Vineyard Homes
with Pools

Displaying 61 - 70 of 70

View Result on Map
Depart OnlyArrive OnlyBookedAvailable
Show Rate Quote
Deep Bottom Custom Contemporary, Heated Pool, Association Tennis Courts, Features Multiple Living Spaces on 3 Levels, A/C WiFi

Custom crafted contemporary home set on lush professionally landscaped grounds. The pool and patio area overlook the large yard with expansive views of the common meadows. There are private association...Read more

Location: 
West Tisbury
Sleeps: 
9
Bedrooms: 
6
Bathrooms: 
4
Price Range:
$7,500 - $11,000
June 2021
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$7,500 /wk
6
7
8
9
10
11
12
$7,500 /wk
13
14
15
16
17
18
19
$7,500 /wk
20
21
22
23
24
25
26
$7,500 /wk
27
28
29
30
 $10,000 /wk
July 2021
SuMoTuWeThFrSaWeek
 1
2
3
$10,000 /wk
4
5
6
7
8
9
10
$11,000 /wk
11
12
13
14
15
16
17
$11,000 /wk
18
19
20
21
22
23
24
$11,000 /wk
25
26
27
28
29
30
31
$11,000 /wk
August 2021
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$11,000 /wk
8
9
10
11
12
13
14
$11,000 /wk
15
16
17
18
19
20
21
$11,000 /wk
22
23
24
25
26
27
28
$11,000 /wk
29
30
31
 $11,000 /wk
September 2021
SuMoTuWeThFrSaWeek
 1
2
3
4
$11,000 /wk
5
6
7
8
9
10
11
$11,000 /wk
12
13
14
15
16
17
18
$11,000 /wk
19
20
21
22
23
24
25
$11,000 /wk
26
27
28
29
30
 
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7

Pool heated to 81 July & August included in rental rate.

Pool heated to 81 June & September additional $275 per week 

Show Rate Quote
Katama Luxury Home - Private Heated Pool with Pool Bar & Patio, Private Landscaped Yard, Screened Porch with Dining Area and Outdoor Living Room, Spacious Deck overlooks Yard & Pool, A/C

Outstanding Katama home set on two private acres and featuring summer living at its best.  Families will enjoy the large screened porch beautifully furnished opening onto the deck overlooking the...Read more

Location: 
Katama
Sleeps: 
14
Bedrooms: 
6
Bathrooms: 
4
Price Range:
$5,000 - $15,000
June 2021
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$6,500 /wk
6
7
8
9
10
11
12
$8,000 /wk
13
14
15
16
17
18
19
$10,000 /wk
20
21
22
23
24
25
26
$11,500 /wk
27
28
29
30
 $13,500 /wk
July 2021
SuMoTuWeThFrSaWeek
 1
2
3
$13,500 /wk
4
5
6
7
8
9
10
$13,500 /wk
11
12
13
14
15
16
17
$12,000 /wk
18
19
20
21
22
23
24
$12,500 /wk
25
26
27
28
29
30
31
$13,500 /wk
August 2021
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$15,000 /wk
8
9
10
11
12
13
14
$15,000 /wk
15
16
17
18
19
20
21
$15,000 /wk
22
23
24
25
26
27
28
$15,000 /wk
29
30
31
 $9,000 /wk
September 2021
SuMoTuWeThFrSaWeek
 1
2
3
4
$9,000 /wk
5
6
7
8
9
10
11
$8,000 /wk
12
13
14
15
16
17
18
$7,000 /wk
19
20
21
22
23
24
25
$6,000 /wk
26
27
28
29
30
 $6,000 /wk
Clean Fee: 
$600 per week
Tax: State & Local: 
9.7

Pool heated to 82 July & August included in the rental rate.

Pool heated to 82 degrees May, June, September & October an additional $250 propane surcharge. No charge on crossover weeks June into July & August into September 

 

woodj14-01-exterior.jpg
Show Rate Quote
Gorgeous Retreat, Pool 18 X 36', Lush Landscaped Yard, Expansive Deck & Patio Areas, Luxury Interior, Media Room, Lambert's Cove Beach 1/2 mile

Gather your family, this gorgeous 5 bedroom home offers all one could want in a vacation home on the Vineyard. Resort like outdoor amenities include pool, stone patio surround,large deck with outdoor...Read more

Location: 
West Tisbury
Sleeps: 
10
Bedrooms: 
5
Bathrooms: 
3
Price Range:
$4,600 - $9,100
June 2021
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$5,100 /wk
6
7
8
9
10
11
12
$6,100 /wk
13
14
15
16
17
18
19
$7,000 /wk
20
21
22
23
24
25
26
$7,800 /wk
27
28
29
30
 $7,800 /wk
July 2021
SuMoTuWeThFrSaWeek
 1
2
3
$7,800 /wk
4
5
6
7
8
9
10
$8,300 /wk
11
12
13
14
15
16
17
$8,300 /wk
18
19
20
21
22
23
24
$8,800 /wk
25
26
27
28
29
30
31
$9,100 /wk
August 2021
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$9,100 /wk
8
9
10
11
12
13
14
$9,100 /wk
15
16
17
18
19
20
21
$9,100 /wk
22
23
24
25
26
27
28
$9,100 /wk
29
30
31
 $8,400 /wk
September 2021
SuMoTuWeThFrSaWeek
 1
2
3
4
$8,400 /wk
5
6
7
8
9
10
11
$7,500 /wk
12
13
14
15
16
17
18
$6,100 /wk
19
20
21
22
23
24
25
$6,100 /wk
26
27
28
29
30
 $4,600 /wk
Clean Fee: 
$700 per week
Tax: State & Local: 
11.7
Show Rate Quote
Lovley Vineyard Haven Home, Heated Pool, AC, Close Proximitity to Towns and Beaches , Perfect Home for Extended Families.

Spacious Vacation Home with heated pool!  This lovely home is perfect for extended families featuring 5 bedrooms, 3 baths, multiple living spaces, and 5 TVs. The pool and deck are perfect...Read more

Location: 
Vineyard Haven
Sleeps: 
8
Bedrooms: 
5
Bathrooms: 
3
Price Range:
$3,500 - $7,800
June 2021
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$5,500 /wk
6
7
8
9
10
11
12
$5,500 /wk
13
14
15
16
17
18
19
$5,500 /wk
20
21
22
23
24
25
26
$5,500 /wk
27
28
29
30
 $6,500 /wk
July 2021
SuMoTuWeThFrSaWeek
 1
2
3
$6,500 /wk
4
5
6
7
8
9
10
$7,000 /wk
11
12
13
14
15
16
17
$7,000 /wk
18
19
20
21
22
23
24
$7,500 /wk
25
26
27
28
29
30
31
$7,500 /wk
August 2021
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$7,800 /wk
8
9
10
11
12
13
14
$7,800 /wk
15
16
17
18
19
20
21
$7,800 /wk
22
23
24
25
26
27
28
$7,800 /wk
29
30
31
 $5,500 /wk
September 2021
SuMoTuWeThFrSaWeek
 1
2
3
4
$5,500 /wk
5
6
7
8
9
10
11
$5,500 /wk
12
13
14
15
16
17
18
$5,500 /wk
19
20
21
22
23
24
25
$5,500 /wk
26
27
28
29
30
 $3,500 /wk
Clean Fee: 
$550 per week
Tax: State & Local: 
11.7

POOL HEATED TO 80 DEGREES JULY AND AUGUST WEEKS INCLUDED IN RENTAL RATE, POOL HEATED TO 80 DEGREES JUNE AND SEPTEMBER WEEKS ADDITIONAL $275 PER WEEK

297.JPG
Show Rate Quote
Main & Guest House, Pool, A/C
Location: 
Edgartown
Sleeps: 
10
Bedrooms: 
5
Bathrooms: 
5
Price Range:
$6,250 - $13,000
June 2021
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$8,750 /wk
6
7
8
9
10
11
12
$8,750 /wk
13
14
15
16
17
18
19
$8,750 /wk
20
21
22
23
24
25
26
$8,750 /wk
27
28
29
30
 $12,250 /wk
July 2021
SuMoTuWeThFrSaWeek
 1
2
3
$12,250 /wk
4
5
6
7
8
9
10
$12,250 /wk
11
12
13
14
15
16
17
$12,250 /wk
18
19
20
21
22
23
24
$12,250 /wk
25
26
27
28
29
30
31
$13,000 /wk
August 2021
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$13,000 /wk
8
9
10
11
12
13
14
$13,000 /wk
15
16
17
18
19
20
21
$13,000 /wk
22
23
24
25
26
27
28
$12,500 /wk
29
30
31
 $12,500 /wk
September 2021
SuMoTuWeThFrSaWeek
 1
2
3
4
$12,500 /wk
5
6
7
8
9
10
11
$8,750 /wk
12
13
14
15
16
17
18
$8,750 /wk
19
20
21
22
23
24
25
$8,750 /wk
26
27
28
29
30
 $6,250 /wk
Clean Fee: 
$350 per week
Tax: State & Local: 
9.7

POOL USAGE IS RESERVED FOR RENTERS OF PROPERTY ONLY

Solar Heated Pool so temperature cannot be guaranteed

0870542821.jpg
Show Rate Quote
Watcha Path, A/C, Hot Tub, Pool - shared with main house

This elegant contemporary home is surrounded by pastoral fields. Private, yet just an eight minute drive to Edgartown Village. Wonderful sun porch for relaxing or dining. Flagstone patio is the...Read more

Location: 
Edgartown
Sleeps: 
6
Bedrooms: 
2
Bathrooms: 
2
Price Range:
$2,500 - $5,500
June 2021
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$3,000 /wk
6
7
8
9
10
11
12
$3,500 /wk
13
14
15
16
17
18
19
$3,500 /wk
20
21
22
23
24
25
26
$3,500 /wk
27
28
29
30
 $4,500 /wk
July 2021
SuMoTuWeThFrSaWeek
 1
2
3
$4,500 /wk
4
5
6
7
8
9
10
$4,750 /wk
11
12
13
14
15
16
17
$4,750 /wk
18
19
20
21
22
23
24
$4,750 /wk
25
26
27
28
29
30
31
$5,000 /wk
August 2021
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$5,000 /wk
8
9
10
11
12
13
14
$5,500 /wk
15
16
17
18
19
20
21
$5,500 /wk
22
23
24
25
26
27
28
$5,000 /wk
29
30
31
 $5,000 /wk
September 2021
SuMoTuWeThFrSaWeek
 1
2
3
4
$5,000 /wk
5
6
7
8
9
10
11
$3,500 /wk
12
13
14
15
16
17
18
$3,500 /wk
19
20
21
22
23
24
25
$3,500 /wk
26
27
28
29
30
 $3,250 /wk
Clean Fee: 
$150 per week
Tax: State & Local: 
9.7

POOL USAGE FOR RENTERS IN MAIN AND GUEST HOUSE ONLY.  NO ADDITIONAL DAY GUESTS PERMITTED.

Solar Heated Pool so temperature cannot be guaranteed

Show Rate Quote
Designer Luxury Katama, Heated Pool, Bluestone Patios, Private Decks, Situated just 1 mile to South Beach and 1.5 miles to Village Area

Beautiful, newly-built luxury home with central a/c in Katama, just a mile from the infamous blue waters and rolling surf of South Beach. You will appreciate the attention to detail...Read more

Location: 
Katama
Sleeps: 
12
Bedrooms: 
5
Bathrooms: 
4
Price Range:
$5,000 - $19,000
June 2021
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$5,500 /wk
6
7
8
9
10
11
12
$6,500 /wk
13
14
15
16
17
18
19
$7,500 /wk
20
21
22
23
24
25
26
$14,500 /wk
27
28
29
30
 $16,500 /wk
July 2021
SuMoTuWeThFrSaWeek
 1
2
3
$16,500 /wk
4
5
6
7
8
9
10
$17,500 /wk
11
12
13
14
15
16
17
$17,000 /wk
18
19
20
21
22
23
24
$15,500 /wk
25
26
27
28
29
30
31
$19,000 /wk
August 2021
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$19,000 /wk
8
9
10
11
12
13
14
$19,000 /wk
15
16
17
18
19
20
21
$19,000 /wk
22
23
24
25
26
27
28
$16,500 /wk
29
30
31
 $9,000 /wk
September 2021
SuMoTuWeThFrSaWeek
 1
2
3
4
$9,000 /wk
5
6
7
8
9
10
11
$8,000 /wk
12
13
14
15
16
17
18
$7,500 /wk
19
20
21
22
23
24
25
$6,500 /wk
26
27
28
29
30
 $6,000 /wk
Clean Fee: 
$450 per week
Tax: State & Local: 
9.7

Propane charge for pool heat is metered see details:

Propane charges for pool heat:.  Owner gives $150 allowance towards pool heat costs during June, July, August & September.  All costs above $150 are billed to the renter.  Note: The higher the pool heat temperature the higher the costs.

Propane charges for pool heat, May and October are metered and charged to the renter.  Note: The higher the pool heat temperature the higher the costs.  

Propane Charges for Pool Heat - May and October, metered propane charges for the use of pool heat,metered and  will be charged to renter  

Show Rate Quote
Deep Bottom Pond, Private Heated Pool, Central Air, WiFi, Gorgeous Views

Contemporary home in Deep Bottom area of West Tisbury. This gracious home with pool and patio overlooks the open meadow land that is deep bottom. The home is professionally landscaped...Read more

Location: 
West Tisbury
Sleeps: 
8
Bedrooms: 
5
Bathrooms: 
4
Price Range:
$5,000 - $11,800
June 2021
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$6,250 /wk
6
7
8
9
10
11
12
$6,250 /wk
13
14
15
16
17
18
19
$6,250 /wk
20
21
22
23
24
25
26
$6,850 /wk
27
28
29
30
 $11,800 /wk
July 2021
SuMoTuWeThFrSaWeek
 1
2
3
$11,800 /wk
4
5
6
7
8
9
10
$11,800 /wk
11
12
13
14
15
16
17
$11,800 /wk
18
19
20
21
22
23
24
$11,800 /wk
25
26
27
28
29
30
31
$11,800 /wk
August 2021
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$11,800 /wk
8
9
10
11
12
13
14
$11,800 /wk
15
16
17
18
19
20
21
$11,800 /wk
22
23
24
25
26
27
28
$11,800 /wk
29
30
31
 $7,100 /wk
September 2021
SuMoTuWeThFrSaWeek
 1
2
3
4
$7,100 /wk
5
6
7
8
9
10
11
$6,100 /wk
12
13
14
15
16
17
18
$6,100 /wk
19
20
21
22
23
24
25
$6,100 /wk
26
27
28
29
30
 
Clean Fee: 
$450 per week
Tax: State & Local: 
11.7

Pool Heated to 82 degrees mid June to mid Sept, pool heat costs included in rental rate.

Show Rate Quote
Spacious Family Home, Pool & Patio Area, Centrally located,

Spacious home with private pool, tucked away in a quiet neigborhood,  central location providing easy access to beaches and towns. This home has been updated with all new hardwood flooring on...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Bathrooms: 
2
Price Range:
$4,775 - $6,500
June 2021
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,775 /wk
6
7
8
9
10
11
12
$4,775 /wk
13
14
15
16
17
18
19
$4,775 /wk
20
21
22
23
24
25
26
$4,775 /wk
27
28
29
30
 $5,500 /wk
July 2021
SuMoTuWeThFrSaWeek
 1
2
3
$5,500 /wk
4
5
6
7
8
9
10
$6,500 /wk
11
12
13
14
15
16
17
$5,500 /wk
18
19
20
21
22
23
24
$5,500 /wk
25
26
27
28
29
30
31
$5,500 /wk
August 2021
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$6,000 /wk
8
9
10
11
12
13
14
$6,000 /wk
15
16
17
18
19
20
21
$6,000 /wk
22
23
24
25
26
27
28
$6,000 /wk
29
30
31
 
September 2021
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: 
$375 per week
Tax: State & Local: 
11.7
297.JPG
Show Rate Quote
Luxury Home, A/C, Out of Town, Idyllic Setting, Pool - shared with Guest House

This gorgeous, award winning design home is set in an idyllic area on the outskirts of Edgartown. Complete with solar heated pool (shared with renters/guests in the guest house), this...Read more

Location: 
Edgartown
Sleeps: 
7
Bedrooms: 
3
Bathrooms: 
3
Price Range:
$4,000 - $8,000
June 2021
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$5,000 /wk
6
7
8
9
10
11
12
$5,500 /wk
13
14
15
16
17
18
19
$5,500 /wk
20
21
22
23
24
25
26
$5,500 /wk
27
28
29
30
 $7,000 /wk
July 2021
SuMoTuWeThFrSaWeek
 1
2
3
$7,000 /wk
4
5
6
7
8
9
10
$7,500 /wk
11
12
13
14
15
16
17
$7,500 /wk
18
19
20
21
22
23
24
$7,500 /wk
25
26
27
28
29
30
31
$8,000 /wk
August 2021
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$8,000 /wk
8
9
10
11
12
13
14
$8,000 /wk
15
16
17
18
19
20
21
$8,000 /wk
22
23
24
25
26
27
28
$8,000 /wk
29
30
31
 $8,000 /wk
September 2021
SuMoTuWeThFrSaWeek
 1
2
3
4
$8,000 /wk
5
6
7
8
9
10
11
$5,500 /wk
12
13
14
15
16
17
18
$5,500 /wk
19
20
21
22
23
24
25
$5,500 /wk
26
27
28
29
30
 $4,000 /wk
Clean Fee: 
$200 per week
Tax: State & Local: 
9.7

POOL USAGE FOR RENTERS IN MAIN AND GUEST HOUSE ONLY.  NO ADDITIONAL DAY GUESTS PERMITTED.

Solar Heated Pool so temperature cannot be guaranteed

Pages