
Vacation rentals with a pool in Westchester
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Top-rated rentals with a pool in Westchester
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Popular amenities for Westchester rentals with a pool
House rentals with a pool

*POOL* |Sleeps 8|Near Coral Gables | Dadeland Mall
Staying at Elsa’s place was wonderful start to finish. Her place is decorated beautifully, with thoughtful amenities placed throughout. The backyard is a peaceful oasis, a hidden gem in the busy hustle and bustle of Miami. This is definitely a place to save for your next trip! It housed 4 women with lots of things and lots of getting ready to do perfectly

Large heated Pool Home (Centrally Located)
The house was absolutely perfect! We stayed in their home and loved every minute. The gardens and pool area were beautiful and very relaxing. They have a very dog friendly house and yard. The hosts were incredibly responsive and very helpful. The house was comfortable and perfect for our family.

Encanto Family, cozy heated pool, center of Miami
Great stay, pool might be a little too hot for summer weather

Ily's House
Great place, and peaceful with great pool

Miami Modern Luxury with Pool & Spa
Pari’s home is even better than described! The backyard, pool and spa felt like our own private slice of paradise. Our hosts were immediately responsive to any questions we had, and even helped me troubleshoot my laptop’s configuration to join their network within a minute of me sending them a question. The house is wonderfully convenient to South Beach and all things east of its location. We stayed there for my daughter’s college graduation from University of Miami, and I have to admit we did not accurately understand how much traffic there can be at all times of the day getting from us to UoM! That just meant we had to adjust our schedules a bit, but everyone agreed there was place better to stay in Miami, and nowhere else we want to stay when we go back!

Luxe collection home in Miami.
Orlando’s place was so nice and looked just like the pictures! We enjoyed the walk-in showers the most! Enough bathroom space for a girls trip is a must lol. The pool was also really nice and heated complimentary which we thoroughly enjoyed. Orlando responded so quickly and was very helpful throughout our stay.

Peaceful Miami Villa/Pool Heated
Yanet is an amazing host! The house was PERFECT for our 10 day stay while my daughter recovered from minor surgery. The home is located in a super quiet and respectful neighborhood where just the two of us felt very safe, plenty of stores nearby, easy to get to everything. Beds were extremely comfortable, pillows were great, home was really clean, pool was beautiful. We settled in very quickly and found it was just an amazing retreat. Lots of spaces to gather and enjoy. I worked from here and the internet was incredibly high speed. Couches were fun to relax on and everything was nicely appointed. Yanet needs more properties as we would rent them!! She’s so quick to respond, very amiable and easy to help with questions. She made this trip so much easier for us. We would definitely stay here again or any properties Yanet hosts. Grateful beyond words.

Emilia Coral villa
Easy s to get there easy to shake in, answer very fast, place very clean, I just didn’t know it was more than one house in the same property
Condo rentals with a pool

Feels Like Summer ~ Panoramic Water Views! 2BR
Amazing place to stay. Very clean, good restaurants, great views. The only issue was the hand scans at the end as they started not working but rather than that 10/10 would stay again.

Chic Studio 5 Icon Brickell Amazing View
The place was beautiful looked even better than the photos, the bed was super comfortable, view was extremely beautiful, only problem was I wish it was more towels I asked for them but nobody ever brought them. Other than that everything was great, also be prepared to pay at least $40-50 a day for parking. Great host he was there right away to help with check in and gave us a better rate for parking which was $40 a day.

Modern and comfortable Studio In Downtown Doral
Great location, parking could be better but no complaints otherwise

Modern DT Studio | Near Port Miami + Free Parking
Host was super helpful and communicative. Apartment was accurately described by the photos. Washer and dryer a huge plus! Convent location and great amenities. Would recommend.

Luxury 5 stars ICON Brickell @46TH 2B/2B, Pool/Gym
I had an amazing stay at Javier’s gorgeous condo in the heart of Brickell! The unit was exactly as pictured—modern, sparkling clean, and equipped with everything I needed. Waking up to sweeping city and bay views from the balcony was such a treat! What I loved most: Prime location: Just steps away from MetroMover, Brickell City Centre, trendy cafes, and top-rated restaurants. Host responsiveness: [Host’s Name] replied almost instantly and provided excellent local recommendations—especially loved the suggestion to visit the rooftop bar nearby. Wonderful amenities: The pool/gym/lounge area in the building was perfect for relaxing after days of exploring. All in all, a top‑notch stay in Brickell. If you’re looking for a stylish, convenient spot to experience Miami’s vibrant urban energy, this is it. Highly recommend—and I’d stay here again in a heartbeat

Best area of Doral with all the services!
Host was very quick to respond, willing to accommodate check in time and very respectful. Condo was just as pictured, spacious, lots of amenities and clean. Surroundings were beautiful at night with plenty of restaurants. Highly recommend this host and will be booking again in the future. My friend and I had an amazing weekend, Thank you!

CityView Balcony Pool& Hottub. Wi-Fi. Full Kitchen
We had a great stay at Joe’s place. Everything was clean, well-organized, and we had everything we needed. The location is excellent, with many good restaurants nearby and a beautiful park by the water. Would definitely stay again!

Design District condo with parking, pool and gym
My family enjoyed our stay in Miami very much. We were able to walk to the grocery stores, the park, and many restaurants around the area. Cory’s place was clean and peaceful. Everyone we met in the building was friendly. Our kids enjoyed swimming in the beautiful pool every day. Thank you!
Quick stats about vacation rentals with a pool in Westchester
Total rentals
50 properties
Nightly prices starting at
G$6,273 GYD before taxes and fees
Total number of reviews
3K reviews
Family-friendly rentals
50 properties are a good fit for families
Pet-friendly rentals
30 properties allow pets
Rentals with dedicated workspaces
40 properties have a dedicated workspace
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- South Beach
- Fort Lauderdale Beach
- Bayfront Park
- Miami Beach Convention Center
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- Everglades National Park
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