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Compare 1153 Vacation Homes in Oak Bluffs with updated reviews, rates, and availability.

4BR Ocean Timberland - Osterville w/ private pool
Backyard w/ pool
4BR Ocean Timberland - Osterville w/ private pool
10.0 out of 10, Exceptional, (10)
"The pool was nice Although the weather was not Very nice layout Had a great time "
4BR Ocean Timberland - Osterville w/ private pool
Coastal chic meets French Provençal in this newly renovated oceanfront home.
Exterior
Coastal chic meets French Provençal in this newly renovated oceanfront home.
10.0 out of 10, Exceptional, (72)
"The home and views were stunning! Clean, comfortable, and plenty of space for everyone. Easy communication with the host. We had a lovely stay!"
The price is AED 1,833
AED 4,292 total
includes taxes & fees
13 Dec - 14 Dec
Coastal chic meets French Provençal in this newly renovated oceanfront home.
Cozy Cape home with outdoor shower and deck - minutes to beach
Cozy Cape home with outdoor shower and deck - minutes to beach
9.8 out of 10, Exceptional, (60)
"House was perfect. Wonderful location. Enjoyed stay so much."
Cozy Cape home with outdoor shower and deck - minutes to beach
Charming cottage with deck, yard, & AC - walk to beach, Main Street, & ferry
Charming cottage with deck, yard, & AC - walk to beach, Main Street, & ferry
9.6 out of 10, Exceptional, (46)
"Lovely visit "
Charming cottage with deck, yard, & AC - walk to beach, Main Street, & ferry
Private suite upstairs: bedroom, office, TV room, bathroom & a large deck.
Tv/media-room.
Private suite upstairs: bedroom, office, TV room, bathroom & a large deck.
10.0 out of 10, Exceptional, (24)
"Nice upper suite. Clean rooms. It was nice that linens were provided. It had a small mini fridge and small microwave stacked on a table. A table to sit at would have been nice. 2 small mugs and 2 plastic wine glasses were supplied as well. I stayed for 6 nights so I just kept rinsing out my mug. 2 separate AC units provided comfortable temperature. Nice quiet area. The deck was nice. It was wet from condensation in the morning and then hot in afternoon with full sun so I didn’t use it. ...
Private suite upstairs: bedroom, office, TV room, bathroom & a large deck.
Spacious cape house near Craigville Beach, downtown Centerville, Hyannis & more!
Exterior
Spacious cape house near Craigville Beach, downtown Centerville, Hyannis & more!
9.6 out of 10, Exceptional, (15)
"A group of friends and I had a lovely long weekend stay here. The yard is so big and perfect for games and relaxing, and the house is close to several beaches, mini golf, restaurants, ice cream, etc. The layout is kind of weird, but we had plenty of space for everything. Would stay here again!"
Spacious cape house near Craigville Beach, downtown Centerville, Hyannis & more!
Immaculate Home, 2 Acres, Short Walk To Beach!
Immaculate Home, 2 Acres, Short Walk To Beach!
10.0 out of 10, Exceptional, (6)
"Our family really enjoyed our stay. Check in and out was easy. House was spacious with lots of room for everyone. Area was gorgeous with plenty to do. Many thanks!"
Immaculate Home, 2 Acres, Short Walk To Beach!
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
Rear view of the house with deck, patio, grill, adirondacks,two tables 12 seats.
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
10.0 out of 10, Exceptional, (188)
"The house was as advertised! Spacious, clean, comfy beds and close to town and beach. Very nice stay. We would definitely rent again! Thank you!"
The price is AED 808
AED 2,114 total
includes taxes & fees
25 Nov - 26 Nov
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
Immaculate Cape Cod Family Retreat- minutes from Ponds, Lakes, and Ocean!
Exterior
Immaculate Cape Cod Family Retreat- minutes from Ponds, Lakes, and Ocean!
10.0 out of 10, Exceptional, (41)
"The house was beautifully clean and well equipped . The central location meant we could fully explore all areas , and enjoy the local hospitality. I would highly recommend this property and its host to friends and family .its a 10 out of 10 from us."
Immaculate Cape Cod Family Retreat- minutes from Ponds, Lakes, and Ocean!
✸Private Sandy Beach✸ Nantucket Sound-2 Min Walk! Kayak & SUP, Near Harbor &Town
Check out our video: https://www.youtube.com/watch?v=6uhi8e5Crgg
✸Private Sandy Beach✸ Nantucket Sound-2 Min Walk! Kayak & SUP, Near Harbor &Town
10.0 out of 10, Exceptional, (80)
"This house and location was beyond our expectations! Beautifully furnished, comfortable and well stocked with anything you would need or want for a perfect vacation. Would love to come back! "
✸Private Sandy Beach✸ Nantucket Sound-2 Min Walk! Kayak & SUP, Near Harbor &Town
Falmouth Cape - Walk to Island Queen ferry to Martha's Vineyard, Beach, Downtown
Falmouth Cape - Walk to Island Queen ferry to Martha's Vineyard, Beach, Downtown
10.0 out of 10, Exceptional, (154)
"This place has everything you need for a very pleasant stay in Falmouth. Communication was great. Check-in was flawless once I figured out which key was which. The location is in a nice quiet neighborhood and just minutes from everything anyone could need, including a GREAT patisserie/boulangerie that I wish we would have found two days earlier. The house itself is a bit older with a few minor, older house issues, none of which are bothersome at all. It is very well equipped. None of the...
Falmouth Cape - Walk to Island Queen ferry to Martha's Vineyard, Beach, Downtown
A Vineyard Home Perfect For Family Gatherings
Exterior
A Vineyard Home Perfect For Family Gatherings
9.0 out of 10, Wonderful, (29)
"In a safe, quiet neighborhood, a true Family beach house/Cabin. Very roomy. "
A Vineyard Home Perfect For Family Gatherings
Location! Location! Location! Steps To Falmouth Heights Beach! CENTRAL AIR
Private kitchen
Location! Location! Location! Steps To Falmouth Heights Beach! CENTRAL AIR
10.0 out of 10, Exceptional, (39)
"Do not hesitate to book this property. We took a family vacation with grandparents, parents, a teen, and a tween. The house would have easily accomodated young children, as well. It was updated, clean, bright, deceptively spacious, and you cannot beat the location. We walked to the beach so many times! There are spaces to watch tv, build a puzzle, sit and read in peace, nap, get some sun on the patio, etc. Parking was easy for two cars, quiet neighborhood, and the owner was kind and...
Location! Location! Location! Steps To Falmouth Heights Beach! CENTRAL AIR
Private Beach Access at Exclusive Oyster Pond Retreat
Private association beach
Private Beach Access at Exclusive Oyster Pond Retreat
10.0 out of 10, Exceptional, (41)
"We had a wonderful time at this beautiful and well-stocked home. The hosts were immediately responsive to all contacts and repeatedly looked to make our stay special. The house and amenities were accurately describe and even understated when you see that the boats, bikes and games were all quality items. The house was impeccably clean and had everything we could possibly need. We had an amazing time. If you rent this house you will want or need for nothing and will probably be writing a...
Private Beach Access at Exclusive Oyster Pond Retreat
Stunning Lake Front House with Private Beach
Living area
Stunning Lake Front House with Private Beach
8.8 out of 10, Excellent, (5)
"We stayed for a weekend with a few adults and a bunch of teenagers - great layout for socializing with the bedrooms on three floors. Lake is gorgeous. Very clean."
The price is AED 2,454
AED 4,116 total
includes taxes & fees
25 Nov - 26 Nov
Stunning Lake Front House with Private Beach
Walk to Town/Golf Club - Renovated Edgartown Home
Interior
Walk to Town/Golf Club - Renovated Edgartown Home
10.0 out of 10, Exceptional, (38)
"Here we found what we hoped for our stay in Martha's. In a quiet residential street, a comfortable, ultra clean house with good size rooms and quality amenities. Cleverly placed skylights illuminate the interior. A supermarket is a corner away and the Edgartown charming historic city center is an easy 15 minutes walk. Who says better? Charles and Andree Sepember 2024"
Walk to Town/Golf Club - Renovated Edgartown Home
Peaceful, dog-friendly home on 3 acres with lovely yard, near beaches
Peaceful, dog-friendly home on 3 acres with lovely yard, near beaches
8.8 out of 10, Excellent, (9)
"We had such a lovely time staying at this house. It was absolutely immaculate inside and appointed with everything we could need and more. The house is light and airy inside, which helped when we had a few days of rain. The location is secluded in the woods (be careful, we did find ticks on us) but a short drive away from the beaches. We will definitely be back "
Peaceful, dog-friendly home on 3 acres with lovely yard, near beaches
Dream coastal dog-friendly vacation 4-bedroom home. Steps from Keyes Beach!
The Keyes Beach is just steps from the house!
Dream coastal dog-friendly vacation 4-bedroom home. Steps from Keyes Beach!
9.8 out of 10, Exceptional, (144)
"The house was very nice and the perfect layout for our gang. The check out pricess briught some grumbles from some family membersas well as the 10 AM check out. I explained its a lot of house to clean before a new group at 4PM. A relative that lives on the Cape said the other side of Sea Street is a bit shady, which is why I gave the 4 star for location. "
Dream coastal dog-friendly vacation 4-bedroom home. Steps from Keyes Beach!
Beachfront On John's Pond, Indoor HEATED Pool, and Dock!
Exterior
Beachfront On John's Pond, Indoor HEATED Pool, and Dock!
9.6 out of 10, Exceptional, (82)
"Wonderful property on the pond. We had a great time. Would rent again. "
Beachfront On John's Pond, Indoor HEATED Pool, and Dock!
Escape on conservation land with furnished deck, pond views, sunroom, & AC
Escape on conservation land with furnished deck, pond views, sunroom, & AC
9.0 out of 10, Wonderful, (14)
"House is great and has everything. The one remote to operate the a/c in one of the upstairs bedrooms needed new batteries (we think). Also we think the entry lock battery is low as it kept going out on us mid code. We wrote the Vacasa people and they wanted us to buy new batteries. NO. It up tk the property manager to take care of this."
Escape on conservation land with furnished deck, pond views, sunroom, & AC
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Oak Bluffs

Cute & cozy cottage with a patio & gas grill in the heart of Martha's Vineyard
Cute & cozy cottage with a patio & gas grill in the heart of Martha's Vineyard
8.4 out of 10, Very Good, (33)
"Perfect escape for three actors coming from a project with an unexpected few days off. We booked last minute and were thrilled to be able to have some things so centrally located"
Cute & cozy cottage with a patio & gas grill in the heart of Martha's Vineyard
Romantic seaside getaway with pool & tennis courts - dog-friendly
Romantic seaside getaway with pool & tennis courts - dog-friendly
9.6 out of 10, Exceptional, (42)
"Nice inn with comfortable and clean units. Not spectacular, but it's one of the few affordable places on the island. Some people might be put off by the location, a mile south of Oaks Bluff. But it's got Noman's, a great restaurant with live music, and it's right on the bus line. Also you can walk 15 minutes to the beach. Units not soundproof, you can here some noise from your neighbors. Great pool and tennis courts."
Romantic seaside getaway with pool & tennis courts - dog-friendly
Luxury home with private pool & foosball - near 3 towns & many beaches
Luxury home with private pool & foosball - near 3 towns & many beaches
8.6 out of 10, Excellent, (36)
"I recently stayed in this lovely OB home with my family. It was me and 9 other people, and there was plenty of room for everyone. The photos are accurate. The pool was clean and heated. The house is located in a private, wooded area but conveniently located to OB, Edgartown, the airport and beaches. The interior/furniture were so cozy. The house came equipped with enough plates, dishes, pots, pans, utensil, towels, etc. It would be helpful if the house came with a book of instructions, so we'd...
Luxury home with private pool & foosball - near 3 towns & many beaches
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.