Holiday rentals with a pool in Estero Island

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Top-rated rentals with a pool in Estero Island

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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, 206 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

Guest favourite
Two comfortable reclining chairs are positioned on a private balcony, facing the beach. A small table is set between them, featuring a pitcher with a garnish and a couple of glasses. Palm trees are visible beyond the railing, framing a distant view of the ocean.
Flat in Fort Myers Beach
4.94 out of 5 average rating, 16 reviews

Salt Air Gulf View Pool Condo Steps from the Beach

This 2-bed, 2-bath condo has EVERYTHING for your sunny beach getaway! The master bedroom has a king bed and ensuite bathroom for privacy, while the second bedroom has 2 twins next to another full bathroom. Just steps from the white sand beaches with beach towels and chairs provided. Enjoy the pool or private balconies while you unwind and soak up the sunshine. A short walk to Publix and the island's favorite hangout, Junkanoo. Note: this second-floor unit’s elevator is currently out of order.

Top guest favourite
Aerial view of a stunning coastline, featuring soft white sand intertwined with turquoise waters. Small boats are anchored near the shore, where a few individuals enjoy the beach. Lush greenery and houses are visible in the background, contributing to the serene landscape.
Apartment in Fort Myers Beach
4.98 out of 5 average rating, 56 reviews

Luxury Beach Condo On The Bay In A tropical Oasis!

Stylish beach condo located on the bay in Estero Island is one of the most beautiful places in all of Florida. There is activities for all ages from fishing, boating, swimming, bicycling and kayaking. You can enjoy World Famous Seafood Restaurants or hang out in the tropical laid back downtown. The condo is walking distance to the beach or a short drive to Lovers Key. Where you can find dolphins exotic shells, manatees, live conch and sea dollars. Memories made here will last a life time!!

Top guest favourite
A glass filled with a refreshing drink is held against a vibrant sunset backdrop. Soft golden light reflects off the surface of the drink, while wispy clouds scatter across the sky, indicating a serene beachfront setting.
Apartment in Fort Myers Beach
4.95 out of 5 average rating, 39 reviews

Vacation Villas #132 Second Floor Beachfront Condo

We are back! Everything in the apartment is all brand new - be the first to experience our newly renovated space! Vacation Villas is the northernmost building on the island, with a secluded beachfront for your enjoyment, but only a short one mile walk to 'Times Square' - the heart of the island. Outdoor living at its best: on the beach, at the pool, on the private lanai, or cooking in the grilling area. Sink your toes in the powdered sugar sand and you will never want to go anywhere else!

Top guest favourite
Home in Fort Myers Beach
5 out of 5 average rating, 29 reviews

Just Beachy • Pool • 2 Kings+ • 3 Min to Beach

Personally hosted by Paul & Alicia of Dancing Palms Vacations, this brand-new home offers Gulf views from the front porch—just steps from the white-sand beach. The 3BR/2BA retreat sleeps 8 with 2 KING bedrooms, a private heated pool, and a fenced outdoor living/dining area with TV and boutique coastal hotel vibe. Enjoy all-new furnishings, games, and beach gear. Open-concept living/kitchen/dining with 85” smart TV. Family-friendly and walkable to bars, restaurants, shops, and the marina.

Top guest favourite
A spacious living area is presented with soft neutral tones and a textured carpet. Large windows furnished with sheer curtains allow natural light to enter. A comfortable sectional sofa occupies one corner, while an entertainment unit holds a flat-screen television, creating a cozy space for relaxation.
Home in Fort Myers Beach
5 out of 5 average rating, 25 reviews

Seabreeze Hideaway

Located in Sun Retreats Fort Myers Beach (formerly Indian Creek), just 3 miles from Fort Myers Beach, Bunche, and Sanibel Island, and Margaritaville. The property offers amenities, including pools, pickleball, tennis, and numerous activities. It’s a great location, away from the main beach traffic but still close to shopping. The trolley also stops right at the entrance. The bungalow features a fully equipped kitchen and allows one pet up to 20 pounds. An occupant must be 35 or older.

Top guest favourite
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
4.97 out of 5 average rating, 134 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!

Top guest favourite
Apartment in Fort Myers Beach
5 out of 5 average rating, 13 reviews

Tide & Seek: Beach-front and Resort Amenities

Welcome to Tide & Seek! This stylish 2 bedroom, 2 bath condo at Gull Wing Beach Resort is perfectly situated on the peaceful south end of Fort Myers Beach. Sleeping 6, this 8th-floor retreat features an open living space, full kitchen with coffee & wine bar, and a screened balcony with angled Gulf views. With resort amenities including a heated pool, spa, grilling area, and direct beach access, it’s the ideal spot for families or friends to unwind in coastal comfort.

Top guest favourite
A dining area features a round marble table surrounded by sleek black chairs, accented by a vibrant arrangement of pink flowers. In the background, a living space includes a luxurious chandelier, comfortable seating, and large windows revealing views of the beach.
Apartment in Fort Myers Beach
5 out of 5 average rating, 19 reviews

Seaside 204 Beachfront condo - Luna Sea on FMB

LunaSea is a well-appointed, breathtaking beach front condo located mid-island on beautiful Fort Myers Beach, FL. This is a 2br/2ba second floor unit with direct beach front views. The condo sleeps up to 6 people. The full kitchen has everything you need from pans to an air fryer and everything else in between. The bedrooms and living room have flat screen 4K HD Smart Tvs for your entertainment. Supermarket is located literally across the street.

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.

Top guest favourite
An open kitchen and dining area features a round glass table surrounded by rattan chairs adorned with tropical patterns. Stainless steel appliances are positioned next to light cabinetry. Expansive windows invite natural light, providing a view of the outdoor scenery.
Apartment in Bonita Springs
4.99 out of 5 average rating, 149 reviews

Casa Bonita - Relax @ The Beach (Newly Remodeled)

Beach within steps of this beautifully remodeled condo! DOC's restaurant & jet ski rentals, directly across the street. Beach gear available along with a cart to transport. Luxurious king size bed with extra plush mattress topper. Queen size sofa bed. Our studio will sleep up to 3 people (2 adults, 1 child) Newly refurbished pools opened April 2nd 2025.

Guest favourite
Apartment in Fort Myers Beach
4.9 out of 5 average rating, 82 reviews

Boutique condo on the bay, short walk to the beach

This beautifully updated Condo sits right on Estero Bay with a beautiful view of the water right outside the back door. The beach, shopping plaza, drugstore, and Marina are within a very short walking distance making this condo perfectly situated in the quiet end of Fort Myers Beach. Kick back, relax, and unwind in this elegant yet casual Condo.

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