Holiday houses in Estero Island

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Top-rated holiday rentals in Estero Island

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Top Guest favourite
A vibrant, two-story house in a coastal hue is displayed, featuring a spacious pool area surrounded by a paved deck. Sun loungers are positioned near the pool, and a covered seating area can be seen. The property is enclosed by white fencing, adding to its privacy.
Home in Fort Myers Beach
5 out of 5 average rating, 20 reviews

New house, pool, views, elevator, steps to beach

Be one of the first families to stay at this Brand New mid island house. Private pool, Elevator, beautiful custom tiled porches, amazing gulf & sunset views. The entire top floor is a master ensuite oasis with large room, spacious bathroom, custom tiled walk-in shower with sunset views, huge custom tiled deck with comfy furniture and amazing views. Perfect mid Island location. Just a mile from all the restaurants and entertainment in Times Square. Linens provided. 3 parking spaces. #19-1352

Top Guest favourite
Aerial view of a stunning coastline, featuring soft white sand intertwined with turquoise waters. Small boats are anchored near the shore, where a few individuals enjoy the beach. Lush greenery and houses are visible in the background, contributing to the serene landscape.
Condo in Fort Myers Beach
5 out of 5 average rating, 51 reviews

Luxury Beach Condo On The Bay In A tropical Oasis!

Stylish beach condo located on the bay in Estero Island is one of the most beautiful places in all of Florida. There is activities for all ages from fishing, boating, swimming, bicycling and kayaking. You can enjoy World Famous Seafood Restaurants or hang out in the tropical laid back downtown. The condo is walking distance to the beach or a short drive to Lovers Key. Where you can find dolphins exotic shells, manatees, live conch and sea dollars. Memories made here will last a life time!!

Top Guest favourite
A clear swimming pool is framed by tropical palm trees, surrounded by lounge chairs. The sunset casts a warm glow over the scene, reflecting off the water's surface. The two adjacent buildings feature balconies with white railings, enhancing the inviting atmosphere.
Condo in Fort Myers Beach
5 out of 5 average rating, 15 reviews

Beachfront condo on 10 acres of pristine beach.

Enjoy the Beach Life! This beautiful one-bedroom condo on the beach with partial ocean views for breathtaking sunsets situated on 10 acres of beauty. Estero Beach & Tennis is ready for a new vacation experience BRAND NEW- heated pool, lobbies, laundry rooms, pool area, BBQ areas, tennis courts, pickleball and bocce ball. Across the street from Santinis Plaza! Our Island is 7 miles of paradise, plenty to do here-enjoy walks on the beach, fishing & watching the dolphins & shelling! Paradise

Top Guest favourite
An open living area features a kitchen island with seating for four, surrounded by white cabinetry and stainless steel appliances. A comfortable seating area with light gray furniture invites relaxation, complemented by natural light streaming through multiple windows. Decorative accents add a welcoming touch.
Home in Fort Myers Beach
4.93 out of 5 average rating, 14 reviews

Paradise Found

Located in Sun Retreats Fort Myers Beach (formerly Indian Creek), just 3 miles from Fort Myers Beach, Bunche, and Sanibel Island, and Margaritaville. The property offers amenities, including pools, pickleball, tennis, and numerous activities. It’s a great location, away from the main beach traffic but still close to shopping, and you can bike or walk to the beach. The trolley also stops right at the entrance. The bungalow features a fully equipped kitchen. Must be 35 to book, park rules.

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, 41 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
A covered outdoor space features a heated saltwater pool bordered by wide stone tiles. Comfortable lounge seating is seen under an umbrella nearby. Lush greenery and canal views are visible beyond the pool area, offering a serene setting for relaxation.
Home in Cape Coral
5 out of 5 average rating, 58 reviews

Coastal Cowgirl - Heated Pool

Have fun with the whole family in Southwest Florida. This bungalow is full of coastal cowgirl vibes and sits right on a gulf access canal. Everything from top to bottom is stocked and brand new. Bring the outdoor oasis in via large panoramic sliders, a covered lanai with a heated saltwater pool and hot tub, outdoor kitchen, and entertainment system. Watch wildlife float by or rent a boat and cruise through the canals to the gulf for amazing beach access. Coastal living at its finest.

Top Guest favourite
The living area features a spacious sectional sofa arranged around a wooden coffee table. A large wall clock is mounted above the seating, adding character. Natural light enhances the cozy ambiance, while a woven area rug complements the warm tones of the wooden furniture.
Apartment in Fort Myers Beach
4.97 out of 5 average rating, 35 reviews

Your Home at the Beach!

Less than a mile from Time’s Square, the beach center, and the remains of the pier. Beach access is a 5 minute walk. Close to public transportation and located on a quiet street with a private backyard on a canal. If you’re lucky, catch a glimpse of a dolphin or manatee. Private entrance. Newly remodeled with full kitchen and shared laundry room. If this sounds like what you’ve been looking for, instant book right now or text me with any questions you might have.

Top Guest favourite
A dining area features a round marble table surrounded by sleek black chairs, accented by a vibrant arrangement of pink flowers. In the background, a living space includes a luxurious chandelier, comfortable seating, and large windows revealing views of the beach.
Condo in Fort Myers Beach
5 out of 5 average rating, 13 reviews

Seaside 204 Beachfront condo - Luna Sea on FMB

LunaSea is a well-appointed, breathtaking beach front condo located mid-island on beautiful Fort Myers Beach, FL. This is a 2br/2ba second 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.

Top Guest favourite
A coastal home is presented with a light purple exterior and spacious covered front porch. A well-maintained lawn features greenery and white stones, bordered by red flowers. Underneath, a paved parking area is visible, with stairs leading to the entrance of the home.
Home in Fort Myers Beach
5 out of 5 average rating, 34 reviews

Grace by The Sea · 2025 Build · Steps to Beach

This stylish coastal home offers a brand-new experience with a spacious lanai and backyard, all with just a 6-minute walk to the sugar sand beach. Start your morning with coffee on the covered front porch, enjoying Gulf breezes. Relax by the pool with a book throw something on the blackstone grill, play corn hole or enjoy cozy outdoor seating for lounging and dining. End the day with a sunset stroll or a short drive to nearby bars and restaurants.

Top Guest favourite
A modern studio apartment features a spacious bed adorned with a blue quilt and colorful pillows. A Smart TV is positioned on a white dresser. Natural light filters through large windows with simple coverings, while a small dining table is visible in the corner.
Apartment in Fort Myers Beach
4.96 out of 5 average rating, 57 reviews

Casa Bella D - 1 Bed/1 Bath - Steps To The Beach

Fort Myers Beach Short Term Rental # 21-0113. Fresh, clean and cozy, Casa Bella D is a modern, newly updated studio apartment located across the street from the Gulf of Mexico and 7 miles of sugar sand beach. This popular ground floor unit features a new Queen bed with a memory foam mattress, a morning kitchen, a full bathroom, and a walk-in closet. The décor is contemporary beach casual and is perfect for 2 people.

Top Guest favourite
An open-concept living area features a light-colored sofa and dark gray armchair, arranged around a circular coffee table. A spacious kitchen with white cabinetry and modern appliances lines the back wall. Natural light filters through large windows, creating a bright and airy ambiance.
Apartment in Fort Myers Beach
4.98 out of 5 average rating, 121 reviews

Fall Specials! Island Paradise Walk to the Beach

Escape to paradise in this beautifully remodeled Fort Myers Beach apartment! Enjoy stunning beaches, a brand new, relaxing pool, and the vibrant island atmosphere with restaurants and bars nearby. This apartment boasts top-quality memory foam mattresses, high-end 100% cotton linens, and fresh towels. Located just one block from the beach, it's the perfect getaway for families and friends.

Top Guest favourite
Condo in Fort Myers Beach
4.82 out of 5 average rating, 113 reviews

Gulf Views & Sunsets | Estero Beach Tennis 206C

☀ Beachfront Bliss at Estero Beach & Tennis Club 206C ☀ Wake up to unobstructed Gulf views in this 5-star Fort Myers Beach condo! Enjoy early check-in, no checkout chores, and every comfort—from a king GhostBed, full kitchen with dishwasher, and high-speed WiFi to pool, tennis, and stocked beach gear. Steps from the sand with sunsets you’ll never forget.

Popular amenities for Estero Island holiday rentals

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Lee County
  5. Fort Myers Beach
  6. Estero Island