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

East Chop Cottage

1 bed
0 bath
2 guests
Average Price:  
$423
41% Cheaper
than normal
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

The Lighthouse

3 beds
2 baths
9 guests
Average Price:  
$458
24% Cheaper
than normal
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

Classic yacht

1 bed
0 bath
2 guests
Average Price:  
$295
18% More
than normal
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