Holiday rentals with a pool in Fort Myers Beach

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!

Family · Location · Cleanliness

100+ 5 Star Reviews and Right on The Beach!

We are a Superhost for a reason! Sanibel Siesta looks amazing! Immaculate beachfront, 2BR, 2BA w/garage, nicely updated beachy unit at sand's edge. Cooks kitchen. Amazing views of the Gulf w/5 star ratings! 3-day min. New hurricane windows, nicely furnished with ELEVATOR IN BUILDING! Discount for weekly/mo. rentals. BR 1:King bed ensuite, smart TV. BR 2: 2 tw. beds, smart TV. Qn. sofa bed in LR. Pool, golf course, bikes, laundry on site. No food or condiments stored in unit. May allow sm. dog.

Family · Location · Indoor spaces

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!

Family · Location · TV

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 · Biking

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 · Comfort

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

We are very excited to update this listing with brand new pictures of this fully renovated home. Everything in Kelsabella is brand new and has plenty of room for everyone. 4 bedroom 2 and 1/2 bathroom with an outdoor heated shower. This is a one story home located in a beautiful neighborhood walking distance to all the activity's and steps away from your beach access . Pool is also heated so it can be used all year round PET OWNERS! Must click on and read “ guest access”

Location · Family · Layout

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!

Family · Location · Hospitality

Whole cozy house

Entire cozy house just for you friends and family. Perfect to spend a pleasant and relaxed moment. If you plan to have a party or event, this place is NOT for you. The neighbors are very strict in terms of noise and large groups of people. Well maintained house. CLEAN POOL BUT NOT HEATED. Walk in to a living area and separated dining. 20 minutes to airport, 25 minutes to the beach, fine dining and entertainment. For a virtual tour, click on the cover photo twice.

Location · Family · Cleanliness

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.

Value · Family · Parking

Luxury pool and spa home - Walk to Time Square

Welcome to Blue Tides, a vibrant, custom 4-bed, 4-bath Fort Myers Beach retreat. Bathed in soothing aqua tones, this home offers open-concept living, multiple balconies with water views, and a private pool & spa. Each beautifully appointed bedroom has an en-suite bath. It’s ideally located in a peaceful neighborhood, steps from the sandy beach and a 5-10 min walk to Times Square. Perfect for groups or book with sister property Pink Star next door!

Family · Location · Cleanliness

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.

Family · Value · Beach

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.

Family · Location · Outdoor spaces