Vacation rentals with a pool in Cypress Lake

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

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.

Palm Palace - Two House Compound Sleeps up to 22!

This property listing includes full access to two separate on-property houses, both with full access to the pool and giant screened lanai! The main house has 3 bedrooms, 2.5 bathrooms and 8 total beds (1 king, 1 queen, 2 double bunk beds & 2 sofa beds). The smaller "pool house" has an additional full kitchen, living room, 2 additional bathrooms & 3 more beds (2 queen & a sofa bed)! This property frequently is booked by multi-generational families, large groups and even entire sports teams!

Mermaids Cove, don't miss this listing!

Mermaid's Cove is a private tropical retreat ready for guests to relax and refresh! It is a beautifully decorated home with a private pool & bedroom /bathroom on opposite ends of the home. The kitchen is fully equipped open concept. It is located in a friendly, family neighborhood near everything Ft. Myers has to offer. If you enjoy palm trees swaying as you float in the pool or sitting under a patio umbrella while grilling dinner, then this home is for you. Come and renew at Mermaid's Cove!

20 min to the beach! Pool, fire pit, 3bd/2.5ba

*Zero damage in all of the hurricanes* Welcome to Double Palm Cottage located at 899 Dean Way, Fort Myers, FL. The 3-bedroom cottage with 2.5 baths and pool is situated in the Historial District directly off picturesque Royal Palm Tree lined McGregor Boulevard leading directly to the Edison and Ford Winter Estates. The cottage just 20 minutes to all the local beaches, shopping, and fine restaurants. Additional entertainment activities include Major League Baseball spring training games.

4BR Waterfront Home w/ Heated Pool & Private Dock

Waterfront Coastal Retreat | Heated Private Pool + Dock | Dining + Beaches Unplug, unwind, and settle into effortless coastal living at this beautifully renovated 4-BR waterfront home in Fort Myers’ quiet, upscale Town & River neighborhood. You’ll enjoy a peaceful setting while staying close to everything—so many local restaurants are just minutes away, and the area’s best beaches are an easy drive: Sanibel Island beaches are about 15 minutes (9.6 mi) & Fort Myers Beach is about 18 mins

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.

Experience of a lifetime

Get ready for the experience of a lifetime at this hidden gem! As you walk through the front door you will begin your journey into the best vacation of a lifetime. Keep on going through the sliders & that will lead you to the incredible resort style pool that will leave you in awe!!! Here you are in the heart of it all. Shopping-dining-entertainment is all within a 5 minute drive. The beautiful beaches just 7 miles away. If you enjoy boating & relaxing this is the place for you.

Swimsational Golf views

Recently updated heated pool home backing to a golf course with private back yard. It has a covered patio area with new furniture and outdoor grill. Both bedrooms have televisions and super comfy pillows / linens. The main area has a coffee/tea bar and island in the kitchen. The garage has a brand new washer/dryer with the latest technology. Located in a great residential neighborhood surrounded by shopping and restaurants. 20 minutes to the beaches or downtown Ft. Myers.

Serene Pool & Spa Home near Beaches & Downtown

Where prime location meets tropical paradise. Welcome to your very own private poolside and spa oasis, minutes from the beach! Close to Sanibel Island, Fort Myers Beach & Bunche Beach, as well as local shopping, amazing restaurants, fun nightlife in Downtown Fort Myers and the winter homes of Thomas Edison & Henry Ford. Fully renovated throughout. This remarkable space can accommodate up to 10 guests, making it the perfect destination for a family or friends vacation!

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.

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.