
Vacation rentals with a pool in Estero Island
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Estero Island
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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

Seaside Resort 210: oceanfront views, heated pool
* This is a corner unit! * Sun-kissed, center-island paradise, * Located directly on the pristine, white sands of Fort Myers Beach. peaceful * Peaceful sounds of ocean waves, panoramic ocean & beach views * Large heated pool. * The island’s only Supermarket, popular bar/restaurant (Junkanoo) & Snook Bight Marina (boat rental, sunset cruises, deep sea fishing) are right across the street! * Comfortable beds, digital locks throughout, 3 new flat screen TV's, 6 beach towels provided.

Plunge in the pool at this Fort Myers Beach home
Tranquility awaits at this newly remodeled vacation rental home. Located in a quiet neighborhood near the white sands of Fort Myers Beach, private screened-in pool, comfortably air-conditioned, 3 bedrooms that sleep up to 6 people, 2 baths, spacious gourmet kitchen, outdoor seating area with tv, beach wagon and more. Local trolley available to take you to Times Square and the famous pier. Tons of shopping and restaurant options. Get away from it all in this little slice of heaven! STR 21-0368

Heated pool home Mid Island Short walk to beach
New to the rental market! This stylish retreat is perfect for families or groups with plenty of space to unwind. Featuring 4 bedrooms with 2.5 bathrooms, you’ll enjoy comfort and privacy throughout your stay. Perfectly located mid-island, just a short walk to the soft sands of FMB. Out back, a huge pool on the canal and large patio provide the ultimate spot for swimming and soaking up sun. Private parking and all the essentials for a seamless stay. Book today. Prime dates won’t last long!

Walk to Times Square, steps to the Beach!
Welcome to your perfect beach getaway! This bright and inviting 2-bedroom, 2-bath vacation rental is ideally located just across the street from the sandy shores of Fort Myers Beach, with easy beach access just a short walk away. You'll also be just a quick stroll from vibrant Times Square—home to great restaurants, shops, live music, and fun nightlife. This comfortable and well-appointed home offers everything you need for a relaxing stay! Come experience the best of Fort Myers Beach!

Beachfront Condo | Gulf Views - Ocean Glass
Beach Villas #503 – Beautiful Beachfront Condo with Screened Lanai. Wake up to the sound of waves and end your day with breathtaking sunsets over the Gulf of Mexico. This 2-bedroom, 2-bath condo is beautifully decorated and perfectly located on the north end of Fort Myers Beach. Sleeps up to 6 with a king bed in the Primary, two double beds in the guest room. Community pool, BBQ grill, and beach chairs available. Free WIFI, keyless entry, and a dedicated parking pass for one vehicle.

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.

Island Gold Steps to the Beach - Heated Pool
No expense was spared in creating this luxurious 2BR/2BA apartment in a 4 plex building. Located in a quiet Fort Myers Beach neighborhood surrounded by nature. Just one block to beach access 23 and a short walk or bike ride to Times Square, this second-floor getaway offers a heated pool with waterfall, multiple outdoor spaces, upscale finishes, and thoughtfully curated comforts for a first-class coastal escape.

Blue Coconut Retreat
Brand-new, custom-built beach house just steps from the sand! Enjoy beach views, a private pool, all-new furniture and bedding, and stylish coastal decor. Relax in comfort with an open, airy layout curated for tranquility. Located just 5 blocks from Publix, Junkanoo, and Fresh Catch Bistro. Whether you're soaking up the sun or dining nearby, this peaceful retreat offers the perfect Fort Myers Beach getaway!

Waterfront Island Oasis w/Heated Pool & Boat Lift!
Come enjoy this waterfront coastal getaway. Equipped with an infinity edge pool, dock with a motorized boat lift, and outdoor dining/grill area. Enjoy your morning sunrise over the water on the widest canal on the island. The stylish interior is spacious with a mix of mid century modern and coastal flare. This is truly your home away from home. Rental License #24-0087

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!

Naples Dream Getaway w/ a view !
!!Book with us and avoid paying Airbnb Fees!!! Luxury Lakeside Villa in Naples – Your Perfect Coastal Escape Welcome to your dream retreat in beautiful Naples, Florida! This stunning luxury villa is perfectly located just 15 minutes from the white sands of Vanderbilt Beach and close to top-tier shopping, dining, and entertainment.
Popular amenities for Estero Island rentals with a pool
House rentals with a pool

Beyond The Sea · 60+ 5-Stars · Walk to Beach-Town

The Great Escape Beach House/ Pool/ Dock

Escape to your Happy Place-pool, 6 bed 2 1/2 bath

Beach Cottage w/ htd pool + The Beach is in sight!

Large Home Steps to Beach, Heated Pool & Game Room

Island retreat - canal, heated pool, walk to beach

Stay and Play 2

Key West–Style Home • Heated Pool • Walk to Beach
Condo rentals with a pool

Beach Sanctuary Condo

Rare walkout condo on Sanibel beach

Boutique condo on the bay, short walk to the beach

206C Gulf Water Views + 2 bikes + beach gear

Ft Myers Beach & Lovers Key State Park- FANTASTIC!

Beach! Beach! Beach! Only 3BR in Island Winds!

Coastal Escape | Walk to Beach | Sunset Views

View of Gulf, Steps to Beach@The Turquoise Turtle
Other vacation rentals with a pool

Luxury Waterfront Home • Pool • Dock • Near Beach

Private Pool & Home 45% off 2026 Ft Myers Beach

The Natural Palm Beach House: Luxurious & Low-Tox

The Wells at Coconut Cove

Island Beach House – Brand New 3-Bedroom Retreat

Sleeps 16 | Bay View | Heated Pool | Walk to Beach

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

Tropical Paradise Home with Pool - Walk to Beach
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