Family-friendly holiday rentals in Estero Island

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Top-rated family-friendly rentals in Estero Island

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Top guest favourite
A spacious living area features a large sectional sofa adorned with cozy pillows. Natural light fills the room from the adjoining dining area, which showcases a wooden table seating six. The modern kitchen with stainless steel appliances is visible in the background, creating an inviting social space.
Home in Fort Myers Beach
4.99 out of 5 average rating, 120 reviews

Private Home and Heated Pool on Virginia Ave

Your Sandy Feet Retreat in Paradise This newly remodeled home offers modern elegance with 3 spacious bedrooms and 2.5 beautifully remodeled bathrooms. Enjoy the private heated pool, perfect for relaxing. Situated in the heart of Fort Myers Beach, this home is just a 5-minute stroll to the powdery, sugar-sand beach and only a 10-minute walk to margaritaville andTimes Square. With a variety of restaurants and bars featuring live music nearly every night, it’s the perfect location for enjoying th

Top guest favourite
An airy kitchen and dining area showcases light wood flooring and a spacious island with bar seating. White cabinetry contrasts with a vibrant blue backsplash. A dining table with blue chairs is accented by natural light from large windows, creating a bright and open space.
Holiday home in Fort Myers Beach
5 out of 5 average rating, 14 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

Superhost
An aerial view of the private pool area features an irregularly shaped pool surrounded by white loungers and a shaded dining table with an orange umbrella. Palm trees provide tropical greenery, and a pink flamingo float adds a playful touch.
Home in Fort Myers Beach
4.76 out of 5 average rating, 29 reviews

Beautiful Pool Home Fort Myers Beach Pet Friendly

Come and Enjoy ultimate relaxation at Ocean Breeze, your perfect getaway on Fort Myers Beach! This stunning home is designed to make your vacation unforgettable, with plenty of space and fantastic amenities for families or groups. Our home comfortably accommodates up to 9 adults up to 11 guests if there are children Upstairs you will find 2 bedrooms and a bonus room with a futon for extra sleeping space Downstairs there is a private suite featuring A kitchenette A Queen sized bed Plus a Futon

Top guest favourite
The screened-in pool area features a serene swimming pool with shimmering water, two blue lounge chairs positioned nearby, and views of a wide canal. A thatched-roof Tiki hut can be seen across the water, surrounded by lush greenery.
Home in Cape Coral
4.99 out of 5 average rating, 248 reviews

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!

Top guest favourite
The living area features a unique sky blue vaulted ceiling, complemented by light gray walls. A spacious gray sofa and a round glass coffee table are positioned around a patterned area rug. A modern kitchen bar with white stools is visible, alongside large windows framing natural light.
Home in Fort Myers Beach
4.95 out of 5 average rating, 40 reviews

Beach Cottage w/ htd pool + The Beach is in sight!

Discover the serenity of The Beached Albatross, a quaint haven just a stone's throw from Fort Myers Beach and it's famous powdered sugar sand. Once you've had your fill of the beach, unwind by the year round heated pool. Inside, a serene sky blue ceiling complements cozy corners, perfect for a morning coffee or evening read. With it's inviting spaces and thoughtful amenities, this is your ideal retreat for creating memories by the ocean. Book your stay and dive into relaxation today!

Top guest favourite
A sunlit pool area is framed by palm trees, with views of the canal and neighboring homes in the background. Comfortable loungers are positioned along the poolside, inviting relaxation amidst the tranquil waterfront setting.
Home in Fort Myers Beach
4.99 out of 5 average rating, 106 reviews

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.

Top guest favourite
A clear blue pool is surrounded by a spacious paved deck, featuring several lounge chairs for relaxation. A covered outdoor area provides additional seating and shade. Lush green grass borders the pool, with palm trees visible in the background under a bright sky.
Home in Fort Myers Beach
4.93 out of 5 average rating, 121 reviews

Escape to your Happy Place-pool, 6 bed 2 1/2 bath

We are very excited to update this listing with brand new pictures of this fully renovated home. Everything in Kelsabella is brand new and has plenty of room for everyone. 4 bedroom 2 and 1/2 bathroom with an outdoor heated shower. This is a one story home located in a beautiful neighborhood walking distance to all the activity's and steps away from your beach access . Pool is also heated so it can be used all year round PET OWNERS! Must click on and read “ guest access”

Top guest favourite
A private heated saltwater pool is surrounded by a paved patio featuring colorful pool floats. A spacious bed is adorned with a light blue quilt, placed against a beach-themed mural. The lower right image displays a brightly colored house exterior with a large garage beneath.
Home in Fort Myers Beach
5 out of 5 average rating, 24 reviews

Oceanview Oasis⁘Heated Pool⁘Grill⁘Screened Porch

🌊 Steps from the Gulf 🏊‍♀️ Private heated saltwater pool 🕶️ Lounge chairs and shaded seating 🍴 Outdoor dining area and grill 🌅 Sunset views from the upper deck 🌴 Huge screened lanai with tropical views 🏖️ We Provide: ✔️ Beach chairs ✔️ Beach towels ✔️ Beach cart Welcome to The Oasis! Whether you're here for rest, adventure, or a bit of both, this peaceful retreat has everything you need for an unforgettable vacation. Town of Fort Myers Beach Registration # 22-0433

Top guest favourite
A screened-in lanai features a tranquil heated pool with a spa, surrounded by paver stones. The sunset reflects on the water, providing a picturesque backdrop. Palms sway gently in the breeze, enhancing the serene setting suitable for relaxation and enjoyment.
Home in Cape Coral
4.97 out of 5 average rating, 306 reviews

Dolphin beach house 2

ONE OF THE BEST WATERFRONTS IN CAPE CORAL! A short walk to the beach a. This 2,500+sq ft home has stunning sunsets and South Western water views from all main living areas,as well as the Master Suite. Heated pool w/ LED colored lighting, built in Spa,Pool bath, full laundry facility, Lanai,Fireplace ,Wi-fi and TVs in every bedroom, private dock . Boat on lift for rent w/RPM rentals . Large 2-car garage w/5 bicycles,beach wagon & cooler on site.

Top guest favourite
Home in Fort Myers Beach
4.96 out of 5 average rating, 27 reviews

Across the beach, free parking, bbq, fits 4, pets

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.

Top guest favourite
A custom-built beach house stands elevated on a stilted structure, showcasing a vibrant blue exterior. The spacious covered area below provides parking and outdoor seating. Steps lead to a welcoming porch adorned with light blue chairs, inviting relaxation in the coastal surroundings.
Home in Fort Myers Beach
5 out of 5 average rating, 7 reviews

Blue Coconut Retreat

Brand-new, custom-built beach house just steps from the sand! Enjoy beach views, a private pool, all-new furniture and bedding, and stylish coastal decor. Relax in comfort with an open, airy layout curated for tranquility. Located just 5 blocks from Publix, Junkanoo, and Fresh Catch Bistro. Whether you're soaking up the sun or dining nearby, this peaceful retreat offers the perfect Fort Myers Beach getaway!

Superhost
Home in Fort Myers Beach
5 out of 5 average rating, 4 reviews

Water Front | Modern Open Concept | Beach Vibes

Deck overlooking a mangrove bay, private dock, abundant wildlife & sea life — this is real Florida. Fish off the dock, watch the birds, or just relax in your own space. Skip the stuffy hotel. Walk to Ft. Myers Beach or hop the golf cart shuttle. Bars & restaurants right on San Carlos Island. Key West Express day trip next door. Nature, beach & nightlife — all from your dock.

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