
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.

Boater’s Paradise-Stunning Sunsets! Games Room!
Renovated lanai! This 3 bed/4 bath home is on the nicest canal with 200+ ft of frontage & gorgeous views of the canal & sunset. The pool, tiki hut & docks have full sun all day. Each bedroom has a private bath & there's a 2 pc powder room off the laundry. The primary has a king bed & walkout to pool. The 2nd bedroom has a queen bed & pool access. Bedroom 3 has a queen & private bath. Fully equipped kitchen with everything you need. And a games room! Enjoy stunning sunsets under the tiki hut.

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!

Central 3BD/2BA •Massive Heated Pool •Golf courses
🌞 Gorgeous Heated Pool Home Near Everything – Perfect for a Relaxing & Convenient Getaway! Welcome to your tropical escape in the heart of SW Florida! This beautifully maintained 3BD/2BA home is located just minutes from world-class beaches, and top local attractions, offering the perfect blend of tranquility, comfort, and accessibility. Whether you're here for a family vacation, a romantic getaway, or a business trip, this home provides everything you need for a restful and memorable stay.

3BR w/HUGE 2k sq ft Lanai & Seasonally Heated Pool
Welcome to your peaceful Bonita Springs retreat, perfectly located near Naples, Ft. Myers, shopping & beaches! This isn’t just a rental, it’s our 2nd home and we treat it as such. You'll experience "exceptional" the minute you enter this stunning, open concept interior. Further, it boasts a striking 2000 sq ft screened-in lanai w a seasonally heated pool. This outdoor oasis doubles your living space and offers a flying pest barrier and significant UV protection. Breathe/Smile/Unwind

Beautiful waterfront home & pool with new interior
This is it!! Your sun & fun get-away! Come for work or come for play to this beautiful waterfront home! 3 Bdrm/2ba open concept with easy access to beaches. It is well stocked with starter supplies for the kitchen/bath & beach needs. The 24' of wall-to-wall window sliders open up to the Lanai overlooking the canal providing sun-kissed waterfront views from the moment you step in the front door. This is the VRBO home you’ve been looking for. It is gorgeous and it's waiting for you!

Peaceful Stay at Cozy Escape
Looking for the perfect escape from the noise and rush of city life? Welcome to your cozy Escape—a peaceful, spacious, and cozy home designed for true relaxation with family or friends. Surrounded by nature and calm, this house offers everything you need to slow down and recharge. Enjoy a refreshing swim in the private pool, share outdoor meals, or simply unwind in one of the comfortable indoor spaces. Experience a stay where time slows down, and every moment is made to be enjoyed.

We Got You! Loaded home w/ Heated Pool & Large Yar
Whatever the reason for your visit, the pool and large yard gives you plenty of space to play and relax! Got a little work to do? No problem. There are two office areas. We made your stay effortless with our fully equipped home in beautiful Southwest Florida! Your pup and kids can have a huge outdoor space along with a brand new bunk room that sleeps up to 6. We do welcome non-shedding dogs for a fee. This home is directly managed. Please note: work crews must be pre-approved.

Beautiful Oasis
Relax at the solar heated pool and enjoy the serenity of the beautiful, and peaceful 0.6 acres of land with a natural pond where different types of birds like egrets, herons, and ducks can be seen. Close to shopping, dining and just 7.5 mi to Bonita Beach Park. If you play Golf, The Bonita Fairways Public Golf Club is 2.8 mi. Or buy a day pass at the Hyatt Regency and spend the day at the lazy river and waterslides. The backyard is all fenced in, ideal to let your dog run.

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 a. 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.

The Palms on Surfside 1004 - SW Cape Coral
Welcome to The Palms on Surfside, a beautiful and super modern designed home located in SW Cape Coral near the Sandoval Community. This 2023 built home will ensure you a vacation in style. You will never want to leave the huge lanai with lots of seating areas overlooking the canal. Spend time fishing in the canal or just relaxing in the heated pool. The living room has 4 large nesting sliding doors that bring the outside in.

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

Waterview, Heated Pool & Spa FREE, Yacht Club

Yacht Club Beauty....walking distance to the beach

Pool | Playground | Foosball, PingPong Table &more

Heated Pool + Hot Tub |3BR | Large Pool|Sleeps 10

Sunny, open 3 BR, 2 BA *pool* home

Paradise on Estero Bay

Salty Dog Hideaway

Coastal Modern Retreat with Heated Pool and Spa
Condo rentals with a pool

Sanibel Harbour Resort - 617: Private Beach

Rare walkout condo on Sanibel beach

Beachfront fully equipped apartment

Gulf Water Views + 2 bikes, beach gear weekly stay

Ft Myers Beach & Lovers Key State Park- FANTASTIC!

Vacation in Paradise

2nd Floor Beachfront Condo Sanibel Harbour

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

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

Serene Modern Oasis | Private Pool in Fort Myers

Catalina Cottage

Waterfront • Heated Pool • Game Room • Mini Golf

Luxury Ocean View

|Heated Pool |Hot Tub |Pickleball |3.5mi to Beach!

Luxury Villa with gorgeous sunrise lake view

Gulf Access, HTD Pool, Kayaks, Bikes, Beach Gear+
When is the best time to visit Gateway?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $272 CAD | $247 CAD | $272 CAD | $172 CAD | $110 CAD | $158 CAD | $137 CAD | $122 CAD | $136 CAD | $158 CAD | $177 CAD | $243 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 50 vacation rentals in Gateway

Nightly prices starting at
Gateway vacation rentals start at $55 CAD per night before taxes and fees

Verified guest reviews
Over 110 verified reviews to help you choose

Family-friendly vacation rentals
40 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
50 of Gateway vacation rentals include wifi access

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

5 Average rating
Gateway stays are highly rated by guests—averaging 5 out of 5!
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- Rentals with pools Lee County
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- Rentals with pools United States
- Naples Beach
- Captiva Island
- Lovers Key Beach
- Englewood Beach
- Stump Pass Beach State Park
- Clam Pass Park
- Bonita National Golf & Country Club
- Tigertail Beach
- Heritage Bay Golf & Country Club
- Blind Pass Beach
- Edison & Ford Winter Estates
- Esplanade Golf & Country Club of Naples
- Florida Gulf Coast University
- Stonebridge Country Club
- Boca Grande Pass
- Del Tura Golf & Country Club
- Jetblue Park
- Bunche Beach
- Delnor-Wiggins Pass State Park
- Talis Park Golf Club
- Bowman's Beach
- Coral Oaks Golf Course
- Manatee Park
- Montura Ranch Estates




