Family-friendly vacation rentals in Milford

4.95 out of 5 average rating, 148 reviews

#2 Milford Beach (across street) Charles Isle 2BR

Welcome to your perfect Milford beachfront escape! This beautifully furnished 2-bedroom, 1-bath 2nd floor unit sits directly across from the beach, with beautiful water views. Just 100 yards from Silver Sands State Park, you’ll have easy access to its beaches, nature trails, and famous boardwalk. This unit offers beach gear, private yard for sunset dining, and proximity to Milford’s lively downtown. Whether here for a romantic getaway or family retreat, this spot offers relaxation or adventure!

FamilyKitchenParking

4.97 out of 5 average rating, 650 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!

Indoor spacesKitchenAccess

4.93 out of 5 average rating, 113 reviews

A spacious deck overlooks the shimmering waters of Long Island Sound, offering both lounge seating and a dining area. The railing lines the edge of the deck, enhancing views of the tranquil waves and bright blue sky, creating a serene waterfront atmosphere.

Home in East Haven

Luxury Beachfront Retreat - Modern Shoreline Villa

Welcome to luxury living and the peaceful beach vibes on Cosey Beach! Jutting out into Long Island Sound, guests will enjoy unparalleled waterfront living as waves break directly under your luxury vacation villa. Breathtaking sunrises and sunsets abound from the main living spaces and multiple decks. Descend to your private beach to use one of the provided kayaks or paddle boards, or wander down the street to family friendly fun, including splash pad, casual restaurants, and ice cream counter.

FamilyKitchenTV

A spacious deck offers a panoramic view of the beach and water, with sunlight reflecting off the surface. Colorful chairs are positioned for relaxation, while shadows created by the railing add depth to the scene. The sandy shore can be seen in the distance.

4.88 out of 5 average rating, 109 reviews

Cheerful 3 Bedroom Cottage with Fire Place

We are happy to still offer some dates for September. Come enjoy the solitude of the beach as the tide ebbs & flows. Reconnect with loved ones in this family-friendly place. Enjoy strolls on the beach located just out the back door or a sunset meal on the back porch. This wonderful cottage offers everything you will need during your stay. Including, comfortable beds, beach strolls and a bright upgraded kitchen with many amenities. The 3 bedrooms will fit up to 8 people comfortably.

Indoor spacesFamilyComfort

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.

4.97 out of 5 average rating, 158 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.

KitchenFamilyBeach

4.93 out of 5 average rating, 191 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.

KitchenFamilyOutdoor spaces

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.

4.93 out of 5 average rating, 157 reviews

SILVER SANDS BEACH COTTAGE MILFORD NEAR YALE/TRAIN

Classic 1920s beach cottage—spend your summer at the shore. Steps to a private neighborhood beach and Silver Sands State Park & boardwalk + walnut beach, this coastal retreat blends vintage charm with modern comfort—perfect for family vacations and girls’ weekends. Walk to downtown Milford Green, shops, restaurants, and the train to NYC for an easy getaway. Enjoy a private, pet-friendly escape surrounded by nature, yet close to New Haven, NYC, and Connecticut’s best shoreline attractions.

FamilyIndoor spacesCheck-in

4.99 out of 5 average rating, 180 reviews

3BR Cottage Walk to Beach and Tyde Wedding Venue

Walking distance from Walnut Beach and Tyde Wedding Venue! Stay at this cozy 3-bedroom (King, Queen + Twin), 1-bath beach cottage in the heart of Walnut Beach. Perfect for family vacations, wedding guests, or Yale visitors, the cottage features a full kitchen, private backyard, fire pit, and peaceful coastal vibes. Walk to the sand, celebrate at Tyde, enjoy coffee on the porch, and relax by the fire pit. Firewood is not provided. Comfort, style, and location — all in one unforgettable stay!

FamilyKitchenWalkability

An aerial view showcases a coastal neighborhood with homes situated along a sandy beach. Vibrant blue waters and marshlands surround the area, emphasizing its seaside location. The arrow points to the property's location within the community, illustrating proximity to the beach.

4.97 out of 5 average rating, 270 reviews

Designer Beach Retreat on Exclusive Cedar Beach

Welcome to your own slice of heaven! Enjoy dinner in your Chef's kitchen while watching one of the most radiant sunsets you will ever see. Stunning views from the private rear deck or snuggled on the couch inside the living room. Wade into Long Island Sound with semi-private beach access 250 feet away. The property is 5 doors down from the CT Audubon Society, known for its epic views and wildlife watching. The sunrises & sunsets are beautiful! 15 minutes to Yale. We can't wait to host you!

FamilyIndoor spacesCheck-in

A comfortable living room is featured, with a gray sofa and two wooden chairs positioned around a small, circular coffee table. Natural light filters through large windows, illuminating light-colored walls and warm wooden flooring.

4.99 out of 5 average rating, 192 reviews

The ARLO - Walk to Brewery & Restaurants

Newly remodeled and designed, The ARLO combines a seamless blend of luxury & comfort for your family. Walking distance to Dockside brewery & stand-out local restaurants, while only 1 mile from the beautiful Walnut Beach. Enjoy a thoughtful & comfortably designed living room, cook in the chef-style kitchen, indoor/outdoor living with a game room and fully-fenced yard. -Less than 2 minutes to The Tyde wedding venue. -15 min to Fairfield U & Sacred Heart -15 min to YALE -0.2 miles off I-95

FamilyIndoor spacesOutdoor spaces

4.99 out of 5 average rating, 108 reviews

A light-filled living space features two skylights allowing natural light to illuminate the wooden floors. A spacious sofa is accompanied by a small coffee table and a seating area is positioned beside a contemporary television. Potted plants add a touch of greenery to the room.

Guesthouse in Milford

The studio downtown

The studio is a new, private, quiet, and peaceful space. It is situated on the second floor of a detached garage with a private entrance. It is located in the historic center of town, within walking distance of the train station, bars, restaurants, and beach. It is ideal for a couple looking for a beach town getaway. The studio has a king-size bed, an eating area, a kitchenette with a fridge, a sink, a double induction cooktop, a seating area, and a bathroom with a rain shower.

Indoor spacesFamilyBiking

A welcoming living area features a comfortable couch and a textured ottoman, complemented by natural wood accents on the ceiling. Light fills the space from multiple windows, highlighting the hardwood floors and decorative stone wall that adds character to the room.

4.94 out of 5 average rating, 419 reviews

Summer Sale! CozyCottage/Pet-friendly/ WalktoBeach

Inspired by my Dad's wanderlust and love of sea & sand. Relax and unwind in this completely remodeled, stylish Cottage a block and a half from Long Island Sound and .9 mile to Walnut Beach - walk to coffee, pizza, lobster shack! We offer a modern kitchen, breakfast nook, dining area, natural stone wall, parking and W/D. Located in a charming coastal town - enjoy quiet neighborhood walks, coastal trails, boardwalk, breweries and restaurants. 15 min to Yale/New Haven, 65 mi to NYC.

Indoor spacesKitchenHiking

Popular amenities for Milford family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.96 out of 5 average rating, 241 reviews

A private hot tub is situated beneath a covered patio, surrounded by blooming azaleas. The inclined garden path leads to a charming wooden house featuring a slate roof, with warm sunlight illuminating the scene. Outdoor seating is available nearby.

Home in Stratford

Cozy Colonial - Private Hot Tub & Entire House

KitchenFamilyNearby

4.95 out of 5 average rating, 211 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

FamilyIndoor spacesWifi

4.99 out of 5 average rating, 181 reviews

The exterior view showcases a charming home surrounded by tall trees and autumn foliage. A circular wooden deck encircles a hot tub, providing an inviting outdoor space. The covered pergola offers shade, while bright flowers add color to the landscaped area.

Villa in New Haven

A Spacious 5BR Near Yale|Ideal For Groups&Family

FamilyKitchenCondition

4.96 out of 5 average rating, 146 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 New Haven

Beach Haven - waterfront, near Yale, sunsets

Indoor spacesKitchenLocation

4.88 out of 5 average rating, 130 reviews

A swim spa with dual zones is shown, featuring illuminated blue and red lights. The adjacent outdoor area includes a large screen displaying a sports event. Steam rises from the hot tub, creating a relaxing ambiance in the evening setting.

Home in Hamden

Sleeping Giant Stay/Swim Spa w/Tread/Tonal/Peleton

KitchenIndoor spacesSleep quality

4.96 out of 5 average rating, 406 reviews

Cabin in New Fairfield

Little Lake Cabin— Lake Access, Hot Tub & Kayaks

Indoor spacesFamilyQuiet

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 Stamford

OCEAN COAST LUXURY BEACH HOUSE/45 min to NYC

FamilyIndoor spacesHot tub

A spacious outdoor deck is furnished with a large sectional seating area, featuring soft cushions for comfort. A glass-top coffee table is positioned at the center. The view includes a glimpse of the nearby beach and coastal structures.

4.95 out of 5 average rating, 97 reviews

Modern Beach Getaway

FamilyKitchenParking

Family- and pet-friendly home rentals

4.82 out of 5 average rating, 260 reviews

A rustic cabin with green log siding is surrounded by tall trees. The front porch features two black chairs, and a storage trunk adds a practical touch. A decorative star and wall clock enhance the inviting exterior, while a garden area complements the natural setting.

Bungalow in Trumbull

Cozy, romantic cabin by the lake.

FamilyKitchenNearby

4.96 out of 5 average rating, 139 reviews

An outdoor seating area is presented with a comfortable couch adorned with colorful throw pillows. A small table features a decorative item, while a vibrant side table adds a pop of color. A patterned rug complements the space, surrounded by greenery.

Apartment in Milford

Downtown | Private balcony | Fast WiFi | King bed

KitchenFamilyLaundry

4.99 out of 5 average rating, 121 reviews

Home in Fairfield

Renovated Cape Near beach, with Fire Pit and BBQ

Indoor spacesFamilyWalkability

4.98 out of 5 average rating, 235 reviews

A serene view of the Long Island Sound showcases several sailboats gently drifting on the blue water. The scene is framed by a simple fence and grassy area, with a clear blue sky above, creating a peaceful coastal atmosphere.

Home in New Haven

WaterviewsTakeWedding pics,CollegeTours Yale&Beach

FamilyIndoor spacesAccuracy

4.83 out of 5 average rating, 182 reviews

The living room features a modern design with a curved green and orange sofa surrounding a light wood coffee table. A striking black fireplace provides a focal point against a light wall. A statue and decorative elements contribute to the welcoming ambience.

Home in West Haven

Westshore Luxury

KitchenIndoor spacesAir conditioning

An aerial view captures the coastal neighborhood, with a sandy beach and clear blue water. The vibrant homes line the shore, featuring varied architectural styles. Lush greenery borders the area, enhancing the sense of tranquility and charm typical of beachside living.

4.99 out of 5 average rating, 127 reviews

Walnut Beach Escape Fenced Oasis Yard

FamilyIndoor spacesBackyard

4.96 out of 5 average rating, 355 reviews

A rustic barn-style home features a wooden exterior with multiple large windows, enhancing natural light. A spacious elevated deck is surrounded by lush greenery, while an outdoor umbrella offers shade. The setting is serene, with a glimpse of the nearby brook and wooded area.

Home in Fairfield

Beautifully Restored Barn With New England Charm

KitchenIndoor spacesNearby

4.99 out of 5 average rating, 191 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

FamilyKitchenDecor

Family-friendly home rentals with a pool

4.98 out of 5 average rating, 164 reviews

Apartment in Milford

The Pond Mill Retreat w/ 2 Bdrms & Pool

FamilyIndoor spacesLaundry

4.97 out of 5 average rating, 119 reviews

A spacious bedroom is presented with a comfortable bed, layered in plush white linens and accented with dark pillows. A wooden dresser sits in front of a large window, allowing natural light to fill the room, while art decorates the walls.

Apartment in New Haven

King 1BR W/ Parking, Pool & Gym

KitchenFamilyAccess

4.97 out of 5 average rating, 214 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

FamilyIndoor spacesLong stay

4.98 out of 5 average rating, 266 reviews

An aerial view showcases the antique farm property set within a spacious landscape. Surrounding areas feature a mix of treed land and open fields. The main house, along with additional structures and a large yard, is visible alongside winding roads, emphasizing the rural setting.

Barn in Bethel

Escape to a Restored New England Antique Milk Barn

Indoor spacesFamilyNearby

4.98 out of 5 average rating, 114 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

Indoor spacesKitchenBathroom

4.92 out of 5 average rating, 91 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

KitchenIndoor spacesDecor

4.94 out of 5 average rating, 96 reviews

A well-maintained pool is surrounded by lush green grass, offering a relaxing outdoor space. Several lounge chairs are positioned around the pool area, and a light stone bench adds a comfortable seating option. Sunlight filters through the trees, enhancing the serene atmosphere.

Home in Redding

Lovely Country Retreat:

Indoor spacesFamilyAccuracy