Vacation rentals with a pool in Westchester

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Popular amenities for Westchester rentals with a pool

House rentals with a pool

Guest favorite
Home in Miami
4.91 out of 5 average rating, 106 reviews

*POOL* |Sleeps 8|Near Coral Gables | Dadeland Mall

LaurenRating, 5 stars1 week ago
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
Top guest favorite
Home in Miami
4.9 out of 5 average rating, 230 reviews

Large heated Pool Home (Centrally Located)

CatherineRating, 5 stars6 days ago
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.
Top guest favorite
Home in Miami
4.98 out of 5 average rating, 125 reviews

Encanto Family, cozy heated pool, center of Miami

DanielRating, 5 stars1 month ago
Great stay, pool might be a little too hot for summer weather
Guest favorite
Home in Miami
4.82 out of 5 average rating, 146 reviews

Ily's House

JernejRating, 5 stars1 week ago
Great place, and peaceful with great pool
Top guest favorite
Home in Biscayne Park
4.97 out of 5 average rating, 115 reviews

Miami Modern Luxury with Pool & Spa

SarahRating, 5 stars1 month ago
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!
Guest favorite
Home in Miami
4.92 out of 5 average rating, 51 reviews

Luxe collection home in Miami.

ChassadiRating, 5 stars2 weeks ago
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.
Top guest favorite
Home in Miami
5 out of 5 average rating, 20 reviews

Peaceful Miami Villa/Pool Heated

MelissaRating, 5 stars1 week ago
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.
Superhost
Home in Miami
4.83 out of 5 average rating, 118 reviews

Emilia Coral villa

AmandaRating, 5 stars2 weeks ago
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

Guest favorite
Condo in Downtown Miami
4.9 out of 5 average rating, 175 reviews

Feels Like Summer ~ Panoramic Water Views! 2BR

JillianRating, 5 stars2 weeks ago
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.
Superhost
Condo in Brickell Business District
4.86 out of 5 average rating, 160 reviews

Chic Studio 5 Icon Brickell Amazing View

NatashaRating, 5 stars1 week ago
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.
Guest favorite
Condo in Doral
4.85 out of 5 average rating, 158 reviews

Modern and comfortable Studio In Downtown Doral

DesmondRating, 5 stars1 month ago
Great location, parking could be better but no complaints otherwise
Guest favorite
Condo in Downtown Miami
4.94 out of 5 average rating, 143 reviews

Modern DT Studio | Near Port Miami + Free Parking

MiraRating, 5 stars3 days ago
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.
Guest favorite
Condo in Brickell Business District
4.92 out of 5 average rating, 555 reviews

Luxury 5 stars ICON Brickell @46TH 2B/2B, Pool/Gym

LeonardoRating, 5 stars4 days ago
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
Top guest favorite
Condo in Doral
4.99 out of 5 average rating, 111 reviews

Best area of Doral with all the services!

LeslieRating, 5 stars3 days ago
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!
Top guest favorite
Condo in Coconut Grove
4.93 out of 5 average rating, 291 reviews

CityView Balcony Pool& Hottub. Wi-Fi. Full Kitchen

IgorRating, 5 stars2 months ago
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!
Guest favorite
Condo in Miami Design District
4.99 out of 5 average rating, 192 reviews

Design District condo with parking, pool and gym

ChauRating, 5 stars1 week ago
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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