Oak Bluffs Luxury Rentals
Where to?
Check in
— / — / —
Check out
— / — / —
Guests
0 rooms, 2+ guests
Bedrooms
Bathrooms
Amenities
Suitability
Property type
Distinctive Features
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.
Rental Home
5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
More info
Check in
Check out
Arrowsmith Cottage - Near Eastville Point Beach - Oak Bluffs-Martha's Vineyard
Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check in
Check out
Private Family Home, Heated Pool, Pets OK, Outdoor Shower, AC, 5 BR 4.5 bath
Rental Home
7 bedrooms
6 bathrooms
Sleeps 16
Match: Sleeps
More info
Check in
Check out
Perfect for Family, Friends, or a Romantic Getaway - Newly Renovated!
Rental Home
4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
Check in
Check out
Your "Vineyard Dream" Vacation (OAK BLUFFS)-Sunny Open Floor Plan Close to Town
Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
Private Meadow View Family Retreat - 4 BR, AC, Tennis, on bike path, large yard
Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
Waterfront. Glorious Sunsets. Private Beach. Kayaks-Paddle boards. Walk to town
Rental Home
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
More info
Check in
Check out
Beautifully Updated Home, Close to Town
Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
Martha's Vineyard Beachfront Condo in Oak Bluffs
Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
The Oak bluffs cottage, Martha’s Vineyard Island.Perfect for. Honeymoon!
Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
Save time - get the best Oak Bluffs rentals sent straight to your email!
Modern 4 bed/3.5 bath Farmhouse with private POOL and AC on bike path
Rental Home
6 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Check in
Check out
Make Lasting Memories In This Adorable Vineyard Cottage!
Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
Beautiful small home w private patio + yardNOW available * WINTER rates !
Rental Home
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
Check in
Check out
Cozy, Clean, Bikes, Kayaks, Laundry, Ferry Tickets, Near Bike Path and Town
Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
Check in
Check out
Location & Charm -- Central AC
Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
Comfortable Island Home, Easy Access to Beaches and Town
Rental Home
2 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
More info
Check in
Check out
'The Carousel House' - Ocean Park - Featured in New York Times
Rental Home
7 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
Check in
Check out
Comfortable townhouse close to town & the beach with outdoor pool & tennis
Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
CENTRAL AIR! Quiet East Chop Retreat Walk 2 Town and Beach.
Rental Home
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
Check in
Check out
Family friendly (1 dog ok); walk to beach, cliff, town, ferries
Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
Check in
Check out
Cozy, dog-friendly condo by the sea with a shared pool, tennis, picnic area
Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
A shared pool, tennis courts, golf, beaches, and more await you at this condo
Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
Now booking for Summer 2023! Remodeled kitchen and bathroom.
Rental Home
4 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
More info
Check in
Check out
Stylish townhouse 1/2 mile from the beach - tennis courts & pool on-site
Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Mid-week turnovers...Great for those who don't have a Monday-Friday workweek
Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
Oak Bluffs Victorian - steps from circuit ave, ocean park, & beach
Rental Home
6 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
Check in
Check out
Sunny coastal retreat with WiFi, pool & tennis - 1/2 mile to beach
Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check in
Check out
Historic Renovated Home in East Chop
Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
Cozy condo with shared pool & tennis - close to beaches, golf, & parks!
Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
Cozy, exceptional view, quiet, high speed WIFI, close to all island attractions
Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
THE PARK ESTATE! Your Martha's Vineyard Getaway!
Rental Home
6 bedrooms
6 bathrooms
Sleeps 16
Match: Sleeps
More info
Check in
Check out
Dog-friendly studio condo w/ shared pool & tennis - close to beaches and golf!
Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
Private Waterfront, Private Beach, Private 90' Dock, Views Views Views
Rental Home
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Charming Sunny Beach House, Walk to Downtown
Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Family-friendly, Island Retreat With Luxurious Amenities
Rental Home
4 bedrooms
5 bathrooms
Sleeps 4
Match: Sleeps
More info
Check in
Check out
Newly renovated, air conditioned cottage close to the beach and town. dogs ok
Rental Home
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
The Island Collection MV: Charming Cottage Located In Heart Of Oak Bluffs
Rental Home
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
More info
Check in
Check out
Charming Artsy Apartment
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
Spacious Waterview Condo - Steps To The Beach, Right Across The Street!
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
**WALK TO BEACHES,HARBOR,EVERYTHING!! *IN-TOWN OB! Deck,A/C,Outdoor Shower, Wifi
Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
Check in
Check out
Oak Bluffs Rental - Walk to the Beach
Rental Home
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
More info
Check in
Check out
Payment Protection
Cozy cottage 3/4 mile from Oak Bluffs harbor
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Martha's Vineyard Oak Bluffs East Chop Summer Vacation Rental Home 4 Bedroom
Rental Home
4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Pristine Retreat - Spectacular outdoor space - New Blue Stone Patio and Fire Pit
Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
New Construction with Patio & Yard - Walk to the Ferry, Downtown & Beaches
Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Check in
Check out
Central location for your vacation
Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Meadow View Farms hideaway. 68 Meadow View Road, Oak Bluffs
Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Check in
Check out
3 Ensuites, Central Air, Perfect Location
Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
Oak Bluffs apartment, walk to town and beaches!
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 2
Match: Sleeps
More info
Check in
Check out
123456…