Holiday rentals in Estero Island

A serene outdoor space is showcased, featuring a sparkling pool surrounded by a stone patio. Several lounge chairs are positioned under a large umbrella, with palm trees swaying gently in the background. A hammock can be seen nearby, adding to the relaxing atmosphere.

4.87 out of 5 average rating, 52 reviews

2 BR w/ Private Pool/Backyard, 2 min walk to Beach

Your getaway awaits in Ft Myers Beach. This upstairs unit has 2 bedrooms with 1 queen bed, 1 full bed, & 1 twin trundle bed; & 1 bathroom. This unit features an open concept living room with 2 futons for additional sleeping space, full kitchen, & dining area. Relax in the private backyard with pool, outdoor shower, games, bbq, & fire pit. Perfect if you’re looking for the best stay just 2 minutes walking distance from the beach. Now with all-in-one washer/dryer in unit & option for pool heating!

4.94 out of 5 average rating, 31 reviews

708A Beachfront Sunrise + Sunset Views

Wake up to stunning sunrises and wind down with breathtaking sunsets in this beautifully renovated beachfront condo on the South End of Ft Myers Beach. Enjoy luxury finishes throughout, including a sleek quartz countertop kitchen, modern appliances, and a spa-inspired walk-in shower. The layout and private balcony offer unbeatable ocean & bay views, making it the perfect escape for relaxation, comfort, and coastal elegance—all just steps from the sand. 708A is where your dream vacation starts!

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.

4.97 out of 5 average rating, 71 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!!

5.0 out of 5 average rating, 11 reviews

Coastal Escape | Walk to Beach | Sunset Views

Sunshine Escape ☀️ Steps to the Beach • Family + Friends Welcome!🌴 100% beachfront, close to restaurants, the marina, nightlife, supermarkets, and more. From the lanai, enjoy the white sands of our prestigious beach and breathtaking sunsets. Master Bedroom: King-size bed (super comfortable) Second Bedroom: Full-size bed + bunk bed (kids absolutely LOVE this room) Living Room: Sofa bed for additional friends or family Don’t wait — book today and be part of an unforgettable vacation! 🌊☀️

Superhost

5.0 out of 5 average rating, 4 reviews

Waterfront Canal Cottage Near Fort Myers Beach

Unwind at this bright, 2020-built canal-front cottage minutes from the sand and surf. The open kitchen and living area feature quartz counters, a cozy fireplace, and comfy furnishings for two bedrooms and two full baths. Soak in the private hot tub on the screened patio, watch boats cruise the canal, or call a golf cart ride to the beach and waterfront restaurants. In-unit laundry, central AC, and great views make this an easy home base for sun, sand, and salt life. Smart TVs in every room.

Superhost

The outdoor area features a heated pool and spa surrounded by a spacious patio. Lounge chairs are positioned beside the pool, providing a relaxing atmosphere. Sunlight reflects off the water, with palm trees and a canal visible in the background.

4.9 out of 5 average rating, 10 reviews

Walk to Beach! Updated home w/ POOL & SPA

Walk to beach- Classic 1950's beach cottage updated with modern conveniences, including newer HEATED pool & spa! Home has 2 bedrooms w/ King & Queen beds, new queen sofa sleeper, updated and fully-equipped kitchen with granite and new stainless appliances, as well a huge island with a wine refrigerator and coffee/bar with a dual Kuerig coffee maker, any glass you will need, juicer for fresh OJ and a beverage refrigerator! TV's in all bedrooms, LR, outdoor TV, firepit & more! FMB Reg#2256

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.

5.0 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.

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.

4.94 out of 5 average rating, 53 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!

5.0 out of 5 average rating, 19 reviews

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.

5.0 out of 5 average rating, 18 reviews

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.

A cozy living room features a light-colored sofa and an accent chair, complemented by a wooden coffee table. A piece of coastal artwork decorates the wall. The space opens to large sliding glass doors, providing views of the ocean and access to an outdoor balcony.

5.0 out of 5 average rating, 16 reviews

Seaside Resort Unit 309

This property requires a 7 night minimum from December- April Welcome to Seaside Oasis, your beachside getaway on the Gulf of America. This newly remodeled 2-bedroom, 2-bathroom condo situated right on the white sandy beaches of Fort Myers Beach is the perfect place for your getaway, offering spectacular beach views, water views and amazing sunsets!