
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.

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 ...

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!

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

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.

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!

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.

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.

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.

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.

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.

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.

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
What Airbnb hosts recommend seeing in Key West
Find unforgettable activities and unique points of interest near you. Our hosts share their favourite things to do and must-visit places to see in Key West.
Fort Zachary Taylor Historic State Park Beach
Historic fort and park with nature trails, a beach, and scenic views
Summarised by AI
Swim, snorkel, and fish at the only natural beach in Key West, then refuel at the on-site snack shack or concession stand for an easy lunch between dips. Rent lounge chairs and snorkel gear, bring water shoes for the coral, and use the park grills for a simple cookout by the water. Explore the Civil War–era fort, see the largest collection of Civil War seacoast guns and cannons, and visit the small museum. Stay for sunset over the Gulf of Mexico, a local favorite view.






The Hemingway Home and Museum
Historic residence featuring guided tours, lush gardens, and famous six-toed cats
Summarised by AI
Tour this National Historic Landmark to see the rooms and writing studio where Hemingway penned some of his most famous works, furnished with much of his original 17th- and 18th-century Spanish furniture. Stroll the lush gardens, visit the Wall of Shame, and browse the on-site bookstore and gift shop. Meet the world‑famous six‑toed cats, whose descendants still freely roam the property and are cared for by a perpetual trust. Bring cash for the entrance fee, then grab a bite at Moondog Cafe next door.






The Key West Butterfly and Nature Conservatory
Enchanting glass conservatory with diverse butterfly species, exotic birds, and flamingos
Summarised by AI
Step into the glass-enclosed conservatory and walk among 50–60 species of butterflies from around the world, all flying freely through lush plants, trees, and cascading waterfalls. Watch for more than 20 species of small, colorful birds and meet the resident flamingos, Rhett and Scarlett, who have become local celebrities. It’s peaceful, fully covered, and great for kids or a rainy-day activity. After exploring, browse the on-site photos and unique gifts, or use your same-day pass to return.






Southernmost Point of the Continental U.S.A.
Iconic concrete buoy marking the southernmost point in the continental United States, 90 miles from Cuba
Summarised by AI
At the Southernmost Point Buoy, you stand at the southernmost point of the continental United States, just 90 miles from Cuba, marked by the big candy-striped concrete buoy and nonstop photo ops. Snap your must-have shot with the bright red, yellow, and black “90 miles to Cuba” marker, turquoise ocean and palm trees behind you, and watch boats drift past. Expect a line, especially after 9am, so go early. Afterward, pair it with nearby “southernmost” spots or the Seaside Café by the Southernmost House.






Other great holiday rentals in Key West

Off Grid Boat "Shanty Pineapple" Key West

Private Pool, 40’ Dock, Tiki Hut, Open Water Views

Luxury Boat Stay | Resort Amenities

Duval Corner - Pet friendly with Balcony

Mellow Macaw @ Old Town - Cozy Condo + Last Key

b watervibe

EYW Getaway

Grouper House: 4 Masters/6 BA, Pool/Dock, BoatRamp
When is the best time to visit Key West?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $496 SGD | $553 SGD | $525 SGD | $448 SGD | $404 SGD | $366 SGD | $375 SGD | $342 SGD | $315 SGD | $388 SGD | $441 SGD | $492 SGD |
| Avg. temp | 21°C | 22°C | 24°C | 25°C | 27°C | 29°C | 30°C | 30°C | 29°C | 27°C | 25°C | 23°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 2,130 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!
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- Bahia Honda State Park
- Fort Zachary Taylor Historic State Park
- Seven Mile Bridge
- Ernest Hemingway Home & Museum
- Sunset Park
- Key West Lighthouse Museum
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- Key West Butterfly & Nature Conservatory
- The Turtle Hospital
- Boyd's Key West Campground
- Southernmost Point
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