Family-friendly holiday rentals in Estero Island

4.93 out of 5 average rating, 875 reviews

The charming exterior of the cottage is highlighted by a blue facade with white trim. Flower boxes adorn the windows, filled with lush greenery. A red door serves as a welcoming entrance. The patio area features stone pavers, surrounded by various plants and comfortable seating.

Tiny home in Fort Myers

Garden Cottage - Tiny House

PLEASE NOTE: The cottage is separate from our house and living quarters. The bathroom is in the back of the main house, just a few steps from the cottage, private and not shared with anyone. We take special precautions to thoroughly clean and disinfect the bedroom and bathroom after each guest. You’ll love our place because of the location, the ambiance, the outdoor space, and the neighborhood. We have a dog and a cat. Our place is good for couples, solo adventurers, and business travelers.

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.

4.93 out of 5 average rating, 14 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.

A heated pool is surrounded by a screened-in enclosure that enhances outdoor enjoyment. An integrated spa complements the pool area, while a tiki hut with a thatched roof offers shaded seating. Lounge chairs are positioned on the tiled deck, providing space for relaxation.

4.93 out of 5 average rating, 14 reviews

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!

5 out of 5 average rating, 22 reviews

An aerial view of the modern coastal home reveals a spacious backyard with a fenced heated pool and jacuzzi. Lounge chairs are arranged around the pool, while the two-story residence features balconies offering views. Palm trees and nearby homes enhance the coastal setting.

Home in Fort Myers Beach

Villa Capri · 2025 Luxury Build · Steps to Beach

Personally hosted by Paul & Alicia of Dancing Palms Vacations, this elevator equipped brand-new experience with a spacious lanai and fenced pool backyard is just a short walk to the white sugar sand beach. Start your morning with coffee on the covered porch, enjoying Gulf views. Relax by the heated pool with a book, fire up the grill, or enjoy cozy outdoor seating for lounging and dining. End the day with a sunset stroll or hop on the open-air free Tram to nearby bars & restaurants.

Guest suite in Fort Myers Beach

A modern kitchen features stainless steel appliances, including a refrigerator and oven. White cabinetry contrasts with a textured brown rug. Natural light flows through large windows, enhancing the bright atmosphere. Potted plants add a touch of greenery to the space.

4.88 out of 5 average rating, 286 reviews

Charming suite w/ private deck Downtown FMB

Discover the perfect blend of modern and tropical charm at our 1BR/1BA loft apartment in Downtown Fort Myers Beach. Just a 2-minute walk to the white sands, this upscale retreat is walking distance to the beach, Times Square, restaurants, bars, and shops. Enjoy water sports, kayaking, parks, and more. Ideal for couples, snowbirds, or anyone seeking a tropical escape, The Loft FMB combines modern comforts with island relaxation truly designed to feel like your home away from home.

The studio apartment features modern furnishings, including a spacious bed with a patterned comforter and a comfortable sofa. A small dining area is visible with barstools at the kitchen counter. Soft lighting enhances the neutral-toned walls, while natural light enters through multiple windows.

4.99 out of 5 average rating, 136 reviews

Ready to Enjoy again! Everything is new!

This vacation rental unit has been totally rebuilt and is now ready to welcome guests again! Nearly everything is new (as of 2024) and it is likely one of the nicest studio apartments now available on the entire island. Skip the dated condos and hotels and get ready to enjoy this newer, nicer option, located just 1 short block (800 feet) from the sand. As you’ll see from the reviews it had a great track record before the storm, and it’s been rebuilt even better! Enjoy NEW!

Campervan/Motorhome in Fort Myers

4.96 out of 5 average rating, 116 reviews

SO "Time to Wander" Pets and free early check in!

Welcome to SO "Time to Wander"! This family and pet friendly beach retreat is beautifully decorated and fully stocked with everything you will need to explore the 3 beautiful beaches that are within minutes of here! There is a outdoor area that has privacy curtains and screens also! This 5th Wheel Camper is VERY spacious and comfortable. We provide everything you need for a day at the beach! I allow free early check in and I do not charge a cleaning fee on this property!

Cottage in Fort Myers Beach

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.

4.93 out of 5 average rating, 133 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!

Apartment in Fort Myers Beach

5 out of 5 average rating, 9 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.

5 out of 5 average rating, 20 reviews

A spacious room is furnished with two queen beds, each set against a light-colored wall. A wooden bench is placed at the foot of each bed. A ceiling fan is mounted above, while the area transitions into a modern kitchen visible in the background.

Home in Fort Myers Beach

1min walk to beach, BBQ, Free Parking, Beachgear

Stay just 600 ft from the beach and a 10-min walk to downtown Fort Myers Beach, with bars and restaurants like Mr. Waves Island Bar. This cozy bungalow sleeps 4 with 2 queen beds, a full kitchen, and a luxurious shower in the full bathroom. Enjoy the patio, grill-ready back porch, and a large garden perfect for outdoor games. We provide beach chairs, umbrella, cooler, and towels—everything you need for a perfect beach day.

4.98 out of 5 average rating, 182 reviews

A compact living area features a light-colored sofa and wooden accents. A sturdy ladder leads to a lofted sleeping area. Natural light fills the space, highlighting a well-equipped kitchenette with modern appliances and a small dining area. A door offers access to the outside.

Tiny home in Cape Coral

Private Hot Tub | King Bed Loft | Hammock Swings

🛜500mbps+ WiFi 🏠Fully private + Private entrance 🌴Hammock Swings ☀️ Outdoor Patio 🦩Private Hot Tub 🥑Kitchenette w/ electric hot plate 😴King Size Bed Loft 📚Work Desk 📺 55 inch Smart TV + Roku ❄️ Cold A/C 🚘 1 parking space NOTE: Accessing the bed requires climbing a ladder. While sturdy and secure, it may not be suitable for guests with mobility limitations, so please consider this before booking.

A serene bedroom is displayed, featuring a spacious bed with a floral patterned comforter. Natural light filters through sheer turquoise curtains. A large mirror and a television are positioned on a dresser, while a lamp provides additional lighting in the softly colored room.