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Holiday houses in Key West

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Top-rated holiday rentals in Key West

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Top Guest favourite
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.
Condo in Key West
4.95 out of 5 average rating, 176 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

Top Guest favourite
A charming cottage features a covered deck with a dining table and chairs, positioned beside a pool. Lush palm trees and tropical plants surround the area, adding greenery. The pool water is clear and inviting, with a depth marking visible at the edge.
Home in Key West
4.95 out of 5 average rating, 370 reviews

Romantic Retreat - 2 person K Suite, Pvt deck/Spa!

Romantic Retreat is an Historic, free standing cottage which, in the 1800's, was the cistern for the Cigar Maker cottages here. It is decorated in a light Caribbean motif, efficiency kitchen (frig, microwave, hot plate) and a very airy bathroom with tub/shower. King memory foam bed and sleeps 2 persons only. 32” Smart TV (bring your Netflix, Amazon UN/PW's). Bose Bluetooth speaker, Amazon Alexa provided. A private adjacent deck with a 2 person Solana spa/seating. Also handicapped accessible.

Top Guest favourite
An Airstream RV is parked under a clear blue sky surrounded by tropical plants and palm trees. A bicycle rests nearby, and a patio area is set up with greenery. The awning extends to provide shade, creating an inviting outdoor space.
Campervan/RV in Key West
4.81 out of 5 average rating, 16 reviews

Airstream Key: you book a campsite &we deliver RV

We will deliver and set up our Airstream at your chosen campsite. To arrange this, you need to make two separate bookings: one with your campsite, and one for Airstream with us. Each booking will require a separate payment. We will ensure everything is ready for your arrival, and check-in times are determined by the campground. Four campgrounds in Key West are listed under the “other details to note.” Campgrounds other than those four are considered case by case with additional delivery fees.

Top Guest favourite
A charming entrance is framed by lush tropical plants and palm trees. The light green door complements the inviting beige exterior of the home. A cozy seating area is situated on the porch, and brick pathways lead through a landscaped yard filled with vibrant foliage.
Condo in Key West
4.95 out of 5 average rating, 64 reviews

Vacation Home Heron Hideaway

Welcome to our unique and charming Airbnb. This cozy retreat offers the perfect blend of comfort and style, featuring a private porch where you can relax and enjoy the island breeze. Take a dip in the refreshing pool or unwind in the private hot jacuzzi after a day of exploring. Enjoy cooking a delicious meal on the grill, and experience a peaceful stay in a one-of-a-kind space. Whether you're here to relax or explore, our home provides everything you need for an unforgettable Key West getaway!

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
4.91 out of 5 average rating, 210 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. 🛥️🌴🎣

Top Guest favourite
An open-concept living area features wraparound seating in dark leather surrounding a polished wooden dining table. Abundant natural light filters through panoramic windows, reflecting off the rich wooden flooring. Tropical-themed wall decor and greenery enhance the inviting aesthetic. A well-equipped kitchen is visible in the background.
Boat in Key West
5 out of 5 average rating, 19 reviews

Sailboat Stay + Resort Amenities

Unplug and unwind aboard The Dream, your own sailboat in Key West, Florida! This is not your typical Airbnb — it's a floating escape on a beautiful 1-bedroom, 2-bathroom 42 foot sailboat docked at the exclusive Perry Hotel & Marina (just minutes from downtown!) Enjoy a queen bed in the spacious Captain’s suite, 2 full-sized paddle boards, snorkel gear, private Wi-Fi, and more. With tropical vibes, luxury touches, and the comforts of home, this is where island adventure meets peaceful retreat.

Top Guest favourite
A spacious sleeping area features a king bed dressed in soft linens and adorned with decorative pillows. Natural light enters through sliding glass doors that open to views of the marina. Warm wood flooring complements the modern design.
Houseboat in Stock Island
4.95 out of 5 average rating, 43 reviews

The Writer's Block- Key West

Discover tranquility aboard this unique floating haven. It's a sleek modern retreat for those who crave space to read, write or find inspiration far from the stresses of the modern world --yet it's steps away from upscale restaurants, two fabulous pools, a gym and so much more. From a king bed to a full-sized shower and kitchenette, you'll enjoy the comforts of home while living directly on the water. Features a large private deck with panoramic views of the marina and its glorious sunsets.

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
4.96 out of 5 average rating, 143 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.

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
4.9 out of 5 average rating, 443 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
A spacious bed is framed by elegant side tables, each topped with a softly glowing lamp. Above the headboard, three framed artworks create a balanced focal point. Decorative pillows add a touch of color, while a leafy plant provides a natural element to the serene space.
Apartment in Key West
4.95 out of 5 average rating, 451 reviews

Studio Blu -Hip Studio/Old Town

*Recent Update (2025): We’ve made a wonderful upgrade to the studio bathroom — it’s now fully enclosed with walls extending to the ceiling and a new exhaust fan for ventilation. Situated in the heart of the Cuban district, just steps from arguably the best café con leche in Key West, this bright and breezy studio apartment is minutes from everything on the island. No car needed — bikes and beach chairs are provided free of charge so you can explore at your own pace.

Guest favourite
A serene pool area features a clear blue water swimming pool surrounded by lounge chairs and umbrellas. A lush landscape of palm trees and green foliage complements the setting, with a charming cottage visible in the background.
Townhouse in Key West
4.91 out of 5 average rating, 187 reviews

Poolside Cottage #411

Welcome! This beautiful cottage is located in the Coconut Mallory Resort & Marina on the eastern end of Key West. This secluded, waterfront oasis includes outdoor pools, hot tub, on-site marina and boat dock. There's also a new bar & grill, Gumbo's, in the resort. When you want to get out and explore KW, you're only minutes from beaches, the Seaport and world famous Duval Street! Bikes, kayaks, paddle boards and golf carts can be rented locally

Guest favourite
An open concept studio apartment features a modern kitchen with stainless-steel appliances, including a coffee maker and oven. A dining table with black chairs is positioned near the kitchen. In the background, a spacious bed is visible, illuminated by natural light from large windows.
Apartment in Key West
4.85 out of 5 average rating, 251 reviews

The Bartlum - Steps to Duval Street

Welcome to the Bartlum, a historic and luxurious studio apartment just steps to Duval Street. This studio, located on Caroline St, has been designed with comfort in mind, offering large windows for natural sunlight and plenty of space to spread out. Enjoy an updated kitchen, spacious bathroom, open concept layout, and all the hot spots of Key west within walking distance!

Popular amenities for Key West holiday rentals

KitchenWi-FiPoolFree parking on premisesAir conditioning

Stay near Key West's top sights

Smathers Beach

56 locals recommend

Key West

389 locals recommend

Key West Lighthouse Museum

51 locals recommend

Southernmost Point

102 locals recommend

Ernest Hemingway Home & Museum

265 locals recommend

Mallory Square

61 locals recommend

Other great holiday rentals in Key West

Superhost
The resort’s exterior is presented with white wooden siding and a classic rooftop structure. Palm trees frame the view, emphasizing the tropical environment. Expansive balconies with white railings offer a welcoming aesthetic, while large windows allow natural light to illuminate the interior.
Hotel room in Key West
5 out of 5 average rating, 5 reviews

Luxurious Stay | Snorkeling. Outdoor Pool

Superhost
Private room in Key West
4.9 out of 5 average rating, 194 reviews

Nuns Room, A single travelers delight!

Guest favourite
Hotel room in Key West
4.88 out of 5 average rating, 645 reviews

The Sanchez House Room #3

Guest favourite
A bright bedroom features a spacious bed against a floral wallpaper backdrop, complemented by colorful decorative pillows. A bedside table with a vintage lamp adds character, while a door opens to a charming balcony area. Natural light fills the room, highlighting the warm wood flooring.
Hotel room in Key West
5 out of 5 average rating, 43 reviews

Marrero's Guest Mansion Adult Only (21+) Room 7

An open-concept interior features a full kitchen with modern appliances and ample cabinetry. A comfortable seating area is present, with a grey sofa and decorative yellow pillow. Natural light floods through the windows, highlighting the wooden beams and white walls that create a bright and welcoming space.
Houseboat in Marathon
4.76 out of 5 average rating, 63 reviews

Tiny Home Aqua Lodges 2/1

A tranquil marina scene is captured at sunset, with colorful clouds reflecting on calm water. A row of Aqualodges is visible along the water's edge, alongside several parked boats and a tiki hut, creating a serene atmosphere.
Houseboat in Key West
4.71 out of 5 average rating, 282 reviews

Deluxe Bungalow

A two-story townhome is depicted, showcasing a light-colored exterior with white railings on the porches. Lush tropical landscaping surrounds the fenced property, with green foliage and colorful flowers visible. A paved pathway leads towards the entrance, framed by palm trees.
Home in Key West
5 out of 5 average rating, 4 reviews

Tropical Townhome On Golf Course

Top Guest favourite
A spacious sleeping area features a colorful patterned bedspread covering a large bed. Wooden accents are presented through side tables, while palm leaves accentuate the walls. Natural light enters from a window, complementing the warm tones of the wooden ceiling.
Private room in Big Pine Key
4.88 out of 5 average rating, 547 reviews

Old Island Life

When is the best time to visit Key West?

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Avg. price$580 AUD$647 AUD$614 AUD$524 AUD$472 AUD$428 AUD$439 AUD$400 AUD$368 AUD$437 AUD$469 AUD$502 AUD
Avg. temp21°C22°C24°C25°C27°C29°C30°C30°C29°C27°C25°C23°C

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 2,180 holiday rentals in Key West

  • Nightly prices starting at

    Key West holiday rentals start at $15 AUD per night before taxes and fees

  • Verified guest reviews

    Over 66,120 verified reviews to help you choose

  • Family-friendly holiday rentals

    1,310 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 680 rentals that welcome pets

  • Holiday rentals with a pool

    1,670 properties feature pools

  • Rentals with dedicated workspaces

    1,070 properties have a dedicated workspace

  • Wi-Fi availability

    2,090 of Key West holiday rentals include Wi-Fi 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!

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