
Holiday rentals with a pool in Key Haven
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Key Haven
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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

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.

Charming Key West Vacation Rental 3bedrm/3bath
Beautiful gated home located in Coral Hammock just minutes away from Key West. It's a spacious 3 bedroom, 3 bath home with a full kitchen, living room, indoor and outdoor dining. With access to shared pool, club house and gym. Everything you need to enjoy vacation. We have also updated the unit with new flooring throughout! Beach Gear is also available Beach towels, beach chairs, beach toys, floats and cooler. Baby / Toddler. Portable Crib, high chair & more. Items available upon request

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.

A Great Escape! Private 2 Bed Rm Beautiful Marina
Our Marina has a pool and a small private beach overlooking the beautiful Keys water! More affordable than most places in Key West while able to reconnect with nature at this private getaway on the Great Escape. As you approach the boat, you feel your dream vacation has come true . One of a lifetime. Staying on a beautiful sportfisher yacht, laying in the waters of the calm keys and in the most beautiful peaceful marina, will definitely set you free from all your worries and stress.

Penthouse in Paradise
Coconut Mallory is a waterfront private community that provides resort amenities. Hop in one of the two on-site pools to cool down after soaking up the sun at Smathers Beach, Key West's largest public beach just 2 miles away. There is also a Jacuzzi and a picnic area with BBQs for guest use. This unit is a two bedroom two bath. It also features two off street parking spaces included. *The Master Tub is not to be used per the community as leaks have occurred in other units before.

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

Tropical Escape at Sunrise
We thoroughly sanitize upon check-out. This luxurious condo features a wonderful tropical interior design. It includes 2 spacious BR's: king bed/ full bath, queen bed/ full bath). Our living room sofa bed accommodates 1 guest. A fully equipped kitchen. Patio overlooks pool. WiFi, basic cable, 3 TV's, A/C, washer-dryer, workout center, BBQ, tennis court, elevator, parking. Accommodates no more than 5 guests. Must be 25 and older.

*Emerald Seas*-Florida Keys Ocean Front Paradise!
Welcome to our Florida Keys Ocean Paradise, Emerald Seas! Truly a special place to get away and relax. Enjoy the crystal-clear waters and amazing views. Bring or rent a boat, look for sea turtles, manatees, dolphins, lobster & tropical fish right from your patio or dock. Take in a glorious sunrise or moonlit night over the water. The amazing, 180 degree panoramic ocean views will take your breath away every moment you are there.

Old Town Key West | Waterfront 2BR | Pool
Bring friends and family to this 1,350 sq ft waterfront corner condo in Downtown Key West. Just 1 mile to Duval Street, the Historic Seaport, and the Hemingway House—more space, more comfort, Key West done right. Enjoy a heated pool, tiki bar, BBQ grills, parking, building elevator, and secure keyless entry. Note: Dock access will be unavailable late April through May due to scheduled improvements; some daytime noise possible.

Castaway Cove: Pet-friendly 2/2 condo near beach!
Welcome to the tranquil, tucked away community of Sunrise Suites in beautiful Key West, Florida. When you choose to spend your vacation with us at the pet-friendly Castaway Cove Condo, you will be just 1 mile from Smather's Beach and a quick 10 minute drive to the fun and excitement of downtown Duval Street with tons of restaurants, bars, art galleries, museums, live music and people watching.

Paradise found
Located on Stock Island this 3 bedroom home is only 8 minutes from Duval street. Walking distance to several great restaurants. Gated community with a gym and large resort style swimming pool. Queen bedroom on first floor with full bath. Second floor King room with private full bath. 3rd bedroom as two twin beds beds with private full bath.
Popular amenities for Key Haven rentals with a pool
House rentals with a pool

Ocean View in Cudjoe Key

Key West Paradise

Tucked away near the Southernmost Point, Louisa's

Gorgeous Romantic Private Villa, Steps from Duval!

Florida Keys Retreat

Ocean~View w/ Dock, Pool, Kayaks, King Bed

White House - Receive $400 towards a Boat Rental!

Passover Cottage | Private Pool & Ideal Location
Apartment rentals with a pool

Condo de Paradise/Salt Water Pool/Boat Dock

Family Suite at Sugarloaf Key Hotel (Pet Friendly)

Magical Sunrises on the Atlantic, Upgraded Condo &

Bright Condo in Paradise

EYW Getaway

Sunrise Suites Resort, Key West FL U #408 2bdr2bth

Hyatt Beach House-Quiet Key West Spot!

Duval Street Suites on Duval Free Parking and heat
Other holiday rentals with a pool

Sentient Waters: 63’ Boat With Full Amenities

43' Classic Yacht Views, Pools, Duval Shuttle

Sunset Harbor 2 bed Ocean views!

Ocean Breeze @ VO - Kayaks, Bikes, 30 Min from KW

Super-Cozy boat in Key West!

Classic 30’ Sailboat

Tropical Paradise

Cottage
When is the best time to visit Key Haven?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | € 672 | € 800 | € 1,083 | € 876 | € 821 | € 717 | € 870 | € 1,015 | € 666 | € 661 | € 897 | € 1,000 |
| 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 |
Quick stats about holiday rentals with a pool in Key Haven

Total holiday rentals
Explore 70 holiday rentals in Key Haven

Nightly prices starting at
Key Haven holiday rentals start at € 77 per night before taxes and fees

Verified guest reviews
Over 1,400 verified reviews to help you choose

Family-friendly holiday rentals
70 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 40 rentals that welcome pets

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wifi availability
70 of Key Haven holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Key Haven rentals

4.9 Average rating
Key Haven stays are highly rated by guests – averaging 4.9 out of 5!
Destinations to explore
- Fitness-friendly rentals Key Haven
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- House rentals Key Haven
- Luxury rentals Key Haven
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- Family-friendly rentals Key Haven
- Rentals with a washing machine and dryer Key Haven
- Rentals with a patio Key Haven
- Pet-friendly rentals Key Haven
- Rentals with pools Key West
- Rentals with pools Monroe County
- Rentals with pools Florida
- Rentals with pools United States
- Sombrero Beach
- Smathers Beach
- Long Beach
- Bahia Honda State Park
- Fort Zachary Taylor Historic State Park
- Ernest Hemingway Home & Museum
- Sunset Park
- Seven Mile Bridge
- Key West Lighthouse Museum
- Florida Keys Aquarium Encounters
- The Turtle Hospital
- Southernmost Point
- Key West Butterfly & Nature Conservatory
- Boyd's Key West Campground
- Calusa Beach & Loggerhead Beach
- Boca Grande Key




