
Family-friendly holiday rentals in Westchester
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Westchester
Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Westchester family-friendly rentals
Family-friendly home rentals with a hot tub

Beautiful Poolside Studio, Heart of Miami

Make It Happen! Brand New with Amazing Water Views

Enjoy our Beautiful Home on a Fun Canal! Hot tub!

Chic Guest house w/pool, hot tub, grill, mini golf

Very Private 1/1 Apt w/Oasis Pool Patio Setting

Escape-5BR-HotTub-Games-FirePit-BBQ-Fun

Guesthome w/ Heated Pool 5 mins from Miami Airport

The Miami Tropic Suite•Private Stay+Free Parking
Family- and pet-friendly home rentals

Coconut Grove Tiny House Solo Retreat near UM MIA

Orismay Luxury Apartment, Miami

Cozy Studio Near Airport | Near Beaches & Downtown

Cozy and private studio.

Cosy Guesthouse Central Located

Miami Stay: 5 Mins to Everything + W/D Inside

Your Cozy Home Away from Home – 10 min to MIA

Modern apartment in Palmetto Bay
Family-friendly home rentals with a pool

Spanish House 3 Bedroom Pool House

Cozy and charming cottage

Sparkling Clean🌟Brand New Luxury Studio with Pool🏊🏼♂️

Encanto Family, cozy heated pool, center of Miami

Condo in Brickell Business District

Oasis Tropical Miami- Fun Mini Golf & Heated Pool

SF Amazing Studio - Walking Distance to Cocowalk

Cozy private guest studio
Quick stats about holiday rentals that are family-friendly in Westchester
Total rentals
90 properties
Nightly prices starting at
$90 SGD before taxes and fees
Total number of reviews
5K reviews
Pet-friendly rentals
50 properties allow pets
Rentals with a pool
50 properties have a pool
Rentals with dedicated workspaces
70 properties have a dedicated workspace
Destinations to explore
- Seminole Holiday rentals
- Miami Holiday rentals
- Central Florida Holiday rentals
- Orlando Holiday rentals
- Saint Johns River Holiday rentals
- Gold Coast Holiday rentals
- Miami Beach Holiday rentals
- Havana Holiday rentals
- Fort Lauderdale Holiday rentals
- Tampa Holiday rentals
- Kissimmee Holiday rentals
- Four Corners Holiday rentals
- Rentals with a patio Westchester
- Rentals with outdoor seating Westchester
- Rentals with a washing machine and dryer Westchester
- Flat rentals Westchester
- Rentals with a hot tub Westchester
- Pet-friendly rentals Westchester
- House rentals Westchester
- Rentals with pools Westchester
- Family-friendly rentals Miami-Dade County
- Family-friendly rentals Florida
- Family-friendly rentals United States
- South Beach
- Fort Lauderdale Beach
- Bayfront Park
- Miami Beach Convention Center
- Hard Rock Stadium
- Everglades National Park
- Haulover Beach
- Port Everglades
- Bal Harbour Beach
- Miami Design District
- John Pennekamp Coral Reef State Park
- Zoo Miami
- Dania Beach
- Ocean Terrace Public Beach
- Trump National Doral Miami
- Phillip and Patricia Frost Museum of Science
- Jungle Island
- Broward Center for the Performing Arts
- Key Biscayne Beach
- Crandon Beach
- Miami Beach Golf Club
- Gulfstream Park Racing and Casino
- Biltmore Golf Course Miami
- Boca Dunes Golf & Country Club