Holiday rentals with a pool in San Carlos Island

Harbour House #312 “Castaway Dreams”

“Castaway Dreams” at Harbour House Resort is a beautifully designed two-bedroom, two-bathroom retreat located in the heart of Times Square Fort Myers Beach. Steps from the sugar-white sand, waterfront dining, and vibrant island entertainment, this prime location puts you right in the center of it all while still offering a relaxing coastal escape. The Harbour House community features a welcoming pool deck and inviting common areas. All linens, beach chairs, and umbrellas are included with your s

Family · Location · Cleanliness

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!

Value · Location · Beach

The Bayview

Welcome to "the Bayview," a stunning getaway minutes from downtown Fort Myers Beach, and a short drive to Sanibel Island. This gorgeous 4 bedroom, 3-bath home has all the amenities to experience the perfect vacation with family and friends. Kick back and enjoy the breathtaking view of Estero Bay from the front porch Lanai, or relax with the family around the rear pool patio. Looking for some fun? Ride an E-bike, rent a golf cart or walk to the nearby "Excursions Marina" and make some memories!

Family · Location · Biking

Luxury Riverfront Retreat • Pool & Spa • 60ft Dock

Luxurious 4BR 3.5Bath villa located in a prime location, directly on the Calosahachee River in a sought-after waterfront area near downtown. Magnificent expansive backyard with high-end amenities and direct river access ✔ 4 bedrooms ✔ Open Design Living ✔ Full Kitchen ✔ Patio (Pool and Hot tub, Bar, Dining, BBQ) ✔ Expansive Tropical Yard ✔ Indoor/Outdoor Surround Sound ✔ 7 Smart TVs ✔ High-Speed Wi-Fi ✔ Large Private pier/dock w/ boat & jet ski lift and a Tiki Hut! See more below!

Location · Family · View

Paradise on canal minutes to Ft Myers Beach/Gulf

Beautiful 3 Bedroom, 3 bath home on a canal with a dock! Bring your boat or jet skis! Enjoy a relaxing stay watching the dolphins and manatee right off the dock. This exquisitely updated home has everything you need for a fantastic vacation. Especially location! 5 minutes to Ft Meyers Beach. Enjoy the resort right in your own backyard. New pool with hot tub and sun shelf. Enjoy beautiful sunsets off the huge patio. Trolly to beach at neighborhood entrance or walk to in minutes.

Location · Value · TV

Sundial E304: Gulf Front 3BR w/Stunning Ocean View

BRAND NEW - RIGHT ON THE BEACH! Enjoy stunning direct gulf-front views from nearly every room at this relaxing 3BR coastal retreat. This luxury residence was fully renovated to include a custom expanded kitchen, 2 gorgeous bathrooms, and washer & dryer. Top of the line coastal furnishings in every room. The large master bedroom offers spectacular gulf views & a full-size desk in case you need a quiet space to work. WiFi has been fully upgraded to make streaming and video a breeze.

Family · Location · View

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.

Value · Family · Shared spaces

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!

Value · Family · Wi-Fi

Fort Myers Beach Sunset Nest

Sunset Nest | Pool, Walk to Beach & Times Square Bright, breezy, and ready for memory-making. This property offers a spacious, sunlit interior with a birds-eye view of the rebuilt, refreshed, thriving Fort Myers Beach neighborhood. Walking distance to the beach and Times Square allows for easy access to shops, dining, and waterfront strolls. The private pool area is just steps away from the main living space. Swim, soak, repeat as you unwind under Fort Myers Beach’s famous skies.

Family · Value · Hospitality

Sunset Canal House - Pool, Spa & Private Dock

Wake up on the water in this bright 4-bedroom Cape Coral home. Twelve feet of pocket sliders open the great room onto a paver lanai with a saltwater pool and spa - sunsets over the canal are the main event. Boaters: a private Trex dock with a 7,000 lb lift on a wide, deep canal, one bridge to open water. Inside: full kitchen, 4 bedrooms, 3.5 baths, laundry, and a fenced yard with room for kids to run. Cape Harbour Marina, shops and restaurants are minutes away.

Value · Location · View

Dolphin beach house 2

ONE OF THE BEST WATERFRONTS IN CAPE CORAL! A short walk to the beach . This 2,500+sq ft home has stunning sunsets and South Western water views from all main living areas,as well as the Master Suite. Heated pool w/ LED colored lighting, built in Spa,Pool bath, full laundry facility, Lanai,Fireplace ,Wi-fi and TVs in every bedroom, private dock . Boat on lift for rent w/RPM rentals . Large 2-car garage w/5 bicycles,beach wagon & cooler on site.

Location · Family · View

Ostego Charm | Fort Myers Beach Coastal Charm

Welcome to Ostego Charm! This beautiful 2 bed, 2 bath Fort Myers Beach home offers an open floor concept filled with natural light and coastal charm. Enjoy breezy evenings on the spacious covered porch or entertain in the bright, modern living space. Elevated for safety and style, and surrounded by lush tropical landscaping, Ostego Charm is just minutes from the beach—your perfect island getaway or vacation rental!

Family · Location · Nearby