
Vacation rentals with a pool in Gateway
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Gateway
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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.

Intervillas Florida - Villa The View
The View – Luxury Waterfront Villa with Infinity Pool & Sunset Views The View welcomes you from the very first moment with breathtaking, wide lake views and spectacular sunsets that turn every day into an unforgettable experience. Perfectly located in a quiet and highly desirable position on one of the lower 8-Lakes, the villa offers direct boat access, allowing you to reach the River and the Gulf of Mexico in a short and scenic ride – ideal for boating enthusiasts and water lovers.

Villa Poolside Paradise: Unwind in Tropical Style!
Welcome to your very own slice of paradise in beautiful Lehigh Acres! Villa Poolside Paradise is more than just a vacation home; it's your ticket to an unforgettable escape in Southwest Florida. This charming and lovely vacation villa is nestled in a serene residential neighborhood, promising tranquility and relaxation. Yet, you're just moments away from the vibrant heart of the region, with shopping, restaurants, bars, and all the entertainment you could desire within easy reach.

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.

Blue Beach Bungalow
3 large bedrooms (3 king sized beds) with TV in everyroom, plus a full den, laundry room, HEATED pool and the house has its own beach with an in-ground fire pit that seats 12, lounge chairs, and sunset views! Walking distance to shopping centers, great restaurants, 20 minutes to RSW Airport and Fort Myers' white-sand beaches, perfect for a romantic get-away and 10 minutes from downtown Fort Myers Completely remodeled in July of 2021 with brand new appliances electronics,

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.

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.

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 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.
Popular amenities for Gateway rentals with a pool
House rentals with a pool

Luxury Riverfront Retreat • Pool & Spa • 60ft Dock

AquaLux Smart Home

Swimsational Golf views

Family Oasis | Heated Pool + Beach Gear, Kid Ready

Luxury Waterfront Escape - Private Pool & Jacuzzi

Luxury Pool Home - South Fort Myers

Charming 3BR Retreat w/ Heated Pool & Lanai

Hidden Gem with Pool. Perfect for Family Getaway
Condo rentals with a pool

Rare walkout condo on Sanibel beach

Beachfront fully equipped apartment

Luxury Gulf View Condo + Steps to the Beach

Ft Myers Beach & Lovers Key State Park- FANTASTIC!

Beachfront Escape w/ Sunset Views, Pool & Hot Tub

Sea Salt Beach Front Condo

Casa Bonita - Relax @ The Beach (Newly Remodeled)

100+ 5 Star Reviews and Right on The Beach!
Other vacation rentals with a pool

Caloosavilla

Luxury Monthly Rental: 3 Bedrooms, 2 bath, sleep 6

Mini Golf • Heated Pool • Near Beach Prime

Riverfront Riviera Outdoor TV's/Hotub/Tanning Deck

Sleep over the water- Boathouse with Private Dock

Close to Cape Harbour western pool and dock, golf

17th Floor Riverfront • Downtown • Pool & Gym

Morning Glory - Walking Distance to Surfside Shops
When is the best time to visit Gateway?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $255 CAD | $326 CAD | $276 CAD | $177 CAD | $113 CAD | $163 CAD | $142 CAD | $126 CAD | $140 CAD | $163 CAD | $183 CAD | $251 CAD |
| Avg. temp | 16 °C | 18 °C | 19 °C | 22 °C | 25 °C | 27 °C | 27 °C | 28 °C | 27 °C | 24 °C | 21 °C | 18 °C |
Quick stats about vacation rentals with a pool in Gateway

Total vacation rentals
Explore 40 vacation rentals in Gateway

Nightly prices starting at
Gateway vacation rentals start at $57 CAD per night before taxes and fees

Verified guest reviews
Over 150 verified reviews to help you choose

Family-friendly vacation rentals
30 properties offer extra space and kid-friendly amenities

Pet-friendly vacation rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
40 of Gateway vacation rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Gateway rentals

4.9 Average rating
Gateway stays are highly rated by guests—averaging 4.9 out of 5!
Destinations to explore
- Miami Vacation rentals
- Orlando Vacation rentals
- Four Corners Vacation rentals
- Kissimmee Vacation rentals
- Miami Beach Vacation rentals
- Tampa Vacation rentals
- Fort Lauderdale Vacation rentals
- Hollywood Vacation rentals
- Jacksonville Vacation rentals
- St. Augustine Vacation rentals
- Key West Vacation rentals
- Davenport Vacation rentals
- Pet-friendly rentals Gateway
- Rentals with outdoor seating Gateway
- Family-friendly rentals Gateway
- Fitness-friendly rentals Gateway
- Rentals with a patio Gateway
- House rentals Gateway
- Rentals with a hot tub Gateway
- Rentals with a washer and dryer Gateway
- Rentals with pools Lee County
- Rentals with pools Florida
- Rentals with pools United States
- Naples Beach
- Captiva Island
- Englewood Beach
- Lovers Key Beach
- Tigertail Beach
- Florida Gulf Coast University
- Stump Pass Beach State Park
- Blind Pass Beach
- Bonita National Golf & Country Club
- Bowman's Beach
- Barefoot beach Bonita Springs,FL
- Boca Grande Pass
- Jetblue Park
- Montura Ranch Estates
- The Naples Pier
- Clam Pass Park
- Bunche Beach
- Edison & Ford Winter Estates
- Yacht Club Public Beach
- Ave Maria University
- Coral Oaks Golf Course
- Delnor-Wiggins Pass State Park
- Lovers Key State Park
- Coconut Point





