Oak Bluffs holiday rentals

We found 1,892 holiday rentals — enter your dates for availability
Discover a selection of 270 homes, 34 apartments and other holiday rentals in Oak Bluffs that are perfect for your trip. Holiday homes offer the best amenities for your family, friends or furry companion, such as parking and a hot tub. At the end of the day, you'll be sure to find a property to rent that has what everyone needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts – Oak Bluffs

Showing deals for:8 Jan - 15 Jan

This is an "upside down house" with the living area on the second floor.
View of living room from dining area. Sun-flooded and relaxing.
New gourmet kitchen
Staircase leads to living room
Exceptional
(51 reviews)

Exclusive Oyster Pond Retreat With Private Beach, New Kitchen and Boat

Edgartown

8% off
S$15,212
for 7 nights, 1 home
S$2,173 per night
includes taxes & fees
Exclusive Oyster Pond Retreat With Private Beach, New Kitchen and Boat
Dining
Living area
Private kitchen
Room
Exceptional
(28 reviews)

Peaceful and Relaxing Cape Cod Ranch located 7 Min. from the Beach.

East Falmouth

7% off
S$8,478
for 7 nights, 1 home
S$1,211 per night
includes taxes & fees
Peaceful and Relaxing Cape Cod Ranch located 7 Min. from the Beach.
Interior
Terrace/patio
Family Room with Panoramic View of the Pool and the Patio
Living area
Exceptional
(5 reviews)

Heated Indoor Pool & Spa - Golf Course View

Mashpee

7% off
S$10,703
for 7 nights, 1 villa
S$1,529 per night
includes taxes & fees
Heated Indoor Pool & Spa - Golf Course View
Outdoor dining
Living area
Dining
Exterior
Exceptional
(17 reviews)

THE PARK ESTATE! Your Martha's Vineyard Getaway!

Oak Bluffs

8% off
S$73,304
for 7 nights, 1 home
S$10,472 per night
includes taxes & fees
THE PARK ESTATE! Your Martha's Vineyard Getaway!
Living area
Exterior
Sun room off the kitchen.
Double sinks for busy kitchens.
Exceptional
(6 reviews)

WALK TO VILLAGE LOCATION, NEW POOL, FAMILY COMPOUND!

Edgartown

8% off
S$32,436
for 7 nights, 1 home
S$4,634 per night
includes taxes & fees
WALK TO VILLAGE LOCATION, NEW POOL, FAMILY COMPOUND!
Large, farmhouse fireplace perfect for chillier seasons.
Meals on the patio are a daily delight- sparkly mornings to ocean dipped sunsets
Exterior
Dining area can seat 8-10 and looks onto patio and water views.
Exceptional
(43 reviews)

Sanctuary House: An ocean-view farmhouse retreat

Vineyard Haven

7% off
S$6,816
for 7 nights, 1 home
S$974 per night
includes taxes & fees
Sanctuary House: An ocean-view farmhouse retreat
family room
Terrace/patio
kitchen
dining room
Exceptional
(34 reviews)

Cotuit Home with an Inground Pool less One Block from the Beach

Cotuit

8% off
S$19,591
for 7 nights, 1 home
S$2,799 per night
includes taxes & fees
Cotuit Home with an Inground Pool less One Block from the Beach
Interior
Living area
Living area
Dining
Exceptional
(48 reviews)

Contemporary and Spacious South Cape Beach Home !!!

Mashpee

8% off
S$8,269
for 7 nights, 1 home
S$1,181 per night
includes taxes & fees
Contemporary and Spacious South Cape Beach Home !!!
Dining
Terrace/patio
Exterior
Interior
Exceptional
(7 reviews)

BRAND NEW!

Oak Bluffs

7% off
S$10,573
for 7 nights, 1 home
S$1,510 per night
includes taxes & fees
BRAND NEW!
Exterior
Outdoor dining
Living area
Private kitchen
Exceptional
(9 reviews)

Charming 4-bedroom house with AC and WiFi in beautiful Edgartown

Edgartown

8% off
S$8,731
for 7 nights, 1 home
S$1,247 per night
includes taxes & fees
Charming 4-bedroom house with AC and WiFi in beautiful Edgartown
Great kayaking down the street to Washburn Island & Waquoit Bay.
Use of clubhouse heated POOL & tennis courts.
Open dining room, living room, kitchen (brand new) 
 & deck.
Out door seating for 8 & gas grill.
Wonderful
(35 reviews)

Minutes to Menauhant Beach - July & August AVAILABILITY clubhouse heated pool.

East Falmouth

7% off
S$4,143
for 7 nights, 1 home
S$592 per night
includes taxes & fees
Minutes to Menauhant Beach - July & August AVAILABILITY clubhouse heated pool.
Outdoor dining
Private kitchen
Private kitchen
Dining
Exceptional
(56 reviews)

Luxurious & Spacious 6 Bed/5 Bath Home with Ocean Views, New Seabury, Cape Cod

Mashpee

15% off
S$8,072
for 7 nights, 1 home
S$1,153 per night
includes taxes & fees
Luxurious & Spacious 6 Bed/5 Bath Home with Ocean Views, New Seabury, Cape Cod
Nice deck right off the kitchen with a grill and exterior furniture
Private kitchen
Interior
Exterior
Exceptional
(25 reviews)

New Home close to Beach, Bike Path, and Sleeps 10! ☀️ 🏖

Falmouth

7% off
S$3,574
for 7 nights, 1 home
S$511 per night
includes taxes & fees
New Home close to Beach, Bike Path, and Sleeps 10! ☀️ 🏖
Your closest neighbors are a family of Osprey!
This unique home was
carefully renovated to maintain its original character.
Choose from a variety of seating areas
overlooking the ocean and harbor.
You will create forever memories in this amazing setting.
Exceptional
(28 reviews)

Oceanfront, Private Dock and Harthaven Private Beach - Walk to Noman's, Inkwell

Oak Bluffs

8% off
S$45,611
for 7 nights, 1 home
S$6,516 per night
includes taxes & fees
Oceanfront, Private Dock and Harthaven Private Beach - Walk to Noman's, Inkwell
Front porch
Kitchen
Dining Room
Living Room
Exceptional
(34 reviews)

Across the street from Old Silver Beach; New house with hot tub. Sleeps 12.

Falmouth

8% off
S$5,390
for 7 nights, 1 home
S$770 per night
includes taxes & fees
Across the street from Old Silver Beach; New house with hot tub. Sleeps 12.
Exterior
Dining
Living area
Interior
Exceptional
(5 reviews)

Beach Getaway - Spacious Katama Beach House

Edgartown

8% off
S$33,053
for 7 nights, 1 home
S$4,722 per night
includes taxes & fees
Beach Getaway - Spacious Katama Beach House
Toasty Fireplace for fall and winter getaways
View from kitchen
Kitchen
View from upper deck
Exceptional
(76 reviews)

Beach Front on Beautiful Jenkins Pond, Quiet Area, Discounted off season rates!

East Falmouth

7% off
S$3,625
for 7 nights, 1 home
S$518 per night
includes taxes & fees
Beach Front on Beautiful Jenkins Pond, Quiet Area, Discounted off season rates!
West wing with futon/sleeper
Plenty of space for dining or lounging on this deck !  Good dogs always welcome!
Spacious wrap around deck with all day sun and shade
Entering from the driveway
Exceptional
(45 reviews)

Striking 5BR/4BA Chilmark Contemporary with Views of the Sound

Chilmark

7% off
S$6,816
for 7 nights, 1 home
S$974 per night
includes taxes & fees
Striking 5BR/4BA Chilmark Contemporary with Views of the Sound
Exterior
Dining
Property grounds
Terrace/patio
Exceptional
(5 reviews)

Water views and a short walk to private beaches, Popponesset Inn and Marketplace

Mashpee

8% off
S$10,943
for 7 nights, 1 home
S$1,563 per night
includes taxes & fees
Water views and a short walk to private beaches, Popponesset Inn and Marketplace
Living area
Property grounds
Living area
Exterior
Exceptional
(18 reviews)

Charming pond front New Seabury resort area

Mashpee

7% off
S$8,747
for 7 nights, 1 home
S$1,250 per night
includes taxes & fees
Charming pond front New Seabury resort area
Private kitchen
Exterior
Interior
Room
Exceptional
(11 reviews)

Immaculate Falmouth Home, short walk to private beach, short drive to Woods Hole

Falmouth

7% off
S$8,996
for 7 nights, 1 home
S$1,285 per night
includes taxes & fees
Immaculate Falmouth Home, short walk to private beach, short drive to Woods Hole
Open floor plan of Living Room/ Dining room & Kitchen.
Kayaks to paddle around Waquoit Bay to Washburn Island
Slate kitchen island & granite dining room table.
Seating for 10.
Deck with outdoor dining & plenty of flowers.
Excellent
(70 reviews)

Steps to the Beach in East Falmouth, PET FRIENDLY & clubhouse heated pool.

East Falmouth

7% off
S$4,143
for 7 nights, 1 home
S$592 per night
includes taxes & fees
Steps to the Beach in East Falmouth, PET FRIENDLY & clubhouse heated pool.
Interior
Interior
Interior
Private kitchen
Exceptional
(51 reviews)

Luxury Loft Historic Center Oak Bluffs

Oak Bluffs

18% off
S$5,952
for 7 nights, 1 home
S$850 per night
includes taxes & fees
Luxury Loft Historic Center Oak Bluffs
Rose covered flower arch next to unit
Living area
Dining table with view of ocean in the sunroom
Exterior
Exceptional
(39 reviews)

Maushop Village Getaway with Ocean Views, Steps to Private Beach

Mashpee

7% off
S$5,564
for 7 nights, 1 cottage
S$795 per night
includes taxes & fees
Maushop Village Getaway with Ocean Views, Steps to Private Beach
  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Explore the beachside setting in Oak Bluffs

Enjoy the wineries and other features of Oak Bluffs. This walkable and scenic city is well known for its beaches, shopping and local tours. With a holiday rental, you get a home away from home – many rentals offer full kitchens and outdoor grills for some home cooking.

Sightseeing in and around Oak Bluffs

Are you hoping to find attractions to visit while you're in town? Venture out of your cosy holiday rental and experience everything that makes Oak Bluffs a one-of-a-kind holiday spot. These are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Cape Cod Winery (8.6 mi / 13.8 km)
  • Shining Sea Bikeway (9.2 mi / 14.8 km)
  • Farm Neck Golf Club (1.2 mi / 2 km)
  • Downtown Library Park (7.3 mi / 11.8 km)
  • Cape Cod Country Club (11.5 mi / 18.5 km)
  • Stand Up & Paddle Cape Cod (15.1 mi / 24.3 km)

Exploring the natural landscape of Oak Bluffs

Whether you're looking for fun outdoor activities or just want to appreciate the scenery, Oak Bluffs is a great place to get outside. These are some of the area's noteworthy natural features, all within 30 miles (48.2 km) of the city centre:

  • Ocean Park (0.3 mi / 0.5 km)
  • Oak Bluffs Town Beach (0.4 mi / 0.7 km)
  • Inkwell Beach (0.5 mi / 0.7 km)
  • Edgartown Beach (2.8 mi / 4.5 km)
  • Lighthouse Beach (4.8 mi / 7.7 km)
  • Lambert's Cove Beach (5.6 mi / 9.1 km)

Seasonal weather in Oak Bluffs

If warm-weather activities are high on your list, August, July, September and June are the hottest months to visit, when temperatures average 20°C.

Transport to and around Oak Bluffs

The nearest airport is in Vineyard Haven, MA (MVY-Martha's Vineyard), located 5.2 mi (8.3 km) from the city centre. If you're unable to find a flight that fits your schedule, you can also fly into Hyannis, MA (HYA-Barnstable Municipal), which is 20.5 mi (32.9 km) away.

Frequently asked questions

What is the best area to stay in Oak Bluffs when booking a holiday rental?
Among the most sought-after neighbourhoods to get a holiday property in Oak Bluffs is Lagoon Heights. Find your perfect stay on Vrbo and experience this area just like a local.
What is the most popular type of holiday rental accommodation in Oak Bluffs?
The most desirable types of holiday rentals in Oak Bluffs are houses. After something a little different? Vrbo has a variety of options to match our guests' requirements, so you'll see holiday homes in all shapes and sizes. The ideal fit is waiting for you — snap up yours today.
How much does it cost to rent a holiday rental in Oak Bluffs?
The average price for a holiday rental in Oak Bluffs is determined by a number of factors, like length of stay, property type and season. Whether you're thinking about a sprawling villa with space for extended family or an apartment for just you and the kids, just add your dates of travel to find stays that offer great value.
How much does it cost to rent a beach house in Oak Bluffs?
The average price for a holiday rental near the beach in Oak Bluffs depends on when you're visiting the area and the style and size of property you're looking for. You can find prices easily and quickly on Vrbo by entering your dates of travel. Then use our filters to choose the number of bedrooms and amenities that you require, like WiFi, air conditioning and a pool.
Are there pet-friendly holiday rentals in Oak Bluffs?
With 310 holiday rentals that welcome four-legged guests, your furry buddy can also come along on your Oak Bluffs holiday. Use the filter tool to browse our pet-friendly holiday rentals and find a holiday home that'll set tails wagging on Vrbo.
Can I rent a house with a pool in Oak Bluffs?
Pack your swimwear and inflatable unicorn, because there are 67 houses with a private pool in Oak Bluffs. Unwind at one of these terrific holiday rentals and every day can be a pool day. Simply enter your travel dates into Vrbo, then use the "pool" filter to find the perfect place for a splashing good time!
What are popular rental amenities in Oak Bluffs?
When it comes to rental amenities that guests are looking for in Oak Bluffs, tennis, a firepit and a chef are at the top of the list. With Vrbo holiday homes, you'll find options to fit your style and taste, whether you're going on a holiday with your partner, family members or even pets.
Are there large group holiday rentals in Oak Bluffs?
You'll find 62 holiday rentals in Oak Bluffs that can host 10 or more people. Whether you're organising a get-together with extended family or a celebration like a birthday, there's ample space to get your group together under the same roof.
Are there holiday rentals in Oak Bluffs that welcome kids?
Bring the entire group together for a fun-packed adventure in Oak Bluffs at one of our 310 family-friendly holiday properties. These stays provide conveniences that are just perfect for getaways with children, such as full kitchens, living rooms and patios. Just click on the "Properties good for families" filter box and pick out your favourite.
What are the top attractions for families in Oak Bluffs?
Keeping the kids happy during your Oak Bluffs holiday is child's play with these top family-friendly attractions:
  • Inkwell Beach
  • Oak Bluffs Town Beach
  • Falmouth Heights Beach
Are there one-bedroom holiday rentals in Oak Bluffs?
There are 30 one-bedroom properties in Oak Bluffs to select from. A one-bedroom holiday rental is a great choice if it's only you and your partner or if you're travelling on your own. Add in more convenience, privacy and space compared to a hotel, and you've got the makings of a break to remember.
Can I find two-bedroom holiday rentals in Oak Bluffs?
Gather your loved ones and experience complete comfort and privacy in one of the 59 two-bedroom holiday rentals Oak Bluffs has to offer.
Are there holiday rentals with WiFi in Oak Bluffs?
Whether you want to keep up with the headlines, make a video call or surf social media, there are 89 holiday homes with WiFi in Oak Bluffs. Check the "WiFi" box when searching on Vrbo and stay connected on your holiday.
How can I find holiday rentals with air conditioning in Oak Bluffs?
There are 280 Vrbo holiday homes with air conditioning in Oak Bluffs providing that gentle, cool breeze and extra bit of comfort. Enter your preferred travel dates and then take advantage of our filters to find stays with air conditioning.
How old do you have to be to rent a holiday rental in Oak Bluffs?
The age limit can differ across properties on Vrbo, so be sure to check the rules of the holiday home in Oak Bluffs you're considering. But normally, it's 16, 18 or 21.
How long can I rent a holiday rental in Oak Bluffs for?
The amount of time you can stay in an Oak Bluffs holiday rental for depends on each property. Just tap in your preferred travel dates to see options that offer long-term stays. They come with everything you need to make your extended trip more comfortable and convenient, such as kitchens and yards. Some holiday homes may also offer discounted weekly or monthly prices, so you can have a longer stay for less.

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