We noticed that you're using an unsupported browser. The Tripadvisor website may not display properly.We support the following browsers:
Windows:
Internet Explorer
,
Mozilla Firefox
,
Google Chrome
. Mac:
Safari
.
Flights
Vacation Rentals
Restaurants
Things to do
Skip to main content
Review
Trips
Alerts
Sign in
Cart
Inbox
See all
Sign in
to get trip updates and message other travelers.
Oak Bluffs
Oak Bluffs Tourism
Oak Bluffs Hotels
Oak Bluffs Bed and Breakfast
Oak Bluffs Vacation Rentals
Oak Bluffs Vacation Packages
Flights to Oak Bluffs
Oak Bluffs Restaurants
Things to Do in Oak Bluffs
Oak Bluffs Travel Forum
Oak Bluffs Photos
Oak Bluffs Map
Oak Bluffs Travel Guide
Hotels
All Oak Bluffs Hotels
Oak Bluffs Hotel Deals
Last Minute Hotels in Oak Bluffs
By Hotel Type
By Hotel Class
Popular Oak Bluffs Categories
Near Airports
Near Colleges
Oak Bluffs Campgrounds
Romantic Hotels in Oak Bluffs
Oak Bluffs Family Hotels
Oak Bluffs Resorts
5-stars Hotels in Oak Bluffs
4-stars Hotels in Oak Bluffs
3-stars Hotels in Oak Bluffs
Oak Bluffs Cheap Hotels
Hotels with Free Wifi in Oak Bluffs
Charming Hotels in Oak Bluffs
Oak Bluffs Clean Hotels
Oak Bluffs Hotels with Restaurants
Oak Bluffs Vineyard Hotels
Wedding Hotels in Oak Bluffs
Oak Bluffs Hotels with Kitchenette
Oak Bluffs Downtown Hotels
Quiet Hotels in Oak Bluffs
Hotels near (PVD) Theodore Francis Airport
Hotels near (MVY) Martha's Vineyard Airport
Hotels near (HYA) Barnstable Airport
Hotels near The National Graduate School of Quality Management
Things to do
Restaurants
Flights
Vacation Rentals
By Vacation Rental Type
Popular Amenities
Places of Interest
Airports
House Rentals in Oak Bluffs
Cheap Oak Bluffs Vacation Rentals
Oak Bluffs Luxury Vacation Rentals
Kid Friendly Oak Bluffs Vacation Rentals
Vacation Rentals near Inkwell Beach
Vacation Rentals near Farm Neck Golf Club
Vacation Rentals near East Chop Lighthouse
Vacation Rentals near Lambert's Cove Beach
Vacation Rentals near Martha's Vineyard Camp meeting Association (MVCMA)
Vacation Rentals near Trinity Park Tabernacle
Vacation Rentals near Shining Sea Bikeway
Vacation Rentals near Nobska Point Lighthouse
Vacation Rentals near Morning Glory Farm
Vacation Rentals near Martha's Vineyard Airport
Shopping
Vacation Packages
Cruises
Rental Cars
Tours
Add a Place
Travel Forum
Airlines
Travelers' Choice
Road Trips
Help Center
Travel Stories
Luxury Rentals and Vacation Rentals in Oak Bluffs, MA
Vacation Rentals
USA
Massachusetts (MA)
Martha's Vineyard
Oak Bluffs
Oak Bluffs Luxury Vacation Rentals
Search
Oak Bluffs Luxury Rentals
List your property
Owner log in
Where to?
Check in
— / — / —
Check out
— / — / —
Guests
0 rooms, 2+ guests
View Map
Bedrooms
Any
Bathrooms
Any
Amenities
Internet (362)
Washer/Dryer (332)
Air Conditioning (331)
Other outdoor space (319)
Show all
Suitability
Kid friendly (286)
Pet friendly (58)
Business Travel (33)
Elder access (11)
Show more
Property type
Vacation Rental House (308)
Condominium/Apartment (59)
Cabin Vacation Rental (0)
Private Room (0)
Show more
Distinctive Features
Waterfront (52)
Water Views (28)
Housekeeping Included (24)
Boat Available (7)
Show all
Distance from
1 mi
367 rentals
in Oak Bluffs.
Sort by:
Tripadvisor Sort
Revenue impacts this sort order.
Learn more.
NEW 5-bed, 4.5-bath w/full basement! Minutes frm downtown Oak Bluffs.
55 reviews
Rental Home
5 bedrooms
5 bathrooms
Sleeps 12
Match:
Sleeps
More info
Check in
Check out
Show Prices
Arrowsmith Cottage - Near Eastville Point Beach - Oak Bluffs-Martha's Vineyard
53 reviews
Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match:
Sleeps
More info
Check in
Check out
Show Prices
Private Family Home, Heated Pool, Pets OK, Outdoor Shower, AC, 5 BR 4.5 bath
53 reviews
Rental Home
7 bedrooms
6 bathrooms
Sleeps 16
Match:
Sleeps
More info
Check in
Check out
Show Prices
Perfect for Family, Friends, or a Romantic Getaway - Newly Renovated!
75 reviews
Rental Home
4 bedrooms
2 bathrooms
Sleeps 7
Match:
Sleeps
More info
Check in
Check out
Show Prices
Your "Vineyard Dream" Vacation (OAK BLUFFS)-Sunny Open Floor Plan Close to Town
79 reviews
Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check in
Check out
Show Prices
Private Meadow View Family Retreat - 4 BR, AC, Tennis, on bike path, large yard
41 reviews
Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check in
Check out
Show Prices
Waterfront. Glorious Sunsets. Private Beach. Kayaks-Paddle boards. Walk to town
29 reviews
Rental Home
5 bedrooms
4 bathrooms
Sleeps 12
Match:
Sleeps
More info
Check in
Check out
Show Prices
Beautifully Updated Home, Close to Town
38 reviews
Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check in
Check out
Show Prices
Martha's Vineyard Beachfront Condo in Oak Bluffs
39 reviews
Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check in
Check out
Show Prices
The Oak bluffs cottage, Martha’s Vineyard Island.Perfect for. Honeymoon!
51 reviews
Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps
More info
Check in
Check out
Show Prices
Save time - get the best
Oak Bluffs
rentals sent straight to your email!
Get the List
Modern 4 bed/3.5 bath Farmhouse with private POOL and AC on bike path
35 reviews
Rental Home
6 bedrooms
4 bathrooms
Sleeps 10
Match:
Sleeps
More info
Check in
Check out
Show Prices
Make Lasting Memories In This Adorable Vineyard Cottage!
99 reviews
Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match:
Sleeps
More info
Check in
Check out
Show Prices
Beautiful small home w private patio + yardNOW available * WINTER rates !
24 reviews
Rental Home
1 bedroom
1 bathroom
Sleeps 3
Match:
Sleeps
More info
Check in
Check out
Show Prices
Cozy, Clean, Bikes, Kayaks, Laundry, Ferry Tickets, Near Bike Path and Town
41 reviews
Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match:
Sleeps
More info
Check in
Check out
Show Prices
Location & Charm -- Central AC
30 reviews
Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check in
Check out
Show Prices
Comfortable Island Home, Easy Access to Beaches and Town
46 reviews
Rental Home
2 bedrooms
1 bathroom
Sleeps 8
Match:
Sleeps
More info
Check in
Check out
Show Prices
'The Carousel House' - Ocean Park - Featured in New York Times
43 reviews
Rental Home
7 bedrooms
3 bathrooms
Sleeps 12
Match:
Sleeps
More info
Check in
Check out
Show Prices
Comfortable townhouse close to town & the beach with outdoor pool & tennis
31 reviews
Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check in
Check out
Show Prices
CENTRAL AIR! Quiet East Chop Retreat Walk 2 Town and Beach.
39 reviews
Rental Home
5 bedrooms
3 bathrooms
Sleeps 12
Match:
Sleeps
More info
Check in
Check out
Show Prices
Family friendly (1 dog ok); walk to beach, cliff, town, ferries
17 reviews
Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match:
Sleeps
More info
Check in
Check out
Show Prices
Cozy, dog-friendly condo by the sea with a shared pool, tennis, picnic area
29 reviews
Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps
More info
Check in
Check out
Show Prices
A shared pool, tennis courts, golf, beaches, and more await you at this condo
35 reviews
Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps
More info
Check in
Check out
Show Prices
Now booking for Summer 2023! Remodeled kitchen and bathroom.
42 reviews
Rental Home
4 bedrooms
4 bathrooms
Sleeps 9
Match:
Sleeps
More info
Check in
Check out
Show Prices
Stylish townhouse 1/2 mile from the beach - tennis courts & pool on-site
24 reviews
Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check in
Check out
Show Prices
Mid-week turnovers...Great for those who don't have a Monday-Friday workweek
23 reviews
Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check in
Check out
Show Prices
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.
21 reviews
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match:
Sleeps
More info
Check in
Check out
Show Prices
Oak Bluffs Victorian - steps from circuit ave, ocean park, & beach
19 reviews
Rental Home
6 bedrooms
3 bathrooms
Sleeps 12
Match:
Sleeps
More info
Check in
Check out
Show Prices
Sunny coastal retreat with WiFi, pool & tennis - 1/2 mile to beach
23 reviews
Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match:
Sleeps
More info
Check in
Check out
Show Prices
Historic Renovated Home in East Chop
41 reviews
Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check in
Check out
Show Prices
Cozy condo with shared pool & tennis - close to beaches, golf, & parks!
36 reviews
Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps
More info
Check in
Check out
Show Prices
Cozy, exceptional view, quiet, high speed WIFI, close to all island attractions
53 reviews
Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check in
Check out
Show Prices
THE PARK ESTATE! Your Martha's Vineyard Getaway!
16 reviews
Rental Home
6 bedrooms
6 bathrooms
Sleeps 16
Match:
Sleeps
More info
Check in
Check out
Show Prices
Dog-friendly studio condo w/ shared pool & tennis - close to beaches and golf!
25 reviews
Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps
More info
Check in
Check out
Show Prices
Private Waterfront, Private Beach, Private 90' Dock, Views Views Views
26 reviews
Rental Home
3 bedrooms
4 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check in
Check out
Show Prices
Charming Sunny Beach House, Walk to Downtown
29 reviews
Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check in
Check out
Show Prices
Family-friendly, Island Retreat With Luxurious Amenities
32 reviews
Rental Home
4 bedrooms
5 bathrooms
Sleeps 4
Match:
Sleeps
More info
Check in
Check out
Show Prices
Newly renovated, air conditioned cottage close to the beach and town. dogs ok
15 reviews
Rental Home
3 bedrooms
4 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check in
Check out
Show Prices
The Island Collection MV: Charming Cottage Located In Heart Of Oak Bluffs
34 reviews
Rental Home
2 bedrooms
3 bathrooms
Sleeps 4
Match:
Sleeps
More info
Check in
Check out
Show Prices
Charming Artsy Apartment
28 reviews
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps
More info
Check in
Check out
Show Prices
Spacious Waterview Condo - Steps To The Beach, Right Across The Street!
61 reviews
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check in
Check out
Show Prices
**WALK TO BEACHES,HARBOR,EVERYTHING!! *IN-TOWN OB! Deck,A/C,Outdoor Shower, Wifi
39 reviews
Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match:
Sleeps
More info
Check in
Check out
Show Prices
Oak Bluffs Rental - Walk to the Beach
8 reviews
Rental Home
3 bedrooms
3 bathrooms
Sleeps 7
Match:
Sleeps
More info
Check in
Check out
Show Prices
Payment Protection
Cozy cottage 3/4 mile from Oak Bluffs harbor
22 reviews
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check in
Check out
Show Prices
Martha's Vineyard Oak Bluffs East Chop Summer Vacation Rental Home 4 Bedroom
22 reviews
Rental Home
4 bedrooms
3 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check in
Check out
Show Prices
Pristine Retreat - Spectacular outdoor space - New Blue Stone Patio and Fire Pit
21 reviews
Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check in
Check out
Show Prices
New Construction with Patio & Yard - Walk to the Ferry, Downtown & Beaches
51 reviews
Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match:
Sleeps
More info
Check in
Check out
Show Prices
Central location for your vacation
32 reviews
Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check in
Check out
Show Prices
Meadow View Farms hideaway. 68 Meadow View Road, Oak Bluffs
25 reviews
Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match:
Sleeps
More info
Check in
Check out
Show Prices
3 Ensuites, Central Air, Perfect Location
20 reviews
Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check in
Check out
Show Prices
Oak Bluffs apartment, walk to town and beaches!
20 reviews
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 2
Match:
Sleeps
More info
Check in
Check out
Show Prices
Previous
Next
1
2
3
4
5
6
…