The Best Airbnb Deals in
Oak Bluffs, Massachusetts
Save money on your trip by finding the biggest discounts for top-rated Airbnb rentals in Oak Bluffs, Massachusetts. Enter your travel dates to find the best deals!
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AirDNA Score: 86
$254/night
Walk to Town, beach and amazing location 113A
2 beds
1.5 baths
4 guests
Average Price:
$731
65% Cheaper
than normal
AirDNA Score: 84
$550/night
The Oak Bluffs House - Walk to Beach & Town
2 beds
2.5 baths
6 guests
Average Price:
$1124
51% Cheaper
than normal
AirDNA Score: 79
$325/night
Sweet little post and beam
1 bed
1.5 baths
2 guests
Average Price:
$346
6% Cheaper
than normal
AirDNA Score: 79
$199/night
Walk to beach and all Oak bluffs has to offer!111D
1 bed
1 bath
4 guests
Average Price:
$406
51% Cheaper
than normal
AirDNA Score: 74
$189/night
Stunning private apartment walk to everything!111C
1 bed
1 bath
4 guests
Average Price:
$397
52% Cheaper
than normal
AirDNA Score: 71
$450/night
Spectacular beach & pool combo; beautiful sunsets!
4 beds
5.5 baths
10 guests
Average Price:
$816
45% Cheaper
than normal
AirDNA Score: 69
$363/night
Beautiful 3 bedroom in Oak Bluffs, walk to beach
3 beds
2.5 baths
8 guests
Average Price:
$394
8% Cheaper
than normal
AirDNA Score: 67
$300/night
Downtown Oak Bluffs, First Floor Harbor House.
1 bed
1 bath
3 guests
Average Price:
$462
35% Cheaper
than normal
AirDNA Score: 66
$1075/night
NEW 5-bd, 4.5-bth home! Minutes from downtown OB.
5 beds
4.5 baths
12 guests
Average Price:
$1454
26% Cheaper
than normal
AirDNA Score: 65
$250/night
AirDNA Score: 64
$295/night
Waterview, Private, Walk to Beach, Mile to Town
2 beds
1.5 baths
4 guests
Average Price:
$477
38% Cheaper
than normal
AirDNA Score: 64
$375/night
WATERFRONT PENTHOUSE OAK BLUFFS
studio
1 bath
2 guests
Average Price:
$404
7% Cheaper
than normal
AirDNA Score: 64
$189/night
Central location for your vacation
2 beds
1 bath
6 guests
Average Price:
$289
35% Cheaper
than normal
AirDNA Score: 64
$325/night
Downtown Oak Bluffs, 2nd floor Harbor house.
2 beds
1 bath
4 guests
Average Price:
$527
38% Cheaper
than normal
AirDNA Score: 61
$488/night
3 beds, 3 baths 1.5 Miles to Downtown and Beaches!
3 beds
3 baths
6 guests
Average Price:
$810
40% Cheaper
than normal
AirDNA Score: 61
$350/night
AirDNA Score: 61
$1500/night
Private Heated Pool, Wifi, AC, Grill & Firepit
5 beds
4.5 baths
16 guests
Average Price:
$4286
65% Cheaper
than normal
AirDNA Score: 59
$263/night
Dog-friendly studio with shared pool, on-site tennis courts, & prime location
studio
1 bath
4 guests
Average Price:
$273
4% Cheaper
than normal
AirDNA Score: 59
$2200/night
Chic Waterfront. 4Bd/4.5bth, Sleeps 11, kayaks A/C
4 beds
4.5 baths
11 guests
Average Price:
$2235
2% Cheaper
than normal
AirDNA Score: 58
$236/night
Romance awaits at this condo near the shore with WiFi, pool & tennis courts
studio
1 bath
2 guests
Average Price:
$249
5% Cheaper
than normal
AirDNA Score: 58
$425/night
impeccable cottage STEPS to downtown OB & beach!
3 beds
1 bath
7 guests
Average Price:
$506
16% Cheaper
than normal
AirDNA Score: 58
$700/night
Newly Renovated Walk Town Oak Bluffs 4B/3b AC
4 beds
3 baths
9 guests
Average Price:
$980
29% Cheaper
than normal
AirDNA Score: 58
$510/night
Bright old-world cottage w/ two porches & large yard - walk to town/beaches!
3 beds
2.5 baths
6 guests
Average Price:
$581
12% Cheaper
than normal
AirDNA Score: 58
$286/night
Charming studio for two with pool & tennis - close to beaches & town
studio
1 bath
4 guests
Average Price:
$283
1% More
than normal
AirDNA Score: 58
$371/night
Charming suite with WiFi, pool & tennis courts - 1/2 mile to the beach
1 bed
1.5 baths
6 guests
Average Price:
$382
3% Cheaper
than normal
AirDNA Score: 58
$267/night
Comfy studio with WiFi, pool, & tennis court - near the beach, dogs OK
studio
1 bath
4 guests
Average Price:
$276
3% Cheaper
than normal
AirDNA Score: 57
$461/night
Dog-friendly townhouse with pool, tennis & more - easy walk to the beach
2 beds
2 baths
6 guests
Average Price:
$449
3% More
than normal
AirDNA Score: 57
$235/night
Dog-friendly studio condo with pool & tennis - close to beaches and golf
studio
1 bath
4 guests
Average Price:
$237
1% Cheaper
than normal
AirDNA Score: 57
$260/night
Martha''s Vineyard studio apartment
1 bed
1 bath
2 guests
Average Price:
$230
13% More
than normal
AirDNA Score: 57
$899/night
First-class 4+ BR Lagoon Pond Camp
5 beds
2 baths
10 guests
Average Price:
$952
6% Cheaper
than normal
AirDNA Score: 52
$900/night
Oceanview Martha''s Vineyard
4 beds
4.5 baths
9 guests
Average Price:
$1026
12% Cheaper
than normal
AirDNA Score: 52
$850/night
In Town Oak Bluffs Cottage - Walk to Everything!
5 beds
1.5 baths
10 guests
Average Price:
$784
8% More
than normal
AirDNA Score: 51
$1400/night
The Island Collection MV: Seascape
7 beds
4 baths
14 guests
Average Price:
$1868
25% Cheaper
than normal
AirDNA Score: 51
$450/night
Serenity on Martha''s Vineyard
2 beds
2 baths
6 guests
Average Price:
$506
11% Cheaper
than normal
AirDNA Score: 51
$1200/night
NEW Modern Waterfront Beauty! "The Harper House"
4 beds
2.5 baths
8 guests
Average Price:
$1461
18% Cheaper
than normal
AirDNA Score: 51
$450/night
FABULOUS OCEAN VIEWS-Oak Bluffs Condo Across Beach
2 beds
2 baths
4 guests
Average Price:
$651
31% Cheaper
than normal
AirDNA Score: 50
$400/night
Your Home Away From Home, newly renovated!!
3 beds
2 baths
6 guests
Average Price:
$448
11% Cheaper
than normal
AirDNA Score: 49
$750/night
Victorian charm, steps to beach
4 beds
3 baths
9 guests
Average Price:
$1035
28% Cheaper
than normal
AirDNA Score: 47
$1000/night
Oak Bluff''s Victorian Near Town & Beaches
4 beds
4.5 baths
11 guests
Average Price:
$1296
23% Cheaper
than normal
AirDNA Score: 47
$750/night
Now booking for Summer 2023! New kitchen & bath!
4 beds
4 baths
9 guests
Average Price:
$1056
29% Cheaper
than normal
AirDNA Score: 46
$20000/night
The Park Estate: Your Martha''s Vineyard Getaway!
6 beds
5 baths
16 guests
Average Price:
$7888
154% More
than normal
AirDNA Score: 46
$800/night
Newly renovated, New Pool 2022! Rest, Relax, Renew
4 beds
2.5 baths
8 guests
Average Price:
$1395
43% Cheaper
than normal
AirDNA Score: 46
$715/night
3brm Walk to town & beach A/C family& pet friendly
3 beds
2 baths
6 guests
Average Price:
$750
5% Cheaper
than normal
AirDNA Score: 45
$220/night
Sunny Private Apartment with Free Kayaking!
1 bed
1 bath
2 guests
Average Price:
$321
31% Cheaper
than normal
AirDNA Score: 45
$525/night
Martha''s Vineyard Vacation Home
3 beds
2 baths
7 guests
Average Price:
$530
1% Cheaper
than normal
AirDNA Score: 43
$349/night
AirDNA Score: 43
$395/night
Vineyard Social
5 beds
4.5 baths
14 guests
Average Price:
$759
48% Cheaper
than normal
AirDNA Score: 41
$350/night
Martha''s Vineyard house near Lagoon Pond Beach
2 beds
2 baths
4 guests
Average Price:
$465
25% Cheaper
than normal
AirDNA Score: 39
$750/night
East Chop Charmer-a/c, big yard, beach, sunsets!
3 beds
2 baths
9 guests
Average Price:
$821
9% Cheaper
than normal
AirDNA Score: 39
$240/night
Cozy Vacation Getaway On Bike Path
3 beds
1 bath
6 guests
Average Price:
$372
35% Cheaper
than normal
AirDNA Score: 38
$300/night
One Bed Apartment 0.8 miles to Farm Neck Golf!!
1 bed
1 bath
4 guests
Average Price:
$426
30% Cheaper
than normal
AirDNA Score: 38
$289/night
Cozy, dog-friendly condo by the sea with pool, tennis, picnic area
studio
1 bath
4 guests
Average Price:
$293
1% Cheaper
than normal
AirDNA Score: 38
$287/night
Cozy condo near the beach with WiFi, pool, tennis, grills, & more
1 bed
1 bath
2 guests
Average Price:
$302
5% Cheaper
than normal
AirDNA Score: 37
$185/night
Vineyard Hills Suite
1 bed
1 bath
2 guests
Average Price:
$197
6% Cheaper
than normal
AirDNA Score: 37
$443/night
Charming townhouse with deck, pool & on-site tennis - walk to the beach
2 beds
2 baths
6 guests
Average Price:
$441
0% Cheaper
than normal
AirDNA Score: 37
$479/night
Renovated townhome with pool & 3 tennis courts - golfing & beaches nearby
2 beds
2 baths
6 guests
Average Price:
$465
3% More
than normal
AirDNA Score: 37
$650/night
Lovely 4 BR house steps from beach
4 beds
2 baths
7 guests
Average Price:
$779
17% Cheaper
than normal
AirDNA Score: 35
$664/night
New Construction with Patio & Yard - Walk to the Ferry, Downtown & Beaches
4 beds
3 baths
10 guests
Average Price:
$828
20% Cheaper
than normal
AirDNA Score: 32
$405/night
Stylish townhouse 1/2 mile from the beach - tennis courts & pool on-site
2 beds
1.5 baths
6 guests
Average Price:
$423
4% Cheaper
than normal
AirDNA Score: 32
$273/night
Cute condo with WiFi, pool & tennis - close to golf & the beach
2 beds
1 bath
6 guests
Average Price:
$324
16% Cheaper
than normal
AirDNA Score: 31
$259/night
Dog-friendly condo with pool & tennis - close to beaches, golf, & parks
studio
1 bath
4 guests
Average Price:
$274
5% Cheaper
than normal
AirDNA Score: 31
$270/night
Charming studio with WiFi, pool, & tennis courts - close to beaches & golf
studio
1 bath
2 guests
Average Price:
$295
8% Cheaper
than normal
AirDNA Score: 30
$287/night
Romantic seaside getaway with pool and community tennis courts - dogs OK
studio
1 bath
4 guests
Average Price:
$279
3% More
than normal
AirDNA Score: 30
$440/night
Superb townhouse close to golf & the beach - deck, tennis, & pool
2 beds
1.5 baths
6 guests
Average Price:
$430
2% More
than normal
AirDNA Score: 30
$412/night
Dog-friendly condo suite with pool, tennis, & picnic area - close to beach
1 bed
1.5 baths
6 guests
Average Price:
$394
5% More
than normal
AirDNA Score: 30
$307/night
Dog-friendly first-floor seaside cottage with WiFi, pool, & tennis courts
1 bed
1 bath
4 guests
Average Price:
$320
4% Cheaper
than normal
AirDNA Score: 30
$400/night
Great Oak Bluffs Vacation Getaway!
4 beds
2.5 baths
6 guests
Average Price:
$587
32% Cheaper
than normal
AirDNA Score: 29
$411/night
Coastal getaway with pool & tennis courts - 1/2 mile from beach, dogs OK
1 bed
1.5 baths
6 guests
Average Price:
$411
0% Cheaper
than normal
AirDNA Score: 29
$367/night
Lovely condo suite, close to golfing & the beach - pool & home comforts
1 bed
1.5 baths
4 guests
Average Price:
$394
7% Cheaper
than normal
AirDNA Score: 29
$325/night
Charming 2 BR Cottage on Brush Pond
2 beds
1 bath
5 guests
Average Price:
$535
39% Cheaper
than normal
AirDNA Score: 29
$268/night
Charming studio condo with pool & tennis - easy access to the beach
studio
1 bath
4 guests
Average Price:
$274
2% Cheaper
than normal
AirDNA Score: 29
$264/night
Dog-friendly condo with shared pool & tennis - close to golf & beach
studio
1 bath
4 guests
Average Price:
$268
1% Cheaper
than normal
AirDNA Score: 29
$482/night
Comfortable townhouse close to town & the beach with outdoor pool & tennis
2 beds
2 baths
6 guests
Average Price:
$469
3% More
than normal
AirDNA Score: 28
$335/night
Family home just 0.8 miles to Farm Neck Golf Club!
3 beds
2 baths
6 guests
Average Price:
$504
34% Cheaper
than normal
AirDNA Score: 27
$400/night
Sweet Second Floor Apartment on Circuit Ave!
1 bed
1 bath
3 guests
Average Price:
$555
28% Cheaper
than normal
AirDNA Score: 25
$472/night
Lovely townhouse with WiFi, deck, pool, & tennis - walk to the beach
2 beds
2 baths
6 guests
Average Price:
$466
1% More
than normal
AirDNA Score: 24
$344/night
Cute & cozy cottage with a patio & gas grill in the heart of Martha''s Vineyard
3 beds
1 bath
6 guests
Average Price:
$415
17% Cheaper
than normal
AirDNA Score: 24
$388/night
Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs
2 beds
2 baths
4 guests
Average Price:
$418
7% Cheaper
than normal
AirDNA Score: 23
$460/night
Deluxe townhouse with WiFi, pool & tennis courts - half-mile to the beach
2 beds
2 baths
4 guests
Average Price:
$462
0% Cheaper
than normal
AirDNA Score: 23
$268/night
Comfortable condo with WiFi, tennis courts, & pool - close to beaches
studio
1 bath
4 guests
Average Price:
$256
5% More
than normal
AirDNA Score: 23
$382/night
Dog-friendly suite with WiFi, pool & tennis - golf & beach nearby
1 bed
1.5 baths
6 guests
Average Price:
$413
8% Cheaper
than normal
AirDNA Score: 22
$543/night
Great Rental on Martha''s Vineyard - Weekly
4 beds
2 baths
8 guests
Average Price:
$554
2% Cheaper
than normal
AirDNA Score: 22
$545/night
Newly remodeled home w/ new furniture, large yard & great porches!
4 beds
3 baths
8 guests
Average Price:
$728
25% Cheaper
than normal
AirDNA Score: 22
$412/night
Dog-friendly condo with pool, tennis courts & home comforts, close to beach
1 bed
1.5 baths
6 guests
Average Price:
$432
5% Cheaper
than normal
AirDNA Score: 22
$284/night
Convenient condo with shared pool, picnic area, tennis - close to golf & beach
studio
1 bath
4 guests
Average Price:
$282
1% More
than normal
AirDNA Score: 22
$281/night
Dog-friendly studio with pool & tennis access - awesome location
studio
1 bath
4 guests
Average Price:
$288
2% Cheaper
than normal
AirDNA Score: 22
$395/night
Sweet Suite Close to Beach and Town
1 bed
1 bath
2 guests
Average Price:
$265
49% More
than normal
AirDNA Score: 22
$431/night
Serene home with backyard barbecue area - bike to Arts District, 1 mile to beach
4 beds
2 baths
8 guests
Average Price:
$524
18% Cheaper
than normal
AirDNA Score: 22
$429/night
Spacious townhouse with pool & tennis courts - close to beach & golf
2 beds
1.5 baths
6 guests
Average Price:
$424
1% More
than normal
AirDNA Score: 22
$411/night
Sunny dog-friendly suite with tennis & pool - close to golf & beach
1 bed
1.5 baths
6 guests
Average Price:
$423
3% Cheaper
than normal
AirDNA Score: 22
$1000/night
Harthaven house 2 acres, 3 br 2 ba plus xtra space
3 beds
2 baths
7 guests
Average Price:
$1009
1% Cheaper
than normal
AirDNA Score: 22
$282/night
Contemporary dog-friendly studio with beach access, pool & tennis courts
studio
1 bath
4 guests
Average Price:
$290
3% Cheaper
than normal
AirDNA Score: 22
$366/night
Ground-floor condo with pool & tennis courts, close to golf & the beach
1 bed
1.5 baths
4 guests
Average Price:
$380
4% Cheaper
than normal
AirDNA Score: 22
$413/night
Comfortable & convenient Martha''s Vineyard condo with pool, close to beach
1 bed
1.5 baths
6 guests
Average Price:
$423
2% Cheaper
than normal
AirDNA Score: 21
$555/night
Spacious Deck, Great Porch - Walking Distance to Beach, Ferry & Town
4 beds
2 baths
10 guests
Average Price:
$602
8% Cheaper
than normal
AirDNA Score: 21
$280/night
Cozy getaway with tennis courts & pool - close to town & beaches - dogs OK
studio
1 bath
4 guests
Average Price:
$289
3% Cheaper
than normal
AirDNA Score: 21
$412/night
Dog-friendly condo with pool & tennis courts - golf and beach nearby
2 beds
1.5 baths
6 guests
Average Price:
$409
1% More
than normal
AirDNA Score: 18
$465/night
Warm, cozy, storybook Cottage near shops & dining
2 beds
1 bath
3 guests
Average Price:
$1116
58% Cheaper
than normal
AirDNA Score: 16
$450/night
Martha’s Vineyard Peaceful Get Away
2 beds
1.5 baths
4 guests
Average Price:
$506
11% Cheaper
than normal
AirDNA Score: 15
$320/night
Oak Bluffs Contemporary Summer Home
3 beds
2 baths
6 guests
Average Price:
$299
7% More
than normal