Vacation Rentals

Depart OnlyArrive OnlyBookedAvailable

Displaying 81 - 90 of 336

Add Favorite
 
<< >>
View Larger Images (23 images)
Get My Quote
Exquisite Designer Home, 10 minute Walk to Oak Bluffs Town Center, Screened Porch, Patio Dining Area, Landscaped Yard, Professionally Decorated, AC

Quietly nestled on a quiet street just on the outskirts of town, this brightly lit home features a mix of coastal details and traditionally styled upscale furnishings for your comfort. The...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$5,050 - $6,000
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$5,300
6
7
8
9
10
11
12
$5,300
13
14
15
16
17
18
19
$5,300
20
21
22
23
24
25
26
$5,400
27
28
29
30
 $6,000
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$6,000
4
5
6
7
8
9
10
$6,000
11
12
13
14
15
16
17
$6,000
18
19
20
21
22
23
24
$6,000
25
26
27
28
29
30
31
$6,000
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$6,000
8
9
10
11
12
13
14
$6,000
15
16
17
18
19
20
21
$6,000
22
23
24
25
26
27
28
$6,000
29
30
31
 $6,000
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$6,000
5
6
7
8
9
10
11
$5,100
12
13
14
15
16
17
18
$5,100
19
20
21
22
23
24
25
$5,100
26
27
28
29
30
 $5,100
Clean Fee: 
$350 per week
Tax: State & Local: 
11.7
Add Favorite
 
<< >>
View Larger Images (24 images)
Get My Quote

DAWSJ

Inquire
Property Details
Recently Updated & Perfect Katama Location, 3 Minute Drive to South Beach, 5 minute Drive to Edgartown Village

Contemporary Beach Home with easy access to South Beach and all that Edgartown Village has to offer.

The modern and bright main living area is an open concept with a...Read more

Location: 
Katama
Sleeps: 
7
Bedrooms: 
3
Baths: 
2
Price Range:
$4,000 - $4,000
June 2027
SuMoTuWeThFrSa
 1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
 
July 2027
SuMoTuWeThFrSa
 1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
August 2027
SuMoTuWeThFrSa
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
 
September 2027
SuMoTuWeThFrSa
 1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
 
Clean Fee: 
$325 per week
Tax: State & Local: 
11.7
Add Favorite
 
<< >>
View Larger Images (27 images)
Get My Quote

DELLA

Inquire
Property Details
Beautiful Newly Updated Cape Style Home, Association Tennis Courts 2 min Walk, Biking & Hiking Trails, Beaches 10 minutes from House

This lovely 3 bedroom, 2.5 bath home features sun-filled rooms, an open floor plan throughout, screened porch set up as a summer living room with a sectional sofa, and a...Read more

Location: 
Edgartown
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$5,000 - $5,400
June 2027
SuMoTuWeThFrSa
 1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
 
July 2027
SuMoTuWeThFrSa
 1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
August 2027
SuMoTuWeThFrSa
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
 
September 2027
SuMoTuWeThFrSa
 1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
 
Clean Fee: 
$400
Tax: State & Local: 
11.7
Add Favorite
 
<< >>
View Larger Images (42 images)
Get My Quote

DELOA

Inquire
Property Details
Ramble House, Lovely, Spacious 3 Bedroom, 3 bath Vacation Home. Tucked on a Tranquil Street in Vineyard Haven, Multiple Living Spaces Indoor & Outdoor, Impeccably Maintained.

A tranquil oasis just outside Vineyard Haven and only one mile from the village center, this spacious and inviting three-bedroom, three-bath home is tucked away at the end of a...Read more

Location: 
Vineyard Haven
Sleeps: 
8
Bedrooms: 
3
Baths: 
3
Price Range:
$3,500 - $6,900
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,000
6
7
8
9
10
11
12
$4,000
13
14
15
16
17
18
19
$4,000
20
21
22
23
24
25
26
$4,000
27
28
29
30
 $5,900
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$5,900
4
5
6
7
8
9
10
$5,900
11
12
13
14
15
16
17
$5,900
18
19
20
21
22
23
24
$5,900
25
26
27
28
29
30
31
$6,900
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$6,900
8
9
10
11
12
13
14
$6,900
15
16
17
18
19
20
21
$6,900
22
23
24
25
26
27
28
$6,900
29
30
31
 $4,000
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$4,000
5
6
7
8
9
10
11
$4,000
12
13
14
15
16
17
18
$4,000
19
20
21
22
23
24
25
$4,000
26
27
28
29
30
 $4,000
Clean Fee: 
$600 per week
Tax: State & Local: 
11.7
Add Favorite
 
<< >>
View Larger Images (39 images)
Get My Quote

DELOR

Inquire
Property Details
Outstanding In-town Home, Gorgeous Professionally Landscaped Yard, 5 Min walk to Main Street Shops & Restaurants

Located on a quiet street in the Edgartown Village area, this lovely 5 bedroom, 3 bath Home has been all newly updated. The home is bordered by lush lawn, privacy fencing...Read more

Location: 
Edgartown
Sleeps: 
9
Bedrooms: 
5
Baths: 
3
Price Range:
$7,000 - $12,500
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$7,000
6
7
8
9
10
11
12
$8,000
13
14
15
16
17
18
19
$8,000
20
21
22
23
24
25
26
$9,000
27
28
29
30
 $10,000
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$10,000
4
5
6
7
8
9
10
$12,500
11
12
13
14
15
16
17
$12,000
18
19
20
21
22
23
24
$12,000
25
26
27
28
29
30
31
$12,000
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$13,000
8
9
10
11
12
13
14
$16,000
15
16
17
18
19
20
21
$16,000
22
23
24
25
26
27
28
$12,000
29
30
31
 $11,000
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$11,000
5
6
7
8
9
10
11
$8,000
12
13
14
15
16
17
18
$7,000
19
20
21
22
23
24
25
$7,000
26
27
28
29
30
 $7,000
Clean Fee: 
$600 per week
Tax: State & Local: 
11.7
Add Favorite
 
<< >>
View Larger Images (45 images)
Get My Quote

DELUP

Inquire
Property Details
Essence of Summer Vacation Home, Edgartown, Katama Area, 4 + Bedroom, 3.5 Baths, Heated Pool, Multiple Indoor/Outdoor Lounge Areas, Seamlessly Connected

Katama Coastal Retreat with Pool, Guest Apartment & Pool House

Welcome to your ultimate island escape in the heart of Katama,  just over a mile from Edgartown Village and two miles...Read more

Location: 
Edgartown
Sleeps: 
10
Bedrooms: 
5
Baths: 
3
Price Range:
$5,900 - $19,500
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$7,900
6
7
8
9
10
11
12
$7,900
13
14
15
16
17
18
19
$8,900
20
21
22
23
24
25
26
$9,900
27
28
29
30
 $16,500
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$16,500
4
5
6
7
8
9
10
$16,500
11
12
13
14
15
16
17
$17,500
18
19
20
21
22
23
24
$17,500
25
26
27
28
29
30
31
$18,500
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$19,500
8
9
10
11
12
13
14
$19,500
15
16
17
18
19
20
21
$19,500
22
23
24
25
26
27
28
$19,500
29
30
31
 $14,500
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$14,500
5
6
7
8
9
10
11
$10,500
12
13
14
15
16
17
18
$8,900
19
20
21
22
23
24
25
$8,900
26
27
28
29
30
 $8,900
Clean Fee: 
$700 per week
Tax: State & Local: 
11.7

Pool Heated to 81 Degrees July & August Weeks, included in Rental Rate

Pool Heated to 81 Degrees, June & September weeks, additional $300 Propane Surcharge.

 

Spa in Pool can be Heated to a Higher Temperature upon request for an Additional Fee. Inquire with agent as to terms. 

Add Favorite
 
<< >>
View Larger Images (22 images)
Get My Quote

DENAL

Inquire
Property Details

Charming, 4-bedroom Oak Bluffs Home, pristinely maintained!  The large wraparound porch and backyard patio areas provide the perfect venue for relaxing when not at the beach or out and about...Read more

Location: 
Oak Bluffs
Sleeps: 
7
Bedrooms: 
4
Baths: 
2
Price Range:
$2,000 - $5,000
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$3,000
6
7
8
9
10
11
12
$3,000
13
14
15
16
17
18
19
$3,000
20
21
22
23
24
25
26
$3,000
27
28
29
30
 $5,000
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$5,000
4
5
6
7
8
9
10
$5,000
11
12
13
14
15
16
17
$5,000
18
19
20
21
22
23
24
$5,000
25
26
27
28
29
30
31
$5,000
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$5,000
8
9
10
11
12
13
14
$5,000
15
16
17
18
19
20
21
$5,000
22
23
24
25
26
27
28
$5,000
29
30
31
 $4,000
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$4,000
5
6
7
8
9
10
11
$2,000
12
13
14
15
16
17
18
$2,000
19
20
21
22
23
24
25
$2,000
26
27
28
29
30
 $2,000
Clean Fee: 
$400 per week
Tax: State & Local: 
11.7

Parking for two cars only, no on-street parking!

 

Add Favorite
 
<< >>
View Larger Images (42 images)
Get My Quote

DESAM

Inquire
Property Details
Luxurious Village Home, Heated Gunite Pool, Acres of Privacy, Walk to Fuller St Beach and Main Street

Edgartown Village Luxury Home featuring a 6 bedroom Main & Guest House, Heated Pool, Cabana & Hot Tub, Water views across Eel Pond to Nantucket Sound and Pristinely Landscaped Grounds. Walk...Read more

Location: 
Edgartown
Sleeps: 
12
Bedrooms: 
6
Baths: 
6
Price Range:
$45,000 - $45,000
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$45,000
6
7
8
9
10
11
12
$45,000
13
14
15
16
17
18
19
$45,000
20
21
22
23
24
25
26
$45,000
27
28
29
30
 $45,000
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$45,000
4
5
6
7
8
9
10
$45,000
11
12
13
14
15
16
17
$45,000
18
19
20
21
22
23
24
$45,000
25
26
27
28
29
30
31
$45,000
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$45,000
8
9
10
11
12
13
14
$45,000
15
16
17
18
19
20
21
$45,000
22
23
24
25
26
27
28
$45,000
29
30
31
 $45,000
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$45,000
5
6
7
8
9
10
11
$45,000
12
13
14
15
16
17
18
$45,000
19
20
21
22
23
24
25
$45,000
26
27
28
29
30
 $45,000
Clean Fee: 
$675 per week
Tax: State & Local: 
11.7

2 week stay required!  

Pool Heated to 82 in July & August included, shoulder weeks please inquire with Agent!

Add Favorite
 
<< >>
View Larger Images (38 images)
Get My Quote

DHANM

Inquire
Property Details
Adorable Oak Bluffs Cottage Just Over a Mile to the Village Center and Town Beaches, Porch, Deck, 4 Bedrooms, 2 Baths

Nestled on a quiet street, this recently updated residence boasts delightful indoor and outdoor living areas. The entrance porch offers cozy seating with wicker chairs and a small dining table that...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$4,950 - $6,700
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
8
9
10
11
12
$4,950
13
14
15
16
17
18
19
$4,950
20
21
22
23
24
25
26
$4,950
27
28
29
30
 $5,300
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$5,300
4
5
6
7
8
9
10
$5,500
11
12
13
14
15
16
17
$5,500
18
19
20
21
22
23
24
$5,500
25
26
27
28
29
30
31
$5,500
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$6,200
8
9
10
11
12
13
14
$6,700
15
16
17
18
19
20
21
$6,700
22
23
24
25
26
27
28
$6,700
29
30
31
 $6,700
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$6,700
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
 
Clean Fee: 
$450 per week
Tax: State & Local: 
11.7
Add Favorite
 
<< >>
View Larger Images (48 images)
Get My Quote

DONAK

Inquire
Property Details
Stunning Luxury Home, Complete Renovation in Main House, Sweet Updated Guest House, Walk to Oak Bluffs Center

Gorgeous Luxury Home, Newly Renovated with Stylish Updates, Walking Distance to Oak Bluffs Center

This stunning bungalow-style home has undergone a complete renovation, blending luxury designer decor with the original...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
4
Price Range:
$6,000 - $17,000
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$6,000
6
7
8
9
10
11
12
$6,000
13
14
15
16
17
18
19
$6,000
20
21
22
23
24
25
26
$7,000
27
28
29
30
 $11,500
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$11,500
4
5
6
7
8
9
10
$11,500
11
12
13
14
15
16
17
$11,500
18
19
20
21
22
23
24
$11,500
25
26
27
28
29
30
31
$15,000
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$17,000
8
9
10
11
12
13
14
$17,000
15
16
17
18
19
20
21
$17,000
22
23
24
25
26
27
28
$15,000
29
30
31
 $7,000
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$7,000
5
6
7
8
9
10
11
$7,000
12
13
14
15
16
17
18
$7,000
19
20
21
22
23
24
25
$7,000
26
27
28
29
30
 
Clean Fee: 
$600 per week
Tax: State & Local: 
11.7

Pages