Vacation rentals with a pool in Estero Island

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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 favourite

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, 120 reviews

Private Home and Heated Pool 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

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.

Condo in Fort Myers Beach

4.92 out of 5 average rating, 211 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

An airy kitchen and dining area showcases light wood flooring and a spacious island with bar seating. White cabinetry contrasts with a vibrant blue backsplash. A dining table with blue chairs is accented by natural light from large windows, creating a bright and open space.

Vacation home in Fort Myers Beach

5 out of 5 average rating, 15 reviews

Heated pool, canal, outdoor kitchen & walk 2 Beach

Relax with the whole family at this peaceful place to stay on Fort Myers Beach. Fully renovated with 3 BR & 2 full bath. New central AC/ Heating unit. Enjoy a day in the heated pool or on your private dock looking out to the bay. 10 minute walk to the beach, Publix or the mid-island restaurants at the marina behind Publix. 3 BR, 2 bath with one room being a twin trundle bed. Enjoy one of the most quiet areas on the island to take walks or morning bike rides. Fully renovated since Ian & Milton

Superhost

An aerial view of the private pool area features an irregularly shaped pool surrounded by white loungers and a shaded dining table with an orange umbrella. Palm trees provide tropical greenery, and a pink flamingo float adds a playful touch.

Home in Fort Myers Beach

4.76 out of 5 average rating, 29 reviews

Beautiful Pool Home Fort Myers Beach Pet Friendly

Come and Enjoy ultimate relaxation at Ocean Breeze, your perfect getaway on Fort Myers Beach! This stunning home is designed to make your vacation unforgettable, with plenty of space and fantastic amenities for families or groups. Our home comfortably accommodates up to 9 adults up to 11 guests if there are children Upstairs you will find 2 bedrooms and a bonus room with a futon for extra sleeping space Downstairs there is a private suite featuring A kitchenette A Queen sized bed Plus a Futon

Top guest favourite

A panoramic view of a sandy beach stretches out towards the horizon under a clear blue sky, dotted with white clouds. Beach chairs are set up along the shore, with lush green vegetation in the foreground, leading to the water's edge.

Condo in Sanibel

4.95 out of 5 average rating, 111 reviews

100+ 5 Star Reviews and Right on The Beach!

We are a Superhost for a reason! Sanibel Siesta looks amazing! Immaculate beachfront, 2BR, 2BA w/garage, nicely updated beachy unit at sand's edge. Cooks kitchen. Amazing views of the Gulf w/5 star ratings! 3-day min. New hurricane windows, nicely furnished with ELEVATOR IN BUILDING! Discount for weekly/mo. rentals. BR 1:King bed ensuite, smart TV. BR 2: 2 tw. beds, smart TV. Qn. sofa bed in LR. Pool, golf course, bikes, laundry on site. No food or condiments stored in unit. May allow sm. dog.

Top guest favourite

The screened-in pool area features a serene swimming pool with shimmering water, two blue lounge chairs positioned nearby, and views of a wide canal. A thatched-roof Tiki hut can be seen across the water, surrounded by lush greenery.

Home in Cape Coral

4.99 out of 5 average rating, 248 reviews

LUX Villa w/ Private Salt Water Pool, Lanai, Canal

Are you looking to swim, relax outdoors, fish and take in beautiful sunsets on a wide gulf access canal? If so you will fall in love with this stunning newly constructed custom built home! The 2750 square foot home is bright & airy with two main bedroom on-suites & a separate family wing! The gourmet kitchen, dining room & great room open via large sliders to the lanai & pool w/ views of the canal in much desired SW Cape! Beach inspired villa! Large captains walk & Tiki! Check out our reviews!

Top guest favourite

The exterior of a two-story beach house is highlighted by a spacious porch with white railings and teal accents. Lush greenery and vibrant flowers frame the landscaped area, providing a welcoming entrance. The stone facade adds a rustic touch to the otherwise modern design.

Apartment in Fort Myers Beach

5 out of 5 average rating, 36 reviews

Beach view Pool Home

Escape to our newly remodeled 1-bedroom apartment with a pool, just steps from the beach. Renovated post-hurricane Ian, it offers easy access to white sand beaches, Lover’s Key State Park, and the lively FMB district. Enjoy the fully stocked kitchen, dishwasher, washer/dryer, and unwind in the serene surroundings. Walk to bay beaches, dine at new restaurants, and experience a perfect blend of relaxation and adventure. High-speed WiFi ensures you stay connected. Book your beachside retreat now!

Top guest favourite

Home in Fort Myers Beach

5 out of 5 average rating, 76 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!

Top guest favourite

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, 106 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.

Top guest favourite

A spacious backyard features a curved in-ground pool, surrounded by a textured paver patio. Lush palm trees offer shade, while outdoor seating is visible in the background. A shed is positioned adjacent to the villa, contributing to the property's inviting outdoor space.

Cottage in Fort Myers Beach

4.94 out of 5 average rating, 146 reviews

Mango Villa - Steps away from beach / private pool

We're Back! Fully Renovated in 2023! Welcome to the Mango Villa located at 150 Mango Street, 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!

Top guest favourite

A custom-built beach house stands elevated on a stilted structure, showcasing a vibrant blue exterior. The spacious covered area below provides parking and outdoor seating. Steps lead to a welcoming porch adorned with light blue chairs, inviting relaxation in the coastal surroundings.

Home in Fort Myers Beach

5 out of 5 average rating, 7 reviews

Blue Coconut Retreat

Brand-new, custom-built beach house just steps from the sand! Enjoy beach views, a private pool, all-new furniture and bedding, and stylish coastal decor. Relax in comfort with an open, airy layout curated for tranquility. Located just 5 blocks from Publix, Junkanoo, and Fresh Catch Bistro. Whether you're soaking up the sun or dining nearby, this peaceful retreat offers the perfect Fort Myers Beach getaway!

Top guest favourite

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, 23 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