
Family-friendly vacation rentals in Westchester
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Top-rated family-friendly rentals in Westchester
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Vacation rentals for every style
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Popular amenities for Westchester family-friendly rentals
Family-friendly home rentals with a hot tub

Finest Bal Harbour Resort by Guaranteed Rental®
absolutely loved our time here! perfect location, amazing amenities, just wonderful ! highly recommend , we will definitely be back !

Golden Bay Club Beautiful Condo! -STR-02901.
The apartment is exactly as described. This is a tremendous place to relax, recover and enjoy the sunny isles of Florida. Fernando and team were incredibly gracious and responsive. Would definitely stay there again (hopefully very soon)

Private Paradise between Miami & the Keys
Great home. The outdoor area was fantastic and the kids loved the pool. BBQ area was perfect for the evenings. The house itself is very spacious and has everything that you need. Perfect for a family getaway, close to the Everglades and the keys

Gorgeous Bay View 1/1.5 Condo in Grove w/ Parking
Beautifully decorated, wonderfully useful design and provisioned. We had a chance to stay at two of Lorelei’s Arya Condo - a 2 bd and a 1 bd. Both were immaculate with nice touches like coffee and creamer to start the stay, some snacks for the hungry traveler. I ask for her to help us smoothly transition from one unit to the other and it was a breeze. Excellent value, fantastic views, perfect location for all the spots in the grove.

Studio #1 hot jacuzzi Miami Center Beach
Tropical Paradise!! This place is exactly what’s needed to kick back and relax. We enjoyed our stay, and will definitely be back.

Tropical RiverHouse w/Spa & Deck
This is our second stay at The Tropical River House, and it is an absolutely wonderful place to relax and take in the beautiful scenery. Located right along a small river, with tropical palm trees framing the most beautiful sunset, all right in the back yard! We were visited by various tropical inhabitants such as ducks, cormorants, a few iguanas sunning themselves on the seawall, and also pods of Manatees slowly swimming by from time to time. It's just wonderful, it's so nice that we spent a couple of days on the back deck relaxing, in lieu of going to the beach. Although we did get some great beach time too! The house is exactly as described, is very clean and organized, and has all the amenities you'll ever need. We "cooked in" on several nights and the kitchen has it all! The neighborhood is quiet, and the home is near to restaurants, shopping, the beach and just about everything. The Tropical River House, once again, exceeded our expectations and we will be back soon.

BRICKELL ARCH LUXURY CONDO 33rd FLOOR+FREE PARKING
I loved the place, it's super well located, I would go back without thinking. Excellent! Highly recommended. It will be our place to go to in Miami.

Amazing View 1 Hotel Corner Unit 2BR/2BA w Balcony
Great stay here! Beautiful place and representative of the photos on the posting. Beautiful views and so centrally located. Huge additive plus to be able to use all hotel accommodations. Thank you for such a fabulous stay!
Family- and pet-friendly home rentals

Grove Central 3Br+ Den Spanish House Patio BBQ
This was exactly what we were looking for. Everything was as advertised and Ana was responsive. Beds were all comfortable and linens were clean. Thanks! We Enjoyed our short stay!

Large heated Pool Home (Centrally Located)
Claudia was a fantastic host! She was very helpful, answering our questions about the neighborhood and where to buy groceries. The house was clean and very comfortable for our group of 6. The garden and pool area were beautifully maintained and the kitchen was well stocked with cooking equipment. Overall we had a great time and felt right at home.

Miami - Group Retreat #1
Amazing hospitality Great location Very quiet neighborhood . Definitely recommended

Breathtaking Pool Home and Backyard by Wilton Mnrs
What an amazing host and fantastic property. Communication was prompt and professional. The host really worked with us to help us to make our experience a great stay! We would stay again and highly recommend this property!

6-BR Vacation Home for Bachelorettes & families
Vischka has a beautiful family home, she was always responsive and ready to help whenever we needed. I would recommend staying at her place!

Cozy 1BR Retreat with Patio, Free Parking & Wi-Fi
I loved the private outdoor living space. Very quiet and comfortable.

• The Captain's Quarters • Home + Guesthouse
Had a great stay! Everyone in my party of 11 enjoyed the property and the amenities. The theme is very cool and elevates activities on premises. The hosts were fantastic and extremely responsive. Would recommend!

Private guest house walk to beach
Marcela was very accessible and extremely helpful. the property was serene, quiet and spacious. the pictures represented the rental very accurately. we really enjoyed our stay
Family-friendly home rentals with a pool

3B Pool Home, King Bed-Priv.Yard-Grill & EVCharger
Everything was nice! Communication from the hosts were great. 10/10 highly recommended! The kids really enjoyed the pool!

4BR Heated Pool Home w/ Tiki Hut!
As perfect as anyone could expect. One minor issue that im sure they were not aware of but jumped to correct it. Two of the most important things for is is there was nothing misleading about the property description and the communication couldn't have been better.

Studio- Between Hard Rock Stadium & Casino
Simply amazing, the smell of jasmine from her tree in the morning by the pool with a cup of coffee was awesome. Judy was absolutely wonderful. he place was clean and the kids loved her pool.

Private Pool | King Bed | BBQ & Hammock
Christina’s place was absolutely lovely! The pool was perfect, and the backyard felt like a little oasis—so peaceful and relaxing. The interior was exactly as expected, super comfortable, and had everything we needed. We had such a great time and would definitely stay again. Highly recommend!

LakeFront - Home Near Casino w private pool
Wow! Just WOW! I appreciate Beatriz deeply, as she was available to accommodate my family and I for a last minute reservation, as my prior plan fell through. Beatriz was easy to communicate with, very thorough, empathic and overall a sweet, genuine spirit. The home was very beautiful and clean! I was very impressed with how everything was organized and decorated. The location was serene as well. I was able to play a little pool and brush up on my skills. I wish I was able to play the other games she had available but didn’t have time. I am so happy that I was able to stay here with family. We all enjoyed it, along with the amenities (my mother was impressed with the availability of kitchen and cooking utensils!). THANK YOU BEATRIZ! I will certainly return whenever I take a trip down to Florida.

The Oasis @ Hollywood, FL (3 miles to the beach)
Excellent comfortable home and wonderful responsive host. One hundred percent would stay again

Waterfront Home 3/3.5 Resort Style-Heated Pool*
We enjoyed our visit, peaceful place, felt like I was home. Everything was clean and very comfortable furniture. We recommend this place and hopefully we can come back soon Thank you for letting us enjoy this stay at your place, we really enjoyed it.

WatersEdge, TropicalHideaway, FLL, MIA, Port, Pool
Lara’s place was hands down the best Airbnb I have ever stayed at. The place was sooo beautiful and CLEAN! It was in a perfect spot, everything about it was amazing and so accommodating for our family. The place was great but so was Lara herself! She’s genuinely someone I could see our family having a friendship with. All in all the place was perfect in all aspects and we already said if we were to ever come back it would be to this home.
Quick stats about vacation rentals that are family-friendly in Westchester
Total rentals
90 properties
Nightly prices starting at
ﺩ.ﺇ257 before taxes and fees
Total number of reviews
4.6K reviews
Pet-friendly rentals
50 properties allow pets
Rentals with a pool
50 properties have a pool
Rentals with dedicated workspaces
60 properties have a dedicated workspace
Destinations to explore
- Gold Coast Vacation rentals
- Miami Vacation rentals
- Miami Beach Vacation rentals
- Fort Lauderdale Vacation rentals
- Florida Keys Vacation rentals
- Key West Vacation rentals
- Central Florida Vacation rentals
- Kissimmee Vacation rentals
- Tampa Bay Vacation rentals
- Four Corners Vacation rentals
- St Petersburg Vacation rentals
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- Apartment rentals Westchester
- Rentals with a patio Westchester
- Kid-friendly rentals Westchester
- Rentals with pools Westchester
- House rentals Westchester
- Pet-friendly rentals Westchester
- Rentals with a washer and dryer Westchester
- Rentals with outdoor seating Westchester
- Family-friendly rentals Miami-Dade County
- Family-friendly rentals Florida
- Family-friendly rentals United States
- Yurt Rentals United States
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- Apartments with a Hot Tub United States
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- Pet-Friendly Vacation Rentals United States
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- Dog-Friendly Cottages United Kingdom
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- Bayfront Park
- Miami Beach Convention Center
- Everglades National Park
- Hard Rock Stadium
- Miami Design District
- Broward Center for the Performing Arts
- Port Everglades
- Key Biscayne Beach
- John Pennekamp Coral Reef State Park
- Trump National Doral Miami
- Crandon Beach
- Zoo Miami
- Hobie Island Beach Park North
- Biltmore Golf Course Miami
- Ocean Terrace Public Beach
- Boca Dunes Golf & Country Club
- Coral Castle
- Gulfstream Park Racing and Casino
- Cannon Beach
- Biscayne National Park
- Miami Beach Golf Club
- Oleta River State Park
- Anne Kolb Nature Center
- Palm Aire Country Club