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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.

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Guest favourite

Home

4.99 out of 5 average rating, 125 reviews

Sea Ray Cove, 75' boat dock, 1 block from beach!

2025 - New concrete dock, fenders & fish filet table. This ground level waterfront home has received a new face lift. Completely remodeled 3 bedroom with bonus room in the well known Sombrero Beach neighborhood. Just a short block walk to the sandy beach shore. Home has an open floor plan overlooking the in-ground pool deck and new tiki hut. Enjoy your morning coffee and happy hour in the screened-in porch with views of the wide lagoon. Come and create your family memories in the fabulous Keys.

Guest favourite

Villa

4.95 out of 5 average rating, 126 reviews

Private 4/3 Pool Heater/Dock/Kayaks/Bikes,etc

Wake up to breathtaking water views at our 4-bedroom, 3-bathroom villa. Enjoy the 1800 sq ft layout, fully equipped kitchen w/stainless steel appliances, and granite countertops. Sleeps 10 with memory foam beds. Outside, relax by your private heated pool (winter) and tiki-shaded area. Fish from the 32' dock or use the BBQ gas grill. Includes 2 kayaks, 2 paddleboards, and 4 adult bikes for a 5-minute ride to Sombrero Beach. Exterior cameras for security. Vacation License #VACA-22-40. Book now!

Guest favourite

Home

4.9 out of 5 average rating, 29 reviews

Sunshine Escape! 2/2 with pool & 10,000lb lift

Create amazing memories at this unique, family-friendly home in the Heart of the Fl Keys! This 2/2 has a complete kitchen,stainless appliances, private pool that can be heated for an extra fee,10,000lb boat lift at dock (no additional space),bait freezer,outdoor shower and much more. Enjoy a cup of coffee on the back patio watching the sunrise! Located on 11th St in Key Colony Beach, a short walk to Sunset Park. On 7th St there's a playground, 9 hole golf,pickle,bocce and basketball courts.

Home

4.72 out of 5 average rating, 18 reviews

Sunset Views, Pool and Dock

Beautiful two bedroom two bath single family home with pool and spa with dock right on the water! Enjoy the beautiful sunset and bay views from our dock, deck or pool! Bring your boat and bathing suits and enjoy this wonderful home in the Heart of the Florida Keys! Pool heat is an additional fee Kayaks and golf carts rental available upon request Saturday to Saturday during busy months except May, September and October. And you can always ask 7 night minimum no exceptions VACA-22-34

Guest favourite

Apartment

4.93 out of 5 average rating, 204 reviews

Anchors Away Condo - Key Colony Beach Oceanfront

Beautiful new renovation in Key Colony Beach ocean front complex. Unit #4 is a studio condo on the 1st floor (no stairs to climb) within steps of the heated pool and private beach. #4 features a crisp, clean white interior with new kitchen, bathroom and furnishings. Kitchen has everything needed to cook a complete meal (dishes, cookware, stove, oven, toaster, microwave, blender, fridge, etc). Guests can enjoy the quiet private beach with lounge chairs, patio tables, tiki's and BBQ grills.

Guest favourite

Villa

5 out of 5 average rating, 7 reviews

Villa Marlin - Perfect Vacation in Florida Keys

Spacious house, newly built with a private outdoor pool in the beautiful Florida Keys. This is the perfect location for boating enthusiasts. There is space for both parking and boat trailers. An exclusive ramp is a block away (30-second drive or 1-minute walk), leads to Gulf of Mexico, and 10 minutes to the Atlantic Ocean. A pool heater is provided for free for renters during the Winter. Outdoor pool shower included. Barbecue gas always provided. Games include corn hole, domino, billard.

Guest favourite

Home

5 out of 5 average rating, 22 reviews

Waterfront Escape -VACA-23-408

Come stay at this brand new home construction on a deep and wide canal leading to the ocean with pool and exotic decor. 75 foot dock with water and electric. Top of the line appliances with a fully stocked kitchen. Spa style showers with high end decor. Luxury at its best. Heated pool with sundeck and lots of seating around the edges. (Pool heater is an additional $100 per stay). Ground level cooking and dining for those beautiful days after boating or while laying around in the pool.

Guest favourite

Home

4.9 out of 5 average rating, 71 reviews

Dream Vacation KCB Marathon with private pool !

Dream Vacation Duplex in Key Colony Beach. Private pool Brand New state of the art house with all commodities and amenities, 3 bicycles 2 kayaks near to restaurants, fast WIFI, washer ,dryer, blue tooth speakers, night mood lights. A modern lift for boat up to 18000 lb Main canal Use of electric golf car Gem and jet sky and boat can be arrange Electric Gem-4 car offered for a minimum extra charge Options of private boat or jet sky (ask) Heated pool on demand (extra cost)

Houseboat

4.75 out of 5 average rating, 144 reviews

2 Bedroom Aqualodge # 11 Grouper

This 2 Bedroom Aqualodge is an adorable accommodation in the Old Wooden Bridge Resort and Marina. You are able to enjoy the resort amenities during your stay. Beautiful Salt Water pool, Fish Cleaning Stations. Renters can also bring their boat or rent a boat from OWB at an additional fee. There is NO Swimming in the Marina Boat Basin. There is a beautiful salt water pool to use for your swimming pleasure. This is a marina with houseboats and rental boats in the slips.

Guest favourite

Townhouse

4.96 out of 5 average rating, 253 reviews

Stunning Townhouse * Full kitchen! * Sleeps 6

This property is a rare find! Sleeping 6 and located over 2 floors, its located in the beautiful resort of Santa Maria. The condo itself is overlooking the pool, enjoys 2 stunning balconies with its own outdoor furniture. Fully equipped kitchen, 21/2 bathrooms, TVs and wifi throughout. The property is located in one of the best destinations within the historic old town. Just 2 blocks from Duval Street, and also just 2 blocks from the beach. You really can have it all!

Guest favourite

Home

4.97 out of 5 average rating, 103 reviews

Anglers Terrace, Condé Nast Traveler's Best Airbnb

As published in Condé Nast Traveler, this is one of the best Airbnb's in Florida. Newly Built two story Tropical Oasis with pool has been thought-out meticulously. An open, very light & spacious floor plan, carefully appointed furnishings, and great location provide the perfect surroundings. Decorated with a Zen sensibility, It’s outdoor Patio deck and Rooftop Terrace extends your living space into the private quiet ocean setting with panoramic views

Home

4.89 out of 5 average rating, 221 reviews

Newly Renovated Oceanside House with Pool

This home is on the Atlantic side of US 1. It is part of Sunrise Beach Resort, a gated community built in 2007 with only 10 other homes. Lounge in your private hammock or enjoy the gorgeous tropical landscaping and cool breezes on one of two balconies, dock or poolside, where you can soak up the sun steps from the house. Breathtaking southwest views of the blue-green ocean and sunsets can be seen from the pool and dock.

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Popular amenities for Key Haven rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Home

4.89 out of 5 average rating, 66 reviews

Casa Loca

Home

5 out of 5 average rating, 7 reviews

Beachy & Bright - 3 BR, Private yard, Heated pool

Home

5 out of 5 average rating, 12 reviews

Waterfront Oasis w/Private Pool-Dockage-Beach

Home

4.85 out of 5 average rating, 27 reviews

Lower Keys Paradise

Home

4.76 out of 5 average rating, 17 reviews

Casa Playa~ Luxury Pool Home Amazing Outdoor Area!

Home

5 out of 5 average rating, 22 reviews

Catherine House: A charming Old Town Key West

Home

4.83 out of 5 average rating, 12 reviews

P22 - Updated 3 bedroom 2 bath duplex with private

Home

4.72 out of 5 average rating, 54 reviews

Gorgeous 3/2 SFH Brand-new pool&spa, 30ft dockage

Apartment rentals with a pool

Apartment

4.74 out of 5 average rating, 150 reviews

2 Bedroom Oceanfront Complex Heated Pool KCB

Apartment

4.68 out of 5 average rating, 80 reviews

BOOK today and enjoy our amazing discounts for yo

Guest favourite

Apartment

4.94 out of 5 average rating, 35 reviews

Condo de Paradise/Salt Water Pool/Boat Dock

Guest favourite

Apartment

4.98 out of 5 average rating, 63 reviews

Oceanfront 3 bed condo Ocean Edge w/ optional slip

Apartment

4.73 out of 5 average rating, 91 reviews

Top floor Ocean Views, Spacious 2 Bedroom Condo, V

Guest favourite

Apartment

4.9 out of 5 average rating, 118 reviews

Tropical Escape at Sunrise

Apartment

4.78 out of 5 average rating, 83 reviews

Pool View Suite | Beachside Resort

Guest favourite

Apartment

4.94 out of 5 average rating, 124 reviews

Fully renovated 2/2 bath condo w/ shared pool!

Quick stats about holiday rentals with a pool in Key Haven

Total rentals
70 properties
Nightly prices starting at
£90 before taxes and fees
Total number of reviews
920 reviews
Family-friendly rentals
70 properties are a good fit for families
Pet-friendly rentals
40 properties allow pets
Rentals with dedicated workspaces
50 properties have a dedicated workspace

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