Holiday rentals in Estero Island

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Top-rated holiday rentals in Estero Island

Guests agree: these stays are highly rated for location, cleanliness and more.

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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, 25 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

Top guest favourite
Aerial view of a spacious waterfront property featuring a pool area enclosed by a screen. Lush palm trees surround the structure, with a boat lift visible along the water's edge. The ocean and distant buildings can be seen in the background.
Home in Fort Myers Beach
5 out of 5 average rating, 18 reviews

Bayfront Bliss

Forget your worries in this spacious & serene home. Boat lift available for renters’ use, able to accommodate up to 24’! Truly relax while watching dolphins and manatees in the back bay of Fort Myers Beach with unmatched panoramic views. The sunrises over the bay are stunning! Take a very short stroll to the other end of the street & find the white sands of FMB where you can enjoy warm sunny days & amazing sunsets! Property is located midland-only 5 streets from Publix! Live like a beach local!

Guest favourite
A private screened-in pool is surrounded by a spacious patio area, featuring sunlight filtering through the mesh enclosure. Brick flooring leads to the turquoise water of the pool, while seating options and a view of palm trees can be seen in the background.
Home in Fort Myers Beach
4.94 out of 5 average rating, 52 reviews

Plunge in the pool at this Fort Myers Beach home

Tranquility awaits at this newly remodeled vacation rental home. Located in a quiet neighborhood near the white sands of Fort Myers Beach, private screened-in pool, comfortably air-conditioned, 3 bedrooms that sleep up to 6 people, 2 baths, spacious gourmet kitchen, outdoor seating area with tv, beach wagon and more. Local trolley available to take you to Times Square and the famous pier. Tons of shopping and restaurant options. Get away from it all in this little slice of heaven! STR 21-0368

Superhost
Flat in Fort Myers Beach
5 out of 5 average rating, 3 reviews

The Wells at Coconut Cove

Welcome to The Wells at Coconut Cove right across from Fort Myers Beach! This comfortable unit puts you just steps from white sand and blue waves. Whether you’re here to relax, explore, or soak up unforgettable sunsets, this beach retreat has everything you need. Start your mornings with coffee, go swimming, shelling, or just lounging under the Florida sun. In the evenings, unwind in your space or head out to enjoy Fort Myers Beach’s famous restaurants, bars, and live music just minutes away.

Top guest favourite
Home in Cape Coral
5 out of 5 average rating, 19 reviews

Villa510~3 En-Suites~Gulf Access, Heated spa~pool

Villa510 is a newly built waterfront retreat ideal for extended stays in Cape Coral. Enjoy peaceful salt canal water views and manatees from the lanai, then relax in your private heated pool and spa—perfect year-round. The outdoor kitchen and lanai create an easy, comfortable daily routine. Inside offers three private en-suite bedrooms, a den with optional airbed, open living space, and TVs in every room. Close to shopping, dining, and beaches—perfect for snowbirds seeking comfort and ease.

Guest favourite
Home in Fort Myers Beach
5 out of 5 average rating, 6 reviews

Heated pool home Mid Island Short walk to beach

New to the rental market! This stylish retreat is perfect for families or groups with plenty of space to unwind. Featuring 4 bedrooms with 2.5 bathrooms, you’ll enjoy comfort and privacy throughout your stay. Perfectly located mid-island, just a short walk to the soft sands of FMB. Out back, a huge pool on the canal and large patio provide the ultimate spot for swimming and soaking up sun. Private parking and all the essentials for a seamless stay. Book today. Prime dates won’t last long!

Top guest favourite
A private pool is enclosed by a glass screen, allowing views of the surrounding tropical plants. The pool features a tiled back wall and a curved edge, set on a patio with textured pavers. Lush greenery is visible beyond the enclosure.
Home in Fort Myers Beach
4.98 out of 5 average rating, 45 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.

Top guest favourite
Home in Fort Myers Beach
5 out of 5 average rating, 78 reviews

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!

Top guest favourite
A waterfront beach house is showcased, featuring a wide driveway and lush green lawn. Palm trees and colorful landscaping surround the entrance, where a welcoming façade is visible under a clear blue sky, creating a relaxing atmosphere for guests.
Home in Fort Myers Beach
4.98 out of 5 average rating, 40 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!

Top guest favourite
Villa in Fort Myers Beach
5 out of 5 average rating, 28 reviews

Luxury Waterfront Home • Pool • Dock • Near Beach

Experience refined coastal living in Siesta Isles, Fort Myers Beach. This 4,000+ sq ft waterfront retreat offers a quick 5-minute drive to the beach and seamless, direct Gulf access by boat. Features include a private dock with lift, heated pool, open-concept design, multiple lounge areas, outdoor kitchen, and a separate TV suite with bar—perfect for families, groups and boaters seeking privacy, comfort, and location.

Top guest favourite
Home in Fort Myers Beach
5 out of 5 average rating, 15 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.

Top guest favourite
A single-level waterfront home is presented with a light green exterior and a blue garage door. Surrounding palm trees and landscaped gardens complement the modern architecture, showcasing a well-maintained lawn. The house overlooks a wide canal, emphasizing its coastal setting.
Home in Fort Myers Beach
5 out of 5 average rating, 24 reviews

Waterfront Island Oasis w/Heated Pool & Boat Lift!

Come enjoy this waterfront coastal getaway. Equipped with an infinity edge pool, dock with a motorized boat lift, and outdoor dining/grill area. Enjoy your morning sunrise over the water on the widest canal on the island. The stylish interior is spacious with a mix of mid century modern and coastal flare. This is truly your home away from home. Rental License #24-0087

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