Family-friendly holiday rentals in Estero Island

Apartment in Fort Myers Beach

4.97 out of 5 average rating, 118 reviews

Summer Specials! Island Paradise Walk to the Beach

Important Note: This apartment had no damage from hurricanes in 2024. Everything is perfect here. Beaches are beautiful, pool is relaxing and welcoming. Thankfully the island restaurants and bars are also back up and going in fun island style! Beaches are beautiful and our brand new pool is complete and ready to enjoy. Be one of the first to enjoy this complete remodel renovation. No expense was spared here. Top quality memory foam mattresses with high end bed linens for a restful sleep. Fres

Holiday home in Fort Myers Beach

5 out of 5 average rating, 11 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

Condo in Fort Myers Beach

4.82 out of 5 average rating, 112 reviews

Oceanfront Views + Balcony Sunsets Bikes Included

“Caihlin, you were a phenomenal host.” – Sandy, May 2025 ☀️ What You’ll Love: • Unbeatable Views: Floor-to-ceiling glass sliders open to the Gulf—watch dolphins, sunsets, and seabirds from your private balcony. • Free Beach Bikes: Cruise the beach or explore nearby Lovers Key with the 2 bikes we provide. • Updated Interior: Modern kitchen, stainless appliances, granite countertops, and a cozy living area with coastal decor. • Comfy King Bed: Sleep to the sound of waves in a plush king-size

5 out of 5 average rating, 14 reviews

New house, pool, views, elevator, steps to beach

Be one of the first families to stay at this Brand New mid island house. Private pool, Elevator, beautiful custom tiled porches, amazing gulf & sunset views. The entire top floor is a master ensuite oasis with large room, spacious bathroom, custom tiled walk-in shower with sunset views, huge custom tiled deck with comfy furniture and amazing views. Perfect mid Island location. Just a mile from all the restaurants and entertainment in Times Square. Linens provided. 3 parking spaces. #19-1352

4.97 out of 5 average rating, 35 reviews

Sea Salt FMB! Stunning pool and island location.

STR #22-0432 Welcome to Sea Salt FMB! This stunningly decorated 4 bedroom and 4 bath pool home is just one block to the beautiful sands of Fort Myers Beach. The unique property features two master suites and two additional king guest bedrooms both incorporating an additional over-the-top bunk that the kids will adore. Side by side living spaces connected via outdoor terrace make Sea Salt FMB an absolute perfect choice for families or groups of friends looking for a perfect beach getaway.

5 out of 5 average rating, 12 reviews

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

Brand new home with Gulf views from the front porch—just steps to the white-sand beach. This 3BR/2BA retreat has 2 KINGS+ sleeps 8 and features a private heated pool, fenced outdoor living and dining area with TV, and a coastal boutique hotel vibe. Designed with all-new furnishings, games, and beach gear. Open concept living/kitchen/dining with 85" smart TV. Family-friendly and fully walkable to bars, restaurants, shops, and the marina. Experience Fort Myers Beach in style and comfort.

5 out of 5 average rating, 38 reviews

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.

Cottage in Fort Myers Beach

4.97 out of 5 average rating, 122 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!

4.97 out of 5 average rating, 115 reviews

Home in Cape Coral

2 Kings, Pool, Gulf Canal, Game Room and Kayaks

Unwind Cape Coral welcomes you to sunny southwest Florida, close to magnificent beaches, fishing, shelling, Minnesota Twins Spring Training & much more. Come enjoy this new construction home with heated pool, Kayaks, heated and cooled game room (PlayStation 5), gulf access - salt water canal, 4k oled tv's & many more refreshing amenities. You will love this clean & bright home with lovely décor. Located in the highly sought after Pelican neighborhood of Southwest Cape Coral!

5 out of 5 average rating, 5 reviews

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!

4.92 out of 5 average rating, 26 reviews

2 BR home w/ private pool, 2 min walk to beach

Your cozy getaway awaits in Fort Myers Beach at this delightful house. With 2 bedrooms including 1 queen bed, 1 full bed, and 1 twin trundle bed, this cool property also features a living room with 2 futons for additional sleeping space. Boasts a big backyard with large pool, outdoor shower, and fire pit. Perfect for a small group of guests looking for a comfortable stay 2 minutes walking distance from the beach. Book now and enjoy everything this house has to offer.