
Vacation rentals with a pool in Gateway
Find and book unique homes with a pool on Airbnb
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!
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.

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.

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.

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.

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!!

Mediterranean Waterfront Estate on Caloosahatchee
Experience Nascosto Estate, a Mediterranean waterfront sanctuary on the Caloosahatchee River. This extraordinary estate offers resort-style amenities, including a heated infinity pool with a cascading waterfall, sanded lounge, fire pit, private pier, and boat lift. Just minutes from Downtown Fort Myers, it provides absolute privacy, breathtaking river views, and magical sunsets—a one-of-a-kind escape where every moment feels unforgettable and memories last a lifetime!

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.

Waterfront with Saltwater Pool, Sauna, Cold Plunge
Experience the epitome of comfort and luxury in our exquisite 4-bedroom, 4-bathroom waterfront wellness retreat. Revel in the tranquillity of water views and be pampered by a host of rejuvenating amenities, including a therapeutic saltwater pool, a soothing sauna, and a refreshing cold plunge. This sanctuary is designed with top-of-the-line features and sumptuous interiors that ensure a restful and revitalizing stay beyond compare.

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

Caloosavilla

AquaLux Smart Home

Swimsational Golf views

Mini Golf • Heated Pool • Near Beach Prime

Luxury Waterfront Escape - Private Pool & Jacuzzi

Salt Water Enclosed Heated Pool, 3BD 2BTH Home

3BR w/HUGE 2k sq ft Lanai & Seasonally Heated Pool

Dive into Luxury: Stunning Tropical Home & Pool
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

2nd Floor Beachfront Condo Sanibel Harbour

Sea Salt Beach Front Condo

Amazing Condo-1 mile from Bonita Beach
Other vacation rentals with a pool

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

Waterfront Villa Capri | Dock + Gulf Access

Sleep over the water- Boathouse with Private Dock

Matlacha Villa- Heated Saltwater Pool

Close to Cape Harbour western pool and dock, golf

17th Floor Riverfront • Downtown • Pool & Gym

Caribbean Gem with Private Pool & Hot Tub

Villa Sunset Serenade II
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 | $277 CAD | $177 CAD | $114 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 |
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- Rentals with pools Lee County
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- 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
- Jetblue Park
- Montura Ranch Estates
- Boca Grande Pass
- 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





