Family-friendly holiday rentals in Fort Myers

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!

3 BR Heated Pool House with Boat Lift

Forget your worries in this spacious and serene space. Total and complete renovation in 2024. Everything is new. Large driveway with the room to park your boat trailer . Gourmet, fully equipped kitchen, including stainless steel appliances, and a Keurig coffee machine . Peaceful location. Private outdoor space. Fully fenced in side garden. Deck with flat top grill and dining area. House is three bedrooms, one king, one queen, and two twin beds. The house is waterfront with the boat lift.

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.

Palmetto Boat House

Escape to your private family oasis along the peaceful Caloosahatchee River, minutes from Babcock Ranch and Fort Myers Beach. Boaters love the nearby public dock—perfect for tying up your boat or jet skis. Unwind in your sparkling private pool with river views, then gather around the fire pit for s'mores under the stars. Whether exploring the water or relaxing poolside, this riverside haven offers families the perfect blend of adventure and tranquility in beautiful Southwest Florida.

Private pyramid home to relax and explore-7021

Relax and enjoy the beauty of sunny southwest Florida in your own unique pyramid! This private vacation home in Pyramid Village features a spring water lake just a short walk from your pyramid (this pyramid has nature views, not lakeside) *Home includes: Free WIFI, private patio with gas grill, washer/dryer, fully equipped kitchen, and 2 queen beds (comfy for 4 guests), 2 Roku TV's, and beach gear (located 15 miles from most popular beaches). * self check in with lock box

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.

Modern City Loft in Downtown River District

Welcome to Gun-Loft, a custom-designed modern sanctuary in the Downtown River District. This expansive 3500 square foot city loft is tailored for those seeking to embrace the cosmopolitan lifestyle, with the perfect blend of urban luxury and cultural richness. Whether it's a leisurely stroll to the Edison Ford Home, an exciting night out, or a culinary adventure in the restaurants nearby, Gun-Loft offers an unparalleled experience in the city's most coveted location.

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.

Dream Villa with Private Pool/Spa

NO HIDDEN FEES. Built on a freshwater canal. Amazing sunset views. Heated pool and waterfall spa with LED lighting. Outdoor Kitchen and TV. This home is perfect for families and infants, and is fully equipped with everything you need for a relaxing vacation. We have a lot of toddler items, including 2 pack and plays, a pool safety gate, a high chair, and a baby bouncer, beach wagon/chairs/tent, beach playpen, books games and toys.

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.

Luxury Heated Pool Villa • No Checkout Chores

Escape to your own private Southwest Florida pool retreat — complete with swaying palms, a heated pool, relaxing lanai, and effortless indoor-outdoor living. No checkout chores. No stress. Just vacation mode from the moment you arrive. IMPORTANT: Please ensure you've read and accept the house rules prior to booking. Thank you. Easy access to Fort Myers (RSW) and Punta Gorda (PGD) Airports – only 24 miles away!