Holiday rentals with a pool in Estero Island

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

Island Beach House – Brand New 3-Bedroom Retreat

Welcome to Island Beach House, a stunning new vacation home built in 2025 right across the street from the beach and located on the highly desirable north end of Fort Myers Beach. This beautifully designed 3-bedroom, 2-bathroom property is perfect for families or groups seeking comfort, style, and the ideal beach getaway. With coastal décor, modern finishes, and an open layout, the home provides a serene, beachy vibe throughout. Onsite management provided by #1 rated: Fort Myers Beach Vacation R

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!

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!

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!

Beachfront! 3BR w/Incredible Gulf Views*Pool

Wake up to breathtaking Gulf views at this beachfront retreat. Just steps from the soft white sand, this coastal getaway offers spacious outdoor decks perfect for enjoying sunrise coffee or sunset skies over the water. Guests can relax by the community pool, unwind to the sound of the waves, and spend their days swimming, shell hunting, or soaking up the sun. Sleeping up to eight guests, this comfortable beach home is ideal for families looking to relax and enjoy the best of the coast.

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.

Intervillas Florida - Villa The View

The View – Luxury Waterfront Villa with Infinity Pool & Sunset Views The View welcomes you from the very first moment with breathtaking, wide lake views and spectacular sunsets that turn every day into an unforgettable experience. Perfectly located in a quiet and highly desirable position on one of the lower 8-Lakes, the villa offers direct boat access, allowing you to reach the River and the Gulf of Mexico in a short and scenic ride – ideal for boating enthusiasts and water lovers.

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.

Sand Dollar View - Beachfront Luxury Living

Located on the North end of Fort Myers Beach, not far from the pier, Sand Dollar View is the most spectacular 5 bedroom beachfront property you'll find! You will be amazed by the views of the ocean from this third floor space. The large deck spans the entire house, with plenty of outdoor furniture for lounging in the warm Florida sunshine. There are two master bedrooms, each with a king size bed and en suite bathroom with huge walk-in showers.

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.

Island Oasis Steps From the Sugar Sand Beach

Just steps from Fort Myers Beach, this beautifully updated duplex offers a serene retreat beside Matanzas Pass Nature Preserve. Enjoy a gourmet kitchen, two king suites, a private fenced pool, and inviting indoor–outdoor living designed for effortless relaxation.