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.

Oak Bluffs Romantic Vacation Rentals

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
Check In Check Out
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    View Map
    Location
    Any Distance
    from
    Price
    per night
    $209 Average
    |||
    |||
    $0$1,000+
    Suitability
    More filters
    Travelers to Oak Bluffs are booking June dates now. Secure your vacation rental today, and have the perfect trip.
    15 Matching Rentals in Oak BluffsView all 231 rentals
    Sort by:
    Default
    2 Bedrooms, 1 Bathroom, Sleeps 3 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    In-Town Historic Property on Martha's Vineyard1 / 20
    (69)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other traveler has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Porch
    • Ocean Views
    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful and spacious 3 bedroom and 2 bathroom. Sunny, open and airy Cape style home. Sleeps 6 people. Comfortably furnished, has air conditioning and has Hi-Speed internet, cable TVs, washer, dryer and parking. Large, private back yard with deck and grill. Convenient location - short walking...
    View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard 02557
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Inquiry
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Wi-Fi
    • DVD Player
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Cute and Cozy guest house with open floor plan in the kitchen, living and alcove sleeping area with queen bed. This cottage is perfect for couples, the owner will consider one additional child. There is a den with futon sofa separate from the main part of the cottage. Relax on the deck while...
    View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard 02568
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Inquiry
    Oak Bluffs Retreat1 / 21
    (5)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Washer
    • Air Conditioning
    • Grill
    • Wi-Fi
    • DVD Player
    • Parking
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 24, 2018
    We are very excited that we booked the house again this summer. We were there in 2016 and loved it. The house is very clean and it exceeded our expectation. it is centrally...
    Reviewed May 22, 2018
    Stayed at a lovely home on the Island..Pleasant grounds with lots of space..Home is in a great location with easy access to every town ..Beachs nearby and a great golf within...
    See all reviews
    About this property
    Welcome to Martha's Vineyard. So many of our guests have returned year after year because they find our property to be centrally located, clean, updated and relaxing. We strive to make our home comfortable, fresh, modern and relaxing. In fact every year we add something new to make our home even...
    View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard 02557
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Inquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Washer
    • Internet Access
    • Grill
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Please note: this house has a new owner and is undergoing major renovations over the winter of 2018. When it’s finished, it will have: a first floor master bedroom with a king-sized bed and a new en-suite double-vanity bathroom with shower, a first-floor laundry room with full-size washer and...
    View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard 02557
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Inquiry
    Studio, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Patio
    • Cable/satellite TV
    • Parking
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Fall in love with Martha's Vineyard during a stay in this lovely first-floor suite by the sea! You'll have access to the grounds' shared pool, kids' playground, BBQ area, and more. Plus, you're only a short drive or a leisurely half-mile walk away from the gorgeous shore. The family dog is also...
    View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard 02557
    Condo/Apartment - 1 Bathroom, Sleeps 4
    Make Inquiry
    Studio, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Internet Access
    • Washer
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Perfect for couples or close friends, this first-floor Island Inn condo has everything you need for a fantastic trip to Martha's Vineyard! Enjoy on-site perks like a shared pool and tennis courts, or venture out to experience New England's beaches, shops, and restaurants. You will enjoy a...
    View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard 02557
    Condo/Apartment - 1 Bathroom, Sleeps 4
    Make Inquiry
    Studio, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    • Parking
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Get ready for a truly memorable vacation in Martha's Vineyard at this cozy studio condo within the wooded Island Inn community. During your stay, enjoy access to a shared pool, tennis courts, and a picnic and BBQ area. Take a short stroll over to the beach to watch the sunrise and then head north...
    View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard 02557
    Condo/Apartment - 1 Bathroom, Sleeps 4
    Make Inquiry
    Save time - get the best Oak Bluffs rentals sent straight to your email!
    Get the List
    Studio, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Cable/satellite TV
    • Washer
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Perfect for couples or close friends, this second floor Island Inn condo is the ideal home base for exploring Martha's Vineyard! From the sights of Oak Bluffs to perks like a shared pool and tennis courts, you'll have everything you need to make your next New England getaway special. The family dog...
    View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard 02557
    Condo/Apartment - 1 Bathroom, Sleeps 4
    Make Inquiry
    Studio, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Washer
    • Parking
    • Air Conditioning
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Book your trip to this seaside Martha's Vineyard retreat for a trip you'll never forget! With room for guests to enjoy the on-site tennis, shared pool, and easy beach access, you may never want to leave! Nestled on the beautiful grounds of the Island Inn on Martha's Vineyard, this second-floor...
    View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard 02557
    Condo/Apartment - 1 Bathroom, Sleeps 4
    Make Inquiry
    Studio, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Cable/satellite TV
    • Air Conditioning
    • Parking
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Whether you're looking for a romantic getaway or a relaxing New England retreat with a close friend, you'll love this walk-up second-floor suite at the Island Inn. Experience an amazing vacation in Martha's Vineyard, with amenities like a shared pool on-site and plenty of sightseeing in nearby Oak...
    View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard 02557
    Condo/Apartment - 1 Bathroom, Sleeps 4
    Make Inquiry
    Studio, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Cable/satellite TV
    • Parking
    • Washer
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy a romantic getaway to Martha's Vineyard at this adorable studio condo for two. With access to a shared swimming pool, tennis courts, and a picnic area, guests of the Island Inn will have a magical time at this rental. This first-floor studio is located along the edge of the highly rated Farm...
    View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard 02557
    Condo/Apartment - 1 Bathroom, Sleeps 2
    Make Inquiry
    Studio, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Internet Access
    • Parking
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Treat your special someone to a stress-free getaway at this Martha's Vineyard seaside condo. Guests will enjoy the shared pristine pool, on-site tennis courts, and easy beach access, making this is the perfect spot to revel in the surrounding beauty. The family dog is also welcome to join you here...
    View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard 02557
    Condo/Apartment - 1 Bathroom, Sleeps 4
    Make Inquiry
    Oak Bluffs Flight and Weather Info
    Low airfares recently found by TripAdvisor travelers
    |
    Local Weather
    Powered by Weather Underground
    39° 24°
    December
    33° 19°
    January
    34° 19°
    February
    39° 24°
    March

    Additional Oak Bluffs Info

    Go to map view
    • Local time: 05:34 PM (EST)
    List your property
    Owner log in