Pet-friendly vacation rentals in Southold

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Top-rated pet-friendly home rentals in Southold

Guests agree: these pet-friendly homes are highly rated for location, cleanliness, and more.

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Guest favorite

Home in North Fork

4.91 out of 5 average rating, 104 reviews

Cozy Farmhouse Retreat in North Fork, NY

A 1905 farmhouse with modern touches, Arthur's Vineyard is a cozy 3-bed, 2-bath home in walking distance of Greenport village's beaches, marina, restaurants and boutiques. An open plan living area, breezy decor and a large landscaped backyard for spending relaxed summer days and nights with your family and friends, including the 4-legged ones. Walk to the train station/jitney or take a short drive to the wineries & farm stands of the North Fork. Recent updates: central heat/AC & new bathrooms.

Top guest favorite

Home in Old Saybrook

4.97 out of 5 average rating, 121 reviews

Year Round Beach House in Old Saybrook, CT.- Pets

Our Beautiful Home is Located in Saybrook Manor Association and only a short walk to the beach . We have 4 Bedrooms that can accomadate 8 people,pull out couch,2 bathrooms, a Dining Room,Kitchen, and Spacious Living room.Our Yard is fenced in for your privacy & pets.Our home comes with many ammenities such as movies,games,kayaks, Clamming &Crabbing tools,Bikes,Floats & Beach Chairs.We have a beautiful backyard to enjoy games,barbecue or just to relax & unwind.Enjoy our beautiful & quaint beach

Top guest favorite

Guesthouse in Hampton Bays

4.97 out of 5 average rating, 184 reviews

WELCOME TO THE LOVE SHACK BY THE SEA

Escape the city, work in nature! Totally private cottage with garden views , central air and heated floors. 1 mile from pristine beaches and center of town, LIRR, Hampton Jitney, 3 large grocery stores, Starbucks, organic market, shopping & restaurants. King bed, cable TV, refrigerator w/ice, microwave, outdoor grill, private yard, Perfect for couples, solo, 1-2 small kids. We welcome small dogs for a $100 fee. Please message us with the size and type. Working couple/owners in main house.

Guest favorite

Cabin in Rocky Point

4.89 out of 5 average rating, 484 reviews

Great little place just for a couple

The outdoor courtyard is especially nice and private-,with a fire pit, grill and comfortable chairs. It is a rustic location easy walking distance to North Shore Beach. If you want an ocean beach you can drive straight south for 20 minutes and reach Smiths Point State Park right on the ocean. The North Fork with its vineyards is a short drive and the Hamptons also only 30 minutes to West Hampton. You can fish, golf, walk among the wooded area and relax in peace. A pleasure. linen 100% cotton!

Guest favorite

Apartment in North Fork

4.94 out of 5 average rating, 94 reviews

Private 1st flr apt w/ patio 3 blocks from beach

We are centrally located in a quiet neighborhood within blocks from the heart of Greenport Village, Peconic Bay Beach, LIRR/Jitney, restaurants, shopping, Mitchell Park, and more! Explore local farms, wineries, breweries and all the North Fork has to offer. Beautifully furnished, ground floor apt with private entrance & patio area comfortably sleeps four, features a queen Tempur-Pedic mattress & convertible couch. Friendly, housetrained pets are welcome for an additional charge.

Top guest favorite

Apartment in Hampton Bays

4.96 out of 5 average rating, 380 reviews

Private & Cozy Cottage with short walk to beach!

Walking distance to Bay Beach & Rumba, & short drive to town & ocean. Quiet neighborhood, great for couples, King bed upstairs, bit of a steep staircase, so may not be suited for anyone with mobility challenges. Kayaks, paddle-boards, available to enjoy. Dog friendly with fenced in patio and doggy door. Private outdoor patio, with charcoal grill. A/C & Heat for year-round enjoyment. Easy to get in/out from the city. Close drive to visit Westhampton and Southampton Main Streets.

Top guest favorite

Home in North Fork

4.95 out of 5 average rating, 20 reviews

Charming Home in Village Center!

Enjoy all that Greenport has to offer by staying in the center of Greenport, less than 2 blocks from the carousel. Relax in the large fenced yard or screened in porch. Effortless walk to shops, great restaurants, coffee spots, night life, the LIRR Station, Jitney, Shelter Island Ferry. Super easy check in and out. Dogs allowed but breed restrictions apply. All pets must be pre approved by the host. I am in the neighborhood and always available by phone or email.

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

Superhost

Home in Hampton Bays

4.79 out of 5 average rating, 106 reviews

Private completely fenced in property. Near beach.

This beautiful custom expanded L ranch of 2800sf nested on a very private flat lot has 4 bedrooms, 3 bathrooms, living room, dining room areas with tons of light and privacy, movie theater. Gym and laundry room. The fenced in back yard comes with a lot of great features such as heated pool, two level pergolas over a 20x40 concrete patio, full play set for the kids, fire pit, hammock area, outdoor shower and a cute pool house/lounge area with a loft!

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 North Fork

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.

Guest favorite

Apartment in Southampton

4.87 out of 5 average rating, 126 reviews

Southampton Village Studio

Location, Location, Location!!!! New renovated stand along Studio Apartment in the heart of Southampton Village. Private with lots of light, Cable TV and living room area. Located in wonderful Southampton Village location, only 1 mile to village shops and 2 miles Coopers Beach. Wi-Fi

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What guests are saying

Total Privacy in Springs.

4.75 out of 5 average rating, 20 reviews6 months ago

The place is roomy and clean. The bed is comfy and the shower is great. There were juices and sodas and water in the mini fridge, a coffee maker with coffee and some wrapped snacks. A comfortable place to stay in a very pricy part of Long Island if you prefer a home over a hotel. We were only there for the 2 nights of our stay since we were out all day and for that it was perfect.

Apartment in East Hampton

What guests are saying

Peaceful and Private 3 bedroom home in the woods

4.88 out of 5 average rating, 26 reviews8 months ago

Maura was an excellent host and the home was perfect! We enjoyed the weekend very much and cannot thank Maura enough for her kindness, responsiveness, warm hearted spirit, and for opening up her home to us. Will always keep this spot in mind for future SI adventures!

Home in Shelter Island

What guests are saying

Bay Breeze-Mins from Beach, Towns and Activities

4.98 out of 5 average rating, 49 reviews7 months ago

We had an amazing stay and highly recommend!!! This was the perfect location for a quick getaway outside the city while still being close to great restaurants, vineyards and beaches! The house was spacious and had everything we needed. The backyard was peaceful, private and we loved the hot tub! Akriti and Scott were extremely responsive and helpful and we can’t wait to return for another trip!

Vacation home in Hampton Bays

What guests are saying

Cozy Springs Getaway

4.71 out of 5 average rating, 7 reviews8 months ago

This house is in a quiet safe neighborhood, 30 mins from Montauk Beach and half the cost for 5 guests. Overall we loved it! The host recommended restaurants which is helpful. When we-reported a problem, someone was there to fix it the next morning. Kitchen well stocked, plenty of outdoor seating, comfy couches. Strange full bathroom cotton curtains a bit long and no liner, difficult to dry. The bath off the master bedroom the floor floods because curtain in there is lined but a bit short. Gotta keep a towel down. Garage is wonderful, laundry in basement handy. Decks off bedroom and patio off dining room both lovely. are beautiful lovely place to stay.

Home in East Hampton

What guests are saying

Stylish Beach Getaway: pool & walking location

5 out of 5 average rating, 9 reviews6 months ago

Maher’s house was an amazing peaceful experience. I enjoyed my time there and he had great recommendations to restaurants and activities! He was very responsive with all questions we had. I will totally stay here in the future if I can get the chance again!! Thank you Maher!!

Home in North Fork

What guests are saying

Southold- Adorable 1 Bedroom Cottage

4.91 out of 5 average rating, 57 reviews1 month ago

Marta & Pete were great hosts. Left helpful instructions and a list of places in the area. The Cottage was definitely a great place to celebrate our anniversary. We wish we could have tried some of their oysters, but look forward to going back during the beach season when they're probably plentiful.

Guesthouse in North Fork

What guests are saying

Adorable Cottage

4.95 out of 5 average rating, 41 reviews3 months ago

This magical cottage is a little slice of paradise. It’s so incredibly cute and cozy but beyond that, Erin Leigh has put in so many thoughtful touches- we wanted for nothing. It’s clean, it’s beautiful, it’s comfortable…truly one of the best places I’ve ever stayed in. Her hospitality was top notch. I felt so spoiled and so sad to leave.

Cottage in North Fork

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