Family-friendly holiday rentals in Milford

4.95 out of 5 average rating, 192 reviews

A spacious studio layout includes a cozy queen bed adorned with a geometric quilt. Nearby, a comfortable seating area features a patterned sofa and a green chair. Natural light flows through large windows adorned with bamboo shades, illuminating the warm wood floor.

Apartment in Milford

The Boathouse, private downtown Harborside suite

The Boathouse is a detached one bedroom studio apartment situated behind our home in the heart of Historic downtown Milford. Through a private entrance you will discover a thoughtfully furnished bedroom (queen bed & pull out couch), dining room, full kitchen & bath. It is ideally suited for a couple/small family looking for a memorable beachtown getaway. Walk, rent bikes/kayaks, shop, dine, enjoy art, music, or a day at the beach… our quintessential New England seaside town is sure to charm you!

5 out of 5 average rating, 129 reviews

Feb/Mar longer stays avail! Inquire! New Firepit!

*Feb and Mar available for longer stays!Inquire!* *Brand New Major Renovation in 2023* • Fully renovated, designer beach house • Steps away from quaint downtown •1 block from water •Walk to beach, restaurants, coffee, ice cream, deli & convenience store, liquor and more... • Luxe, white, 100% cotton sheets & fluffy duvets •FULLY FENCED backyard with outdoor seating, BBQ grill, & fire pit .Easy drive to Sacred Heart, Fairfield, & Yale .STEPS to Tyde wedding venue .Fiber internet for fast speed

4.97 out of 5 average rating, 613 reviews

An expansive patio extends towards the shimmering waters of Long Island Sound, featuring lounge chairs and a dining table with an umbrella. Decorative planters and lanterns are arranged along the patio edge, complementing the serene waterfront view.

Apartment in Milford

Water front studio apartment with fireplace.

This is a beautifully appointed studio apartment located off the patio level of a water front home. Guests enjoy a large private patio over looking gorgeous sweeping views of Long Island Sound. A private entrance and off street parking. The amazing views and amenities make this space the perfect romantic getaway! Close to I95 and Metro North railroad. Ten minutes to great dining in downtown Milford. A true waterfront oasis! Come and experience this beautiful retreat! You won't be disappointed!

4.95 out of 5 average rating, 329 reviews

An open living space features a bright white interior with large windows allowing natural light. Seating includes a plush sofa and wicker chairs. A modern kitchen with stainless steel appliances is visible. The dining area showcases a table for six, enhancing a communal atmosphere.

Bungalow in Woodmont

Fall Sale! Cozy Bungalow/Walk2Beach/Pet-friendly

Welcome to the Beach Bungalow, completely remodeled to the studs in '21! This Woodmont by the Sea home is a 3 block stroll to Anchor Beach & the walkway along beautiful Beach Ave. The home offers a modern kitchen, dining for 6, private back porch & outdoor shower. This +775sf bungalow has a driveway & on-street pkg. It's located in a charming coastal town, walking distance to restaurants, grocery store & Robert Treat Farm and is 2 mi to I95, 10 mi to Yale/New Haven...and mins to breweries.

A vibrant sunset fills the sky with hues of pink, orange, and purple, reflecting on the tranquil water. Silhouettes of two birdhouses are visible on posts in the foreground, framed by lush vegetation along the shore.

4.98 out of 5 average rating, 138 reviews

3 Bedroom Beach House with Hot Tub!

Enjoy breathtaking sunset views in our spacious beach house while dining or relaxing in the hot tub. Snuggle up in front of the fireplace while watching a movie on the frame TV. Wake up in the master suite to spectacular marsh views while listening to birds from the Audubon Society. Steps to a white sand beach, heated bathroom floors, luxury bathrobes, linens, and organic mattresses. 6-bikes for exploring. A true resort-like experience with a chef's kitchen making a home away from home.

4.98 out of 5 average rating, 135 reviews

Apartment in Milford

The Pond Mill Retreat w/ 2 Bdrms & Pool

Catch up on a little work or simply unwind. Everything is waiting for you in this cozy, yet functional space surrounded by a beautiful wooded area with pond. Your private entrance accommodations include a finished, walk-out lower-level apartment (~730 sq ft) containing thoughtfully appointed bedrooms, living room, kitchen, and full bathroom. Experience solitude while enjoying the convenience to Rt 15, I-95, & Boston Post Rd destinations. And if you require assistance, we live right upstairs.

4.93 out of 5 average rating, 169 reviews

A serene waterfront view is presented, showcasing calm waters reflecting a soft pink sky. Lush green grasses frame the foreground, while a tree line marks the horizon, creating a tranquil landscape. A few ducks can be seen gently floating on the water.

Loft in Milford

Lovely water front lower-level loft, free parking

This unique centrally located water front loft is located on the second Gulf Pond 1.5 miles from historic Milford center buzzing with water front restaurants and downtown shopping. This one bedroom, one bath, has a private entrance and free off street parking. Outdoor patio & grill with kitchenette, enjoy a waterfront view throughout the 400 sq ft space. Close to I-95, the Merrit Parkway, and Milford train station. Explore 17 miles of beaches in this New England town by bike, kayak, or foot.

Two wicker chairs with patterned cushions are positioned beside a large window, offering a panoramic view of the sandy beach and ocean. The serene landscape includes gentle waves and distant beachgoers, framed by a bright sky.

4.99 out of 5 average rating, 146 reviews

Serene Waterfront Retreat - 400 ft Private Beach!

Welcome to a slice of waterfront heaven! Located on Milford's Cedar Beach, this newly renovated 3 bedroom / 1.5 bath home features over 400 feet of private beach. Enjoy breakfast prepared in the Chef's kitchen while watching one of the most radiant sunrises you will ever see. Stunning views from every room in the house. Wade into Long Island Sound with your own private beach. Located 3 doors down from the CT Audubon Society, known for its views & wildlife. We can't wait to host you!

4.99 out of 5 average rating, 151 reviews

A cozy bedroom features a spacious bed adorned with a textured neutral blanket and decorative pillows. Two bedside tables flank the bed, holding matching cups and a small vase of flowers. Natural light filters through the window, accentuating the warm wood floor and soft, light-colored decor.

Cottage in Milford

3BD Modern Cottage | Walk 2 Beach + Tyde Wed Venue

Walking distance from Walnut Beach and Tyde Wedding Venue! Stay at this cozy 3-bedroom, 1-bath beach cottage in the heart of Walnut Beach. Perfect for family vacations, wedding guests, or Yale visitors, our modern farmhouse-style home features a full kitchen, a private backyard with a fire pit, and peaceful coastal vibes. Walk to the sand, celebrate at Tyde, enjoy coffee on the porch, and end the day by the fire. Comfort, style, and location — all in one unforgettable stay!

A two-story oceanfront home features a light gray exterior with large windows and a turquoise front door. A spacious ground level is accessible via white railings, leading to an outdoor sitting area. The serene beach and water views are visible in the background.

4.95 out of 5 average rating, 127 reviews

Oceanfront Retreat with Hot Tub

Escape to this luxurious 4-bedroom, 2.5-bath oceanfront home on the stunning Long Island Sound. Enjoy direct beach access, a private hot tub, and a fully equipped patio with a gas grill and dining area. Perfect for families or groups, this retreat offers breathtaking views, a full kitchen, arcade games, and modern amenities. Located minutes from restaurants and shops, it’s ideal for relaxation or adventure. Book now for a perfect blend of comfort and coastal charm.

4.92 out of 5 average rating, 334 reviews

A cozy living area features mid-century modern furniture, including an orange armchair and a sleek glass coffee table. A gallery wall displays various artworks, complemented by natural light from two windows. A small dining area with a round table and four chairs contributes to the inviting layout.

Guesthouse in Westville

Square6ix Stylish Guesthouse in Westville

Inviting, eclectic, and completely private, this single family stand-alone guest house is an intimate and engaging haven. A serene private guesthouse perfect for couples, creatives, and travelers. Stylishly decorated with modern amenities, this space is a cozy retreat just a short walk to Westville Village and Edgewood Park. Ideal for weekend getaways, local visitors, or professionals seeking a quiet base with fast WiFi and free parking.

4.93 out of 5 average rating, 137 reviews

The exterior of a beach cottage is shown, featuring light-colored siding and blue shutters. A white railing surrounds a small porch, leading to a front door. Lush greenery and a few decorative elements enhance the inviting appearance of the home.

Cottage in Milford

SILVER SANDS BEACH COTTAGE MILFORD NEAR YALE/TRAIN

Peaceful Classic1920s Milford beach cottage steps from Silver Sands Beach & boardwalk. Blending coastal charm with modern comfort, it’s perfect for vacations, remote work, or longer stays. Walk to downtown shops, restaurants, and train. Ideal for Yale visitors, travel nurses, or weekend getaways. Enjoy a private, pet friendly retreat surrounded by nature yet close to New Haven, NYC, and Connecticut’s best shoreline attractions

Popular amenities for Milford family-friendly rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.95 out of 5 average rating, 191 reviews

A spacious pool area is framed by well-maintained greenery and flowering plants. Two large umbrellas provide shade over lounge chairs beside a sparkling pool, with expansive coastal views and a serene landscape of grasses and trees beyond.

Cottage in Guilford

Luxury cottage by the sea with hot tub and pool

4.94 out of 5 average rating, 120 reviews

Sailboats glide across a calm blue sea, with distant shorelines visible under a clear sky. The tranquil waters reflect shades of blue, creating a serene nautical setting that accentuates the beauty of the surrounding landscape.

Home in Shippan Point

OCEAN COAST LUXURY BEACH HOUSE/45 min to NYC

4.92 out of 5 average rating, 110 reviews

Home in Bedford

Bedford Paradise Getaway | Hot Tub | Town Center

4.96 out of 5 average rating, 369 reviews

Cabin in New Fairfield

Lake Cabin with Hot Tub, Fire pit and Kayaks

4.9 out of 5 average rating, 128 reviews

A cozy living area is furnished with two armchairs featuring floral patterns and colorful cushions. A wooden coffee table rests on an area rug, and a brick fireplace is situated beneath a wall-mounted clock. Large windows allow natural light to illuminate the space.

Apartment in Brewster

The Hideaway

4.96 out of 5 average rating, 116 reviews

A spacious living area features a large, comfortable sofa facing a stone fireplace with a modern television mounted above it. A skylight allows natural light to brighten the room, and an open kitchen is visible in the background with sleek cabinetry and barstool seating.

Guesthouse in Guilford

Guilford Lakes Cottage, with hot tub and fire pit.

4.88 out of 5 average rating, 145 reviews

A comfortable living space is presented, combining a light-colored sofa and a larger grey sectional couch. A wooden coffee table sits centrally, with artwork displayed on the wall above. Soft lighting is provided by overhead fans, enhancing the cozy atmosphere.

Guest suite in Waterbury

Private cozy getaway

4.95 out of 5 average rating, 126 reviews

A vibrant sunset reflects on calm waters, with shades of orange and purple illuminating the sky. Silhouettes of small boats are visible along the sandy shoreline, while gentle waves create a serene atmosphere. The scene offers a tranquil view of Long Island Sound at dusk.

Home in East Shore

Beach Haven - waterfront, near Yale, sunsets

Family- and pet-friendly home rentals

4.95 out of 5 average rating, 333 reviews

A spacious bedroom features a large bed with crisp white linens, surrounded by vibrant artwork and colorful cabinetry. Warm wood paneling lines the ceiling, and two bedside lamps provide soft illumination, contributing to a bright and inviting environment.

Apartment in Southport

2BR Flat above Historic Cider Mill

5 out of 5 average rating, 159 reviews

Home in North Haven

Luxury Stay in Expansive Historical Home

4.89 out of 5 average rating, 137 reviews

A corner of the apartment features unique hand-tinted windows that create colorful reflections. A cozy armchair sits beside a fireplace, surrounded by potted plants. The space is complemented by a woven area rug and a light-colored bed with a simple texture.

Apartment in Bridgeport

Stylish Sheek Loft Ricport Studio 2, Downtown

Place to stay in Fair Haven Heights

A view from the backyard showcases the Quinnipiac River with a fishing boat navigating the water. East Rock is visible in the background, framed by lush trees. Two red Adirondack chairs are positioned on the green grass, inviting relaxation by the riverside.

4.95 out of 5 average rating, 145 reviews

“Old Shell Fisherman’s Q River Speakeasy”

4.99 out of 5 average rating, 119 reviews

A cottage nestled in a lush green setting is highlighted, surrounded by trees. The lawn is spacious and well-maintained, featuring a hammock between two trees. The structure showcases a simple facade with light blue siding, white window frames, and a chimney.

Home in Newtown

Comfortable home away from home- near everything

4.99 out of 5 average rating, 134 reviews

A charming red exterior features white window treatments and a rustic door. Decor elements include a wooden wagon wheel and an artistic iron wall hanging. Lush greenery and flowers are visible in the garden area, enhancing the welcoming entryway.

Guesthouse in Newtown

Guest Suite at Wisteria Gardens

4.99 out of 5 average rating, 145 reviews

A timber-style cottage is surrounded by landscaping featuring stones and low shrubs. A spacious deck with white railings leads to a welcoming entrance. Light-colored siding and multiple windows enhance the two-story structure, set against a backdrop of trees and open land.

Home in Southbury

The Cottage at Cedar Spring Farm

4.8 out of 5 average rating, 255 reviews

A sunlit bedroom features a spacious bed topped with a neutral blanket and decorative pillows. Large windows allow natural light to filter in, casting soft shadows across the room. A wooden dresser with plants and framed artwork adds warmth to the inviting space.

Guest suite in Wilton

Guest suite with private enter

Family-friendly home rentals with a pool

Apartment in Harbor Point

An open-concept living area is presented, featuring a modern TV stand with a television, a circular dining table, and sleek kitchen appliances. Neutral tones blend with wooden flooring, while a decorative area rug adds texture. The space is well-lit by natural light from nearby windows.

4.75 out of 5 average rating, 4 reviews

Luxury Apt In Harbor Point with Balcony

4.97 out of 5 average rating, 209 reviews

A serene pool area features a clear blue in-ground pool surrounded by lounge chairs with red cushions. A vibrant hibiscus flower adds a splash of color, and a slide is visible for added fun. The area is enclosed for safety.

Guest suite in Monroe

Garden Level Suite with Beautiful Pool

5 out of 5 average rating, 45 reviews

Home in Redding

Renovated Retreat with Heated Pool

4.95 out of 5 average rating, 262 reviews

A spacious outdoor pool is surrounded by natural greenery, featuring a stone patio and a diving board. A covered lounge area with large windows overlooks the pool, providing a serene setting for relaxation and leisure.

Home in Stamford

Midcentury Modern ZenHouse Sculptor Studio

4.92 out of 5 average rating, 61 reviews

A bright sleeping area features a spacious bed adorned with various pillows in shades of gray and white. Two table lamps flank the bed, providing soft illumination. The warm wall color enhances the cozy ambiance of the room.

Apartment in Trumbull

Cozy studio unit

4.98 out of 5 average rating, 106 reviews

A spacious loft area features high ceilings with exposed beams and warm wooden accents. Two comfortable leather sofas face a central ottoman, surrounded by artwork and decor. Natural light floods in through large windows, highlighting the rich wooden floors and a decorative rug.

Cottage in Black Rock

Spacious Cottage Loft

5 out of 5 average rating, 176 reviews

A serene outdoor space features a heated saltwater pool surrounded by a spacious lawn. Sun loungers are positioned near an umbrella for shade, with lush greenery and a wooden fence creating a tranquil backdrop.

Home in Pound Ridge

Peaceful Light-Filled Guesthouse 1 Hour From NYC