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Pet-friendly vacation rentals in Sag Harbor

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Top-rated pet-friendly home rentals in Sag Harbor

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

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Home in Sag Harbor

4.82 out of 5 average rating, 132 reviews

New! Sag Harbor Village Pool, Hot Tub &Beach House

New, immaculate, all-season home by the beach with crisp designer details. Every detail was considered for maximum enjoyment. The heated saltwater pool (open April-Nov) hot tub, fenced in yard & deck gets sun all day. Located in the village of Sag Harbor, steps from the Bay and Main Street & all the Hamptons has to offer. Come feel the vacation vibes as soon as you arrive. The central location, luxurious finishes, breathtaking sunsets on the sandy beach make this the perfect year-round getaway.

Oct. 31 – Nov. 7

$1,146 CAD per night

Guest favourite

Home in East Hampton

4.94 out of 5 average rating, 202 reviews

Private beach Historical House with large property

Entire three-story house. 3 large bedrooms and 3 FULL BATHROOMS on a very private, 2+acre wood lot on the bay in Historical East Hampton with private beach access. Fully renovated in 2018 with modern amenities while preserving the original charm. A/C and heating. Private upper floor with bedroom + sitting area for office and extra sleeping. Modern kitchen with island that opens to living room with fireplace. Walk through the secluded backyard to enjoy the amazing sunsets. Ideal for fishing.

Apr. 28 – May 5

$1,231 CAD per night

Guest favourite

Apartment in Sag Harbor

4.92 out of 5 average rating, 133 reviews

Whaling Captain Pierson's Apartment TOO

Whaling Captain Pierson's Apartment TOO is at a waterfront property. An apartment in one of the contributing homes which define Sag Harbor as a historic village. The house is a 7 minutes’ walk from the center of historic Sag Harbor Village. It is the only house and apartment offering a vast, picturesque, panoramic view of beautiful Sag Harbor Cove from Main Street as well as spectacular sunsets. (See my other listings of Whaling Captain Pierson's Apartment and Whaling Captain Pierson's Cottage)

Jan. 30 – Feb. 6

$550 CAD per night

Guest favourite

Guesthouse in Hampton Bays

4.96 out of 5 average rating, 146 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.

May 1 – 8

$509 CAD per night

Guest favourite

Apartment in Sag Harbor

4.84 out of 5 average rating, 172 reviews

Pet friendly, artists apartment & guest cabin.

Artists apartment and cabin located on quaint cul-de-sac just outside Sag Harbor Village, minutes from Long Beach. Centrally located. Free bikes, surf boards, 3 stand up paddle boards and a large canoe. Minutes from most beaches. A shaded, fenced in dog run. The cabin is a separate sleeping space from the apartment and has a 2 person SAUNA recently installed. Used if you bring more guests or if the two primary guests require separate rooms. WIFI AC and heat but No bathroom in the cabin.

Aug. 27 – Sep. 3

$1,041 CAD per night

Guest favourite

Home in East Hampton

4.97 out of 5 average rating, 120 reviews

East Hampton (walking distance to village)

Relax by the hot tub and fire pit with local wines or walk to the village for shopping and dining. House is just a few blocks from Serafina and the famous Nick and Toni’s. Complimentary cruiser bikes included to get around town. IGA supermarket is around the corner and gas grill is on site and ready to use. The house is also walking distance to the train station if your coming from Manhattan. The second bedroom features a Murphy Bed that folds out of the wall and over the couch pictured.

Oct. 15 – 22

$1,002 CAD per night

Guest favourite

Apartment in Hampton Bays

4.97 out of 5 average rating, 340 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.

Apr. 2 – 9

$406 CAD per night

Guest favourite

Cottage in Southampton

4.96 out of 5 average rating, 101 reviews

Charming Southampton Light filled Cottage

Escape and relax in this beautiful tranquil Southampton retreat! Newly remodeled cottage just blocks from the water. The home is nestled on 1/2acre quiet park-like setting located at the end of a long gravel driveway. Enjoy the private outdoor space with a fire pit, outdoor dining table, new dual BBQ and lounge chairs. Inside, the large dining room table easily sits 8. This stylish Coastal farmhouse has all new beds and furniture. Complete with Wifi, Cable, AC and Nespresso maker!

Oct. 13 – 20

$1,136 CAD per night

Guest favourite

Home in East Hampton

4.97 out of 5 average rating, 116 reviews

Explore the Water & Woods at a Relaxing Retreat

Flick through records under soaring ceilings and hang out in the year-round hot tub at this East Hampton open-plan retreat. Unwind in the wooded backyard, take a dip in the pool or spa, detox in the sauna, grill on BBQ, relax in the movie-theatre seats to watch a film, then snuggle up to fireplace or firepit before drifting to sleep in super comfy beds. Minutes to village, beaches and hiking trails. Terrific for families & friends looking for a relaxing getaway.

Nov. 9 – 16

$1,315 CAD per night

Guest favourite

Apartment in Sag Harbor

4.98 out of 5 average rating, 117 reviews

Sag Harbor Retreat

Experience the many wonderful things the Hamptons has to offer in the Summer in centrally-located Sag Harbor. Our place is a professionally-decorated luxury apartment with its own entrance, yard and two parking spaces. This home-away-from-home is an immaculate and well-appointed retreat located in Sag Harbor. Great for couples and solo adventurers. Close to Sag Harbor's Main Street with abundant recreational activities, shopping and restaurants.

Jan. 5 – 12

$1,079 CAD per night

Guest favourite

Home in Water Mill

4.91 out of 5 average rating, 110 reviews

Beach Barn w/ Sauna and Heated Pool - Dog Friendly

Dog friendly (upon request) Hampton Beach Barn with heated pool and infrared sauna. POOL OPEN - May 3, 2024 - October 28, 2024 This impressive house, nestled within a rustic, woodland plot, promises a tranquil stay. Eclectic modern decor is complemented by striking rustic touches, such as Dutch-style farm doors, exposed beams, and vintage wood-burning stove.

Nov. 16 – 23

$1,394 CAD per night

Guest favourite

Guest suite in Cutchogue

4.88 out of 5 average rating, 587 reviews

Walk to Vineyards, Beaches, Farms & Town

Private bungalow with a separate entrance in a historical tudor home. Spacious bedroom with king-sized bed, kitchenette and bathroom. Two bikes, cable TV, internet, AC, beach towels, parking, snacks, coffee and water all provided. Walking distance to the beach, restaurants, shops, vineyards, grocery, farms and fish market. Jitney stop is one block away!

Aug. 12 – 19

$285 CAD per night

Vacation rentals for every style

Get the amount of space that is right for you.

Apartments

Convenient locations with everyday essentials

Houses

A space that's all yours, with room for everyone

Cottages

Quaint homes, peaceful surroundings

Popular amenities for Sag Harbor pet-friendly home rentals

Free parking on premises

Air conditioning

Pet-friendly house rentals

Guest favourite

Home in Sag Harbor

4.84 out of 5 average rating, 151 reviews

Sag Harbor House for rent.

Aug. 1 – 8

$1,117 CAD per night

Guest favourite

Home in East Hampton

4.92 out of 5 average rating, 128 reviews

Heated pool, games room, near beach, kid-friendly

Oct. 23 – 30

$1,012 CAD per night

Guest favourite

Home in Montauk

4.91 out of 5 average rating, 418 reviews

DITCH PLAINS SURF HOUSE

Oct. 30 – Nov. 6

$411 CAD per night

Guest favourite

Home in Southampton

4.88 out of 5 average rating, 193 reviews

Secluded Southampton Luxury Estate. 286

Oct. 25 – Nov. 1

$1,634 CAD per night

Guest favourite

Home in Southampton

4.96 out of 5 average rating, 130 reviews

Waterview, PoolOpenNow! DogsFree+Kayaks+PingPong

Jun. 7 – 14

$1,559 CAD per night

Home in East Hampton

4.88 out of 5 average rating, 101 reviews

Gorgeous East Hampton Getaway

Nov. 8 – 15

$1,158 CAD per night

Guest favourite

Home in Brookhaven

4.95 out of 5 average rating, 127 reviews

Beautiful & Independent Guest House near the water

Mar. 24 – 31

$253 CAD per night

Guest favourite

Home in Montauk

4.87 out of 5 average rating, 181 reviews

Laid-Back Bungalow. 10 min Walk to Beach & Town!

Oct. 19 – 26

$675 CAD per night

Pet-friendly home rentals with a pool

Guest favourite

Guesthouse in Southampton

4.96 out of 5 average rating, 136 reviews

Wonderful Private Spacious Pool House

Mar. 21 – 28

$767 CAD per night

Guest favourite

Bungalow in Montauk

4.91 out of 5 average rating, 529 reviews

Montauk Oceanview with Fireplace (2)

Jan. 1 – 8

$292 CAD per night

Guest favourite

Home in Manorville

4.98 out of 5 average rating, 199 reviews

Ultimate House with Heated Pool, Hot Tub and Sauna

Oct. 3 – 10

$890 CAD per night

Guest favourite

Apartment in Sag Harbor

4.95 out of 5 average rating, 83 reviews

PRIVATE BASEMENT APARTMENT WITH POOL IN SAG HARBOR

May 15 – 22

$345 CAD per night

Condo in Bridgehampton

4.92 out of 5 average rating, 13 reviews

Bridgehampton w/ Pool steps to town 3 bd 2.5 Bath

Nov. 15 – 22

$681 CAD per night

Guest favourite

Home in Southampton

5.0 out of 5 average rating, 22 reviews

Renovated Southampton Home+Pool

Feb. 17 – 24

$560 CAD per night

Guesthouse in Bridgehampton

4.82 out of 5 average rating, 61 reviews

Central Hamptons Guesthouse

May 7 – 14

$407 CAD per night

Guest favourite

Home in Sag Harbor

4.84 out of 5 average rating, 45 reviews

Modern Home in Sag Harbor, NY

May 29 – Jun. 5

$1,445 CAD per night

Private, pet-friendly home rentals

Guest favourite

Apartment in Southampton

4.86 out of 5 average rating, 107 reviews

Southampton Village Studio

Apr. 11 – 18

$461 CAD per night

Guest favourite

Cottage in Riverhead

4.98 out of 5 average rating, 126 reviews

Savor Blazing Ocean Sunsets at a Soothing Beachfront Haven

Jan. 3 – 10

$1,057 CAD per night

Apartment in Sag Harbor

4.88 out of 5 average rating, 16 reviews

Well-appointed one bedroom Apt

May 14 – 21

$278 CAD per night

Guest favourite

Cottage in East Hampton

5.0 out of 5 average rating, 20 reviews

Chic cottage on lush, secluded acre by the beach.

Oct. 22 – 29

$503 CAD per night

Guest favourite

Condo in Sag Harbor

4.95 out of 5 average rating, 19 reviews

Charming Sag Harbor Condo right in town/Main St!

May 15 – 22

$495 CAD per night

Guest favourite

Guesthouse in Sag Harbor

4.96 out of 5 average rating, 95 reviews

Sag Harbor's Secret by the Bay ❤️ | Walk to beach 🏖

Sep. 2 – 9

$762 CAD per night

Guest favourite

Cottage in Bridgehampton

5.0 out of 5 average rating, 50 reviews

Bridgehampton Cottage Close to Town, South of HWY

Guest favourite

Apartment in Sag Harbor

5.0 out of 5 average rating, 74 reviews

Private Country Studio ~Warm Fireplace

Nov. 29 – Dec. 6

$569 CAD per night

Quick stats about vacation rentals that are pet-friendly in Sag Harbor

Total rentals
110 properties
Rentals with dedicated workspaces
60 properties have a dedicated workspace
Rentals with a pool
50 properties have a pool
Family-friendly rentals
90 properties are a good fit for families
Total number of reviews
2.4K reviews
Nightly prices starting at
$273 CAD before taxes and fees

Destinations to explore