Pet-friendly vacation rentals in Osterville

4.83 out of 5 average rating, 509 reviews

The image displays four sections of the cottage. A cozy sleeping area features a full-size bed with soft linens. A bright kitchen with marble counters is visible, alongside a comfortable living space with seating. An outdoor deck with furniture showcases a partially fenced yard.

Tiny home in Dennis Port

★TINY HOUSE★4/10mi Beach & Village★Pet OK★2 Bikes

Welcome to SAND PEBBLE COTTAGE! We are PET FRIENDLY! ($25/nt) This 300sq.ft "TINY HOUSE" is 0.4 mi from the ocean beach & 1/2 mi from Dennisport village At the end of a cul-de-sac, this tiny cottage has everything you need ✅ 4/10mi to beach & village ✅ Kitchen w/marble counters ✅ 2 Bike ✅ Deck w/furniture & charcoal BBQ ✅ Parking-2 cars ✅ Separate bedroom ✅ Full A/C ✅ Bring your sheets/towels-we do not provide linens ✅ Pet friendly-only 1 pet as the cottage is tiny $25/nt

5 out of 5 average rating, 178 reviews

An outdoor dining setting features a table with a plate of salad and wine glasses, accompanied by a bottle of white wine. In the background, a charming shed displays ‘Cape Away’ signage, surrounded by well-maintained greenery and a cozy lounge area.

Home in South Yarmouth

Relaxing Retreat | King Beds * Sauna * Bar Shed

Welcome to Cape Away, your charming family & pet-friendly retreat! Enjoy a fully stocked kitchen, cozy fireplaces, sauna, and outdoor shower. Unwind with dozens of board games, dart board, fire pit, and BBQ. The fully fenced private backyard offers beach gear, a bar shed and lounge area. We are perfectly located just 5–20 minutes from top rated restaurants and beaches, making it your ideal home base. With premium amenities, thoughtful touches it’s the perfect space to escape, explore and relax.

5 out of 5 average rating, 286 reviews

The exterior of a classic Cape Cod home is framed by a grassy yard under a partly cloudy sky. White wooden adirondack chairs sit on the lawn, and the house features a cozy front porch, shutters in a deep hue, and multiple windows allowing natural light.

Home in West Yarmouth

The Pearl: 3 Bedroom 500 steps to Englewood Beach!

The Pearl is a classic Cape Cod 3-bed home 500 steps to Lewis Bay. Walk through the marsh path on your way to Englewood Beach, a number of small beaches, & Colonial Acres! Seagull Beach is 2 miles away. • Mesh WiFi, 2 Smart TVs • Central Air Conditioning • Large 2nd-floor bedroom • Big yard on a quiet dead-end street • Original wood floors/trim • Living/Dining rooms • Outdoor shower, grill, deck, firepit • Equipped kitchen • Linens/towels provided • Washer/Dryer in basement • Work from home

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 bright living room features light blue walls and hardwood flooring, with natural light streaming through skylights. A cozy seating area includes a grey sectional and a light-colored side table, while a fireplace is adorned with decorative art. A television is positioned across from the seating arrangement.

4.89 out of 5 average rating, 150 reviews

1-level fenced in yard Craigville Beach 2200sqft

Welcome to Midori On The Cape! This modern 4-bedroom, 2-bath, Cape-style house features ~2200 sq ft one-level Cape-style living in a quiet neighborhood, Free EV charging. 15000 sqft lot with fenced in flat grassy backyard, fire pit, swing set. Centrally located near Craigville Beach, Cape Cod Mall, vibrant Hyannis downtown and ferry terminal to Martha's Vineyard and Nantucket Island 1 living room, 2 dining areas, 4 super-sized bedrooms. Perfect for family staycation and gathering.

5 out of 5 average rating, 332 reviews

A wooden outdoor table and benches are positioned on a stone patio, overlooking a serene pond. Lush greenery lines the water's edge, and white flowers in a planter enhance the natural setting. The calm water reflects the surrounding trees and sky.

Home in West Yarmouth

gorgeous waterfront cottage w/4kayaks and 2 SUPs

Small 500 sq ft gem . Quintessential Cape Cod cottage WATERFRONT on big Sandy Pond. Step back in time and enjoy being on Cape Cod in your own Camp. Come enjoy this charming cottage with 2 bedrooms and views of the pond throughout. Kayak, fish and swim from your front door. *1 Paddle Bd *4 kayaks- 4 adult/4 child life vests *Gas Fire-pit *Gas Grill *XL outdoor shower *Quiet lakeside hood *Gorgeous marble counters in the new kitchen *Remote control heating & cooling system *WiFi

4.98 out of 5 average rating, 330 reviews

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.

Home in Falmouth

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!

Home in West Hyannis Port

A spacious living room is captured, featuring light-toned sofas arranged around a wooden coffee table. A large television sits on a stand, with natural light streaming through tall, arched windows. A patterned rug adds color beneath the furniture, and indoor plants enhance the ambiance.

4.83 out of 5 average rating, 183 reviews

Spacious house steps to Craigville beach! Dog ok!

Welcome to our Craigville retreat, close walk (0.3 mi) to one of the most beautiful beaches on the Cape. We are close to other beaches, ferry to Islands, food, hiking/kayaking/biking, Melody tent. You’ll love it because of the location and lots of natural light. If you want to stay in-enjoy private fenced backyard w/ fire pit, porch furniture and a hammock. Stocked with all you need to relax. We can host one dog. *Read/Agree to Pet policy bfr booking w dog*

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!

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!

4.85 out of 5 average rating, 252 reviews

The cottage exterior features a shingle facade with flower boxes adorned with colorful blooms. Two large windows provide natural light, while a wooden step leads to the entrance. The surrounding yard is well-kept, with green grass and vibrant hydrangeas adding to the inviting atmosphere.

Cottage in West Yarmouth

Charming Cottage near Beach and Ferry.

2022 renovation (floors, bathroom, cabinets) The cottage is only 150 yards from a sandy residential beach. Good for couples, families (with kids), and furry friends (pets). Enjoy a great outdoor shower, grill and deck, wifi, central AC/heat, cable TV, linens, washer/dryer. Additional Beach gear. No host interaction required. Great place to work remotely. Private yard and picnic table with lots of takeout options nearby.

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.

Popular amenities for Osterville pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.95 out of 5 average rating, 96 reviews

A charming path leads to the entrance of a house, framed by a white picket fence and lush greenery. Flowering plants line the walkway, which is paved with bricks and gravel. Solar panels are visible on the roof, complementing the natural surroundings.

Home in Mashpee Neck

Cozy garden retreat close to it all! Pet friendly

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

The sunlit sunroom features a light-colored sofa and an egg chair, creating a relaxed seating area. Large windows provide views of the outdoors, while a round area rug and a decorative coffee table enhance the inviting atmosphere.

4.94 out of 5 average rating, 54 reviews

Walk2Lake | Fence | Cragiville | 3Livings | Pet AC

5 out of 5 average rating, 25 reviews

The two-story house is presented with a white exterior, set against a golden sunset. Large windows adorn the front, with a welcoming door at the center. The surrounding yard features mature trees, creating a serene outdoor environment.

Home in Hyannis Port

Baby & Pet Friendly, Solar, AC, Lo $

A spacious living area features neutral-toned walls and light hardwood flooring, with comfortable seating arranged around a coffee table. Natural light floods through large windows, and decorative plants add a touch of greenery. A staircase leads to the upper level, enhancing the home's inviting layout.

4.92 out of 5 average rating, 60 reviews

5mins2Beach,Fenced Yard,Central AC,Pet,Firepit,5BR

4.88 out of 5 average rating, 17 reviews

Aerial view captures the serene landscape surrounding the property, featuring lush green trees and a tranquil pond. The area is dotted with homes along the water's edge, contributing to the peaceful atmosphere of the setting.

Home in Centerville

Spacious Home w/ Beach Pass & Private Pond Access

5 out of 5 average rating, 31 reviews

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.

Home in Falmouth

Cape Fall Family Retreat+ Pet +FirePit +EVCharger

Pet-friendly home rentals with a pool

5 out of 5 average rating, 18 reviews

Home in East Dennis

Sleeps 12 near beach. Hot tub game room

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

A heated saltwater pool glistens under the sun, surrounded by a spacious paver patio. The fenced backyard provides privacy, while a light-colored house with a deck offers a welcoming ambiance. Lush trees stand in the background, enhancing the serene outdoor space.

4.82 out of 5 average rating, 17 reviews

Centerville Oasis, Heated Saltwater Pool!

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

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.

4.86 out of 5 average rating, 7 reviews

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

4.92 out of 5 average rating, 49 reviews

A spacious outdoor area is highlighted by a seasonal heated pool surrounded by a wooden deck. Multiple blue lounge chairs are arranged around the pool, and a fire pit table is situated at the center. A large checkers board and garden beds add to the inviting atmosphere.

Home in Yarmouth Port

Winslow Acres [heated] Pool Escape; pool May 15

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 exterior of the home showcases a spacious, two-story design with a large deck wrapped around the back. White railing surrounds the deck, where comfortable seating is provided. Lush green grass covers the backyard, accentuated by trees in the background, creating a serene outdoor environment.

5 out of 5 average rating, 12 reviews

*Large Group Escape w/ 4 BR & Fire Pit

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

4.93 out of 5 average rating, 15 reviews

Home in West Falmouth

Serene Beach House Retreat near Chappy, Old Silver

5 out of 5 average rating, 57 reviews

The exterior of the apartment is shown, featuring a two-story building with textured wooden siding. The backyard presents a grassy area with seating options, including patio furniture. Access to balconies is visible, along with pink umbrellas and several windows that allow natural light into the units.

Apartment in Centerville

Modern Luxury, Central Location, Bikes & Kayak

5 out of 5 average rating, 19 reviews

An aerial view captures the serene coastline, highlighted by sandy shores and gentle waves. The landscape features a mix of open land and scattered homes, with clear blue waters extending to the horizon under a bright sky dotted with clouds.

Home in Fairhaven

Waterfront Island Oasis w/Breathtaking Sunsets

The home is set on a gently sloping green lawn, showcasing a classic Cape-style exterior. White siding is complemented by navy blue shutters, while a welcoming front porch features comfortable seating. Lush trees surround the property, creating a serene atmosphere.

4.94 out of 5 average rating, 18 reviews

Osterville House on the Hill! Beach Pass included!

5 out of 5 average rating, 72 reviews

A backyard space is equipped with a fire pit surrounded by four white Adirondack chairs, providing a cozy gathering area. String lights hang overhead, illuminating the outdoor dining table set for a meal. A charming cottage is visible in the background, enhancing the inviting atmosphere.

Home in West Dennis

Sunset Sabbatical Cape Cod