Family-friendly holiday rentals in Gateway

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

Private farmhouse stay at Dim Jandy Ranch.

Take it easy at this unique and tranquil getaway. A beautifully appointed bed and bath in a separate building from the house. We have goats, donkeys and chickens and a Highland cow, all super friendly. Sit and relax on your private, beautiful lanai or any of our farm tables placed around the property. Join us as we feed the animals. Or even join in one of our Goat Yoga classes! We're easily located close to I-75, airports, shopping, beaches, downtown. Perfect for couples or solo travelers.

Modern 3BR Retreat • Near RSW Airport & Beaches

Relax and unwind in this stylish, spacious 3-bedroom retreat just minutes from RSW Airport, shopping, dining, hospitals, and Southwest Florida’s top attractions. Whether you’re visiting with family, traveling for work, or enjoying a Florida getaway, you’ll love the bright open-concept layout, high ceilings, fast WiFi, and fully equipped kitchen. Located in a quiet, safe neighborhood, this home offers the perfect blend of comfort, convenience, and everything you need for a stress-free stay.

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

Sunny Lakefront Retreat.

Sunny Lakefront Retreat 🌞🌊 | Fort Myers Gateway Welcome to Sunny Lakefront Retreat — your perfect getaway in the heart of Fort Myers Gateway! This spacious 4-bedroom, 3-bathroom lakefront home comfortably sleeps up to 10 guests, making it ideal for families, groups, or a relaxing escape with friends. The open-concept living space is designed for comfort and connection, featuring cozy seating, a fully equipped kitchen, and plenty of room for everyone to relax and unwind.

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 Spacious Cabin Nature Preserve Fort Myers

Take it easy at this unique and tranquil getaway. An experience like no other. Get connected to nature and enjoy the wildlife in a private nature preserve. Spacious 1 bedroom with queen bed and queen sleeper sofa in the living room. Unwind on the hammock listening to the sound of birds. Relax and recharge in this beautiful and peaceful retreat. Cleaning included no need to do anything at checkout. Located on a 9.3 acre private nature preserve and palm tree farm.

Pool | Playground | Foosball, PingPong Table &more

“The 1 Acre House” offers you all the luxuries and amenities your friends and family could desire, all while being conveniently located in the heart of Lehigh Acres and just at 25 minutes from the airport. ⭐️ Game room inside the garage, with pool table, foosball table, air hockey table, arcades & TV. ⭐️Huge deck with seats & all light on. ⭐️ Sand volleyball. ⭐️ Mini golf. ⭐️ Playground. ⭐️ Ping Pong Table. ⭐️ Trampoline.

Super Clean-3 Bdrm-Home-Coffee Bar -Canal View

Relax with the whole family at “The Resting Place.” RSW-Airport is 14 minutes away, Casino is 20 mins away, Shopping Center is 3 mins away, West minister Golf Coarse is 4 mins away & Edison Mall is 15 mins away. We pride ourselves on having a clean & replenishing environment. Our Duplex is Surrounded by nature, our back yard is right on the canal. We can meet you upon arrival or we can be non-existent. The choice is yours.

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!

Family Villa w/ private pool and hot tub!

Relax with the whole family at this peaceful place to stay. Pool + Hot tub with temperature control 3 Car Garage, 3 bedrooms plus den acting as bedroom. TV in all bedrooms. High speed Wifi, garage and driveway parking. Available Amenity center with Full bar and restaurant, resort style pool + hot tub, gym and arcade center. Timber Creek application fee for amenity center $50. Please message with any questions.