Holiday houses in Key West
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Quick stats about holiday rentals in Key West
Total holiday rentals
Explore 2,110 holiday rentals in Key West
Nightly prices starting at
Key West holiday rentals start at $17 NZD per night before taxes and fees
Verified guest reviews
Over 74,900 verified reviews to help you choose
Family-friendly holiday rentals
1,250 properties offer extra space and kid-friendly amenities
Pet-friendly accommodation
Find 730 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
Wi-Fi availability
2,050 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!
Top-rated holiday rentals in Key West
Guests agree: these stays are highly rated for location, cleanliness and more.
Boat Slip - Waterfront Condo - Key West Pool
Be among the first to experience this spacious waterfront Key West getaway, newly available as a vacation rental! Enjoy a heated pool, marina views, an oversized private balcony, and over 1,200 sq ft of living space, all just minutes from Duval Street. Complete with a full kitchen, free parking, elevator access, pet-friendly accommodations, high-speed WiFi, and a private boat slip. Perfect for boating, fishing, beaches, and everything Key West has to offer. Pet friendly. 10-min from EYW airport.
FamilyLocationHospitality
KW CanalFront 3BR: Htd Pool, Boat Tie-Up, Pet OK
Your own private Key West hideaway awaits. Surrounded by lush tropical landscaping, this peaceful home offers a large pool, outdoor shower, grill, and fire pit — perfect for relaxing days and starlit evenings. Enjoy complete privacy indoors and out, with three comfortable bedrooms, a fully equipped kitchen, washer/dryer, and 66' of canal frontage- bring your own boat or ask one of our favorite captains to pick you up! Whether out on the town or relaxing in your own home, you will love it here!
LocationValueHeating
Casa Rosa: 4BR/4BA house, pool, near Duval
Casa Rosa, a historic eyebrow home in Key West, offers 4 bedrooms, 4 bathrooms, a private pool, hot tub, and prime location just a block from Duval Street. Enjoy charming décor, a fully equipped kitchen, and outdoor dining surrounded by tropical foliage. Relax in the serene backyard oasis or explore nearby attractions like the Hemingway Home, Mallory Square, and Southernmost Point. Pool heat available for $250+ tax per week. Book now for an unforgettable stay! Saturday-to-Saturday Rentals Only.
LocationValueIndoor spaces
Gorgeous Ocean View in Paradise, Close to Key West
This is paradise! Wake up to a gentle breeze and birds singing just outside your balcony. Watch the sunrise over the ocean and mangroves from your private balcony. Enjoy your privacy as you start your day, then venture out to explore all that Key West has to offer: water sports, quaint shops, delicious food, history all around you, and so much more! On property features: Pool, Hot Tub, Yellowfin Bar & Kitchen and Parking. Beach supplies included: Coolers, Snorkel Gear and Beach Towels.
LocationFamilyPool
Lagoona-Matata
A truly magical place "Lagoona-Matata" sits on the edge of Vaca Cut showcasing fabulous views of the Gulf. The outdoor area flows from the patio to the pool deck, private sandy beach, tidal pool and then to the pier dock. "Vaca Cut" is a fast-moving body of water from incoming to outgoing tides with fish of every kind moving through that makes fishing from the dock great entertainment. The continuous plethora of sea life in the lagoon makes this property an experience unlike any other.
FamilyLocationPool
Starlight Serenity - Hideaway with Stunning Views
Escape to paradise at this serene 1-bedroom, 1-bath home in beautiful Sugarloaf Key sleeping up to four guests. Enjoy breathtaking views from the expansive wrap-around balcony, perfect for sunrise coffee or sunset cocktails. The spacious outdoor area is ideal for dining, lounging, and soaking in the tropical ambiance. Whether you're relaxing indoors or savoring the outdoors, this home offers the perfect blend of comfort and tranquility. Book your next getaway for 3 nights or more!
LocationValuePets
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.
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Palm Breezes! Room for Everyone on the Ocean.
This 5 bedroom 3 bath house with pool on Ocean front property on Highway 1.. This lovely home has its own huge pool area with full lounge chairs all the way around pool area, the pool is heated. Grill, Jacuzzi. Full WiFi. TVs in every bedroom! Travel down our private dock way to the beautiful Cudjoe Bay, hop one of the many kayaks and take a healthy paddle with your friends/family or just enjoy the breathtaking ocean view while you sit on the porch.
LocationValueSleep quality
Tropical Heron Hideaway w/ Hot Tub + Pool
Welcome to our charming 1932 Key West retreat in the peaceful Meadows neighborhood. This unique getaway features a private porch, a private hot tub, access to a shared pool and BBQ grill, and all the comforts of home. Blending historic island charm with modern amenities, it’s just minutes from Duval Street, the Historic Seaport, beaches, restaurants, and local attractions—the perfect place to relax and experience authentic Key West.
LocationFamilyWalkability
Sunset Suite-Historic 2 BR, K/Q, Sleeps 4, Spa!
Historic 1880's Cigar Maker's cottage completely renovated. 1 K and 1 Q BR’s, half bath upstairs between BR’s, 32” Smart TV's, Full kitchen with granite counter tops, new stainless steel appliances. A newly remodeled bath with tumbled marbled tile, hairdryer. Also a totally private outdoor shower located in your private patio. All bath amenities provided, plus pool towels and daily housekeeping!
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Tiki Suites ~ Original Tiki ~ Floating Bungalows
Stay on the water in this one-of-a-kind Tiki Suite in Key West. This private floating bungalow blends boat life with comfort, featuring a custom bed, panoramic views, and direct access to the ocean. Swim, paddle, or relax in a hammock surrounded by nature. A peaceful, off-grid glamping experience you won’t find anywhere else. Accessible by boat only.
LocationValuePool
Wake Up On The Water | Luxury Marina | Key West
Wake up to the rhythm of the water and experience Key West from a completely different perspective. Stay aboard a 45-ft sailing yacht at the Perry Hotel & Marina. Enjoy 2 pools, gym, fine dining, and a free shuttle to Old Town. Ideal for couples or close knit groups: intimate, memorable, and all part of the yacht lifestyle.
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Popular amenities for Key West holiday rentals
Other great holiday rentals in Key West
Sandbar Suite | 2 bed near Duval & waterfront
LocationValuePool
Cozy Tiny Houseboat: Find Your Peace and Balance
ValueLocationLayout
At Mine | Lovely Suite steps from Duval Street
LocationFamilyBiking
3BR In Resort Village, Pools, Free Kayak & Shuttle
LocationFamilyHospitality
Newly Renovated 2/2 Bath Condo, with shared pool
LocationFamilyCheckout
Searenity Vacation Rental! Pool, Tiki Hut, Dockage
LocationFamilyBackyard
Keys Marathon Oceanfront, 4BR, 3.5 Bath Pool Home.
LocationFamilyView
Gorgeous Ocean View Home!
ValueFamilyCheck-in
When is the best time to visit Key West?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $760 NZD | $881 NZD | $818 NZD | $684 NZD | $579 NZD | $516 NZD | $497 NZD | $453 NZD | $418 NZD | $514 NZD | $584 NZD | $652 NZD |
| 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.
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