Vacation rentals with a pool in Estero Island

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Estero Island

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

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Top guest favorite

A spacious living area features a large sectional sofa adorned with cozy pillows. Natural light fills the room from the adjoining dining area, which showcases a wooden table seating six. The modern kitchen with stainless steel appliances is visible in the background, creating an inviting social space.

Home in Fort Myers Beach

4.99 out of 5 average rating, 124 reviews

Sandy Feet Retreat on Virginia Ave

Your Sandy Feet Retreat in Paradise This newly remodeled home offers modern elegance with 3 spacious bedrooms and 2.5 beautifully remodeled bathrooms. Enjoy the private heated pool, perfect for relaxing. Situated in the heart of Fort Myers Beach, this home is just a 5-minute stroll to the powdery, sugar-sand beach and only a 10-minute walk to margaritaville andTimes Square. With a variety of restaurants and bars featuring live music nearly every night, it’s the perfect location for enjoying th

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Guest favorite

A private screened-in pool is surrounded by a spacious patio area, featuring sunlight filtering through the mesh enclosure. Brick flooring leads to the turquoise water of the pool, while seating options and a view of palm trees can be seen in the background.

Home in Fort Myers Beach

4.94 out of 5 average rating, 52 reviews

Plunge in the pool at this Fort Myers Beach home

Tranquility awaits at this newly remodeled vacation rental home. Located in a quiet neighborhood near the white sands of Fort Myers Beach, private screened-in pool, comfortably air-conditioned, 3 bedrooms that sleep up to 6 people, 2 baths, spacious gourmet kitchen, outdoor seating area with tv, beach wagon and more. Local trolley available to take you to Times Square and the famous pier. Tons of shopping and restaurant options. Get away from it all in this little slice of heaven! STR 21-0368

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Top guest favorite

Home in Cape Coral

5 out of 5 average rating, 20 reviews

Villa510~3 En-Suites~Gulf Access, Heated spa~pool

Villa510 is a newly built waterfront retreat ideal for extended stays in Cape Coral. Enjoy peaceful salt canal water views and manatees from the lanai, then relax in your private heated pool and spa—perfect year-round. The outdoor kitchen and lanai create an easy, comfortable daily routine. Inside offers three private en-suite bedrooms, a den with optional airbed, open living space, and TVs in every room. Close to shopping, dining, and beaches—perfect for snowbirds seeking comfort and ease.

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Guest favorite

Home in Fort Myers Beach

5 out of 5 average rating, 6 reviews

Heated pool home Mid Island Short walk to beach

New to the rental market! This stylish retreat is perfect for families or groups with plenty of space to unwind. Featuring 4 bedrooms with 2.5 bathrooms, you’ll enjoy comfort and privacy throughout your stay. Perfectly located mid-island, just a short walk to the soft sands of FMB. Out back, a huge pool on the canal and large patio provide the ultimate spot for swimming and soaking up sun. Private parking and all the essentials for a seamless stay. Book today. Prime dates won’t last long!

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Top guest favorite

A private pool is enclosed by a glass screen, allowing views of the surrounding tropical plants. The pool features a tiled back wall and a curved edge, set on a patio with textured pavers. Lush greenery is visible beyond the enclosure.

Home in Fort Myers Beach

4.98 out of 5 average rating, 46 reviews

Sea Salt FMB! Stunning pool and island location.

STR #22-0432 Welcome to Sea Salt FMB! This stunningly decorated 4 bedroom and 4 bath pool home is just one block to the beautiful sands of Fort Myers Beach. The unique property features two master suites and two additional king guest bedrooms both incorporating an additional over-the-top bunk that the kids will adore. Side by side living spaces connected via outdoor terrace make Sea Salt FMB an absolute perfect choice for families or groups of friends looking for a perfect beach getaway.

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Top guest favorite

Home in Fort Myers Beach

5 out of 5 average rating, 78 reviews

Walk to Times Square, steps to the Beach!

Welcome to your perfect beach getaway! This bright and inviting 2-bedroom, 2-bath vacation rental is ideally located just across the street from the sandy shores of Fort Myers Beach, with easy beach access just a short walk away. You'll also be just a quick stroll from vibrant Times Square—home to great restaurants, shops, live music, and fun nightlife. This comfortable and well-appointed home offers everything you need for a relaxing stay! Come experience the best of Fort Myers Beach!

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Top guest favorite

The living area features a unique sky blue vaulted ceiling, complemented by light gray walls. A spacious gray sofa and a round glass coffee table are positioned around a patterned area rug. A modern kitchen bar with white stools is visible, alongside large windows framing natural light.

Home in Fort Myers Beach

4.94 out of 5 average rating, 50 reviews

Beach Cottage w/ htd pool + The Beach is in sight!

Discover the serenity of The Beached Albatross, a quaint haven just a stone's throw from Fort Myers Beach and it's famous powdered sugar sand. Once you've had your fill of the beach, unwind by the year round heated pool. Inside, a serene sky blue ceiling complements cozy corners, perfect for a morning coffee or evening read. With it's inviting spaces and thoughtful amenities, this is your ideal retreat for creating memories by the ocean. Book your stay and dive into relaxation today!

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Top guest favorite

A sunlit pool area is framed by palm trees, with views of the canal and neighboring homes in the background. Comfortable loungers are positioned along the poolside, inviting relaxation amidst the tranquil waterfront setting.

Home in Fort Myers Beach

4.99 out of 5 average rating, 114 reviews

Paradise on canal minutes to Ft Myers Beach/Gulf

Beautiful 3 Bedroom, 3 bath home on a canal with a dock! Bring your boat or jet skis! Enjoy a relaxing stay watching the dolphins and manatee right off the dock. This exquisitely updated home has everything you need for a fantastic vacation. Especially location! 5 minutes to Ft Meyers Beach. Enjoy the resort right in your own backyard. New pool with hot tub and sun shelf. Enjoy beautiful sunsets off the huge patio. Trolly to beach at neighborhood entrance or walk to in minutes.

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Top guest favorite

The outdoor area features a spacious paved patio surrounding a private heated pool. Lounge chairs are positioned by the poolside, and a grill is visible nearby. The pink-hued villa and a screened lanai area can be seen in the background.

Cottage in Fort Myers Beach

4.96 out of 5 average rating, 145 reviews

Coral Reef Villa - Steps from beach / Private Pool

We're Back! Fully Renovated in 2023! Welcome to the Coral Reef Villa located at 213 Fairweather Lane, Fort Myers Beach. 2 bedroom and 1 full bathroom villa. Steps away from the beach where paradise is waiting for you. Centrally located at the North end of the island. Walk to Times Square to enjoy shopping and dining. Close to all Fort Myers Beach has to offer while also located on a quiet residential street, this home is perfect for those that demand both proximity and tranquility!

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Top guest favorite

A clear blue pool is surrounded by a spacious paved deck, featuring several lounge chairs for relaxation. A covered outdoor area provides additional seating and shade. Lush green grass borders the pool, with palm trees visible in the background under a bright sky.

Home in Fort Myers Beach

4.93 out of 5 average rating, 131 reviews

Escape to your Happy Place-pool, 6 bed 2 1/2 bath

We are very excited to update this listing with brand new pictures of this fully renovated home. Everything in Kelsabella is brand new and has plenty of room for everyone. 4 bedroom 2 and 1/2 bathroom with an outdoor heated shower. This is a one story home located in a beautiful neighborhood walking distance to all the activity's and steps away from your beach access . Pool is also heated so it can be used all year round PET OWNERS! Must click on and read “ guest access”

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Top guest favorite

Condo in Fort Myers Beach

4.84 out of 5 average rating, 126 reviews

206C Gulf Water Views + 2 bikes + beach gear

Beachfront & Gulf Water Views at Estero Beach & Tennis Club 206C Wake up to unobstructed Gulf views in this 5-star Fort Myers Beach condo! Enjoy early check-in, no checkout chores, and every comfort—from a king GhostBed, full kitchen with dishwasher, free high-speed WiFi, heated pool, tennis/pickleball courts, BBQ grills, free parking, and stocked beach gear. Steps from the sand with sunsets you’ll never forget.

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Top guest favorite

A single-level waterfront home is presented with a light green exterior and a blue garage door. Surrounding palm trees and landscaped gardens complement the modern architecture, showcasing a well-maintained lawn. The house overlooks a wide canal, emphasizing its coastal setting.

Home in Fort Myers Beach

5 out of 5 average rating, 24 reviews

Waterfront Island Oasis w/Heated Pool & Boat Lift!

Come enjoy this waterfront coastal getaway. Equipped with an infinity edge pool, dock with a motorized boat lift, and outdoor dining/grill area. Enjoy your morning sunrise over the water on the widest canal on the island. The stylish interior is spacious with a mix of mid century modern and coastal flare. This is truly your home away from home. Rental License #24-0087

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