Holiday rentals with a pool in Punta Rassa

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

Family · Location · Solo travel

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!

Location · Value · Decor

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.

Value · Family · Sleep quality

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.

Family · Location · Air conditioning

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.

Value · Family · Cleanliness

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.

Value · Family · TV

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 · Value · Walkability

2BD Half Duplex Fort Myers - Private Swimming Pool

🌅 Welcome to your perfect Fort Myers vacation rental — a stylish, sun-filled 2-bedroom duplex with a private screened-in pool! Located in a quiet, safe neighborhood just 15 minutes from Fort Myers Beach and 10 minutes to Sanibel ⛵️, this family-friendly home offers easy access to shopping (7 mins), dining, golf (10 mins), and major highways. Whether you're visiting for a weekend getaway or an extended stay, this is your ideal Southwest Florida escape. 🍍

Family · Location · Access

Amazing View of Sanibel Harbour

This charming 2nd-floor condo in Sanibel Harbour offers a relaxing retreat with easy parking and elevator access. Enjoy a private beach, swimming pool, and hot tub just steps from your door. Explore nearby attractions like Sanibel Island Lighthouse, J.N. “Ding” Darling Wildlife Refuge, and kayak tours. Located near the Sanibel Causeway with shops and dining, it’s the perfect base for your Sanibel getaway. Book today and start making memories!

Location · Family · Hospitality

Impulse 25 Beach Cottage

⸻ All age community! Welcome to your brand-new home in an all-age community in Sun Retreats Fort Myers Beach! Ideally located within 3 miles of Fort Myers Beach, the Sanibel Island entrance, and Bunche Beach, this beautifully upgraded 2-bedroom, 2-bathroom home offers everything you need for a perfect vacation getaway. Thoughtfully decorated and fully equipped, it’s the ideal place to relax and enjoy the Florida lifestyle.

Family · Location · Decor

Dive into Luxury: Stunning Tropical Home & Pool

Escape to a tropical paradise in this stunning 1952 midcentury modern home, perfectly located in the heart of historical McGregor Boulevard - home to the famous palm trees planted by Thomas Edison. Indulge in delicious meals at local restaurants like McGregor Cafe and McGregor Pizza, or tee off at the nearby public golf course. And if you're looking to hit the beach or explore downtown, both are just a short drive away.

Family · Location · Air conditioning

Waterfront Pool Home. Minutes to Sanibel & Beaches

Where prime location meets tropical paradise. Welcome to your very own lakefront, poolside oasis, less than 10 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. The perfect destination for a family or friends vacation!

Family · Location · Indoor spaces