Vacation rentals in Deep Pond

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Deep Pond

Guests agree: these stays are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Superhost

Home in Milford

4.92 out of 5 average rating, 26 reviews

Light-filled Beach House Steps from the Sand

Located in prime Bayview Beach, a one min stroll to the sandiest beach in Milford. Two floors with private patio. Main level: half-bath, Cooks kitchen with a 6 person dining area, living room with flatscreen. Upstairs: master w/king size bed & en-suite bath, kids bedroom w/ bunkbed, another full bath w/ tub. 3rd bedroom with queen bed and trundle twin. If you want a get-a-way from the city, or just an escape then come to this tucked-away home. Enjoy all that this coastline gem has to offer.

Superhost

Home in West Haven

4.79 out of 5 average rating, 43 reviews

Beachside Retreat

***Brand new to Airbnb, the Beachside Retreat is perfect for a quick getaway or a longer short term stay. Gorgeously renovated home has 4 spacious bedrooms, living room & dining room large enough to entertain and kitchen perfect for making those home-away-from-home meals. Across the street from the beach, wake up to stunning sunrises with your morning coffee or relax on the wrap around porch and watch the sunset. With walking trails, restaurants and shops close by you never have to go far.

Top guest favorite

Home in Northport

4.94 out of 5 average rating, 114 reviews

Cool pad, Private Rms, Walk to village, Wtr view

Beautiful pad on a tranquil street and walkable neighborhood. 5-10 minute walk to the village and 2-minute walk to the cliffs overlooking the bay and sound. Water view from one bedroom, great outdoor yard - very private. Updated amenities, marble bathroom, cozy indoor living area and very comfortable beds. The rental space is private and is the entire first floor of the home. The home is a two-story duplex with a shared entrance and private locking doors to each space. Wonderful location.

Superhost

Home in Baldwin

4.85 out of 5 average rating, 133 reviews

Clarissa's Paradise

RESERVE NOW: This ideally located five-bedroom totally renovated home is the perfect spot for a family fun vacation. Located within walking distance of the well known playground and spray ground. The home features a spacious patio, central air conditioning, baseboard heating, WiFi, and Cable tv. The open layout provides perfect gathering spaces for your family, and all bedrooms are spacious and comfortably appointed. 4 full bathrooms . Sleeps 10. PLEASE NO PARTIES ARE STRICKLY PROHIBITED

Top guest favorite

Home in Ocean Beach

5 out of 5 average rating, 43 reviews

Sunny Spacious Pet Friendly Steps from the Beach

This ideally located four-bedroom home is the perfect spot for your family's vacation. The home features a spacious deck, central air conditioning, WiFi, 4 Smart TV's, a Sonos sound system and YouTube TV. The open layout provides perfect gathering spaces for your family, and all bedrooms are spacious and comfortably appointed. There are 2 full bathrooms as well as an outdoor shower. Fully equipped including beach chairs, towels, 5 bikes, 2 wagons and beach toys for the kids. Sleeps 10.

Superhost

Guest suite in Branford

4.9 out of 5 average rating, 99 reviews

Granite Bay Getaway - Private Studio Apartment

Enjoy Long Island Sound in this cozy getaway. Three block walk to shore. Quiet residential neighborhood. Private deck with lovely afternoon light. Private entrance. Fully equipped eat in kitchen. Picturesque shoreline town of Branford. Many wonderful restaurants, 2 within walking distance. Land trust hiking trails at end of street. Ten minutes to New Haven, Yale & Avelo airport. Train station 2 miles away with connections to New York City and Boston. ½ mile from CT Hospice.

Guest favorite

Home in Mastic

4.88 out of 5 average rating, 102 reviews

Cozy home. Comfy living

The whole group will enjoy access to everything from this centrally located home. three comfy bedroom, two bathrooms, large living room, dining and kitchen. close to the beach, nature reserved, kayaking, sky diving and Tanger outlet mall, restaurant and all the fast food located nearby. long island vast array of winery and farms stand etc. Guest is expected to follow house rules. 15 mins after check out time is given after that fees will incur at nightly rate

Guest favorite

Houseboat in Riverhead

5 out of 5 average rating, 11 reviews

Peconic River Boatel

Perfectly updated nautical houseboat situated on the scenic Peconic River. Featuring two picturesque bedrooms, a full service eat-in kitchen and a living room with panoramic river view. Enjoy your morning coffee on the outside deck while taking in the sunrise. This historic waterfront town was named to Forbes Advisor’s “Best Places to Travel in 2023” — one of just 11 U.S. destinations on this year’s list. A must see for adventurers and families alike!

Superhost

Home in Hampton Bays

4.82 out of 5 average rating, 68 reviews

Spacious Hamptons Oasis | Perfect for Families

Escape to our stunning year-round retreat in Hampton Bays' Red Creek area. With over an acre of lush land, our charming residence offers unparalleled serenity and tranquility just minutes from local bay, beaches, and wineries. Ideal for family fun, friend retreats, and exquisite dining in the Hamptons. For off-season activities, explore wineries, animal feeding farms, apple and pumpkin picking, breweries, and more. Book now for your dream getaway!

Superhost

Home in Shelter Island

4.9 out of 5 average rating, 115 reviews

There's a Beach Getaway!

Welcome to our family-friendly oasis just two blocks from beautiful beaches! Our house offers an open space living area, an expansive yard, fire pits, and a basement with a playroom and workout area. Enjoy our quiet neighborhood. We provide kid-friendly toys, beach gear, bicycles, and more. Sleeps six, with additional options available for larger parties. Cleaning fees for winter stays are 0$.

Top guest favorite

Home in Greenport

4.98 out of 5 average rating, 179 reviews

Greenport Village walking distance to all

Large spacious home in the heart of wine country. Roomy den for relaxing after the wineries. Screened in patio for al fresco dining and enjoying the spacious yard. Hot tub operational year round! Strong, fast wifi with multiple extenders. Message me with any questions or for special offers on 4/5 day stays or midweek 2/3 night specials.