
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.
Vacation rentals for every style
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Popular amenities for Gateway rentals with a pool
House rentals with a pool

Gorgeous 5 Star POOL/HOT TUB on a Canal
This was exactly what we needed for our getaway! The pool and hot tub were amazing, and so relaxing! We loved being able to swim whenever we wanted, and Jesse made it so convenient with the app to heat the pool / spa. He had everything imaginable for our beach day (and this was for a beach day with an infant, including a beach wagon to haul all of our things) - we were surprised and really thankful for this! The house itself was spacious, and checked the boxes of things that we needed. It was close to grocery stores and a couple of good restaurants. The neighborhood was quiet and easily accessible as well. Jesse was very communicative. Jesse checked in on our stay, ensured that we had recommendations (if we wanted them), and even let us know when a pool tech was coming out as well. We would definitely rent here again!

Private Heated Pool and Spa
Great place! Very clean and dog friendly. Alex was responsive within minutes of any questions. Would definitely stay again

Beautiful Home w/ Pool & Spa, Pet Friendly!
Beautiful home in peaceful neighborhood with great location! The home was very clean, had nice amenities, and we felt right at home. Loved the pool and private back yard. Dara was quick to respond to any questions and made the rental a 5 star experience.

Tropical House with Pool
We loved staying at Elle’s house!!! The pool and the park was ideal for my kids. The house was clean and had everything we needed. The area was so peaceful but yet only a few minutes drive to shops and restaurants. We had a fabulous stay and wished we would have stayed longer. Ele was very friendly and helpful. There was a plumbing issue in the bathroom and she came promptly to deal with it. The double beds were a little soft to our taste but other than that we had a great experience. Thank you Ele!

Whole cozy house for group of 5
the place was nice and clean. Jose gave clear instructions and the house was exactly what we expected! we would book again! 5 stars

Spacious Canal Oasis with Pool, BBQ & Mini Golf
We had a fantastic week stay on kids Spring Break! Beautiful property, comfortable bedrooms and bathrooms, spacious well equipped kitchen. Amazing pool and hot tub, canal and yard. Mini golf, pool table, foosball table - added tons of fun to our stay. Thank you!

Family Villa w/ private pool and hot tub!
Caleb's place was beautifull, spacious, and clean. The community center amenities were fantastic! Our family had a wonderful time and would definitely stay there again.

The Parsonage-Private Villa-Heated Pool & Spa.
This place was perfect for our bachelorette party! Plenty of space and beds for everyone and a short 10-15 min walk from the restaurants and bars in downtown Fort Myers. We loved relaxing by the pool during the day. It felt private, secluded, and safe. Michelle was very helpful and friendly and we greatly appreciated her flexibility during the check in process. Highly recommend this place for large groups!
Condo rentals with a pool

Sunny Florida condo!
One of my favorite Airbnb rentals to date. The condo was clean, quiet and had everything we needed/wanted. On top of the space being great, Ken and Becky were amazing hosts. I usually stay in different places each time, but I'll be staying here anytime I'm in or near Fort Myers it's that good. 100% recommend booking with them !!

Charming Townhouse close to Sanibel and FMB
Everything worked out very well. Highly recommended for a relaxing stay with the family.

Sanibel Harbour Resort - 216: Colorful condo
Everything was perfect, the place, the atmosphere, the spacious Apartment, very crean, perfect. I Would return

Park Shore Resort-Top Floor BLDGJ #457 Water Views
We had a wonderful stay at Josh’s place! It was a perfect fit for our family. The location was ideal — just minutes from the beach, grocery stores, restaurants, and parks. The apartment was well-equipped with all the amenities we needed and was very peaceful at night. We’re already looking forward to our next visit to Naples and will definitely consider staying at this condo again.

Beach condo on yachat marina
Karley’s place exceeded our expectations. Very peaceful neighborhood. Very friendly people in the neighborhood. The condo had everything that we needed. The lanai was my favorite spot! We even got to fish just a few steps from the door. Very comfortable and super clean condo. We rented e-bikes just a 5 minute walk away. They were great for passing backed up traffic going towards Times Square at the beach. We also rode them all the way back on the shoreline. It was awesome! We would definitely not hesitate to stay there again. Any questions that we had were answered super quick. Great host and co-host! Thanks again Karley and Kelly for letting us stay at your place!

Park Shore Resort Modern Top Floor 2 Bed 2 Bath
Lauren has done up the place very well and having beach towels and beach chairs really helped us. The place is clean and the view from the balcony overlooking the water body is gorgeous. Having a pull out sofa in the living area is an added bonus. The best part is that good eateries and a grocery store are walking distance from the apartment. Lauren is extremely responsive and helped us whenever we needed it. We would certainly like to stay here again if we visit Naples.

Amazing Condo-1 mile from Bonita Beach
Our family had a wonderful week long stay at Susan’s condo. She supplied everything we needed for great beach days and the pool was clean and warm! It is within walking distance to a bunch of restaurants and ice cream spots. Would definitely recommend to anyone looking for a quiet, yet fun place to stay in Bonita!

1st Fl Condo, 2 Kings, Beach, Golf Supplies, Bikes
This is a great apartment with large bedrooms and comfy beds, a very very well equipped kitchen and a garage full of surprises including a gas grill and beach stuff. Stacey was great from the beginning and was very helpful and immediate with any question. We’ll decently stay again when in the area. Thanks Stacey!
Quick stats about vacation rentals with a pool in Gateway
Total rentals
50 properties
Nightly prices starting at
$55 CAD before taxes and fees
Total number of reviews
90 reviews
Family-friendly rentals
40 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
30 properties have a dedicated workspace
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- Tigertail Beach
- Clam Pass Park
- Englewood Beach
- Panther Run Golf Club
- Talis Park Golf Club
- The Club at The Strand
- Lovers Key Beach
- Worthington Country Club
- Esplanade Golf & Country Club of Naples
- Bonita National Golf & Country Club
- Seagate Beach Club
- Moorings Beach Private Park
- Boca Beach
- Tarpon Bay Beach
- Del Tura Golf & Country Club
- Stonebridge Country Club
- Residents' Beach
- Delnor-Wiggins Pass State Park
- Naples Botanical Gardens
- Mediterra Golf Course
- Cypress Woods Golf & Country Club
- Stump Pass Beach State Park
- Barefoot beach Bonita Springs,FL
- Bonita Beach Dog Park