Family-friendly vacation rentals in Milford

4.95 out of 5 average rating, 146 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!

FamilyIndoor spacesAmenities

4.97 out of 5 average rating, 640 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 spacesKitchenDecor

4.99 out of 5 average rating, 178 reviews

3BR Modern Cottage | Walk 2 Beach & Tyde 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, 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!

KitchenIndoor spacesCondition

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.

4.89 out of 5 average rating, 108 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.

FamilyKitchenBeach

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, 155 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.

Indoor spacesFamilyOutdoor spaces

4.94 out of 5 average rating, 188 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.

KitchenIndoor spacesCleanliness

An aerial view captures the surrounding residential neighborhood with close proximity to Long Island Sound. The property is highlighted in a circular outline, showcasing its location relative to nearby homes and the shoreline.

4.98 out of 5 average rating, 123 reviews

2 Bedroom with sweeping views of Long Island Sound

Entire 1st floor apartment with private entrance. A spacious layout with spectacular views of Long Island Sound from your private deck. Convenient location; minutes to downtown Milford, train station, beaches, restaurants, and shopping. 15 minutes to Yale and famous New Haven landmarks. Walking distance to local restaurants, beaches, and an ocean-side playground. Public Beach: 7 minute walk - 0.4 mi Restaurants: 6 minute walk - 0.3 mi Playground: 2 minute walk - 250' *NO SMOKING*

FamilyKitchenCheck-in

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!

KitchenIndoor spacesNearby

4.99 out of 5 average rating, 106 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.

KitchenIndoor spacesCheck-in

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, 413 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.

KitchenFamilyOutdoor spaces

4.94 out of 5 average rating, 145 reviews

Oceanfront Beach House w/ Private 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.

KitchenFamilyAccuracy

4.98 out of 5 average rating, 156 reviews

Fully renovated/Walk to water & shops/fenced yard!

*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

KitchenIndoor spacesView

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, 236 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

FamilyKitchenAccess

4.96 out of 5 average rating, 142 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

KitchenIndoor spacesParks

Superhost

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

4.88 out of 5 average rating, 128 reviews

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

FamilyIndoor spacesLocation

4.95 out of 5 average rating, 208 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

Indoor spacesKitchenOutdoor spaces

4.96 out of 5 average rating, 402 reviews

Cabin in New Fairfield

Little Lake Cabin— Lake Access, Hot Tub & Kayaks

KitchenFamilyQuiet

4.99 out of 5 average rating, 179 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

FamilyKitchenWalkability

4.96 out of 5 average rating, 118 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.

KitchenFamilyHot tub

Superhost

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

4.94 out of 5 average rating, 120 reviews

OCEAN COAST LUXURY BEACH HOUSE/45 min to NYC

FamilyIndoor spacesQuiet

Family- and pet-friendly home rentals

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.

5.0 out of 5 average rating, 124 reviews

Walnut Beach Escape Fenced Oasis Yard

Indoor spacesFamilyPets

4.96 out of 5 average rating, 137 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

FamilyIndoor spacesBathroom

4.99 out of 5 average rating, 178 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

Indoor spacesKitchenLaundry

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, 155 reviews

SILVER SANDS BEACH COTTAGE MILFORD NEAR YALE/TRAIN

Indoor spacesKitchenSleep quality

4.98 out of 5 average rating, 228 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

Indoor spacesKitchenDecor

Superhost

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

4.84 out of 5 average rating, 172 reviews

Westshore Luxury

FamilyKitchenBeach

4.93 out of 5 average rating, 288 reviews

Loft in Southport

Historic Loft, Co-Work, River View

FamilyKitchenAccess

4.99 out of 5 average rating, 117 reviews

Home in Fairfield

Renovated Cape Near beach, with Fire Pit and BBQ

KitchenIndoor spacesLocation

Family-friendly home rentals with a pool

4.98 out of 5 average rating, 159 reviews

Apartment in Milford

The Pond Mill Retreat w/ 2 Bdrms & Pool

FamilyKitchenValue

4.97 out of 5 average rating, 117 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

FamilyKitchenDecor

4.98 out of 5 average rating, 265 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

KitchenIndoor spacesQuiet

4.98 out of 5 average rating, 112 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 spacesKitchenLayout

4.97 out of 5 average rating, 213 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

FamilyKitchenBiking

4.96 out of 5 average rating, 269 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

KitchenIndoor spacesPets

4.93 out of 5 average rating, 84 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

FamilyIndoor spacesPets