Family-friendly vacation rentals in Wakefield

Find and book unique family-friendly homes on Airbnb

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

  • Total vacation rentals

    Explore 40 vacation rentals in Wakefield

  • Nightly prices starting at

    Wakefield vacation rentals start at G$8,376 GYD per night before taxes and fees

  • Verified guest reviews

    Over 1,390 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    40 of Wakefield vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Wakefield rentals

  • 4.7 Average rating

    Wakefield stays receive an average rating of 4.7 out of 5 from guests

Top-rated family-friendly rentals in Wakefield

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Guest favorite
A modernist house is surrounded by vibrant autumn foliage, showcasing a blend of red, orange, and green leaves. The structure features large glass windows and a roof that floats above the walls, offering scenic views of the lush forest.
Home in Rye
4.91 out of 5 average rating, 140 reviews

1956 House of the Year Award. Easy commute to NYC.

Architectural masterpiece, designed by famous architect Ulrich Franzen. House of the year awarded in 1956 by Architectural Record, featured in LIFE and House and Garden magazines. Taste the unique experience of modernist living, surrounded by nature yet walking distance to the beautiful town of Rye, the beach, natural parks and 45m by train to NYC. The house is filled with light,all the rooms have forest views,you feel inmersed in nature while enjoying the magical experience of modernist living!

Guest favorite
An outdoor area is illuminated by a vibrant red fireplace, surrounded by cozy seating arrangements with cushions and throws. Potted flowers add color, while string lights gently glow above, enhancing the serene atmosphere of the deck. A natural stone backdrop is visible in the distance.
Cottage in Greenwood Lake
4.98 out of 5 average rating, 382 reviews

Luxury Cottage with Spectacular Lake Views

Ultra Chic Cottage set high above Greenwood Lake with Private beach and lake front community access. Minutes away from Mountain Creek Ski Resort, Spa & Water park, Mt. Peter Ski & Tubing, Warwick creameries, breweries & vineyards & apple picking. 1 BR, 1 Bath, play/office/common room. Huge wrap around fenced in deck with Mid century modern fireplace allows for scenic dining, lounging and around the fire gatherings. #LakeViewCottage_GWL Town of Warwick Short Term Rental Permit #P25-0245

Top guest favorite
A shaded gazebo features a comfortable eight-seat patio lounge set arranged around a fire table. The surrounding area is well-maintained grass, providing a spacious setting for outdoor relaxation.
Home in Mount Vernon
4.97 out of 5 average rating, 119 reviews

Backyard Gazebo in Quiet NYC Suburban Stay

Welcome to our private split-level home with a fenced-in backyard! Enjoy this entire single-family home and never walk more than 8 steps between levels! This is a year-round perfect spot - enjoy the outdoor patio and indoor electric fireplace during your short term or midterm stay. We are located in Westchester County, just outside NYC. The house is 1.5 mi from 3 Metro-North stops and a 30-minute ride to Manhattan. Send us a message and we will let you know how far it is to your event.

Guest favorite
An open floor plan showcases a cozy living space. A comfortable seating area is paired with a wooden coffee table, while a small kitchen with stainless steel appliances is visible. A spacious bed is positioned in the background, creating an inviting atmosphere.
Guest suite in Mount Vernon
4.84 out of 5 average rating, 315 reviews

Cozy Studio Getaway w/easy access to NYC/CT

Enjoy a relaxing stay with a home away from home; in this 1 bedroom studio apartment. Equipped with a comfortable bed, clean bathroom, kitchen, fridge, microwave, sink, counter top & stove. - 1 bedroom apartment with open floor plan (Fits 1-2 adults) - Private Individual Entrance (basement level) - Convenient & easy street parking - 5 minute drive from Metro North Railroad (Mount Vernon East station) which gives access to other parts of Westchester, Manhattan, and CT areas.

Guest favorite
Ranch in Mount Vernon
4.89 out of 5 average rating, 199 reviews

Private Studio Apt. close to NYC

A Private and unique studio apartment with its own entrance. It offers a peaceful retreat away from the busy city of New York. Free parking and luxurious furnishing. A comfortable queen size bed. A TV with basic cable. An electric fireplace for those romantic evenings. A jacuzzi for Unwinding and soaking after a long day. A HVAC system for heating/cooling. Stroll over to Pelham Village for breakfast or dinner. Enjoy Time Square only 20 mins away via Metro North train.

Top guest favorite
A view of the exterior of the property is framed by lush greenery, featuring a stone wall with a potted plant. Beyond, expansive views of the lake and surrounding mountains are visible beneath a clear sky.
Home in Greenwood Lake
5 out of 5 average rating, 216 reviews

Spectacular Lake Views from Every Room & Garden

Our property boasts unparalleled views of Greenwood Lake and the mountains beyond. Our private garden features a seasonal waterfall cascading into a lily pond with fish and frogs. The shaded patio offers panoramic views and a gas grill. During the winter months, after skiing at nearby slopes, unwind in the claw foot tub or retreat to the cozy ambiance of our living room, with exposed wooden ceilings, a welcoming fireplace, a smart TV, a record player and board games.

Guest favorite
The living area features a sectional sofa and a coffee table, arranged on a neutral-toned rug. A dining table with four stools is set near the kitchen, which includes modern appliances and ample cabinetry. Soft lighting highlights the open floor plan.
Apartment in Yonkers
4.78 out of 5 average rating, 178 reviews

Cozy 1Br Garden Apt w/ Private Backyard

Nice and Cozy lower level basement apartment centrally located in Yonkers in close proximity to NYC. Apartment offers a full size kitchen, a bedroom with a Queen bed for 2 and a Pull out sofa for 1 additional guest. The unit has a private entrance on the lower level of a private home along with a backyard exclusively for this unit only. Plenty of street parking in the area 30 min drive to NYC (Grand Central) Plenty of bars restaurants and malls in the area

Top guest favorite
The lakeside property features a well-manicured lawn leading to the water's edge, complemented by a dock and a single kayak. Lounge chairs are arranged near a shaded gazebo, with a stone pathway guiding guests towards the house, which is framed by lush greenery.
Home in Greenwood Lake
4.97 out of 5 average rating, 101 reviews

Luxury Lakefront w/ Beach, Dock & Kayak • 1h NYC

Escape to our modern, year-round lakeside paradise on Greenwood Lake, just 1 hour from NYC. This bright, airy home offers stunning lake views, a private dock, and a sandy beach area. Perfect for families or couples, enjoy seasonal activities from swimming and kayaking in the summer to skiing just 10 minutes away in the winter. Relax by one of two fireplaces or on the spacious deck. A tranquil retreat for relaxation and adventure. Permit N. 23-225

Guest favorite
A small living area features a pair of brown leather sofas, including a reclining chair. A coffee table with a marble top is positioned between the seating. Natural light filters through the sheer window treatments, illuminating the polished wooden floor.
Apartment in Mount Vernon
4.95 out of 5 average rating, 153 reviews

Todds Comfortable, Cozy and welcoming 3bdr Apt

Convenient to all transportation Shopping Centers/Malls, Restaurants/Dining, Empire City Casino, Cross-County, Bay Plaza, City Island Seafood, Glen Island Park, Memorial Field, are all located 15 minutes or less from the apartment. 20 minutes from Laguardia Airport by car/40 minutes from Kennedy Airport by car. 35 minutes from New York City by Metro North Train. 30 minutes or less from all Lower Westchester Parks, Pools, Waterfronts etc.

Top guest favorite
A spacious sleeping area is highlighted by a large white bed with a patterned quilt. Two decorative lamps are positioned on either side of the bed. A dresser and a decorative shelf with small plants and art are visible against the blue wall, enhancing the room's appeal.
Apartment in Yonkers
4.89 out of 5 average rating, 228 reviews

Near Empire Casino Cross County Mall Yonkers

This is a private one-bedroom apartment perfect for a comfortable stay. The unit features a cozy bedroom and a pull-out sofa in the living room, allowing the space to accommodate up to four guests. Enjoy the privacy of your own apartment while being just minutes from New York City, with easy access to transportation, dining, and local attractions. Parking: Street parking is available. Please do not park in the driveway.

Top guest favorite
A stained glass welcome sign is displayed, featuring a design of green shamrocks. The word 'Fáilte' is prominently featured in an elegant font, complemented by warm shades of amber and green in the background.
Home in Yonkers
4.95 out of 5 average rating, 319 reviews

Conefrey's.

Spacious, bright, comfortable, 1 bedroom apartment. Walking distance to all public transport, 10 minutes walk to Cross County Shopping Center. Only 20 minutes from Grand Central station and only 7 minutes from Sarah Lawrence College. Quite neighborhood, close to all amenities including McLean Avenue.

Top guest favorite
A cozy living area showcases a dark sofa adorned with green pillows, complemented by a sleek kitchen bar with three stools. Natural light streams through sliding glass doors, leading to an outdoor space with a stone patio and greenery.
Apartment in Yonkers
4.96 out of 5 average rating, 134 reviews

Cozy and beautiful garden apartment

Keep it simple at this peaceful and centrally-located place. Beautiful and cozy ground level apartment with private entrance in a quiet and secure neighborhood just a few minutes from the Empire Casino, Cross County mall, Lawrence hospital and many diners and restaurants.

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