Holiday rentals with a pool in Lee County

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

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!

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.

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.

Heated Pool + Hot Tub |3BR | Large Pool|Sleeps 10

•Prime Location: Just minutes from Sanibel & Captiva Islands • 10-minute walk to movie theaters, shops, and restaurants • 8 min to Fort Myers • 10 min to Cape Coral Water Park • 25 min to the airport • Perfect for families & remote work • 5 Smart TVs • Fast Wi-Fi • Family-friendly amenities & games • Fully equipped kitchen • Washer & dryer • Sofa bed • Beach towels & bathrobes • Outdoor living: • BBQ grill • Outdoor dining area • FREE onsite parking • Easy self check-in

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

Villa510 is a newly built waterfront retreat ideal for extended stays in Cape Coral. Enjoy peaceful salt canal water views and manatees from the lanai, then relax in your private heated pool and spa—perfect year-round. The outdoor kitchen and lanai create an easy, comfortable daily routine. Inside offers three private en-suite bedrooms, a den with optional airbed, open living space, and TVs in every room. Close to shopping, dining, and beaches—perfect for snowbirds seeking comfort and ease.

Bonaire Grand Luxury Villa

Experience a 5 star Luxury experience at the Bonaire Grand Villa. The villa was designed as a vacation rental with high end finishes and the ultimate guest experience in mind. The location is perfectly situated in an upscale riverside hamlet, 10 minutes from Fort Myers Beach and Sanibel Island with downtown Fort Myers 15 minutes away. The 5 bedrooms and 3 bathrooms provide ample space for a large group to enjoy. The heated pool and 3 balconies that over look scenic views do not disappoint.

Luxury Mansion! 6ksqft, Pool, Gym, Near Beach

Welcome to Your Fort Myers Dream House! • Luxe 6000 sq ft. 6BR home. 1 acre flat grass yard, fully equipped gym, game room & 8 smart TVs. • Ideal for large groups or 2-4 families with 10 beds, sleeps 16+ & multiple dining areas. • Great location: 5-15 minutes to beaches, 5 golf courses, dining/restaurant areas, nearby grocery stores • Pool table, pingpong table, Playstation 4, foosball, basketball mini game, BBQ grill, poker mat & chips, pool basket and volley net, yard soccer set

Countryside Luxury Villa with Pool, Bbq

Enjoy with the entire family at this gorgeous, luxurious & modern lodge in La Belle, with Pool, BBQ area, firepit, a picnic area, a canal perfect for fishing and a basketball court, this amazing home welcomes up to 10 guests as it has 5 bedrooms and 5 full bathrooms. It's peaceful and at the same time perfect for family gatherings, celebrations and events. Near by The Labelle Brewing Co. and The Launch at LaBelle Yacht Club. Live the countryside experience with style!!

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.

Luxury Riverfront Estate & Pool

Your Property This spacious waterfront home features a bright open floor plan with expansive water views throughout the main living areas. Guests can enjoy a fully equipped chef’s kitchen, large dining area, comfortable living room, private pool, dock, outdoor entertainment spaces, and a dedicated game room. The home was thoughtfully designed to maximize the waterfront setting, with large windows showcasing beautiful bay views from sunrise to sunset.

Luxury Riverfront:Pool, Tiki Bar & Outdoor Kitchen

Reconnect and relax at this spacious riverfront retreat, perfect for gathering with family and friends. This custom coastal home offers 4 bedrooms, 4 bathrooms, and 3 separate living areas, giving everyone room to spread out and unwind. Enjoy morning coffee while watching boats, dolphins, and manatees pass by, then spend the day soaking in the heated saltwater pool and spa. Guests may enjoy the views, but the dock is not available for boat use.