
Holiday houses in Estero Island
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Top-rated holiday rentals in Estero Island
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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

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!

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

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.

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!

Poolside Retreat l Walk to Beach l Sleeps 8
Enjoy poolside relaxation from this private villa in Fort Myers Beach, just a 7-minute walk to the beach. This modern retreat is perfect for couples or small families. The spacious villa offers privacy, comfort, and an elevated setting above it all. Start your mornings on the sand, spend your afternoons in the heated pool and spa, and unwind in the evenings with bay breezes from upstairs. STR Registration Number: R260539 *Under 25 please message before booking *NO Elevator

Chateau Bleu ·2026 Luxury· Rooftop Deck Gulf View
Personally hosted by Paul & Alicia of Dancing Palms Vacations, this elevator equipped brand-new experience with covered porches on all levels including a panoramic gulf view from a roof top deck. The oversized TV is perfect for watching movies or sports and the house has 4 KING beds. The backyard features a spacious lanai and fenced heated pool with sun loungers and a putting green. Just across the street awaits the white sugar sand beach. All beach equipment is provided.

Seaside 408 - Beachfront 2BR/2BA Sea La Vie on FMB
Sea La Vie is a well-appointed, breathtaking beach front condo located mid-island on beautiful Fort Myers Beach, FL. This is a 2br/2ba third floor unit with direct beach front views. The condo sleeps up to 6 people. The full kitchen has everything you need from pans to an air fryer and everything else in between. The bedrooms and living room have flat screen 4K HD Smart Tvs for your entertainment. Supermarket is located literally across the street.

Tangerine Tides: Resort Pool/Spa, On Beach, Lanai
Welcome to Tangerine Tides! This bright & colorful 2BR/2BA Gulf-view condo on Fort Myers Beach sleeps 6 with a king, queen & sleeper sofa. Enjoy direct beach access, a community pool & hot tub, beach chairs and beach towels, pickleball, tennis, BBQ grills, plus Gulf views from your private balcony. With a fully equipped kitchen and plenty of space to unwind, it’s the perfect island escape for families, couples & friends!

Oceanfront Condo 201 | 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.

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.

Beach escape! Walk to the square! Steps to beach!
Modern 3BR/2BA home with an industrial-chic vibe, perfectly located just a short walk down the street from the beautiful Fort Myers Beach. Enjoy a fully equipped kitchen, open living space, and private outdoor area—ideal for relaxing after a day in the sun. Walk to the beach in minutes or explore nearby Times Square for dining and entertainment. Comfort, style, and unbeatable location all in one!
Popular amenities for Estero Island holiday rentals
Other great holiday rentals in Estero Island

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

The Great Escape Beach House/ Pool/ Dock

Beachfront Bliss!

Seaside Resort Unit 309

Pink Star | Coastal Chic - Walk to Town Square

Renovated 1BR Beach Condo |Walk to Sand| Sleeps 4

Private Pool - Bay Views - Club 205 At Bayview

“Steps to Sand! Modern Cozy Apartment
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