Waterfront holiday rentals in Estero Island

5.0 out of 5 average rating, 39 reviews

Tide & Seek | 8th-Floor Beachfront, Pool, 2BR

Welcome to Tide & Seek! This stylish 2BR/2BA condo at GullWing Beach Resort on the peaceful south end of Fort Myers Beach sleeps 6 and features an open living space, fully outfitted kitchen + gourmet style coffee & wine bar, and a large screened balcony with Gulf & beach views. Enjoy direct beach access and resort amenities including a heated pool, spa, grilling area, beach-cruiser bikes, newly renovated tennis & pickleball courts (equipment provided for guest use) for a relaxed coastal getaway!

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.

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, 69 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 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.

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

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 two-story beachfront home features a pastel green exterior with white accents and a welcoming front porch. Lush landscaping surrounds the property, and a flag is displayed proudly from the garage. Palm trees sway gently in the foreground, while a clear blue sky complements the vibrant setting.

5.0 out of 5 average rating, 34 reviews

Casa Mia - heaven on the beach STR# 20-0043

Welcome to our beach front home with private walk to the beach. Perfect location. Publix grocery store and restaurants just one block away. The beach is coming back to life. The beach looks great, restaurants and bars are opening and parasailing is back. Food truck courts are now a new addition to the beach. Live outdoor music is back. The Yucatán, Wahoo Willys, Bonita Bills, Dixie Seafood, Fresh Catch Bistro and Junkanoo are some of restaurant’s now open. Beach trolley is running.

A waterfront beach house is showcased, featuring a wide driveway and lush green lawn. Palm trees and colorful landscaping surround the entrance, where a welcoming façade is visible under a clear blue sky, creating a relaxing atmosphere for guests.

4.98 out of 5 average rating, 42 reviews

The Great Escape Beach House/ Pool/ Dock

Escape to this waterfront beach house in sunny Fort Myers Beach! Perfect for families and friends, it features a private pool, a 50ft private dock with direct gulf access. House is only 1/2 a block from beach access. Plenty of outdoor entertainment areas including a large game room, with an outdoor ping pong table and beach accessories. Just minutes from beaches, shops, and dining this is your perfect Florida getaway for fun, relaxation, and unforgettable memories!

Superhost

5.0 out of 5 average rating, 3 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.

A stylish living area is arranged with a leather sofa and chairs, facing a large flat screen TV. Natural light floods the space through glass doors leading to a balcony with ocean views. A dining table with seating for four is placed near a decorative plant and vibrant pink flowers.

5.0 out of 5 average rating, 26 reviews

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.

5.0 out of 5 average rating, 16 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.

4.84 out of 5 average rating, 128 reviews

206C Gulf Water Views + 2 bikes + beach gear

Beachfront & Gulf Water Views 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, free high-speed WiFi, heated pool, tennis/pickleball courts, BBQ grills, free parking, and stocked beach gear. Steps from the sand with sunsets you’ll never forget.

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.