
Holiday 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.

Golf & Pool Views! Close to FGCU and Airport.
Perfectly located 2 Bedroom 2 Bath condo! Nestled on a public golf course with a wonderful pool area, it is the perfect combination for a peaceful vacation. The condo is centrally located by everything one needs to relax and enjoy the Fort Myers area. We have gone the distance to make your vacation memorable. The spacious condo has adjustable beds, which will provide you sweet dreams. Close to the beaches, shopping, airport, golf, and tons of restaurants. Guests can also enjoy the pool area.

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.

Heated Saltwater Pool + Playset | 4 br| No stairs
One-level, no-stairs Cape Coral home built with you in mind. Private heated saltwater pool with fountains + sun bench, fenced backyard, loungers Playset, and smart TVs in every bedroom. Sleeps 10 with 4 bedrooms & 2 full baths - has crib, pool toys, games, grill, and outdoor dining -easy self check-in, lounge chairs, umbrellas, gas grill. You will be close to lots of different cuisines within 5-10mins drive, 30 mins to the Gulf Shores beaches, 30 mins to the airport. Relax. Refresh. Rewind.

The Pool House
Welcome to The Pool House. Wether you're looking for a private relaxing getaway, a family vacation in florida's sunny weather, or a cool dip in the pool you've found the right house. You'll discover a fully stocked kitchen, 2 grills to choose from, private master bed and bath, large open floor concept kitchen, dining and living. Complimentary Netflix and other free channels on smart TV with onn speaker. 5-7 minutes from Walmart and shopping centers. 38-50 minutes from Fort Myers beach.

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 Cape Coral Villa with Private Heated Pool
Escape to your own private pool oasis in sunny Southwest Florida—where swaying palms, crystal-clear water, and warm coastal breezes set the stage for relaxation, family fun, and unforgettable memories. Hassle-Free Stay: NO CHECKOUT DUTIES – just enjoy your stay! 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!

Cozy studio 1.3 miles to Barefoot Beach
Very inexpensive way to get close to the beach and still have complete privacy! Whole unit-Share nothing. Small and cozy studio/room 12x19 with a refrigerator, microwave, air conditioner, full bath, suitable to more or less sleep. Queen size bed. Closet and dresser. This is a separate guest room with a private entrance not connected to another unit. Located in an adorable tropical feel complex in a seafoam green building.

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.

Casa Capri | Heated Pool | No Service Fee
Escape to Luxury! We've got you covered - no service fees! Discover our 5-star Cape Coral retreat: high-speed WiFi, smart TVs, premium bedding, and more. Unwind in style and serenity. Your peaceful haven awaits! Nestled in the heart of Cape Coral, our meticulously designed space promises an unforgettable stay for the discerning traveler. Relax with the whole family at this peaceful place to stay.

Casa Bonita - Relax @ The Beach (Newly Remodeled)
Beach within steps of this beautifully remodeled condo! DOC's restaurant & jet ski rentals, directly across the street. Beach gear available along with a cart to transport. Luxurious king size bed with extra plush mattress topper. Queen size sofa bed. Our studio will sleep up to 3 people (2 adults, 1 child) Newly refurbished pools opened April 2nd 2025.

Luxury Villa: Pool, Hot Tub And Amazing Lake View
Escape to a private waterfront paradise on the famous Eight Lakes! This luxurious home offers spectacular sunset views from your private infinity pool and hot tub. Perfect for a relaxing retreat, it features seamless indoor-outdoor living, a gourmet kitchen, and high-end amenities. Ideal for couples or small groups seeking an unforgettable getaway.
Popular amenities for Gateway rentals with a pool
House rentals with a pool

Resort Living in Heritage Palms

Peaceful Stay at Cozy Escape

Luxe Unique: Close to Beach, Hot Tub, Heated Pool

3BR Home w/ Pool near downtown Fort Myers & Edison

Sunny Pool Beach/Island Escape in Comfy Canal Home

Dive into Luxury: Stunning Tropical Home & Pool

3 BR Heated Pool House with Boat Lift

Pool, space, privacy, location!
Apartment rentals with a pool

Beachfront @ Elevate in the Sun!

Cozy Coastal Escape. Close to FMB and Sanibel

Rare walkout condo on Sanibel beach

Gulf Water Views + 2 bikes, beach gear weekly stay

Ft Myers Beach & Lovers Key State Park- FANTASTIC!

Oceanview unit. Completely remodeled pool is open!

2nd Floor Beachfront Condo Sanibel Harbour

Easy Breezy Too
Other holiday rentals with a pool

Resort Life in Heritage Palms

Caper Beach Club Penthouse 2 - Gulf View

Waterfront • Heated Pool • Game Room • Mini Golf

Seahorse Studio

Stylish 2 Bedroom 2 Bath Townhome with Pool!

Blue Fish Apt 4- Downtown Blue Resort-Heated Pool

Paradise Found

Sunny Florida Oasis with Heated Pool & Hot Tub
When is the best time to visit Gateway?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $251 SGD | $228 SGD | $251 SGD | $158 SGD | $101 SGD | $146 SGD | $127 SGD | $113 SGD | $125 SGD | $146 SGD | $163 SGD | $224 SGD |
| 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 holiday rentals with a pool in Gateway

Total holiday rentals
Explore 50 holiday rentals in Gateway

Nightly prices starting at
Gateway holiday rentals start at $51 SGD per night before taxes and fees

Verified guest reviews
Over 110 verified reviews to help you choose

Family-friendly holiday rentals
40 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
50 of Gateway holiday 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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- 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
- Del Tura Golf & Country Club
- Esplanade Golf & Country Club of Naples
- Boca Grande Pass
- Bunche Beach
- Delnor-Wiggins Pass State Park
- Talis Park Golf Club
- Stonebridge Country Club
- Jetblue Park
- Florida Gulf Coast University
- Manatee Park
- Bowman's Beach
- Sun Splash Family Waterpark
- The Naples Pier




