozy Studio

Experience the ultimate romantic getaway at Key West Bliss, a cozy one-bedroom condo just steps from Duval Street, Hemingway’s Home, and the best of Key West’s attractions.

Popular amenities for Key West holiday rentals

When is the best time to visit Key West?

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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 € 9 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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  3. Florida
  4. Monroe County
  5. Key West