Oak Bluffs vacation rentals
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Top-rated vacation rentals in Oak Bluffs
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
Home in Mashpee
4.94 out of 5 average rating, 110 reviewsNewly Renovated! Seconds to sand, fire pit, A/C
Recently Renovated! This Cape Cod Cottage is completely refreshed top to bottom. Less than 60 seconds to the sand. Cape cod vacations do not get any better than this! Located on idyllic Monomoscoy Island known for its gorgeous wildlife and stunning waterways, our home is the perfect choice to rent on Cape Cod. We are less than 10 Mins to Mashpee Commons and famous Mashpee Town Beach, Less than 5 mins to New Seabury and the Popponesset Inn, and only 15 mins to downtown Falmouth. Linens included!
Home in Falmouth
4.85 out of 5 average rating, 33 reviewsCape Vacation in style! Close to Main St & Beaches
We affectionately call this house 'The Local,' as it sits in the heart of beautiful Falmouth, within short walking distance to the quaint Main St. shops, delectable restaurants, fish markets, entertainment like bowling and axe-throwing (!), and is a short drive to Woods Hole and many of the Cape's most breathtaking beaches along the coast. Great summer or off-season destination, the house is complete with high-end finishes and furnishings to make your vacation especially comfortable. Enjoy!
Apartment in Oak Bluffs
4.95 out of 5 average rating, 167 reviewsBeautiful private apartment walk to everything!
This is an incredible property! Renovated and spotless with all the amenities to make your stay feel like home, only better. Downtown Oak Bluffs and her beautiful beaches are within a five-minute walk. There is a local market and deli right next door where you can find anything you need in a pinch, and a great BBQ restaurant across the street. This second floor apartment has one bedroom with a queen-sized bed and a queen pullout couch. Smart TVs, full kitchen and laundry plus much more!
Home in Oak Bluffs
4.92 out of 5 average rating, 166 reviewsimpeccable cottage STEPS to downtown OB & beach!
Unique opportunity to stay in an impeccable cottage in Downtown Oak Bluffs. With a front porch with rocking chairs, a back deck & grill, & an outdoor shower, and A/C! - this is the ideal oasis for your Vineyard Vacation. Turn right and find yourself steps from restaurants & shops on Circuit ave. Turn left and walk 5 mins to beautiful beaches. Everything you want out of vacation at your fingertips. Relax, and truly experience the Vineyard the way it was meant to be, at the @WeePackemInn
Home in Mashpee
4.94 out of 5 average rating, 36 reviewsTranquil Cape getaway#2 with AC Kid & Pet friendly
Welcome to this peaceful Cape retreat! With its charming Cape style home and serene surroundings, this two-level residence offers a perfect getaway for relaxation and quality time with loved ones. Property Features: Four Cozy Bedrooms Outdoor Deck and Grill Complete Fenced-In Yard Swing Set Whether you're looking to relax indoors, enjoy outdoor activities, or spend quality time with family and friends, this idyllic haven offers all the necessary amenities for a memorable vacation.
Home in Edgartown
4.95 out of 5 average rating, 111 reviewsWalk To Town - Beautiful Edgartown Cottage
Walk to downtown Edgartown in minutes while staying in this newly renovated 2-story home in the heart of Upper Main St. The 3-bedroom, 2-bathroom house has been completely renovated, with brand new bathrooms, kitchen appliances, etc. You cannot beat the location of this home! You're a short 10 min walk from Edgartown's amazing restaurants & shops, in addition to a short bike ride to Katama's famous South Beach or Oak Bluff's State Beach. Both easily accessible via bike paths.
Home in Oak bluffs
4.81 out of 5 average rating, 107 reviewsBeautiful 3 bedroom in Oak Bluffs, walk to beach
Located in Martha's Vineyard, close to beach, bike path, oak bluffs center, art and culture, parks,and the airport. You’ll love my place because of the outdoors space with a wrap around farmers porch, the proximity to the ferry, walking distance to neighborhood beach, less than 2 miles from ferry, screened in porch, central a/c, hardwood floors and an open floor plan. Real Cape Cod feel with modern amenities. Most of my guest come back year after year!
Home in Edgartown
4.91 out of 5 average rating, 53 reviewsUpdated Beautiful Cottage in Edgartown AC
Light, airy and central-air-conditioned home offers all the comforts of modern living centrally located in Edgartown. A true island charmer. Recently completed extensive upgrades completed enhance all of the space, including a new kitchen, both bathrooms, basement, and more. A spacious outdoor furnished deck with enclosed outdoor shower and an expansive grassy lawn make for a great space to relax. Great location makes Island travel a breeze.
Home in Edgartown
4.98 out of 5 average rating, 171 reviews20-minute walk to Edgartown Village!
This 1550 square foot Ranch-style Condo with loft was built in 2018 and is set on a large nicely landscaped lot with plenty of room inside and out. It has It has 3 bedrooms and sleeps 8. It’s a 20-minute walk to the Edgartown village center, a 10-minute walk to Morning Glory Farm, and just a 10-minute drive to South Beach! All updated furnishings, beds, linens, appliances. Read our reviews! Immaculate!
Home in Falmouth
4.94 out of 5 average rating, 304 reviewsAbsolutely Adorable 4 Bedroom Ranch
Property is very close to beach at lovely, freshwater Jenkins Pond. This nicely furnished rental has a fabulous lower level family/TV room with add'l sleeping area and a full bath. Outdoors there is a large yard with a large deck and outside shower during the summer season. Minimum 2-night stay, rates may vary depending on season, weekly and monthly rate available.
Home in Mashpee
4.96 out of 5 average rating, 185 reviewsGorgeous sunsets! Private family beach - Cape Cod!
Saturday to Saturday weekly rental during summer months. Wrap around deck, beach and waterfront. Open layout. Perfect for families & Couples with a family beach . Stunning sunsets, very private and close to Mashpee commons, Falmouth and New Seabury all 10 minutes away. We are happy to have you for stays longer than 7 days! Just send us a note!
Guesthouse in Tisbury
4.86 out of 5 average rating, 251 reviewsAdorable Vineyard Haven Cottage
Booking for 2025 season; Spring, Summer and Fall is OPEN. 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!
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Oak Bluffs vacation rentals
Oak Bluffs house rentals
Home in Edgartown
4.97 out of 5 average rating, 226 reviewsBrand new gorgeous 2 bedroom guest house.
Home in Marstons Mills
4.88 out of 5 average rating, 133 reviewsThe Mills Retreat- 3BR/2Bath - Beach pass included
Home in Oak Bluffs
4.94 out of 5 average rating, 131 reviewsThe Lighthouse
Home in Oak Bluffs
4.83 out of 5 average rating, 193 reviewsWaterview, Private, Walk to Beach, Mile to Town
Home in East Falmouth
5 out of 5 average rating, 36 reviewsSpacious and immaculate custom home.
Home in Sandwich
4.7 out of 5 average rating, 20 reviewsHoliday in the sun!
Home in Mashpee
4.83 out of 5 average rating, 153 reviewsNew Seabury & South Cape Beach State Park
Home in Teaticket
4.93 out of 5 average rating, 123 reviewsCute Single Family Home in Nice Neighborhood
Oak Bluffs cottage rentals
Cottage in Falmouth
4.86 out of 5 average rating, 106 reviewsSpectacular Beach- front home, includes linen
Cottage in Woods Hole
4.97 out of 5 average rating, 90 reviewsCape Cod Cottage Getaway!
Cottage in East Falmouth
4.93 out of 5 average rating, 162 reviews“Cozy Cottage” on Great Bay
Cottage in Tisbury
4.98 out of 5 average rating, 331 reviewsMartha's Vineyard Getaway Cottage
Cottage in Pocasset
4.81 out of 5 average rating, 109 reviews* Rustic Cape Cod Captain's Quarters Cottage
Cottage in Sandwich
4.95 out of 5 average rating, 209 reviewsLakefront cottage, Private Beachfront, Wow View!
Cottage in Edgartown
4.98 out of 5 average rating, 97 reviewsLovely two - story private cottage.
Cottage in Mashpee
4.95 out of 5 average rating, 341 reviews★The Islander | Steps From Water, Fire Pit, AC★
Oak Bluffs condo rentals
Condo in Tisbury
4.98 out of 5 average rating, 50 reviewsShort Walk into Town - Nice Comfortable Reasonable
Condo in Vineyard Haven
5 out of 5 average rating, 21 reviewsRelax....You're on Island Time......
Condo in Tisbury
4.91 out of 5 average rating, 47 reviewsPrivate 3bdrm Condo Tashmoo Woods
Condo in Tisbury
4.9 out of 5 average rating, 72 reviewsSunny 2bedroom condo w pool, walk to town
Condo in Oak Bluffs
4.96 out of 5 average rating, 27 reviewsLOCATION LOCATION!! Ocean- View TOP Floor Condo
Condo in Falmouth
4.73 out of 5 average rating, 15 reviewsCondo in Falmouth MA
Condo in Tisbury
4.77 out of 5 average rating, 13 reviewsMartha’s Vineyard Ground Floor Condo * Near Ferry
Quick stats about vacation rentals in Oak Bluffs
Total rentals
670 properties
Nightly prices starting at
$10 before taxes and fees
Total number of reviews
24K reviews
Family-friendly rentals
480 properties are a good fit for families
Pet-friendly rentals
140 properties allow pets
Rentals with a pool
30 properties have a pool
Frequently Asked Questions
What types of vacation rentals are available in Oak Bluffs?
Uncover the perfect home-away-from-home with our diverse selection of vacation rentals in Oak Bluffs. From over 50 cottage rentals, over 30 condo rentals to over 460 house rentals, we've got you covered. For even more variety, explore our Airbnb Categories to find the ideal space for your getaway.
Where should I stay in Oak Bluffs?
Make yourself at home in Oak Bluffs by choosing from our most frequently booked neighborhoods. We have over 630 vacation rentals in East Chop, over 630 vacation rentals in West Chop, and over 630 vacation rentals in Eastville.
Are there vacation rentals with a dedicated workspace in Oak Bluffs?
Yes! Work meets play with ease at over 350 vacation rentals in Oak Bluffs featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Oak Bluffs?
Four-legged friends are welcome in Oak Bluffs. Choose from more than 170 vacation rentals for guests traveling with pets.
How much does it cost to stay in house rentals in Oak Bluffs?
Experience the best of Oak Bluffs with our house rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Oak Bluffs have a bbq area?
Absolutely! We offer over 250 house rentals with a bbq area in Oak Bluffs. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Oak Bluffs have self check-in?
Absolutely! We offer over 160 house rentals with self check-in in Oak Bluffs. Enjoy a tailored experience with all the comforts you desire.
Are there Oak Bluffs house rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 20 house rentals with pools in Oak Bluffs, available on Airbnb. Make a splash and soak up the sun in style!
Do house rentals in Oak Bluffs have wifi?
Absolutely! We offer over 460 house rentals with wifi in Oak Bluffs. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Oak Bluffs have a gym?
Absolutely! We offer over 30 house rentals with a gym in Oak Bluffs. Enjoy a tailored experience with all the comforts you desire.
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