Vacation rentals with a pool in Windley Key

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Windley Key

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

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, 132 reviews

Sea Ray Cove, Mini Lobster week NOW OPEN!

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 favorite

A modern kitchen features white cabinetry and stainless steel appliances. A wooden cutting board is placed on the counter, complemented by cooking utensils. Soft lighting illuminates the space, enhancing the clean and functional design. A window with shutters allows natural light to enter.

Condo in Key Largo

4.95 out of 5 average rating, 99 reviews

Gorgeous lagoon-front 2BR Townhouse with 2 pools

Kawama Yacht Club is situated between an extension of John Pennekamp Coral Reef State Park and a salt-water, filtered, tidal snorkeling lagoon! Two pools, tennis courts, private beach, a waterfront (lagoon) will keep you busy on site, while the neighborhood offers boating, many great restaurants and you may even swim with dolphins just outside the gates to the community. The townhouse comes equipped with two bicycles and two kayaks. All brand new appliances throughout + extra lg washer/dryer.

Guest favorite

A private heated pool is surrounded by a spacious patio with laid brick flooring. Palm trees frame the scene, while a vibrant sunset casts warm colors across the sky. Lounge chairs are positioned by the pool, inviting relaxation by the serene water view.

Villa in Marathon

4.95 out of 5 average rating, 136 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 favorite

A serene pool area is visible, featuring a clear blue pool with a surrounding deck. Lounge chairs are arranged along the edge, and a large umbrella provides shade. Lush greenery and a clear sky contribute to a tranquil outdoor environment.

Vacation home in Key Largo

4.94 out of 5 average rating, 116 reviews

Ocean Shores Villa 3 with pool and boat slip

This centrally located boater's paradise is the perfect place to relax. Walk to restaurants, cook in kitchen or grill downstairs. With only 4 units in the building the guests have half an acre of waterfront entertainment (boat slip, Kayaks, Bikes, Hammock and Pool). 32ft Dock Slip and Trailer Parking are included in the rental. Relaxing Balcony that looks down the Ocean Canal is the perfect place to have your morning coffee. Conveniently located near Sandbars, State parks and many attractions.

Superhost

A refreshing swimming pool is surrounded by palm trees, offering a relaxing area for guests. Lounge chairs are placed around the pool deck, and the clear blue sky is visible above, creating a bright and inviting setting. Tropical landscaping provides privacy and enhances the tropical feel.

Home in Key Largo

4.91 out of 5 average rating, 101 reviews

New Oceanside Casa Azul! Voted #1! Golf Cart-Beach

No hidden fees! Casa Azul blends luxury and laid-back island vibes in the heart of Key Largo. With Superhost status and hundreds of 5-star reviews, a perfect escape. Voted the #1 Vacation Rental in Key Largo, it’s ideal for families, couples, and groups alike. Enjoy a free golf cart, fast Wi-Fi, 2 pools, private beach, saltwater lagoon, kayaks, tennis and pickleball courts with gear, marina access, boat ramp, trailer parking, and optional slip rentals. Salt Life meets luxury - this is the one.

Top guest favorite

Condo in Tavernier

4.96 out of 5 average rating, 186 reviews

Best View Ocean Pointe Pool Beach King Bed, Gated

***IMPORTANT*** The pictures you see here are of OUR unit. What you see is what YOU GET. No surprise when you arrive at Ocean Pointe. NO bait and switch. We own in the Prominent Building #3 just steps from the Pool & Jacuzzi. Wireless Internet Netflix & Cable TV, XBOX ONE. ***Most of our guests (99%) claim this is the cleanest Airbnb they have ever stayed in.*** You will get a TRUE UNIMPEDED OCEAN VIEW in our unit. Read our reviews, our past guests tell it all. ⭐ 5 STAR ⭐ Get what you pay for.

Top guest favorite

An aerial view captures the coastal complex featuring turquoise roofs and landscaped grounds. The private beach is visible, lined with palm trees, lounge chairs, and tiki huts. The calm waters reflect the blue sky, while boats can be seen in the distance.

Condo in Key Colony Beach

4.93 out of 5 average rating, 215 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 favorite

A brightly lit living area features a comfortable blue sofa and a tropical-print armchair. A glass coffee table is positioned in front, with a basket of colorful towels visible. Large windows offer a view of the outdoors, while a palm tree artwork adds a serene touch.

Condo in Tavernier

4.97 out of 5 average rating, 108 reviews

Modern and Coastal 3212 is Across from Pool

Are you looking for a Caribbean Vacation in a tropical resort without leaving the USA? Look no further than our Ocean view 2 bedroom and 2 bath condo at Ocean Pointe Suites! Our property offers: 24 hour front gate security, Heated Junior Olympic Pool with 15 person hot tub, tropical Beach, Marina, Tennis/Pickle ball courts. Enjoy the newly re opened ISLAND GRILL pool bar! We are located 60 miles from Miami International Airport and 90 miles from Fort Lauderdale International Airport.

Superhost

A scenic pool area is visible, featuring a hot tub adjacent to the water's edge. Palm trees sway gently in the breeze, providing a tropical atmosphere. The blue sky reflects on the tranquil water, enhancing the serene setting.

Home in Marathon

4.75 out of 5 average rating, 24 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 September and October. And you can always ask 7 night minimum no exceptions VACA-22-34

Guest favorite

Home in Marathon

4.9 out of 5 average rating, 72 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)

Guest favorite

A sunny view of the salt-water pool area features several lounge chairs arranged around the pool. Lush greenery borders the space, and buildings in the background are visible under a clear sky. The atmosphere reflects a relaxed outdoor setting.

Houseboat in Big Pine Key

4.75 out of 5 average rating, 147 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 favorite

A serene pool area is surrounded by lush tropical landscaping and palm trees. Lounge chairs are positioned around the pool, along with blue umbrellas providing shade. The clear water sparkles under the bright sun, creating an inviting space for relaxation.

Cottage in Islamorada

4.96 out of 5 average rating, 110 reviews

2br/1ba w heated pool, 1 mile to robbies marina

Your slice of Islamorada awaits at the Key Lime Cottage! Step inside this charming 2 bedroom cottage and you will instantly feel at home. Located in the heart of the Florida Keys yet nestled in a serene neighborhood, it offers the perfect blend of comfort and relaxation. With a full kitchen, access to a gorgeous pool shared with only 6 other homes, outside seating with grill and a fire pit, beach chairs and key lime treats - there is something for everyone!

0 of 0 items showing

What guests are saying

Waterfront Escape -VACA-23-408

5 out of 5 average rating, 33 reviews2 weeks ago

We loved staying at this home in Marathon. My family of 5 (three young kids; 9, 6 & 1) plus 4 other adults all stayed here comfortably and thoroughly enjoyed ourselves. We all felt right at home! The home was spotless and kept very clean. The location was great and we LOVED the backyard with everything it offered. The kids especially loved the yard. There are numerous marinas right by the home, which made renting a boat very convenient. Highly recommend doing so! We loved having the extra amenities like the kayak and paddle boards as well! Whenever I needed to get in touch with the host Carmen, she was very communicative and responded right away. Would definitely stay here again and highly recommend! Thank you again!

Home in Marathon

What guests are saying

Oceanfront with Pool near Sombrero Beach

4.98 out of 5 average rating, 45 reviews3 weeks ago

We had an amazing time at Seascape Point during our first family trip to Marathon! The home was absolutely perfect for our crew—my wife, our three kids, and me. The kids had an absolute blast hunting for crabs, fishing, and swimming all week long. The property was well-suited for our family’s needs, and it made for a memorable vacation. Thank you for helping make this trip such a great one—we’d love to come back!

Home in Marathon

What guests are saying

Paradise Palms~ Open Water Views w/ 40' Dock, Pool

5 out of 5 average rating, 3 reviews5 days ago

This home and location are exceptional!!! Everything about it exceeded our expectations, and I wouldn’t hesitate to rent a vacation home from Coco Plum again. It is expensive, but when you look at all you get and the location, it’s actually a bargain. The owner really has an exceptional home! Our family had a great time, and we will be back next year. Thank you!

Home in Marathon

What guests are saying

Serenity Bay Estate-FL Keys Best Kept Secret! Beau

4.93 out of 5 average rating, 29 reviews4 months ago

Stunning location, very comfortable with plenty of space for 10 people. When we arrived we never felt like leaving. Beautiful pool and hot tub surrounded by palm trees, sandy area with great fire pit, gorgeous outdoor eating area and kayaks to drop from pier. Very private location with spectacular sunsets! Fabulous!!!!

Home in Marathon

What guests are saying

Venetian Tropics private heated pool at 82 degrees

4.86 out of 5 average rating, 7 reviews7 months ago

I’d like to start this review with JoAn is amazing and super responsive. If you need anything, she will ensure that you will get it. This house is the epitome of what you would expect for a Florida keys home. If you’re looking for a house with a lot of character, in a phenomenal location for Atlantic access and fuel, this is the place. We throughly enjoyed our time staying here and will be back next year. The pool was nice to get into after diving every day, there was a fresh water hose on the dock, a freshwater outside shower and even a fish cleaning station. There is a deep freezer for ice and a tiki bar outside with a sink. Couldn’t be any happier with the house or the host. Thanks again JoAn for letting us use your house.

Home in Islamorada

What guests are saying

A motorhome in paradise

4.78 out of 5 average rating, 18 reviews3 weeks ago

We stayed here over spring break 2025- and it was very fun. It has such close proximity to John Pennekamp State Park.. so if you are an avid snorkeler, this is the place for you. My kids loved the pool, and went for night swims every night. It's very safe, and the neighborhood can be a little loud at night, but if you close the windows it's so peaceful. We weren't here often ( out doing adventures on the Florida Keys) but it was a nice place to come back to after a long day. The hammocks are very very nice and the marina has a gorgeous view. Thank you!

Camper/RV in Key Largo

What guests are saying

Superb Keys home w/heated pool

5 out of 5 average rating, 13 reviews3 weeks ago

This was the perfect home base for our Florida Keys vacation. My family of five (3 teenage girls) were very comfortable and loved the pool/hot tub. The bathrooms were clean with the showers having great pressure and the beds were super comfortable. The house was just as described and the neighborhood was quiet, peaceful and perfect for a run/walk. We were able to visit Everglades NP, Biscayne NP, and Key West during our stay. Would highly recommend!

Home in Tavernier

1 of 12 pages