Holiday rentals with a pool in Estero Island

McGregor’s Gem• Heated Pool 3BR/2BA River District

🌴 Welcome to McGregor’s Gem—your ideal Southwest Florida retreat! Dive into relaxation in your private heated pool, spread out across three bedrooms and two baths, and enjoy the perfect blend of peaceful tree-lined neighborhood living just minutes from the charming Downtown Fort Myers River District, world-class beaches, and top local attractions.☀️ Whether you’re traveling with family, friends, or on business, this home offers all the modern comforts you need for a relaxing, stress-free stay

Island Oasis Steps From the Sugar Sand Beach

Important Note: This apartment had no damage from hurricanes in 2024. Everything is perfect here. Beaches are beautiful, pool is relaxing and welcoming. Thankfully the island restaurants and bars are also back up and going in fun island style! Beaches are beautiful and our brand new pool is complete and ready to enjoy. Be one of the first to enjoy this complete remodel renovation. No expense was spared here. Top quality memory foam mattresses with high end bed linens for a restful sleep. F

Boater’s Paradise-Stunning Sunsets! Games Room!

Renovated lanai! This 3 bed/4 bath home is on the nicest canal with 200+ ft of frontage & gorgeous views of the canal & sunset. The pool, tiki hut & docks have full sun all day. Each bedroom has a private bath & there's a 2 pc powder room off the laundry. The primary has a king bed & walkout to pool. The 2nd bedroom has a queen bed & pool access. Bedroom 3 has a queen & private bath. Fully equipped kitchen with everything you need. And a games room! Enjoy stunning sunsets under the tiki hut.

LUX Villa w/ Private Salt Water Pool, Lanai, Canal

Are you looking to swim, relax outdoors, fish and take in beautiful sunsets on a wide gulf access canal? If so you will fall in love with this stunning newly constructed custom built home! The 2750 square foot home is bright & airy with two main bedroom on-suites & a separate family wing! The gourmet kitchen, dining room & great room open via large sliders to the lanai & pool w/ views of the canal in much desired SW Cape! Beach inspired villa! Large captains walk & Tiki! Check out our reviews!

Beachfront, Water Views Estero Beach Tennis 708A

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!

AquaLux Smart Home

Unwind in style in this spacious and modern home. Here's what awaits you: Smart Home Technology: Control lights, temperature, and even the front door with voice commands or your smartphone for a seamless experience. Heated Saltwater Pool: Take a refreshing dip in the sparkling pool, perfect for year-round enjoyment. Dedicated Workout Area: Maintain your fitness routine with a private space equipped for exercise. Freshwater Canal Views: Wake up to calming water views and the sounds of nature.

Beachfront @ Elevate in the Sun!

Welcome to ELEVATE IN THE SUN! Where an elevated experience is waiting. Premier Host (Other Site)-4.8* The unit boasts a completely remodeled kitchen with quartz countertops, brand new appliances including a dishwasher (very rare), brand new living room furniture, and new A/C and music surround sound streaming via Amazon Alexa and Apple Music. Sunrises are included each morning on your private balcony and sunsets are breathtaking down on the beach with toes in the bright white sand.

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!

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.

Coral Reef Villa - Steps from beach / Private Pool

We're Back! Fully Renovated in 2023! Welcome to the Coral Reef Villa located at 213 Fairweather Lane, 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!

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!

Tide & Seek: Beach-front and Resort Amenities

Welcome to Tide & Seek! This stylish 2 bedroom, 2 bath condo at Gull Wing Beach Resort is perfectly situated on the peaceful south end of Fort Myers Beach. Sleeping 6, this 8th-floor retreat features an open living space, full kitchen with coffee & wine bar, and a screened balcony with angled Gulf views. With resort amenities including a heated pool, spa, grilling area, and direct beach access, it’s the ideal spot for families or friends to unwind in coastal comfort.