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Family-friendly vacation 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.

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Top guest favorite

A serene lakeside view shows a white heron standing on a sandy beach. Two lounge chairs are positioned nearby, surrounded by lush greenery and reflecting the peaceful atmosphere of the lake. The water exhibits calm, clear hues, enhancing the natural setting.

4.97 out of 5 average rating, 116 reviews

Miami 3/2 Lakeside, Designed for Max Comfort

Lakefront home w/Beach in Kendall that's Spacious, Clean and Designed for Extra Comfortable Sleeping. Located in a very safe, family friendly neighborhood w/playground. I live in the same neighborhood & love it here. New AC+fans in all rooms. Peaceful back yard on lake that has lots of ducks, turtles, iguanas, ibis and egrets (no snakes/gators). Very desirable location, central to attractions/highways and walking distance from a lot. High Quality Beds, Super Fast Internet, Fully Stocked Kitchen.

Top guest favorite

A spacious bedroom is furnished with a large bed covered in a light-colored blanket. Soft, ambient lighting is provided by bedside lamps. A window with blinds allows natural light to brighten the room. A decorative orchid adds a touch of greenery to the space.

Condo in South Beach

5 out of 5 average rating, 290 reviews

5 star Apt+Free Parking+Beach Service-South Beach.

Beautiful apartment located in the heart of South Beach. Steps away from Convention C, tropical beaches, cafes, restaurants, Lincoln Rd Mall, and all means of transportation. Love to be active? Our apartment is a walking distance from Flamingo Park with swimming pool, tennis courts, running track, basketball courts, pull up bars, and best of all, a positive vibe for a great time in South Beach!!! Free Beach Service at any Esteban's station,1umbrella 2chairs 9am-5pm. Closest station 15mins walk.

A bright and airy bedroom features a charming house-shaped bed adorned with a patterned blanket and cushions. Decorative banners hang above, complemented by soft lighting from pendant fixtures. A cozy atmosphere is enhanced by indoor plants and accent furniture, providing a welcoming feel.

Apartment in Hollywood Beach

4.92 out of 5 average rating, 261 reviews

The best view in Miami!

Best view ever! You’ll love my place because of its location. This apartment is great for families! The unit is super spacious!! 1070 square feet!! Right on the beach! You’ll find everything you’ll need for a perfect stay. Quiet by night, fun by day Please be aware that both check in and check out must take place with the host . Additional fees Fob: USD 30 every 2 adults Weekly Parking: USD 100 (1-7 nights) Please note that parking pass reimbursable deposit will be charged only in cash ($20)

The living area is furnished with light-colored sofas and accent pillows, arranged around a round, textured coffee table. A patterned rug covers the tiled floor, while natural light streams through large windows, complemented by soft, neutral curtains. A decorative wall feature adds visual interest.

Apartment in Fort Lauderdale

4.8 out of 5 average rating, 281 reviews

01 Cozy Portside Apartment - close to everything!

Look no further! Conveniently located minutes to restaurants, the beach & downtown, this apartment embodies the Florida way of life! Steps away from restaurants, stores & free public transportation, it doesn’t get more convenient than this! With a fully equipped kitchen, comfortable queen beds & an eclectically decorated environment, we look forward to hosting you! If you are planning to bring your furry friend with you please reach out as we do have to adhere to our insurance policy on breed

Top guest favorite

A bright indoor space features a sleek red sofa adjacent to a foosball table. Natural light fills the room through a window, enhancing the modern design. Light wood flooring complements the clean, minimalistic aesthetic, with cabinets visible in the background.

Villa in Hollywood Lakes

5 out of 5 average rating, 107 reviews

Alluring Villa, Stroll to Stunning Hollywood Beach

Please do not book this place for parties. Lovely spacious private villa on quiet street with heated salt water pool, jacuzzi and toddler pool. 12 minute easy walk to Hollywood Beach, named one of the top 10 beaches in the USA, with a 2 mile boardwalk with restaurants, live music and loads of fun! The pretty canal is one short block away and makes for a very lovely walk around the rim. 25 Minute walk to downtown Hollywood. Community shuttle to Hollywood or beach on demand by call via the app.

Top guest favorite

Condo in Sunny Isles Beach

4.93 out of 5 average rating, 129 reviews

Stunning direct ocean front 2 bed / 2.5 bath condo

The condo is in Sunny Isles Beach Florida's Riviera, safe, clean, family friendly. On the beach and stretching across the whole beach front of the building. Offering 180 degree direct ocean views from both bedrooms and living room. 2 ensuite bathrooms plus half bathroom. No Carpeting. No resort fees. Full service building on a pristine beach in an upscale area. Super comfortable, 600 thread count sheets, 86" TV for cinema experience, fully equipped kitchen. Valet parking only $40+tax per day

A modern kitchen area features a sleek countertop with an integrated induction cooktop, a kettle, and kitchen essentials. Stainless steel appliances include a refrigerator and microwave. Natural light filters in through horizontal window blinds, illuminating the stylish, light-colored cabinetry.

Apartment in South Beach

4.9 out of 5 average rating, 192 reviews

SoFi Villa #5, 4 Beds - FREE Parking, Kitchen

Unit 5, 1st Floor unit. ADA Compliant. SoFI Villas is a Vacation Rental - located in the wonderful neighborhood of South of Fifth Street. We have a total of 5 apartments with a private outdoor courtyard. 5 Minute walk to Ocean Drive and the beach! Lovely restaurants and stores, Parking- Residential street pass, for Zone 1, Free Parking for one car. We follow the City of Miami Beach Code laws, No loud Noise/ music, No parties. Quiet time after 10 pm- as this is a residential neighborhood.

The image captures a corner of the studio featuring a neutral-colored wall, two sets of double white doors, and a tall vase with decorative elements. A small dining area with dark wooden stools and decorative items is visible, creating a simple and functional space.

4.78 out of 5 average rating, 402 reviews

⭐⭐⭐⭐⭐5 MINUTES MIAMI AIRPORT 10 MINUTE MIAMI BEACH

⭐⭐⭐⭐⭐10 Minutes to Miami beach - (5 star rating) - 10 blocks from (Miami Airport), Large Studio ( for non smokers ) with 2 beds- independent private entrance your own key and Free parking space in front of the house with a gate. The Studio is attached to a house. 10 BLOCKS from 20 car rental companies, 5 BLOCKS FROM Water Park. Perfect for couples, business travelers, 10 minutes from (Miami cruise ships). Tip: a lot of guest take an Uber and save money. Address - very centralized- Enjoy!

An outdoor shower with a vibrant blue tiled wall is positioned next to a pathway leading to the beach. Palm trees are visible in the background against a bright blue sky, creating a refreshing atmosphere by the ocean.

Apartment in Mid Beach

4.86 out of 5 average rating, 103 reviews

Stunning Beachfront in Miami Beach + free parking

Enjoy the comfort & tranquility of this beautiful modern condo with full panoramic ocean views! Savor your morning coffee on your private balcony, overlooking the sparkling ocean water with private access to the beach. Features a spacious master bedroom with 1 king, 2 twin beds, w/ a room divider that slides open/close to transform the room into 2 private spaces or 1 large room that sleeps 4. In-suite washer\dryer. Free valet parking for 1 car. Free cable+Wi-Fi BTR01258709-2022 RT 2406711

A neatly arranged living area features a light-colored sectional sofa adorned with pillows in warm hues. A wooden coffee table holds decorative items, while a large flat-screen TV is positioned against the wall. Light enters through multiple windows, complemented by ceiling light fixtures.

Apartment in Miami

4.84 out of 5 average rating, 389 reviews

Enjoy A Tropical Retreat in Coral Gables

Lovely Private Apartment nestled in lush tropical gardens, comfort abounds in this beautiful & historic Coral Gables home. Everything you need is here to make this your home away from home. Safe neighborhood, in the center of Miami within walking distance to over 200 restaurants, shops, art galleries, bars, & entertainment. Just minutes to Brickell, South Beach, Miami Beach, Key Biscayne, University of Miami, Coconut Grove & more...! Enjoy, relax, or let you adventurer spirit soar!

A light-filled living area features a spacious sectional sofa with a tufted design, complemented by a wooden coffee table. A standing lamp provides additional lighting, while vinyl records are displayed on the wall. Sheer curtains frame the windows, offering a view of the outside.

4.87 out of 5 average rating, 315 reviews

Boutique and stylish home - saltwater POOL

This stylish and charming Mediterranean home is located on a quiet residential street in Miami. The residence has 3 bedrooms, 2 bathrooms, a bonus room, a full kitchen and laundry. A private back yard is fully fenced and hosts a newly built 15x30ft salt-water pool - heated November through end of April - a wooden deck, covered patio, outdoor dining set and a gas grill. The residence is 20min drive to either Miami International or Fort Lauderdale airports

A spacious studio layout features a stylish white sofa adorned with patterned cushions, complemented by a sleek coffee table. A comfortable bed is positioned against a subtle patterned wall, with soft lighting providing a calming atmosphere. Nearby, a dedicated area for storage and a closet are visible.

Apartment in South Beach

4.9 out of 5 average rating, 252 reviews

Seagrass Studio w/ pool, 2 blocks to beach

The comfortable condo is in an Art Deco building in the heart of South Beach, next to Española Way, and just two blocks to Lincoln Road, Ocean Drive, the Convention Center, and the magnificent beach. You’ll love the pool - a rare find in this neighborhood. The space offers great value in an ideal location. Good for couples, solo adventurers, and business travelers. You must be 25 or older to rent here.

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Popular amenities for Westchester family-friendly rentals

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

A spacious living area is featured with a modern glass dining table surrounded by upholstered chairs. Large windows allow natural light to fill the space, revealing views of the outside greenery. Designer lighting fixtures hang elegantly above, complementing the contemporary décor.

Condo in Bal Harbour

4.89 out of 5 average rating, 204 reviews

Finest Bal Harbour Resort by Guaranteed Rental®

A clean and modern bathroom is presented with a white vanity featuring a sink and ample counter space. A shower stall with sliding glass doors is visible, alongside a toilet. A bright teal towel adds a pop of color to the neutral tones.

Condo in Sunny Isles Beach

4.88 out of 5 average rating, 107 reviews

Golden Bay Club Beautiful Condo! -STR-02901.

A spacious outdoor area features a saltwater pool and a hot tub surrounded by lush tropical plants. A thatched tiki hut provides shaded seating, while a patio with lounge chairs is situated nearby. The home's façade is visible, highlighting large windows.

Home in Homestead

4.93 out of 5 average rating, 397 reviews

Private Paradise between Miami & the Keys

A colorful playground is nestled under large trees, featuring multiple slides and climbing structures. Soft green turf surrounds the play area, providing a safe environment. In the background, a building emerges among the trees, contributing to the family-friendly atmosphere.

Apartment in Coconut Grove

4.93 out of 5 average rating, 137 reviews

Gorgeous Bay View 1/1.5 Condo in Grove w/ Parking

A private outdoor area features a spa jacuzzi surrounded by a lush garden, providing a serene environment for relaxation. Two wicker chairs with colorful cushions are positioned nearby, and a small side table is visible. A secure gate offers access from the patio.

Guesthouse in Flagami

4.86 out of 5 average rating, 342 reviews

Studio #1 hot jacuzzi Miami Center Beach

A squash court is depicted, featuring four individuals engaged in play. The foreground shows a player preparing to serve, with a partially visible racket. The backdrop includes additional players and the court's walls, emphasizing an active and energetic atmosphere.

Apartment in Coconut Grove

4.84 out of 5 average rating, 229 reviews

Amazing City View Sleeps 3, Pool, Free Pkg, Pool

Condo in Coconut Grove

4.73 out of 5 average rating, 163 reviews

Incredible Studio, on the 10th FL

A tall skyscraper named 'Brickell Arch' is depicted, featuring a sleek glass facade reflecting the sky. Tall palm trees are positioned in the foreground, complementing the modern architectural design of the building.

Apartment in Brickell Business District

4.78 out of 5 average rating, 303 reviews

BRICKELL ARCH LUXURY CONDO 33rd FLOOR+FREE PARKING

Family- and pet-friendly home rentals

Home in Coral Way

4.89 out of 5 average rating, 289 reviews

Grove Central 3Br+ Den Spanish House Patio BBQ

A cozy bedroom features a king-size bed with white linens and fluffy pillows. Natural light flows through the window, illuminating the space. A flat screen TV is mounted on the wall, and a small bedside table and lamp are positioned beside the bed. A full-length mirror reflects the cozy ambiance.

Guest suite in Hollywood Lakes

4.92 out of 5 average rating, 355 reviews

Near Beach, Private Entrance, 1 mile from Downtown

Top guest favorite

4.89 out of 5 average rating, 225 reviews

Large heated Pool Home (Centrally Located)

A bright, modern bathroom features a walk-in shower with a glass enclosure and a pebble stone floor. A white vanity with a sink and minimalist decor complements the clean design. Natural light enters through a window, illuminating the space.

4.85 out of 5 average rating, 111 reviews

Miami - Group Retreat #1

Home in Hollywood

4.89 out of 5 average rating, 170 reviews

3B Pool Home, King Bed-Priv.Yard-Grill & EVCharger

A comfortable living room is displayed, featuring a television on a white media console. Two windows with blinds allow natural light in, illuminating the space. A woven chair complements a dark sofa, while a coffee table holds a decorative tray and a remote.

Home in Hollywood Lakes

4.85 out of 5 average rating, 179 reviews

Coastal Living for Four

The exterior of the duplex features a well-maintained garden with lush green grass. A concrete walkway leads to the entrance, framed by two large windows. The front door is white with a small window, complemented by a subtle doormat. A red vehicle is parked nearby.

Guesthouse in Coral Way

4.84 out of 5 average rating, 329 reviews

Stylish Stay Close to UM & City Vibes

A studio space is presented with a spacious bed in the foreground, accompanied by a small desk and a bistro table. A microwave, fridge, and coffee maker are visible on a shelf, with a private bathroom entrance at the rear. Natural light enters through glass doors leading to a patio.

Apartment in Coconut Grove

4.9 out of 5 average rating, 310 reviews

Tropical Bungalow Hideaway, Spacious Patio

Family-friendly home rentals with a pool

A serene outdoor space is highlighted by a heated saltwater pool surrounded by lush palm trees. Poolside seating includes elegant iron chairs and tables. Soft lighting enhances the tranquil ambiance, creating a welcoming atmosphere for relaxation and enjoyment.

4.93 out of 5 average rating, 190 reviews

Private Pool and Tropical Garden Oasis

A modern living area features a comfortable sectional sofa and a low coffee table, complemented by colorful wall art. The open kitchen with white cabinetry and bar seating connects seamlessly to the living space, enhancing the flow and accessibility of the area.

Apartment in Mid Beach

4.81 out of 5 average rating, 107 reviews

Unique and exotic beach front townhouse

A heated saltwater pool is surrounded by a screened patio, featuring several lounge chairs positioned along the edge. The water reflects the surrounding foliage, creating a serene environment. A fence provides privacy, ensuring a tranquil space for relaxation.

Home in Pembroke Pines

4.74 out of 5 average rating, 177 reviews

Entire 3/2 with private heated salt water pool

A modern bathroom features a glass-enclosed shower with marble tile and a dual sink vanity with dark wood cabinetry. Soft lighting illuminates the space, while window shutters allow for privacy and natural light.

Loft in South Beach

4.92 out of 5 average rating, 199 reviews

Luxury Residence in South Beach - Roof Top Pool

Top guest favorite

A bright area displays a wooden shelving unit alongside a small table. Potted plants are set atop the shelves, which hold various kitchen appliances and decorative items. A woven basket and magazines are visible on the table, complemented by a colorful textile underneath.

Guesthouse in Biscayne Park

4.95 out of 5 average rating, 494 reviews

Cozy and charming cottage

Guest suite in Pembroke Pines

4.94 out of 5 average rating, 706 reviews

Studio- Between Hard Rock Stadium & Casino

Top guest favorite

A well-organized sleeping area features a bed dressed with a light blue comforter. Tropical-themed wall art adds a decorative touch. A bedside table holds a lamp, and natural light filters through sheer curtains covering a window.

Apartment in Flagami

4.83 out of 5 average rating, 150 reviews

Tamiami Guest House- Studio #2

A spacious living area features large windows allowing natural light to brighten the space. A comfortable couch is positioned around a glass coffee table, complemented by a decorative rug. A pool table is visible in the background, alongside tasteful artwork and indoor plants.

4.9 out of 5 average rating, 145 reviews

LakeFront - Home Near Casino w private pool

Quick stats about vacation rentals that are family-friendly in Westchester

Total rentals
90 properties
Nightly prices starting at
G$14,687 GYD 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