Vacation rentals with a pool in Estero Island

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.

Gorgeous Beach Residence with Pool, Spa, and Bikes

Welcome to Margarita Mansion! This intimate four-condo development features a large heated pool, spa, and bikes, all within walking distance to the beautiful white sandy beaches of Fort Myers Beach, FL. This listing is for unit 3 at Margarita Mansion, which is a 2/2 apartment with kitchen and pool/spa access. Pet friendly with a sleeping capacity of up to four guests, this property is perfect for those seeking an amenity rich accommodation with private patio and close proximity to the beach!

Luxury Beachside House W/ Heated Pool & Elevator

261 Key West is a luxurious Oceanside single-family pool home with private elevator that will satisfy the most exquisite taste. You will not only enjoy the fine quality and style of the home, you will enjoy the Gulf waters and the soft white sandy beaches of the Gulf just footsteps from your door. Your stay will include beach chairs, umbrellas, sand toys, fishing rods, kayak, paddle boards, and bicycles for your enjoyments. Enjoy a stylish experience at this centrally-located place.

Waterfront 2/2: Beach .4mi+Shared Pool+Dock+Gym

Embrace a week-long getaway in this waterfront & elevated 2BD/2BA unit, with a brand new pool, along with a workout room! The new dock is ideal for fishing and launching kayaks or paddle boards, ensuring memorable waterfront adventures. Located in the heart of Fort Myers Beach, you'll enjoy easy access to vast beaches, lively restaurants, & bars w/ live bands. Unwind in the pool, on the expansive lanai, the spacious living rooms, or the well-equipped kitchens! FMB STR rental #22-0317

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.

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!

The Great Escape Beach House/ Pool/ Dock

Escape to this waterfront beach house in sunny Fort Myers Beach! Perfect for families and friends, it features a private pool, a 50ft private dock with direct gulf access. House is only 1/2 a block from beach access. Plenty of outdoor entertainment areas including a large game room, with an outdoor ping pong table and beach accessories. Just minutes from beaches, shops, and dining this is your perfect Florida getaway for fun, relaxation, and unforgettable memories!

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.

Grace by The Sea · 2025 Build · Steps to Beach

This stylish coastal home offers a brand-new experience with a spacious lanai and backyard, all with just a 6-minute walk to the sugar sand beach. Start your morning with coffee on the covered front porch, enjoying Gulf breezes. Relax by the pool with a book throw something on the blackstone grill, play corn hole or enjoy cozy outdoor seating for lounging and dining. End the day with a sunset stroll or a short drive to nearby bars and restaurants.

Beach escape! Walk to the square! Steps to beach!

Modern 3BR/2BA home with an industrial-chic vibe, perfectly located just a short walk down the street from the beautiful Fort Myers Beach. Enjoy a fully equipped kitchen, open living space, and private outdoor area—ideal for relaxing after a day in the sun. Walk to the beach in minutes or explore nearby Times Square for dining and entertainment. Comfort, style, and unbeatable location all in one!

Canal-front Paradise Retreat

Discover family-friendly serenity at our Fort Myers Beach retreat! With direct canal access to the Gulf, unwind by the pool or set sail from your own boat slip. Just a short stroll from the beach, this 3-bed, 3-bath haven offers relaxation and adventure for all ages. Enjoy outdoor dining and modern comforts for an unforgettable, stress-free Florida getaway.

Cozy Condo on the Gulf

Escape to breathtaking Gulf views from your private balcony! Start your day with coffee and sunrise, or relax with evening cocktails as the sunset dazzles. Watch for dolphins and the amazing seabirds in the sanctuary below. While the island recovers, your perfect beach getaway is here and waiting. Book your unforgettable vacation now!