
Holiday rentals with a pool in Gulf Gate Estates
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Top-rated rentals with a pool in Gulf Gate Estates
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.
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Popular amenities for Gulf Gate Estates rentals with a pool
House rentals with a pool

Your DreamOasisAwaits: SiestaKeyEscape with Pool!
A beautiful home with a private, relaxed atmosphere and all the amenities you could need.

SPACIOUS 2bed/2bath house - 5 min to SIESTA KEY!
Great place with everything you need!! Felt like home! Roma was very responsive and let us check in a bit earlier!

Paradise Getaway Pool house
We had an amazing stay! Marcos’ place was beautiful, peaceful, and met our needs. It was only minutes away from the beach, which made it nice. Also very close to restaurants, shops, and activities. The best part of the house was the pool and back patio area. Planning to return next year!

Private Home near Siesta Key
I traveled with my whole household my husband and I and our kids ranging from ages 15 down to six a set of twins at that. this house was perfect for us because it was safe and quiet and clean very roomy and came with the pool which was a plus when the kids were done with the ocean

Spectacular Sunsets! 15 min Siesta Key!
We loved the villa and would gladly stay here again. The community was wonderful, and the location provided ready access to everything that we wanted to see during our stay. The host was responsive to every question. We were very thankful that we found this home!

House of Peace oasis,heated pool, pool table, fire
We had an amazing stay! The house was cozy, spacious, and had everything we needed. We loved the pool and how close it was to Siesta Key—only about 15 minutes, which was perfect since our friends were staying there. The location was great, and the amenities made it feel like home. Stephanie was such a friendly and helpful host. We'd definitely stay here again!

3 bedroom Heated salt water pool close to Siesta
I stayed here with my family to visit Siesta Key Beach. The house was absolutely beautiful and had everything you could possibly need to accommodate your stay. I tend to over pack and i caught myself not needing to use a lot of my stuff because Sergey already provided them. The backyard was absolutely beautiful. My toddler did not want to get out of the heated pool. The house was nicely decorated and super clean! We appreciated the beach chairs and umbrella. The worst part of our stay was leaving those comfortable beds. Thank you Sergey for a wonderful stay. We cannot wait to return!

Captain's Cottage
The house was just perfect for us, our son and grandkids. The supplies were bountiful, including beach towels, bikes, sand toys, beach chairs and umbrellas, paper goods, a whole cabinet of spices and condiments, and an entire bookcase of games. Our grandkids were ecstatic about the pool and the giant inflated flamingo. Everything was just lovely, and the hosts were most accommodating. We would definitely stay here again!
Apartment rentals with a pool

Gateway to Siesta Key - 1/2 Mile to the Beach
Excellent place, unbeatable location, very cozy and comfortable. Chris let us know we could check in early without even asking. I would gladly come back!

Best Siesta Key Condo
We had a very good time at Siesta Key and enjoyed our time at Maureen's place. The building is older, the amenities are well maintained and the condo itself is well cared for. I did find some mystery stains on the mattress and the decorative pillows in my room, but I'm guessing they are just spills that were difficult to get out. More importantly, the boat dock is usable, albeit with some difficulty if the boat is larger than 22 feet or so. We figured out on the second day that the best way to dock was parallel to the intracoastal between the posts and to tie off with lines on either side of the stern and with a single line on the bow. I would check ahead to make sure the dock is available, but we had no other boats docked there on a holiday weekend. The private beach access was a lifesaver on a holiday weekend, despite the short walk required to get there. Having both intracoastal and beach access is the biggest value of the place in my opinion.

Sea Shell Ocean view On Beach Walk everywhere Pool
Amy was the most responsive host I have ever had on Airbnb. I appreciated her hospitality.

Sea Club 2-Relaxing Siesta Key Condo-Siesta Sky
Absolutely love Sea Club. This was our second stay there. Will always come back. Walk to the beach is not bad at all. Condo is next to the road but still quiet. Really enjoyed our stay!

Crystal House on Siesta Key Beach
Our stay with Eric was amazing! We needed a quick beach weekend and this exceeded our expectations. His unit was as described with luxury towels and bed linens. Beach closet was bonus…the cart, cooler and chairs was much needed and appreciated! I messaged Eric prior to our arrival asking if there was a volleyball in the closet so I could add to our grocery order if not. First thing I saw as we walked in the unit was a new volleyball sitting on the table awaiting our arrival! Way above and beyond! Easy check in and check out. Actually, our flight was ahead of schedule and Eric allowed us early entry to get our trip started a bit sooner! This was our first time visiting the area and definitely plan on returning and will stay here again. Thanks for a great stay!

Siesta Key - 1/2 Mile to the Beach!
This condo was the perfect place to stay for my trip to Siesta Key. This condo is private in a neighborhood far enough from the hustle and bustle but close enough to get to the beach within a 5 minute drive. The condo was equipped with beach gear and all kitchen necessities. Very clean, comfortable, and felt right at home. I will definitely be booking this condo again for my next trip to my favorite beach!!

Siesta Key Ground Floor Condo 2BR On Trolley Line
Great stay, the location, the amenities all were wonderful. Melissa and Brandon were super responsive and the place had more essential stocked than most of the other places we have stayed, which was very thoughtful. Melissa also had a regular coffee pot sent out to us right away, since we don’t use Keurig’s which was super nice and very much appreciated. We would definitely come back!

Siesta Key Beach Front Condo
Our stay was exactly what we wanted. Our host, Evan, was great and quick with any questions we had. The condo was located very close to Siesta Key Beach, and we didn't have to drive more than 20 minutes to get to anything that we wanted to around that area, some things even within walking distance. Everything we could have possibly wanted was provided in our home, which really made the week stress-free. We would definitely stay here again!
Quick stats about holiday rentals with a pool in Gulf Gate Estates
Total rentals
120 properties
Nightly prices starting at
₹4,282 before taxes and fees
Total number of reviews
3.3K reviews
Family-friendly rentals
110 properties are a good fit for families
Pet-friendly rentals
40 properties allow pets
Rentals with dedicated workspaces
70 properties have a dedicated workspace
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- Anna Maria Island
- Siesta Beach
- Anna Maria Public Beach
- Crescent Beach
- John's Pass
- Turtle Beach
- Caspersen Beach
- Bean Point Beach
- Raymond James Stadium
- Cortez Beach
- Lido Key Beach
- Amalie Arena
- Coquina Beach
- Gulfport Beach Recreation Area
- Vinoy Park
- North Beach
- Fort De Soto Park
- Manasota Key Beach
- Streamsong Resort
- Tampa Theatre
- Jannus Live
- Curtis Hixon Waterfront Park
- Splash Harbour Water Park
- River Strand Golf and Country Club