Holiday rentals with a pool in Estero Bay

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Top-rated rentals with a pool in Estero Bay

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

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Guest favourite
A sparkling pool features a waterfall and is surrounded by palm trees. Lounge chairs are positioned around the pool area. In the background, views of the bay are visible under a clear blue sky, creating a serene vacation atmosphere.
Apartment in Fort Myers Beach
4.92 out of 5 average rating, 207 reviews

Ft Myers Beach & Lovers Key State Park- FANTASTIC!

BEACHES ARE OPEN! Beautiful Views, large unit, Enjoy the sun, beach, and excitement of Florida. Lovers Key State Park, beautiful beaches, hiking & biking trails, Ft Myers Beach, white sand, many activities. Views of the gulf & bay area. Exercise room, wifi, great swimming pool- the beaches & trails you come to Florida for. Ft Myers beach has the white sand you think of when visiting Florida. The Gulf Coast Beach, and Lovers Key State Park are there for your enjoyment. Great place for Memories

Top guest favourite
A clean outdoor pool is surrounded by a safety fence, with clear blue water reflecting the sky. Several lounge chairs are positioned nearby for relaxation, while lush greenery and an open landscape are visible in the background, creating a serene atmosphere.
Flat in Fort Myers
4.93 out of 5 average rating, 118 reviews

Golf & Pool Views! Close to FGCU and Airport.

Perfectly located 2 Bedroom 2 Bath condo! Nestled on a public golf course with a wonderful pool area, it is the perfect combination for a peaceful vacation. The condo is centrally located by everything one needs to relax and enjoy the Fort Myers area. We have gone the distance to make your vacation memorable. The spacious condo has adjustable beds, which will provide you sweet dreams. Close to the beaches, shopping, airport, golf, and tons of restaurants. Guests can also enjoy the pool area.

Guest favourite
The beachfront view reveals several multi-story condominiums lining the shore, surrounded by sandy areas populated by beachgoers. Gentle waves lap at the shoreline, while a sky filled with soft clouds adds to the serene coastal atmosphere.
Apartment in Bonita Springs
4.91 out of 5 average rating, 128 reviews

Ken & Gina's Beach Condo (#2301)

Due to hurricane Ian, the courtyards and tennis courts are under repair. Pools are open. 2 of 4 entrances are open. Studio condo across the street from Bonita Beach. 3rd floor unit offering partial views of the gulf. Being able to walk to the beach (2 mins) and 2 restaurants while centrally located between Ft. Myers and Naples makes this a great location. Local bike rental shops offer delivery of bicycles. Bonita beach offers jet ski, paddle board and catamaran rental. Parking is free

Guest favourite
A living area is seen featuring large glass doors that offer a view of the waterfront. Rattan furniture, including a sofa and coffee table, complements the room. Decorative sea-themed artwork adorns the walls, creating a bright and airy atmosphere.
Apartment in Fort Myers Beach
4.95 out of 5 average rating, 120 reviews

Romance! Awesome Beach & Views! 5 Stars

Feeds the senses & nourishes the soul! Away from the crowds and noise is this spectacular, waterfront (on the beach) 5 Star corner condo allowing you private unobstructed views of the Gulf, San Carlos Pass, Fort Myers Beach, City Lights, Back Bays, wildlife and is on Lover’s Key State Park Beach (#4 in US & 3 miles of pristine white sand shelling beach and 700 acres of nature). Don't risk your chance for a lifetime memorable experience anywhere else. There is bridge construction currently.

Top guest favourite
A spacious outdoor area encompasses a newly heated pool, surrounded by tropical landscaping. Lounge chairs are positioned near the pool, while dining tables and colorful umbrellas provide shade. A BBQ grill is accessible, with additional seating visible under the covered patio area.
Home in Naples
4.93 out of 5 average rating, 150 reviews

606 SeaRenity Resort • Designer Home w/Heated Pool

Welcome to 606 SeaRenity! This completely remodeled home features a SOUTHERN EXPOSURE, HEATED POOL & is surrounded by lush tropical landscaping! Located in the heart of the Vanderbilt Beach area meaning world class, white sand beaches are easily accessible by walking, biking or driving. Near the Ritz Carlton, Turtle Club & LaPlaya this home is sure to please. Supermarkets, Shopping, Dining & Nightlife including Mercato Shopping & Dining District, Naples best attractions just minutes away.

Top guest favourite
The open living area features a comfortable gray sofa adorned with decorative pillows. A wooden coffee table sits in the center, surrounded by a vibrant area rug. The dining area includes a round table with four chairs, and a well-equipped kitchen is visible in the background.
Apartment in Fort Myers Beach
5 out of 5 average rating, 15 reviews

Beachfront @ Elevate in the Sun!

Welcome to ELEVATE IN THE SUN! Where an elevated experience is waiting. Premier Host (Other Site)-4.8* The unit boasts a completely remodeled kitchen with quartz countertops, brand new appliances including a dishwasher (very rare), brand new living room furniture, and new A/C and music surround sound streaming via Amazon Alexa and Apple Music. Sunrises are included each morning on your private balcony and sunsets are breathtaking down on the beach with toes in the bright white sand.

Top guest favourite
Home in Bonita Springs
4.99 out of 5 average rating, 71 reviews

Tropical Oasis: Stunning Pool Home in Bonita

Welcome to your tropical getaway in Bonita Springs! This stunning 4-bedroom, 2-bathroom home features a heated pool with a sunshelf, offering the perfect spot to soak up the Florida sunshine. Centrally located near the Coconut Point Mall, you'll have easy access to shopping, dining, and you're located just 15 minutes from Bonita Beach. Inside, enjoy spacious, coastal-themed living areas ideal for gatherings with family and friends. Your private oasis awaits—book now for a memorable stay!

Top guest favourite
A screened patio overlooks a serene swimming pool surrounded by lush greenery. Two lounge chairs are positioned nearby, with a small table featuring colorful drinks. A few inflatable toys float in the water, offering a casual ambiance for relaxation.
Home in Bonita Springs
4.97 out of 5 average rating, 115 reviews

3BR w/HUGE 2k sq ft Lanai & Seasonally Heated Pool

Welcome to your peaceful Bonita Springs retreat, perfectly located near Naples, Ft. Myers, shopping & beaches! This isn’t just a rental, it’s our 2nd home and we treat it as such. You'll experience "exceptional" the minute you enter this stunning, open concept interior. Further, it boasts a striking 2000 sq ft screened-in lanai w a seasonally heated pool. This outdoor oasis doubles your living space and offers a flying pest barrier and significant UV protection. Breathe/Smile/Unwind

Top guest favourite
A serene pool area features a champagne-style hot tub connected to a shimmering pool, surrounded by a marble deck. A vibrant mural of a sea turtle decorates the wall, while lounge chairs are positioned nearby, inviting relaxation amidst lush tropical landscaping.
Home in Bonita Springs
4.98 out of 5 average rating, 148 reviews

Luxe Unique: Close to Beach, Hot Tub, Heated Pool

Step into the luxurious 2BR 2BA oasis in the heart of Bonita Springs, FL. It promises a relaxing retreat just a few minutes from the pristine Bonita Beach, restaurants, shops, exciting attractions, and natural landmarks. The stylish design and a rich amenity list will leave you in awe. ✔ 2 Comfortable Bedrooms ✔ Open Design Living ✔ Fully Equipped Kitchen ✔ Backyard (Pool, Hot Tub, Swim-Up Bar, BBQ) ✔ Lounge Pool House ✔ Workspace ✔ Smart TVs ✔ Wi-Fi ✔ Parking See more below!

Guest favourite
Home in Fort Myers
4.94 out of 5 average rating, 370 reviews

Whole cozy house

Entire cozy house just for you friends and family. Perfect to spend a pleasant and relaxed moment. If you plan to have a party or event, this place is NOT for you. The neighbors are very strict in terms of noise and large groups of people. Well maintained house. CLEAN POOL BUT NOT HEATED. Walk in to a living area and separated dining. 20 minutes to airport, 25 minutes to the beach, fine dining and entertainment. For a virtual tour, click on the cover photo twice.

Top guest favourite
A cozy sleeping area features a queen size bed dressed in a nautical-themed quilt. A small refrigerator and microwave are visible, along with a dresser and television. Light enters through a shuttered window, complementing the soft blue walls.
Apartment in Bonita Springs
4.83 out of 5 average rating, 232 reviews

Cozy studio 1.3 miles to Barefoot Beach

Very inexpensive way to get close to the beach and still have complete privacy! Whole unit-Share nothing. Small and cozy studio/room 12x19 with a refrigerator, microwave, air conditioner, full bath, suitable to more or less sleep. Queen size bed. Closet and dresser. This is a separate guest room with a private entrance not connected to another unit. Located in an adorable tropical feel complex in a seafoam green building.

Top guest favourite
Apartment in Fort Myers Beach
4.83 out of 5 average rating, 118 reviews

Gulf Water Views + 2 bikes, beach gear weekly stay

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.

Popular amenities for Estero Bay rentals with a pool

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