Vacation rentals in Long Island Sound

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Top-rated vacation rentals in Long Island Sound

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Top guest favorite

A serene view of the shoreline at dusk, showcasing gentle waves lapping against the sandy beach. A wooden railing leads down the steps to the water's edge, with smooth stones lining the path. A remote island can be seen in the distance, against a softly colored sky.

Apartment in Milford

4.95 out of 5 average rating, 161 reviews

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!

Top guest favorite

A modern living space features a comfortable sofa, a circular coffee table, and a television unit. Large sliding glass doors create a seamless view of the outdoors, with natural greenery visible beyond the private deck. Soft natural light fills the room, enhancing its inviting ambiance.

Guesthouse in Guilford

4.99 out of 5 average rating, 496 reviews

Get Back to Nature at a Modern Wood Clad Getaway

SPRING IS HERE--Glorious spring birds. Come and enjoy a wonderful time in our guest house--warm days, cool nights. You can Hike on the trails, and Stroll along the ocean. Ospreys; hawks; cardinals, blue jays, bluebirds, gold finches and more are here year round. Great places to shop and eat or catch a show at one of New Haven’s renowned museums or broadway theatres or relax. Enjoy! We want you to have a relaxing stay with us, free from worry. We are located in a private area, away from public.

Top guest favorite

A functional laundry area is showcased, featuring a washer and dryer side by side. The space is well-organized, with a metal shelving unit positioned above, storing cleaning supplies. Exposed utility lines and concrete walls provide a utilitarian background, contributing to the overall practicality of the area.

Apartment in Milford

4.98 out of 5 average rating, 104 reviews

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.

Guest favorite

A serene view is captured through a large window, framing a tranquil lake surrounded by lush greenery. A potted plant is positioned in the foreground, while a wooden chair sits on the patio outside. Soft curtains drape, accentuating the bright, sunny atmosphere.

Loft in Milford

4.94 out of 5 average rating, 144 reviews

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.

Superhost

A private yard features a small patio area with white folding tables and chairs surrounded by lush greenery. Sunlight filters through the trees, creating a serene outdoor space for relaxation or al fresco dining.

Apartment in Ridge

4.74 out of 5 average rating, 163 reviews

The Silver Pine Cone

Welcome to the hamlet of Ridge. The gateway to Long Islands many treasures. Whether you are venturing out to the North Fork wineries or a scenic drive on the south shore beaches on your way to the Hamptons. A beautiful cozy private (not a shared space) full one bedroom downstairs lower level apartment, living room w/full size sofa sleeper, kitchen/dining room, full bathroom and a completely separate yard with patio furniture exclusively for your use. Everything you need to enjoy your stay.

Top guest favorite

Home in Milford

4.99 out of 5 average rating, 111 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

Guest favorite

A calm beach scene at dusk is presented with soft hues of pink and blue in the sky. The sandy shore is visible, with a large rock positioned near the water's edge. Two signs marked 'PRIVATE BEACH' stand upright in the foreground.

Guest suite in Wading River

4.9 out of 5 average rating, 271 reviews

Beachy En Suite /Gateway to The North Fork

Adorable,quiet,clean, w private entrance, private bedroom and bathroom,breakfast nook and patio.We are located in a beach front town dubbed“Gateway to the North Fork”.Walking/driving directions to local beaches,15minute walk to our community beach,Wildwood StPk(.6mi away).Niks deli nearby.Minutes by car to wineries,breweries,farm stands,EastWind,TangerOutlets15min away,35min to Hamptons,Greenport!Hosts live in adjoining house.NoTV but Wifi is good so bring your device for entertainment.

Top guest favorite

The spacious living room is designed with modern décor, featuring a leather sofa and a glass coffee table. A large Roku TV is prominently displayed against the wall, and natural light filters in through a nearby window. A dining area with sleek barstools complements the space.

Apartment in Norwalk

5 out of 5 average rating, 15 reviews

The Design Studio Suite | 2 Beds | Spacious | Luxe

Private one bedroom apartment with modern decor offers everything you need for a short or long term stay. Space includes a full kitchen separate from studio area, & washer + dryer. Studio offers a Queen Sized bed, pull-out bed, workspace, 70 inch Roku Smart TV & hand painted artwork. The Location Less than two miles from Merritt Parkway, near I-95 & East Norwalk train station. One mile away from large shopping center and less than half a mile away from local convenience center.

Superhost

An outdoor seating area is illuminated by string lights and lanterns, creating a cozy atmosphere. Two chairs are positioned around a circular table on a gravel surface, surrounded by lush greenery and potted plants. A chiminea stands nearby, adding character to the inviting space.

Apartment in Rocky Point

4.72 out of 5 average rating, 192 reviews

Juniper Hollow

You are just a stone’s throw from the beach in this two-guest suit. Beach key provided! This indoor space measures 400 sf but you’ll find it well laid out with twice as much private outdoor space (for you warmer weather travelers). Older reviews are from 4 years ago and pre renovation, we are refreshed. Feel free to roam the rest of the 1/3 acre property of rolling hills, old growth trees, a hammock house, tree swings on the hill, and water views from the driveway.

Guest favorite

A welcoming sign stands prominently along the walkway, displaying the words 'Welcome to the RiverWalk.' Lush green trees frame the pathway, complemented by a clear blue sky, creating an inviting atmosphere for visitors exploring the area.

Apartment in Calverton

4.94 out of 5 average rating, 108 reviews

J&J's BnB Lovely, BR/Bath w/ Private Entrance!

Welcome to Jeanette and Jims Airbnb! We are avid travelers and look forward to hosting you on your trip to beautiful Long Island! Lovely, clean updated private room with private separate entrance and bathroom. Great location on a quiet wooded acre. 2 miles from Splish Splash. 3.6 miles from the Long Island Aquarium. 8.7 miles from Cupsogue Beach. 4.8 miles from Baiting Hollow Farm Vineyard. So much to do near by. Head easily to the north or south fork!

Guest favorite

A spacious beachfront property is showcased, featuring a well-maintained lawn and a patio area with outdoor seating. The ocean is visible in the background, providing serene water views. The home is characterized by its coastal architecture and nearby neighboring structures.

Home in Branford

4.97 out of 5 average rating, 34 reviews

Adorable Beach House on LI Sound

Beach House with incredible views of the Thimble Islands - 4 min walk to Restaurants including Lenny’s, Zagat award winner for fresh local seafood - 1 min walk to Bud’s Fish Market - 3 min walk to Indian Neck Liquor - 3 min drive to brewery w/ food trucks & music - 4 min drive to Branford Green w/ specialty stores, coffee & ice cream

Guest favorite

The image captures a nighttime view of a well-kept backyard featuring a swimming pool surrounded by a stone patio. Lush green plants and colorful flowers line the area, while string lights provide soft illumination. A few lounge chairs are positioned nearby, enhancing the outdoor setting.

Apartment in Rocky Point

4.94 out of 5 average rating, 156 reviews

North shore Guest Room.

This apartment is our guest room with outside private entrance and off street parking. Apartment has a refrigerator, microwave, coffee maker, and toaster oven. Queen bed and a twin pullout couch bed is provided. The place is appropriate for a short stay as an affordable alternative to hotel stay.

Vacation rentals for every style

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Cabins

Kick off your hiking boots at these rustic lodgings

Bungalows

Intimate homes. inviting architecture

Apartments

Convenient locations with everyday essentials

Popular amenities for Long Island Sound vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Long Island Sound

Top guest favorite

A balcony features four wooden chairs, two with soft cushions, surrounding a central glass table. Lush greenery is visible in the background, providing a serene atmosphere. Potted plants add a touch of nature to the space, inviting relaxation in a calm setting.

Private room in West Haven

4.93 out of 5 average rating, 181 reviews

Cozy bedroom near the beach.

MariusRating, 5 stars1 week ago

We only came to sleep basically for one night before we moved up north. But we felt very comfortable and had a very pleasant stay! Freddy welcomed us friendly and everything was nice and clean!

Guest favorite

Guesthouse in Middle Island

5 out of 5 average rating, 12 reviews

Private newly renovated apt

CharlotteRating, 5 stars6 days ago

Very clean and quiet, had all of the amenities we needed for a short weekend stay. Arielle was very friendly and accommodating. Parking and check in/out was easy. Nicely renovated space!

A well-lit bathroom features light blue patterned wallpaper, a sleek white door, and a vintage-style sink. A mirror with a decorative frame is mounted above the sink, while a towel holder and a cushioned bench add functional elements to the space.

Home in Bellport

5 out of 5 average rating, 4 reviews

Bellport Village Retreat

Dean And AnneRating, 5 stars1 month ago

Karen’s home was so beautiful, well decorated and comfortable. The home was very well equipped with everything we needed including high end amenities all throughout the home and a chefs kitchens dream. We have stayed in Airbnb’s in many parts of the country and the home far exceeded our expectations. On top of that Karen was a kind and responsive host. We really would give this host and home 10 stars if that was possible. Highly recommend that you book the home of you have the opportunity.

Guest favorite

A white shelving unit features neatly arranged, packaged slippers. Two gray slippers with a soft fabric surface are placed side by side, while a single black slipper with a patterned bottom is positioned on the left.

Home in Coram

4.88 out of 5 average rating, 8 reviews

Luxe Home Escape

CrystalRating, 5 stars2 weeks ago

Nerlly's space was exactly how she described it. Plenty of space for my family and I of 3. We had everything we needed for our stay and more. The basement unit was very clean upon arrival and Nerlly allowed us to check in early. It was very comfortable and peaceful. Her and her husband are so sweet and very attentive hosts! Our stay couldn't have been any better. Thank you so much for being awesome hosts! We would definitely recommend them and their home to anyone looking for a comfortable, clean and friendly stay.

Top guest favorite

A charming alleyway is lined with warm string lights, highlighting the entrance to South Lane Bistro. Colorful mums in orange and yellow pots complement the rustic decor. Brick pathways guide visitors through a quaint setting filled with greenery and inviting outdoor seating.

Home in Guilford

5 out of 5 average rating, 7 reviews

Mulberry Seaside Cottage

EmilyRating, 5 stars2 weeks ago

This home was exactly as described and pictured. The home is tastefully decorated and comes with everything you need. Not to mention the beautiful views, the easy walks to either beach, and bikes in the basement to explore the neighborhood. You will not be disappointed with Carol's place! Even with unpredictable weather we still had a great restful vacation! I would book here again!

Luxe

A bright living space features bamboo flooring, with an open layout that connects areas for relaxation and dining. Comfortable seating options include a white sofa and wooden chairs. Light streams through multiple windows, enhancing the tranquil ambiance, complemented by decorative artwork on the walls.

Home in East Quogue

5 out of 5 average rating, 6 reviews

Charming, Modern Hamptons Gem

EmilyRating, 5 stars4 weeks ago

We had a lovely stay at Christine’s for a family wedding at the Westhampton Country Club. Our family is from out of town and had my mother and our kids in tow. The property was quiet and peaceful. Its location close to town was perfect. The house itself was adorable, nicely furnished and very clean. My kids loved the toys in the kids room and the swingset. Couldn’t ask for more. Thank you Christine!

Top guest favorite

Stairs lead up to a light-filled door featuring a window, offering natural illumination. The wooden steps are complemented by fresh white walls, creating a clean aesthetic. A handrail is mounted for safety, and sunlight casts shadows on the floor.

Apartment in Fairfield

5 out of 5 average rating, 14 reviews

New & Modern Studio Apartment in Fairfield

Stephanie and BillRating, 5 stars1 week ago

We were very happy here, the place was spotless and had all the important amenities to be comfortable and feel at home. Hosts were very responsive and communicative which was much appreciated. Very convenient location for a visit with family/friends in Fairfield.

Top guest favorite

A garden area is visible, featuring lush greenery and colorful flowers. A decorative stone element stands prominently among the plants. The entrance of the cozy apartment is shown, leading to a wooden deck with railings, surrounded by vibrant plants and shrubs.

Apartment in East Haven

5 out of 5 average rating, 5 reviews

Unique & Cozy Apartment

StephanieRating, 5 stars1 week ago

I absolutely loved my stay at this adorable apartment! It was spotless and had every amenity you could possibly need — they really thought of everything. The location was a dream! Right next-door is the cutest little coffee shop (I went every morning), and we found the most charming Asian market nearby that made us feel like we were transported straight to Tokyo — the food was incredible. One of my favorite parts? The peaceful Zen Garden in the back. It’s private, beautifully maintained, and perfect for relaxing or snapping some great photos. We also saw bunnies and even deer during our stay — such a magical touch. The house itself was amazing — super comfortable, easy to settle into, and it worked perfectly with our crazy schedule and late hours. I truly can’t wait to come back to this area and specifically stay here again. It felt like a little hidden gem!

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Vacation rentals in Long Island Sound

Top-rated vacation rentals in Long Island Sound

Vacation rentals for every style

Popular amenities for Long Island Sound vacation rentals

Other great vacation rentals in Long Island Sound

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