Holiday houses in Estero Island

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Top-rated holiday rentals in Estero Island

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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, 19 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!

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, 262 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
Home in Cape Coral
5 out of 5 average rating, 21 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
A spacious outdoor area features a sparkling heated pool surrounded by sun loungers. The large two-story home showcases multiple balconies and expansive windows, with tropical greenery accentuating the inviting atmosphere. The patio is completed with a barbecue grill, ideal for alfresco dining and relaxation.
Home in Fort Myers Beach
4.95 out of 5 average rating, 22 reviews

Waterfront Luxury | Walk to Beach | Heated Pool

For a true luxury escape look no further than this modern waterfront 3 bedroom home with spacious sun lit rooms, a large chefs kitchen and a sparkling heated pool overlooking the canal. Located right in the heart of Fort Myers Beach house is within walking distance to the beach, beach shops and 5 min from the grocery store. Sit at the balcony and watch out for manatees or if you're really lucky the occasional dolphin making their way up the canal while enjoying the views. Lic # STR 22-0028

Guest favourite
An open-concept living space features light wood flooring and modern furnishings. A spacious kitchen with white cabinetry and stainless steel appliances is complemented by a dining area with seating for six. A large television is mounted on the wall, enhancing the inviting atmosphere.
Apartment in Fort Myers Beach
4.89 out of 5 average rating, 19 reviews

Coastal Luxe Retreat steps from the sugary sand

Welcome to Coastal Luxe Retreat, a beautifully appointed ground-floor residence just steps from the beach — where luxury meets laid-back coastal charm. Designed to comfortably sleep six, this stylish escape offers an effortless blend of comfort, convenience, and refined design. The open-concept living and dining area is filled with natural light and sophisticated décor, perfect for relaxed gatherings or quiet evenings in. Coastal Luxe Retreat is your front-row seat to seaside serenity.

Top Guest favourite
A serene pool area is framed by palm trees, with crystal-clear water reflecting the blue sky. A safety railing surrounds the pool, while grassy areas extend beyond. The horizon showcases the Gulf waters in the background, providing a tranquil setting for relaxation.
Home in Fort Myers Beach
5 out of 5 average rating, 68 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.

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
4.94 out of 5 average rating, 51 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!

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

The Woods at Coconut Cove

Welcome to The Woods at Coconut Cove right across from Fort Myers Beach! The Woods is one of our 2nd floor units with 1 full bath and 1 bedroom with a queen bed. The living room features a vaulted ceiling and a shared balcony with direct-view of the pool. There is a pull out couch (queen) in the living room that provides extra sleeping space well. The Woods has an open floor plan highlighting the fully stocked kitchen, ready for your cooking needs while you visit!

Guest favourite
Home in Fort Myers Beach
5 out of 5 average rating, 9 reviews

Luxury pool and spa home - Walk to Time Square

Welcome to Blue Tides, a vibrant, custom 4-bed, 4-bath Fort Myers Beach retreat. Bathed in soothing aqua tones, this home offers open-concept living, multiple balconies with water views, and a private pool & spa. Each beautifully appointed bedroom has an en-suite bath. It’s ideally located in a peaceful neighborhood, steps from the sandy beach and a 5-10 min walk to Times Square. Perfect for groups or book with sister property Pink Star next door!

Top Guest favourite
Condo in Fort Myers Beach
5 out of 5 average rating, 9 reviews

Oceanfront Condo 210 | Heated Pool + Gulf Views

Rare corner-unit beachfront retreat directly on the white sands of Fort Myers Beach! Enjoy panoramic Gulf views, ocean breezes, beautiful sunsets & a large heated pool. Bright, comfortable and perfectly located mid-island. Supermarket, Junkanoo restaurant/bar & Snook Bight Marina are right across the street. Walk to dining, boat rentals, sunset cruises & deep-sea fishing. Keyless entry, 3 TVs & 6 beach towels included.

Top Guest favourite
Villa in Fort Myers Beach
5 out of 5 average rating, 31 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.

Guest favourite
Condo in Fort Myers Beach
4.86 out of 5 average rating, 95 reviews

Boutique condo on the bay, short walk to the beach

NOTE: the pool will be closed until the end of August for repairs. 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.

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