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Vacation 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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Top guest favorite

An outdoor space features a sparkling in-ground pool surrounded by a sun deck with several lounge chairs. A shaded screened-in porch is visible in the background, along with a gas grill and a cornhole game set nearby. Lush palm trees provide a tropical atmosphere.

Home in Marathon

4.99 out of 5 average rating, 144 reviews

Cancellation Deal; Sept 27 thru Oct 04; Save now!

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.

A spacious outdoor pool area is surrounded by lush greenery and palm trees. Lounge chairs are positioned around the pool, reflecting a serene atmosphere. A shaded gazebo offers a relaxing spot nearby, while the clear water invites refreshment under the bright sky.

Condo in Key West

4.95 out of 5 average rating, 163 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

The image captures a circular pool surrounded by palm trees and a wooden deck. Lounge chairs in blue are arranged for relaxation. A light-colored cottage is visible in the background, creating an inviting atmosphere. The sky above is bright and partly cloudy.

Home in Key West

4.95 out of 5 average rating, 352 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.

Cottage in Cudjoe Key

4.93 out of 5 average rating, 135 reviews

King Master, 2BR, 2BA, 35' Seawall, SUP, Kayaks

Updated, waterfront, 2BR, 2BA with King Master and a 35' seawall.Bring your boat!Fully stocked kitchen w stainless appliances. So much to do here for up to 6 at this family-friendly, quiet resort-Venture Out, a gated,secure community. Fishing, lobstering, oversized pool, children's pool, hot tub, pickleball, tennis and basketball courts.Rec center. Bike, kayak, and SUPs.Between Key West(20Mi)and Marathon, this property and area is not to be missed! Free WIFI; Both bedrooms and LR have Roku TVs.

An aerial view of the beachfront complex showcases a vibrant landscape with lush palms surrounding the property. The well-maintained grounds feature lounge areas and tiki huts adjacent to the sandy beach. The ocean's gentle waves are visible along the shoreline, reflecting the clear blue sky.

Condo in Key Colony Beach

4.91 out of 5 average rating, 191 reviews

Exquisite Oceanfront Paradise - Key Colony Beach

Exquisite renovation just completed (Nov 2024). Unobstructed ocean views from our beachfront condo in Key Colony Beach. Ground floor and just a few steps away from our private beach and heated pool. Location just does not get any better. Stunning, clean white interior - kitchen stocked with everything (dishes, cookware, utensils, glassware, stove, oven, toaster, microwave, blender, fridge, etc). Guests can enjoy the quiet private beach with lounge chairs, patio tables, tiki's and BBQ grills.

The image showcases a bright pool area surrounded by lush tropical foliage. A two-story wooden building features multiple balconies, enhancing the serene environment. Several lounge chairs are positioned on the pool deck, inviting relaxation under the sunlight.

Vacation home in Key West

4.86 out of 5 average rating, 332 reviews

Historic Cigar House. 3rd floor Suite W/Kitchen

This unit is located in the historic "Cigar House" of the Island City House Hotel. Unit 12 is on the 3rd floor and is one of the most requested units in the entire hotel. Your private balcony overlooks the pool. Only 3 blocks from Duval street so close everything, yet quiet enough for a good nights sleep. You will have your own private entrance and use of all the hotel amenities. The space is a private 1BR with a kitchen and NEW sleeper sofa (12/23). In Old Town, walk to everything.

A private balcony is shown, featuring colorful patio chairs and vibrant tropical plants. The space is framed by white railings and light blue shutters, creating a fresh and inviting setting for relaxation.

Condo in Key West

4.89 out of 5 average rating, 249 reviews

Tropical Old Town Bungalow

Great Location, Close to Duval & Beach Welcome to paradise! This Tropical Old Town Bungalow is located perfectly between Key West’s best beaches and the best restaurants and nightlife! The rental unit sits right between the White Street Art Gallery District and the Historic District, which features some of Key West’s most historic homes and properties. Whether you are walking, riding bikes or grabbing a quick cab, no destination is too far from this conveniently located rental.

A serene waterfront scene is captured at sunset, featuring palm trees, boat docks, and a gently reflecting harbor. A large boat is tied up alongside the dock, with colorful lights and silhouettes of the surrounding structures visible in the background.

Condo in Key West

4.9 out of 5 average rating, 218 reviews

"Abaco" Key West • 2/2 End Unit Waterfront+Dockage

Time to fish & relax! Bring your family & friends to this 1350 sqft waterfront corner condo home. Boat slip available on-site with commercial ice machine and fish cleaning station. Located in historic Downtown Key West. Walk/Bike everywhere less 1mi to Duval Street, Seaport, Hemingway House, etc. On-site amenities: heated pool, boat slip, tiki bar & grills, parking, secure keyless entry, & building elevator. Large Park adjacent with tennis courts. 10min from airport (EYW).

A tranquil outdoor pool is surrounded by palm trees, with lounge chairs and tables positioned for relaxation. Umbrellas provide shade near the water, while a charming cottage can be seen in the background under a clear blue sky.

Townhouse in Key West

4.86 out of 5 average rating, 202 reviews

Poolside Cottage #412

Welcome! This beautiful cottage is located in the Coconut Mallory Resort & Marina on the eastern end of KW. This secluded, waterfront oasis includes outdoor pools, hot tub, on-site marina and 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, golf carts, kayaks, stand-up paddleboards and other watercraft can all be rented locally!

A spacious living room is furnished with a soft blue sofa and matching armchair. Light wooden flooring complements the room's bright atmosphere, and a coffee table sits in the center. Large sliding glass doors lead to a patio area, allowing natural light to fill the space.

Condo in Key West

4.89 out of 5 average rating, 147 reviews

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.

Home in Cudjoe Key

4.9 out of 5 average rating, 113 reviews

*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.

A spacious houseboat is moored at the marina, featuring multiple deck levels and seating areas for relaxation. The surrounding water reflects a clear blue sky, while neighboring yachts are visible in the background. This inviting setting showcases the boat's modern design.

Houseboat in Key West

4.88 out of 5 average rating, 252 reviews

Key West Luxury Houseboat at Yacht Club Resort

PANORAMIC Ocean Views - POOL 200+ FIVE STAR Reviews- FIVE YEARS SuperHost Rated ~ SUN DECKS on All Levels, 500 square foot Rooftop Sky-Deck - 2x Queen Bedrooms 2x Ensuite Full Bath Queen Sleeper Sofa and 1/2 Bath Ocean-View Living Room ~ Floor-to-Ceiling Windows ~ 50 inch TV, 42 inch TV, 32 inch TV ~ Granite Countertops Throughout ~Full Kitchen, Full Size Appliances ~

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Popular amenities for Key Haven rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Top guest favorite

Home in Marathon

5 out of 5 average rating, 42 reviews

Brand New Luxury Oceanfront Home w/ Pool, 38' Slip

A clear blue sky with scattered clouds is visible above the pool area. Palm trees line the edge of the space, providing a tropical feel. A rectangular pool and a smaller octagonal pool are present, surrounded by lounge chairs and an open expanse of sandy ground.

Home in Cudjoe Key

4.97 out of 5 average rating, 167 reviews

Cudjoe Key Home with a View

A collage highlights an inviting outdoor space featuring a heated pool, hot tub, and two putting greens on lush lawn. The open living area showcases comfortable seating, light-colored furnishings, and ocean-themed decor. Exterior views reveal spacious patios and well-maintained landscaping under a colorful sunset.

Home in Marathon

4.95 out of 5 average rating, 138 reviews

Paradise - Pool, Hot tub, Mini Golf, Dockage, Fish

Top guest favorite

Home in Key Colony Beach

4.95 out of 5 average rating, 123 reviews

Waterfront Home 37.5-ft dock, Cabana Club Included

An aerial view captures the waterfront property with a heated pool and outdoor seating areas, surrounded by lush palm trees. The private canal is visible, along with neighboring homes. Blue skies enhance the tropical setting, creating a serene atmosphere perfect for relaxation.

Home in Marathon

4.86 out of 5 average rating, 7 reviews

The Keys Grand Blue/ 120'Dock/Mini Golf/ GameRoom

Top guest favorite

A serene outdoor pool is surrounded by lounge chairs and umbrellas, with palm trees swaying gently nearby. The expansive water reflects the clear blue sky, while the ocean can be seen in the background, enhancing the inviting atmosphere for relaxation.

Home in Key Colony Beach

4.98 out of 5 average rating, 112 reviews

Waterfront House with 37 ft Dock & Cabana Club

The living area features a spacious sectional sofa facing a large window with multiple shutters, allowing natural light to fill the room. A modern coffee table is situated on a soft area rug, complemented by dining stools near the open kitchen with updated appliances.

Home in Cudjoe Key

4.86 out of 5 average rating, 106 reviews

Waterfront Sanctuary in the Keys!

A community pool is surrounded by lush greenery and palm trees, featuring a paved patio with several chaise lounges. The pool's water sparkles under the sunlight, and a thatched-roof cabana adds a relaxing touch to the outdoor space.

Home in Key West

4.86 out of 5 average rating, 111 reviews

Your clean and cosy family home in Key West

Condo rentals with a pool

A community pool is shown, featuring a clear blue water surface with visible lane markings. Surrounding the pool are lounge areas with light-colored decking and palm trees in the background, adding to the open and airy feel of the space.

Condo in Key West

4.82 out of 5 average rating, 284 reviews

La Dolce Vita, Old Town Steps to Duval! 3 blks bch

A swimming pool is surrounded by lush greenery and lounge chairs. Tall palm trees provide shade next to the clear blue water. The pool area features a small staircase for easy access, with a sunny atmosphere inviting relaxation.

Condo in Key West

4.9 out of 5 average rating, 89 reviews

Ocean Front Studio private Sandy Beach in Key West

A spacious outdoor area is depicted, with an Olympic-size swimming pool surrounded by lounge chairs and umbrellas. Lush palm trees and landscaped gardens frame the scene, while a sandy beach and ocean are visible in the background, enhancing the resort-like atmosphere.

Condo in Key West

4.78 out of 5 average rating, 300 reviews

Affordable Beachfront Luxury Condo Sleeps 6

Top guest favorite

Aerial view of the condominium complex showcases a large pool surrounded by palm trees and lounge chairs, with direct access to a private beach. Calm turquoise waters extend beyond, and a wooden dock is visible in the distance under a clear blue sky.

Condo in Marathon

5 out of 5 average rating, 46 reviews

Beach Heaven-Private Beach, Pool

Top guest favorite

A light-filled living area features a comfortable sofa paired with accent tables. Soft blue walls create a calming backdrop, while stylish decor elements, such as framed artwork and lamps, add character. A mirror reflects the space, enhancing its openness and inviting ambiance.

Condo in Key West

5 out of 5 average rating, 40 reviews

EYW Getaway

A clear, inviting outdoor pool is surrounded by lush tropical landscaping. Palm trees are scattered around, softening the edges of the pool area. A multi-story building with a light-colored exterior provides a backdrop, featuring several balconies with white railings.

Condo in Key West

5 out of 5 average rating, 8 reviews

Hyatt Beach House-Quiet Key West Spot!

A clear pool glimmers under the sun, surrounded by palm trees. Lounge chairs are positioned by the poolside, while tiki huts can be seen in the distance. The condominium buildings frame the view, creating a peaceful outdoor space.

Condo in Key Colony Beach

4.86 out of 5 average rating, 131 reviews

Beachside Unit 33-Private Tropical Beach Plus Pool

Top guest favorite

An aerial view showcases the beachfront location of the condominiums, with a gleaming pool surrounded by well-kept lawns. White sandy beaches meet the clear turquoise waters, while tropical palm trees sway gently in the breeze. Nearby canals and homes create a serene coastal community.

Condo in Marathon

4.96 out of 5 average rating, 23 reviews

*NEW* Private Beach, pool & fully loaded kitchen

Other vacation rentals with a pool

A private heated pool sits on a wooden deck, showcasing clear turquoise water. Lush greenery surrounds the area, and the ocean is visible in the background. Two lounge chairs invite relaxation, while the distant shore features gentle waves under a bright blue sky.

Home in Cudjoe Key

4.84 out of 5 average rating, 32 reviews

Yellow Home - Receive $400 towards a Boat Rental!

Top guest favorite

The expansive outdoor area is surrounded by lush palm trees and colorful umbrellas. A sparkling pool reflects the sky, flanked by lounge chairs. The house stands in the background, offering a vibrant yet tranquil environment, with a stone pathway leading to the pool area.

Home in Marathon

4.98 out of 5 average rating, 52 reviews

Oceanfront with Pool near Sombrero Beach

Condo in Key West

4.88 out of 5 average rating, 34 reviews

New Listing! Key Lime Paradise/Condo

The outdoor area features a charming pool surrounded by lush tropical landscaping and palm trees. A view of the two-story home is visible in the background, showcasing its inviting exterior. Several loungers are strategically placed beside the pool, offering a relaxing space.

Apartment in Key West

5 out of 5 average rating, 17 reviews

Horse Conch~ Amazing Location With Shared Pool

Top guest favorite

A spacious swimming pool is surrounded by lush tropical greenery and lined with lounge chairs. Tiki-style huts provide shaded areas for relaxation, while the pool's clear blue water reflects the vibrant sky, creating a serene and inviting environment.

Home in Key West

5 out of 5 average rating, 25 reviews

Funky Chicken Cottage with Shared Pool in Paradise

A spacious pool area features a large swimming pool surrounded by lounge chairs and vibrant blue umbrellas. Lush palm trees provide shade, and ocean views are visible in the background, enhancing the tranquil atmosphere of the outdoor space.

Apartment in Key West

5 out of 5 average rating, 7 reviews

Henry's Penthouse On The Ocean

The modern home is showcased from an aerial view, featuring a spacious pool area surrounded by palm trees. A rooftop lounge is visible, with stairs leading up. The layout highlights the pool, outdoor seating, and ample outdoor amenities, with clear blue skies above.

Home in Marathon

5 out of 5 average rating, 24 reviews

Off the Hook~ Luxury Pool Home, 30' Dock & Kayaks!

Top guest favorite

A large swimming pool is surrounded by palm trees, creating a tropical atmosphere. The pool features a hot tub integrated into the pool area, with comfortable lounge chairs positioned around it. The sky is clear, and sunlight reflects off the water's surface.

Home in Key Colony Beach

5 out of 5 average rating, 28 reviews

Boat Dock+King Beds & Cabana Club

Quick stats about vacation rentals with a pool in Key Haven

Total rentals
60 properties
Nightly prices starting at
R1,588 ZAR before taxes and fees
Total number of reviews
1.1K reviews
Family-friendly rentals
60 properties are a good fit for families
Pet-friendly rentals
40 properties allow pets
Rentals with dedicated workspaces
40 properties have a dedicated workspace