Vacation rentals with a pool in Estero Island

5.0 out of 5 average rating, 5 reviews

Private Pool & Home 45% off 2026 Ft Myers Beach

STR#R250080Month of April & Dec$3000+fees. Discounts in August to Dec. Fort Myers Beach - ALL NEW inside and out - Equipped Kitchen TWO MINUTE walk across street to beach and a heated pool to yourself. This one story home has 3 bedrooms - 2 full baths, LR kitchen, breakfast room Canal front,3 blocks from Publix & restaurants. Driveway parking or park a car in the garage. Washer, Dryer and two bicycles in the garage. Beach chairs and bikes included. Minutes to the beach. License No:DWE4607658

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!

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.

4.99 out of 5 average rating, 70 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!!

A spacious pool area is visible, featuring lounge chairs arranged around a clear blue pool. Palm trees provide a tropical feel, and the beach is accessible through a wooden pathway in the background. Clear skies contribute to the inviting atmosphere.

4.91 out of 5 average rating, 87 reviews

3BR BeachCondo | Gulfside Pool | Hot tub | Sleep 8

Welcome to GullWing 202! Experience the comfort of our OWNER-MANAGED 3-bedroom, 2-bath condo situated on Estero Island's broadest white-sand beach. Unwind and bask in the sunshine on the beach or beside the pool, all while supporting the restoration of Fort Myers Beach! Our pool area is ready for enjoyment, featuring brand-new loungers and fresh BBQ grills. Plus, with Publix and CVS open, as well as a growing selection of restaurants, you'll have all the essentials for an ideal getaway.

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! 🌊☀️

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!

Cottage in Fort Myers Beach

A spacious backyard features a curved in-ground pool, surrounded by a textured paver patio. Lush palm trees offer shade, while outdoor seating is visible in the background. A shed is positioned adjacent to the villa, contributing to the property's inviting outdoor space.

4.94 out of 5 average rating, 154 reviews

Mango Villa - Steps away from beach / private pool

We're Back! Fully Renovated in 2023! Welcome to the Mango Villa located at 150 Mango Street, Fort Myers Beach. 2 bedroom and 1 full bathroom villa. Steps away from the beach where paradise is waiting for you. Centrally located at the North end of the island. Walk to Times Square to enjoy shopping and dining. Close to all Fort Myers Beach has to offer while also located on a quiet residential street, this home is perfect for those that demand both proximity and tranquility!

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.

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.

5.0 out of 5 average rating, 32 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.

5.0 out of 5 average rating, 17 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 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.