Pet-friendly holiday rentals in West Tisbury

4.96 out of 5 average rating, 113 reviews

A clear view of Vineyard Sound is visible through the surrounding trees, showcasing the serene blue waters extending to the horizon. The gentle outlines of land can be seen in the distance, framed by lush greenery and a tranquil atmosphere.

Home in West Tisbury

Lambert's Cove Retreat, Water view, Beach pass

Enjoy stunning views of Vineyard Sound from this cozy three bedroom two bath home in a quiet neighborhood just minutes from Lambert's Cove Beach. This upside down house has one bedroom on the main level along with a full bath and open kitchen, dining, and family room. The downstairs has another living space, two bedrooms, laundry room, and full bath. Enjoy family time in the open upstairs with water views, or retreat to the lower level living room for some separation, quiet time, or work space.

4.97 out of 5 average rating, 155 reviews

A charming post and beam house is set back from a sandy driveway, surrounded by lush greenery and colorful flowers. Large windows on the upper level allow for natural light, providing a welcoming entrance to the home.

Home in West Tisbury

Secluded Up Island Cottage

Charming Martha's Vineyard post and beam house on two secluded acres with two bedrooms in West Tisbury. The master bedroom has a queen bed, the second bedroom has a full bed, the loft has a full size futon. It is peacefully tucked away at the end of a road with only three other houses on it. It has easy access to beaches, bike paths and walking trails. Enjoy some family time in the wooded backyard grilling or relaxing with an outdoor shower or napping in the hammock after a day at the beach.

A single-story ranch home is set against a clear blue sky, featuring a neatly landscaped front yard with low shrubs and grass. The entrance includes a welcoming front door with decorative trim and steps leading up to it. Mature trees provide shade around the property.

4.91 out of 5 average rating, 133 reviews

Fiddler's Green - families and pets welcomed!

Get ready to put your feet in the sand, then return to our outdoor shower, spacious deck & hammock to lounge your evening away! Enjoy our fire pit and grill. Walk 1 mi to Town Dog Park or Cape Cod Winery. Make Fiddler's Green your home base for Falmouth's dozen public beaches (three of which are less than 3 mi away), and Falmouth's quintessential town green (2.5 mi away), stores, churches, library, and epic local spots for food & beverages - Liam's Irish Pub, Añejo Mexican Bistro, etc.!

4.98 out of 5 average rating, 312 reviews

A cozy living space features a striped sofa and a round table set near a rug. Light from the windows brightens the room, which leads to a bedroom visible in the background, adorned with a patterned quilt and vibrant pillows.

Cottage in Pocasset

Upper Cape Cozy Cottage

Simple but cozy cottage on an acre property next to the main house. Moderate sized bedroom and living room. Small kitchen and bathroom. The kitchen is fully equipped for cooking. Air conditioning is a portable unit and only in the bedroom. Games, books, and puzzles provided. There is no cable but a smart TV is included with access to Netflix etc. if you have an account. Outdoor area includes charcoal grill and seating . Large back yard with yard games, basketball hoop and fire pit.

A spacious living room features modern furnishings arranged for comfort. A large flat-screen TV is mounted above an electric fireplace. Natural light enters through multiple windows, and a playful dog portrait decorates the wall. A patterned rug anchors the seating area.

4.98 out of 5 average rating, 330 reviews

The Driftwood Home, 5 min from Mashpee Commons, AC

- NOW PET FRIENDLY! - 15 min to Old Silver, South Cape, and Falmouth Heights beaches - 5 min to Mashpee Commons - 15 min to Falmouth Main St - 1600 square feet, built in 2014, w/ central AC - Large kitchen w/ all cookware and utensils - Outdoor deck with seating, fire pit, and grill - 55” Smart TV - 10 min to Shining Sea Bike Trail - Less than 10 min to Falmouth, Cape Cod, and Quashnet Valley Country Clubs - Centrally located to all of the Upper Cape - No parties or events!

4.91 out of 5 average rating, 129 reviews

The front exterior of the house is shown surrounded by lush greenery, featuring a well-maintained lawn. A pathway leads to the entrance, and the porch offers seating. Two sun loungers are positioned on the grass, inviting relaxation in the open space.

Home in Oak Bluffs

** Vineyard Vacation Retreat ** with HOT TUB

Gated 2br house with lots of different places to lounge and relax. Drive through the 10’ granite gate onto the shell driveway. The house is filled with art from local artist Alan Whiting, Colin Rule, Kara Taylor and Scott McDowell. There is so much to do and explore. The adventure is just starting so make sure to pack up your swimmers, suntan lotion and get out the door. Kick back and relax, you're home. Updated 7/25/2025 we do not have any more firewood on the property.

4.96 out of 5 average rating, 159 reviews

A modern kitchen features a spacious island with two black bar stools. Stainless steel appliances, including a microwave and toaster, complement quartz countertops. Natural light fills the space through large windows, revealing a glimpse of greenery outside.

Cottage in Oak Bluffs

Beautiful and walk to everything Oak Bluffs!

This is a beautiful cottage in the heart of Oak Bluffs! Walk to town, the inkwell beach and the harbor! This modern and comfortable space will be the perfect home base for you and your family. Enjoy all the amenities including central air. Coffee maker, full laundry, outdoor shower and a beautiful patio too. We are on property eager to make your stay as magical as possible. Please check the reviews of our other listings to see how guests enjoy our properties.

4.99 out of 5 average rating, 274 reviews

A brick patio is seen outside the private entrance of the apartment, featuring two blue lounge chairs and a small table with a potted plant. Lush greenery surrounds the patio, enhancing the tranquil outdoor space.

Apartment in Barnstable

Your dog will love it here and you will too.

If you love to travel with your dog (dogs), like I do, then this is the perfect place for you and your dog. We have a large fenced in yard for your dog to play in and for you to relax in with your dog. We have a one bedroom apartment with a full kitchen, bath, living room and dining area When you book would you PLEASE let me know whether or not you will be traveling with a dog and if you are what breed of dog will you be bringing. Thanks!

4.9 out of 5 average rating, 154 reviews

Two wooden adirondack chairs are positioned on a grassy area, facing a tranquil lake surrounded by trees. Bright yellow daffodils bloom nearby, adding a touch of color to the natural landscape under a clear blue sky.

Guesthouse in Dartmouth

Lovely Lakeside Cottage

Keep it simple at this peaceful and centrally-located cottage. Lovely lakeside cottage with open floor plan. Centrally located in southeastern Massachusetts with short drives to Boston, Providence, Newport, and Cape Cod. Several beaches within 20 minutes. Washer/ Dryer on site and California King Size bed. A simple five (5) minute ride to UMass Dartmouth. Cottage has a living room, full kitchen, bedroom, full bath, and small dining area.

Guest suite in West Falmouth

A cozy living area features a comfortable gray sofa with decorative pillows and a wooden coffee table. Natural light fills the space, highlighting a dining table with four chairs. A doorway leads to the kitchen, while a wall-mounted TV provides entertainment options.

4.99 out of 5 average rating, 190 reviews

The Sea-Cret Garden, Guest Apartment

Kick back and relax in this calm, stylish space! This comfortable and peaceful guest apartment is situated in an ideal location in a quiet, beautiful neighborhood that is close to beaches and a short drive to downtown. Take a quick stroll to the West Falmouth Market or the Shining Sea Bike Path. With easy access to Chapoquoit & Old Silver Beach, this perfectly situated apartment is in an ideal spot for your next Falmouth getaway!

4.94 out of 5 average rating, 114 reviews

A historic lighthouse stands beside a renovated white keepers home, both set on a lush green lawn. The Atlantic Ocean stretches out in the background under clear blue skies, offering a serene coastal view.

Lighthouse in Pocasset

Wings Neck Lighthouse

Once in a lifetime experience to stay in a Lighthouse. Historic, unique and charming but with all of the conveniences that make a great vacation. Just feet from the Atlantic with 360 degrees of ocean view. Beautiful, peaceful and memorable all year long. Sandy private association beach just steps away. Expansive lawn and patio for enjoying salt air, waves, boats and sunsets.

Guesthouse in Vineyard Haven

A charming cottage is surrounded by lush greenery and blooming hydrangeas. A small Weber grill is positioned on the stone patio, and a wooden pathway leads to the covered porch. The facade features multiple screened doors and windows, inviting natural light into the space.

4.85 out of 5 average rating, 275 reviews

Sweet Vineyard Haven Cottage

Booking for Fall 2025 is still OPEN. BOOKING for 2026 season to OPEN Oct. 15th Walk to Main Street Vineyard Haven and ferry from this classic, comfy cottage with great screened porch and well equipped kitchen. No car, no problem. Upgraded A/C, premium cable and a new outdoor shower!

Popular amenities for West Tisbury pet-friendly home rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.89 out of 5 average rating, 9 reviews

An outdoor deck showcases a circular table surrounded by chairs, with an umbrella providing shade. Comfortable seating areas feature cushioned chairs, adding to the inviting ambiance. Planters with flowers are positioned near the house, enhancing the natural setting among trees.

Home in Vineyard Haven

Renovated Vineyard Retreat

4.98 out of 5 average rating, 53 reviews

A charming coastal home is presented in a scenic setting, featuring a light grey exterior and a welcoming front porch. Brick walkways lead to the entrance, flanked by well-maintained gardens and landscaped shrubs. A gravel driveway provides ample parking alongside the property.

Home in Pocasset

Coastal Retreat Near Saltwater Beaches & Boating

4.83 out of 5 average rating, 23 reviews

A spacious deck extends from the cottage, offering unobstructed views of Buzzards Bay. The serene water reflects a clear blue sky, while a sandy beach and distant island can be seen in the background. A picnic table is positioned nearby on the shore.

Home in Mattapoisett

Oceanside Cottage with Private Beach

4.98 out of 5 average rating, 47 reviews

The exterior of the home is shown, featuring a well-manicured lawn with stone pathways leading to the entrance. Blue shutters frame the windows, and a bright red door adds a pop of color. The serene lake is visible beyond the property.

Home in Centerville

Lake charm

4.68 out of 5 average rating, 184 reviews

A spacious living area is highlighted by a large blue sectional sofa, complemented by several accent pillows. Large glass doors provide a view of the deck, while pendant lights hang from a vaulted wooden ceiling, enriching the open atmosphere.

Home in Vineyard Haven

Carolyn's Vineyard Haven

4.93 out of 5 average rating, 15 reviews

Home in West Falmouth

Serene Beach House Retreat near Chappy, Old Silver

4.89 out of 5 average rating, 36 reviews

A cozy kitchen area features a rustic wooden island surrounded by two woven bar stools. A vintage white refrigerator and a classic black stove are complemented by open shelving adorned with plants and kitchenware. Bright light streams through a window, enhancing the inviting atmosphere.

Home in West Tisbury

Greenehill~ Up-island 1800's Vineyard farmhouse.

4.83 out of 5 average rating, 210 reviews

A grassy outdoor space features two blue Adirondack chairs and a small fire pit, surrounded by trees and overlooking a serene pond. A hammock hangs in the distance, while the deck is visible on the right, extending from the house.

Home in Eastville

Waterview, Private, Walk to Beach, Mile to Town

Pet-friendly home rentals with a pool

4.89 out of 5 average rating, 88 reviews

A lagoon-style pool surrounded by a concrete deck provides lounge chairs and shaded areas under umbrellas. A gazebo is visible in the background, complementing the lush greenery that borders the property.

Villa in Wareham

Perfect Farmhouse for groups-golf/trails/beach

4.95 out of 5 average rating, 22 reviews

An aerial view reveals a spacious bay front home surrounded by lush greenery. A large pool is visible in the backyard, with steps leading down to a beach area featuring kayaks. The residence is set in a tranquil, wooded environment.

Home in Cotuit

ShoestringBayHouse, waterfront & pool in Cotuit

4.85 out of 5 average rating, 65 reviews

A charming Cape-style house is surrounded by lush green grass, featuring a well-maintained front yard adorned with flower beds and small American flags. The entrance is highlighted by a decorative door with a wreath, framed by neatly arranged bushes. A single-car garage is visible on the right.

Home in Mashpee

Sunny Cape w/Private Pool, Steps to Private Lake

4.92 out of 5 average rating, 49 reviews

A clear blue swimming pool is surrounded by lounge chairs positioned for relaxation. Lush greenery provides a natural backdrop, while a shaded area offers protection from the sun. Steps lead from the pool to a nearby structure, adding convenience for guests.

Condo in Tisbury

Private 3bdrm Condo Tashmoo Woods

4.67 out of 5 average rating, 615 reviews

A sunlit corner of the guesthouse features a dining area with a round table and four wooden chairs, surrounded by large windows that offer views of the ocean. A decorative cabinet and television are positioned nearby, enhancing the inviting space.

Cabin in Falmouth

Waterside Guest House

4.86 out of 5 average rating, 7 reviews

A serene outdoor space features a private saltwater pool surrounded by a stone patio. Colorful lounge chairs await relaxation beside the pool, while large umbrellas provide shade. A fenced area enhances privacy, with additional seating options visible nearby.

Home in Barnstable

Private Saltwater Pool, Game Room, near Beaches!

4.95 out of 5 average rating, 56 reviews

A view from the deck reveals a well-maintained pool area surrounded by lounge chairs and umbrellas. Adjacent to the pool is a tennis court, framed by greenery, providing a serene backdrop. The water sparkles under a clear blue sky, inviting relaxation.

Home in East Falmouth

Dog Friendly Cape Oasis | Pool+Beach |Tennis Court

4.91 out of 5 average rating, 34 reviews

An aerial view of a spacious property featuring a uniquely shaped heated saltwater pool surrounded by a stone patio. A large deck is positioned next to the pool, with several lounge chairs arranged nearby and greenery framing the area.

Home in New Seabury

Home w/ golf view, salted heat pool, mins to beach

Private, pet-friendly home rentals

The den features a cozy seating arrangement with two light gray chairs facing a white-brick fireplace. The fireplace has flickering lights for ambiance. Shelves are visible, adorned with plants and decor, beside a window allowing natural light into the space.

4.93 out of 5 average rating, 94 reviews

Comfortable Cape House In E. Falmouth

Guesthouse in West Tisbury

A rustic studio cottage is presented with a sloped roof and blue siding. A wooden deck leads to the entrance, flanked by a garden with flower beds. A grill is visible on the deck, and a stone pathway meanders through the green yard.

5 out of 5 average rating, 37 reviews

Charming W. Tisbury Studio Guest Cottage

5 out of 5 average rating, 21 reviews

A charming Cape Cod cottage is displayed with cedar shake siding and a welcoming front porch. Planted flower boxes adorn the windows, while a neatly trimmed hedge and stone pathway lead to the entrance. Lush green grass and vibrant landscaping enhance the outdoor space.

Cottage in Teaticket

Saltwind Cottage | beach • firepit • movies

4.9 out of 5 average rating, 21 reviews

A charming cottage is framed by lush greenery and features a welcoming front porch. Bright yellow siding and black shutters create a pleasant contrast. An American flag is displayed near the entrance, and a well-maintained path leads to the door, inviting guests to explore further.

Home in Teaticket

Pretty Cottage Steps From Ocean!

4.85 out of 5 average rating, 53 reviews

Cottage in Falmouth

Berry Bog Bungalow - serenity close to everything!

4.96 out of 5 average rating, 24 reviews

The exterior of a spacious single-story home is presented, featuring a blend of shingle and wood siding. A covered entryway is framed by greenery, while a stone pathway leads to the front door. Large windows reflect natural light, contributing to the inviting ambiance.

Home in Centerville

Sunny Cape Home, Bike to Beach, Central AC

Apartment in West Tisbury

4.73 out of 5 average rating, 11 reviews

Bright loft apartment COMES WITH FREE USE OF CAR!!

An open living area features a sectional sofa and a coffee table on a light area rug. Large windows allow natural light to fill the space. A dining area with a table for four is visible in the background, adjacent to a fully equipped kitchen with modern appliances.