Holiday rentals with a pool in Estero Island

Paradise on Estero Bay

Welcome to Mullock Creek a Boater's dream! Southwest views boasting breathtaking sunsets overlooking gulf access canal from your spacious backyard, just minutes away from shopping and dining at Coconut Point, and Gulf Coast Town Center. This stunning Key West Style home has been beautifully maintained and updated offering a lovely front entrance, fully equipped kitchen, spacious Living Room, dining room, Wi-Fi, private driveway with access to the open garage, fully furnished and private pool.

Sunny Sanibel - Gorgeous Loggerhead Walkout Unit

Loggerhead Cay 351 is a fantastic ground floor walk out condo residence in the sought after Loggerhead Cay development of Sanibel`s East End. "Sunny Sanibel" features two spacious bedrooms and bathrooms, a fully equipped kitchen, direct Gulf views, and a walk out patio, this residence is both beautiful and functional! With resort grade amenities including tennis, pickleball, Olympic sized heated swimming pool, shuffleboard, and community grills, guests will surely return year after year!

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!

Blue Mermaid

Fully stocked, and beautifully renovated and furnished 4 BR/ 3 bath direct access waterfront Villa with heated pool, dock, kayaks, fishing poles and much more. Located on a great saltwater canal minutes away from open water. Close to shopping, restaurants, and entertainment. Sleeps 8 The booking price includes full electricity - incl. pool heat. No further fees will occur after booking. Owners allow 1 non-shedding dog up to 40 lbs. Pre-approval needed and pet fee applies.

Seaside 302 - Beachfront 2BR/2BA - Solmate on FMB

Solmate 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.

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.

The Coconut Shack

Welcome to Fort Myers Beach! At the Coconut Shack, enjoy an AMAZING SALTWATER POOL with sun on the lanai all afternoon. Grill out, relax, or head down to the BEACH - beach gear included! AMAZING outdoor KITCHEN/BAR. Rent a BOAT and park at the end of the street and WALK to the house! Fresh coffee is stocked before you arrive, and you're just 20 mins from the airport. Everything you need, nothing you don’t—just sunshine, water, and pure relaxation.

555 Royal Palm Villa | Luxury Heated Pool Home

Luxury resides at this 3 Bed/2 Bath with Heated Pool. You'll surely be happy spending your stay at this single family home located on the most desired block of the popular Naples Park neighborhood, only a 3 minute drive from Vanderbilt Beach and Wiggins Pass Beach. Xfinity Comcast Cable & Internet service Free to our guests. Beach chairs, umbrellas and towels are available to make your trip to the beach an easy one.

Lovers Key Resort Suite 5 - Bay View

Enjoy this 5th floor condo at Lovers Key Resort, with breathtaking views of Estero Bay! Take in the view from inside through the floor to ceiling windows or sit out on the balcony. Admire the gorgeous sunrise over the bay as you sip your morning coffee! This fully furnished 1 bedroom, 1 bath condo features a king size bed, TV in the bedroom, and an extra large bathroom with garden tub and a walk-in shower.

Villa Seascape-on lake, infinity pool, spa, modern

With its unforgettable cotton candy sunrises, Villa Seascape is a lakeside delight. Offering a blend of luxury and location, you can relax and rejuvenate during your holiday experience. Step inside your waterfront getaway and you will immediately be met with widewater views from it's central viewpoint on Lake Britannia.

Gullwing Beach Resort 1002

Gullwing 1002 is a partial beachfront view condo, with a heated pool, whirlpool spa, elevated tennis courts, and private beach access. Take in the views from the beach to Estero Bay from the private screened in balconies on the 10th floor, accessible from every room. Located on the south end of the island.

Island Paradise Walk to the Beach-Heated Pool

Just a block from white-sand beaches and only 1.2 miles to the vibrant heart of Times Square (Fort Myers Beach), this peaceful 2-bed, 2-bath home sleeps up to 6 and offers stylish updates, high-speed internet, and a secluded backyard pool to relax in after your Gulf-coast adventures.