Family-friendly holiday rentals in Middletown

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Middletown

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

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Top guest favourite
A spacious room with a queen size bed dressed in yellow accents is shown.  A small dining table is positioned nearby, surrounded by four chairs. In the background, a shelving unit holds storage bins and decorative items, while light filters through sheer window coverings, creating a bright atmosphere.
Guest suite in Portsmouth
4.93 out of 5 average rating, 148 reviews

By the Sea BnB - Portsmouth RI

By the Sea Air BNB is the perfect location for your stay! Located in our home with a private entrance you'll have the entire space with all the amenities you'll need to make for an enjoyable & relaxing break. Within walking distance to the local beach & restaurants. Spend a day in Newport & your night relaxing by the firepit, play a game or watch TV. We're 25 mins. to Newport, 15 mins. to their beaches, 10 mins. to Bristol's famous 4th of July celebration & close to Roger Williams University.

Top guest favourite
An outdoor space features a custom bar with nautical-themed decor and a green lawn. Brightly colored outdoor games are set up nearby, along with lounge chairs for relaxation. String lights are draped overhead, creating an inviting atmosphere for leisure and entertainment.
Home in Middletown
4.97 out of 5 average rating, 184 reviews

Ideal Location - Family Friendly - KING BED -

Welcome to CAPE NEWPORT! Stay with us knowing EVERYTHING is less than 2 miles away and there are no crazy checkout rules... lock up and go! Seriously no stripping beds, or taking out the garbage - we do it all! Beaches, Downtown Newport, Breweries, Newport Vineyards, Cliff Walk, Mansions, Golf, Groceries & takeout! Perfect spot for a mix of downtown & quiet small town vibes. You have your own PRIVATE fully fenced in backyard - 5 off street parking spots & Custom Backyard Bar & Picnic Table.

Guest favourite
A private deck is shown, featuring two lounge chairs positioned on a lightly textured rug. The deck is surrounded by white railings with a clear blue sky in the background, offering ample sunlight and a spacious area for relaxation.
Flat in Newport
4.87 out of 5 average rating, 190 reviews

CHIC on Thames St Deck & free parking

Our WHARF SUITE : stay in Newport's most desirable hot spot! 🐶💕. Our recently renovated 1 bedroom 1 bath condo sits directly on Thames Street, you can't beat the location! The rental also comes with 1 FREE parking space 300 feet away from us. The large windows throughout allow for plenty of sunshine and great lighting. The renovated kitchen attaches to a walkout private deck with views of downtown Newport. Go out, have some fun and don't worry about getting around. AC in bed & living room.

Top guest favourite
A manicured outdoor space features a grassy lawn framed by vibrant flower planters. Lounge chairs are positioned for relaxation, and a cozy seating area invites gathering. Natural stone pathways lead to a covered porch with wooden pillars, creating an inviting connection between the indoor and outdoor environments.
Home in Middletown
4.99 out of 5 average rating, 170 reviews

Walk to the Beach - Serene Coastal Country Cottage

Relax with ocean breezes. A 13 minute walk to pristine second beach and a short drive to everything Newport has to offer. Recently refreshed, and nestled within the famous Paradise farm setting, this home will keep you perfectly comfortable amid your Island exploration downtime. A full kitchen with Gas range and beautifully kept grounds will allow for alfresco summer dining. The home is Immaculately kept and spaciously sleeps max 6 adults and 2 children under 13yrs for a maximum of 8 guests.

Top guest favourite
The kitchen features modern white cabinetry and marble countertops, equipped with essential appliances including a stove, microwave, and refrigerator. Natural light fills the space, highlighting the decorative elements such as houseplants and tableware. A functional island provides additional counter space and organization.
Cottage in Portsmouth
5 out of 5 average rating, 221 reviews

Cozy Cottage Near Newport. Water Views. Fireplace

Welcome to Aquidneck Cottage! Relax in our charming 3BR retreat, just a short walk to Island Park beach. This sun-drenched cottage features an open layout & well appointed kitchen, perfect for families or friends to unwind together. Explore the stunning Newport & Bristol coastline before returning to the comforts of the cottage including water views, fireplace, and a private backyard. Perfectly located near beaches, vineyards, breweries, shopping, golf courses, colleges, wedding venues, & more

Top guest favourite
A two-story house is depicted with a welcoming front porch featuring white railings and columns. Lush greenery surrounds the property, with neatly trimmed grass and various plants enhancing the outdoor space. The house's siding is light-colored, complemented by shaded areas from nearby trees.
Casa particular in Newport
4.95 out of 5 average rating, 153 reviews

Cozy Den, steps to Cliff Walk, Beaches & Downtown

+PLEASE READ ENTIRE LISTING before booking and ALL pre/post check in/out info after. Thank you. Hello! This is a perfect little weekend getaway spot for two adults. You will be in walking distance to downtown, the Wednesday Farmer's Market, Salve, Cliff Walk, Mansions, Easton's Beach, a grocery store, coffee shops, and a pharmacy. We are an owner-occupied multi-generational Newporter (+ 1 dog from Tennessee) home. LGBTQ+ friendly. We know the vegan spots if you need them. All are welcome!

Top guest favourite
A charming entrance to a tiny house is bordered by vibrant flowers and greenery. Two blue chairs provide a seating area by the door, complemented by potted plants. The wooden deck appears inviting and well-maintained, enhancing access to the home.
Tiny home in Middletown
4.99 out of 5 average rating, 154 reviews

Cozy coastal tiny house getaway

Situated on Easton's Point, brand new ocean front tiny house looks across to Mansion Row with access to a rocky beach for lounging, swimming, or fishing. The property is close to downtown Newport & ideally located between three beaches. The cozy unit has a queen bed, full bath & kitchenette with coffee maker, fridge, and toaster oven. There is a small deck with ocean views, access to ocean front, outdoor shower and off street parking. We provide beach chairs, a beach umbrella and towels.

Top guest favourite
Guest suite in Middletown
4.95 out of 5 average rating, 362 reviews

Traveler's Guest Nest, special winter rates

Off-Season Special – Cozy Coastal Getaway Near Newport Escape the crowds and experience Newport in its quiet season. Our private studio offers peace, comfort, and easy access to the area’s best trails and beaches, just 3 miles from downtown. Perfect for a weekend getaway, nature walks, or a cozy couple’s retreat. Features: • Private entrance & patio • Easy parking • Quiet+safe Special off-season rates for fall and winter stays. A perfect little escape by the sea, without the Newport prices.

Top guest favourite
A garden archway frames a stone pathway leading to a wooden deck and outdoor seating area. Brightly colored red patio umbrellas provide shade for the dining set, while well-maintained greenery and flowers enhance the inviting atmosphere of the private outdoor space.
Guest suite in South Kingstown
4.96 out of 5 average rating, 205 reviews

Sunny Wakefield studio apartment

Attached to a family home but its own private space—including a private entrance, dedicated parking space, small deck, and lawn area with seating—this sunny studio is in the walkable heart of Wakefield, near URI, beaches, Newport, bike path. Queen bed; queen sleeper couch; best suited to 2 adults (the sleeper couch works best for children). Fridge, micro, coffee, grill (no oven). Allergy friendly: Free & Clear laundry products; no pets. Self check-in. Automatic discount for longer stays.

Top guest favourite
A lush green yard is framed by a flowering tree and manicured bushes, leading to a scenic view of the water. A series of stone steps creates a pathway, with the tranquil cove visible in the background under a partly cloudy sky.
Guest house in Portsmouth
4.94 out of 5 average rating, 114 reviews

Blue Bill Bungalow-Waterfront year round studio

A room with a view! Unwind and relax in your private waterfront guest suite located in a separate building on our property. Whether you're here to explore or just for a change of scenery....we believe you will truly enjoy your stay. Enjoy gazing at the water in your backyard, take a stroll down to the beach or walk to several local eateries. Whether you are in the mood for burgers and wings, surf and turf, or just want to grab a drink, Island Park has it all! Gov't ID required.

Guest favourite
The bedroom features a spacious bed with a white headboard set against warm beige walls. A bedside lamp provides soft illumination. A folded gray blanket is placed on the bed, while a dresser adds storage space. Natural light filters through curtains, enhancing the serene setting.
Flat in Middletown
4.88 out of 5 average rating, 229 reviews

Stay At Merhalla!

Welcome to Merhalla! Located minutes to downtown Newport and Broadway, 1.6 miles to the Naval War College. Everything you need for your Island vacation is within 2 miles! You will have a 1,000 sq ft open floor plan apt decorated with original, local art. The open concept layout has a private bedroom with an additional open air suite. I would love to share recommendations for some great spots, and want to make your stay the best on the island! State Registered: RE.00672-STR

Top guest favourite
A bright living room features a navy futon and a light-colored armchair, offering a cozy seating arrangement. Natural light filters through two white-curtained windows, illuminating the warm wooden floor. A simple white coffee table stands at the center, enhancing the inviting space.
Home in Middletown
4.97 out of 5 average rating, 116 reviews

Settle Inn-Cozy newly renovated house near beaches

Quaint, restful 1950's cottage located btwn two beaches within 2 miles. Located 1 mile from historic Newport. Two parking spaces on premises. Centrally located near restaurants, bars, grocery stores, breweries, and vineyards. Comfortable queen bed on level 2, full bathroom, fully equipped kitchen, grill, outdoor sitting & dining, air conditioners, washer & dryer, WIFI. Beaches chairs & towels available. Perfect for romantic couples getaway. Sorry, no pets.

Popular amenities for Middletown family-friendly rentals

When is the best time to visit Middletown?

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Avg. price$345 SGD$346 SGD$372 SGD$450 SGD$553 SGD$621 SGD$739 SGD$757 SGD$621 SGD$495 SGD$396 SGD$379 SGD
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Quick stats about holiday rentals that are family-friendly in Middletown

  • Total holiday rentals

    Explore 940 holiday rentals in Middletown

  • Nightly prices starting at

    Middletown holiday rentals start at $90 SGD per night before taxes and fees

  • Verified guest reviews

    Over 43,220 verified reviews to help you choose

  • Pet-friendly holiday rentals

    Find 260 rentals that welcome pets

  • Holiday rentals with a pool

    220 properties feature pools

  • Rentals with dedicated workspaces

    500 properties have a dedicated workspace

  • Wifi availability

    940 of Middletown holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Middletown rentals

  • 4.9 Average rating

    Middletown stays are highly rated by guests – averaging 4.9 out of 5!

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