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Pet-friendly vacation rentals in Shelter Island

Find and book unique pet-friendly homes on Airbnb

Top-rated pet-friendly home rentals in Shelter Island

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

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Rental unit in Sag Harbor

4.83 out of 5 average rating, 183 reviews

Pet friendly Apt. Plus cabin, EV charger & sauna.

Artists apartment and cabin located on quaint cul-de-sac just outside Sag Harbor Village, minutes from Long Beach, pet friendly beaches are even closer. Centrally located for easy commutes to all towns and even ocean beaches. Free bikes, surf boards, 3 stand up paddle boards and 2 canoes. Life vests for you and pets A large tick free, shaded, shaded dog run. The cabin is a separate sleeping space from the apartment and has a 2 person SAUNA recently installed. WIFI AC and heat but No bathroom!.

Home in Sag Harbor

4.9 out of 5 average rating, 182 reviews

Kiddo Approved! Heated Pool/Hotub Renovated Home

Family friendly Sag Harbor one level beach house close to Main Street. Heated pool (for a fee), hot tub, enclosed grass yard, kids play area with sandbox and toys, crib, highchair, outdoor fireplace, outdoor shower, yard is fenced and gated with separate safety fence and gates around pool. Backs up to a nature preserve for privacy. Quiet Neighborhood. Short drive to the beach and Main Street. Pool open April 13th-Oct 1. Pool can be heated June-August (for a fee). Hot Tub open April- November.

Guesthouse in Hampton Bays

4.97 out of 5 average rating, 179 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.

Rental unit in Hampton Bays

4.96 out of 5 average rating, 375 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.

Cottage in Southampton

4.96 out of 5 average rating, 123 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!

Tiny home in Mastic

4.94 out of 5 average rating, 102 reviews

Cozy craftsman style home close to beaches

Feel refreshed when you stay in this rustic gem. 10 minutes from the fire island beaches this newly renovated home will take your breath away. 20 minutes from local wineries theres no shortage of things to do. This is a single dwelling home. There is a basement apartment with a separate entrance. The tenant does not have access to the house. Everything pictured is yours to use! Kick your feet up and enjoy the details of this handcrafted home. Tree house inside and out!

Home in North Fork

4.91 out of 5 average rating, 101 reviews

North Fork Escape - Walk To Village, Beach, Parks

Modern & cozy 3-bedroom, 2-bathroom farmhouse, dating back to 1905 and in walking distance of Greenport village and its many attractions. Large, landscaped & fully fenced private backyard for relaxed summer days and nights. Wood burning fireplace for the cooler months. Walk to the great bars & restaurants, beaches, train station/jitney & a short drive to the wineries & farm stands of the North Fork. Central heat & AC with new baths added in 2022.

Home in North Fork

4.9 out of 5 average rating, 200 reviews

Greenport Beach House

Nestled steps from the beach, and all that Greenport and the North Fork has to offer, this exquisitely charming 3 bedroom 2 bathroom waterfront home is absolutely delightful.. You’ll love my place because of the views, the location, the people, the ambiance, the outdoors space, and the Saltwater pool.. My place is good for couples, solo adventurers, business travelers, families (with kids), groups, and furry friends (pets).

Home in Shelter Island

4.9 out of 5 average rating, 115 reviews

Hay 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. Monday-Thursday stays February through June no cleaning fees!!!

Home in Mastic

4.95 out of 5 average rating, 129 reviews

Paradise Citadelhottub, heated pool golf

Welcome to Paradise Citadel. Have a family gathering in this beautiful property. Minimum 2 nights for the July 4th weekend Respect our neighbors. General rule; there is a $500 fee for smoking inside the property. This property offers 2 firepits, swing set for kids to enjoy themselves Basketball court Golf lovers will love this large putting green 6person hot tub 18 round pool for kids and adults.

Home in Water Mill

4.92 out of 5 average rating, 120 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 (please ask for closing date) 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.

Home in North Fork

4.98 out of 5 average rating, 171 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.

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Popular amenities for Shelter Island pet-friendly home rentals

Free parking on premises

Air conditioning

Pet-friendly house rentals

Home in Wading River

4.96 out of 5 average rating, 488 reviews

Your Zen Retreat

Home in Southampton

4.9 out of 5 average rating, 247 reviews

PICTURE PERFECT SOUTHAMPTON HOME-

Home in North Fork

4.94 out of 5 average rating, 33 reviews

Bailey House

Home in Sag Harbor

4.85 out of 5 average rating, 159 reviews

Sag Harbor House for rent.

Home in North Fork

4.98 out of 5 average rating, 243 reviews

The Greenport Bungalow

Home in Shirley

4.9 out of 5 average rating, 134 reviews

Cope near the beach

Home in East Hampton

4.95 out of 5 average rating, 225 reviews

Private beach Historical House with large property

Home in Water Mill

4.99 out of 5 average rating, 84 reviews

Pristine 5 bedroom Home - South of the Highway

Pet-friendly home rentals with a pool

Bungalow in East Hampton

4.93 out of 5 average rating, 107 reviews

East Hampton Ranch with Access to Clearwater Private Beach

Home in East Hampton

4.85 out of 5 average rating, 68 reviews

East Hampton Home Minutes to Village w/heated pool

Home in Water Mill

4.91 out of 5 average rating, 106 reviews

Peaceful 1850s barn w/Pool

Home in East Hampton

5 out of 5 average rating, 5 reviews

The Hideaway

Home in Southampton

4.94 out of 5 average rating, 52 reviews

Amazing Home in SH with private Pool

Home in East Hampton

4.98 out of 5 average rating, 64 reviews

Stylish Oasis, Gorgeous Pool, Private Beach Access

Home in East Hampton

4.94 out of 5 average rating, 16 reviews

Walk to Water. Stunning Home with Gorgeous Pool & Grounds.

Home in Southampton

4.95 out of 5 average rating, 151 reviews

Waterview, DogsStayFree! Kayaks, Ping-Pong

Private, pet-friendly home rentals

Rental unit in East Hampton

4.75 out of 5 average rating, 20 reviews

Total Privacy in Springs.

Cottage in North Fork

4.97 out of 5 average rating, 149 reviews

Savor Blazing Ocean Sunsets at a Soothing Beachfront Haven

Cottage in Hampton Bays

4.96 out of 5 average rating, 67 reviews

Hamptons Cottage.

Home in Hampton Bays

4.75 out of 5 average rating, 75 reviews

Cozy 4-bedroom home close to the beach & town

Home in North Fork

5 out of 5 average rating, 9 reviews

Stylish Beach Getaway: pool & walking location

Home in East Hampton

4.83 out of 5 average rating, 6 reviews

Peaceful, Summer Pool, Close to Ocean & Village

Cabin in North Fork

4.86 out of 5 average rating, 97 reviews

Beach & Forest: Cozy Cabin, Hot Tub, Peloton

Guest suite in North Fork

4.92 out of 5 average rating, 155 reviews

GREENPORT RETREAT- PRIVATE 2 BR APT w/ PRIV BEACH

Quick stats about vacation rentals that are pet-friendly in Shelter Island

Total rentals
50 properties
Nightly prices starting at
$180 before taxes and fees
Total number of reviews
1.2K reviews
Family-friendly rentals
50 properties are a good fit for families
Rentals with a pool
20 properties have a pool
Rentals with dedicated workspaces
30 properties have a dedicated workspace

Destinations to explore