Rentals

Pool

The vacation rentals below all have pools. Take a quiet dip in the privacy of your own back yard or enjoy gathering around the pool with family and friends. Please note that most homes are booked for a two-week minimum and that we recommend “cancel for any reason” trip insurance to protect your investment.

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Search Pool Vacation Rentals

43 results
Walk to Beach Chilmark
 
$10,000 - $20,000/wk
Rental #115121
7 Bed
| 5+ Bath
Details
Near Bike Path Oak Bluffs
 
$9,100 - $20,000/wk
Rental #154897
6 Bed
| 4 Bath
Details
South Shore Chilmark
 
$12,000 - $20,000/wk
Rental #115712
4 Bed
| 3+ Bath
Details
Waterview West Tisbury
 
$12,500 - $20,000/wk
Rental #158141
3 Bed
| 3 Bath
Details
Down-Island Oak Bluffs
 
$8,000 - $19,500/wk
Rental #155922
4 Bed
| 3+ Bath
Details
South Shore Edgartown
 
$18,000 - $18,000/wk
Rental #116713
4 Bed
| 4 Bath
Details
Up-Island Chilmark
 
$18,000 - $18,000/wk
Rental #122079
5 Bed
| 4+ Bath
Details
Up-Island Chilmark
 
$12,500 - $18,000/wk
Rental #158931
5 Bed
| 3+ Bath
Details
Near Bike Path Edgartown
 
$5,500 - $17,750/wk
Rental #145492
6 Bed
| 4+ Bath
Details
Up-Island West Tisbury
 
$10,000 - $17,500/wk
Rental #134414
4 Bed
| 3+ Bath
Details
Near Bike Path Edgartown
 
$8,000 - $17,500/wk
Rental #136255
5 Bed
| 5 Bath
Details
Up-Island Chilmark
 
$8,000 - $15,000/wk
Rental #157652
3 Bed
| 2 Bath
Details
Down-Island Vineyard Haven
 
$9,000 - $15,000/wk
Rental #147472
4 Bed
| 3+ Bath
Details
Up-Island West Tisbury
 
$11,500 - $15,000/wk
Rental #148208
4 Bed
| 3 Bath
Details
Up-Island Chilmark
 
$4,800 - $13,500/wk
Rental #116622
4 Bed
| 3 Bath
Details
Waterfront Edgartown
 
$10,000 - $13,500/wk
Rental #122875
4 Bed
| 3 Bath
Details
Down-Island Vineyard Haven
 
$12,000 - $12,500/wk
Rental #154309
5 Bed
| 2 Bath
Details
Up-Island West Tisbury
 
$8,000 - $12,000/wk
Rental #144426
6 Bed
| 2+ Bath
Details
Walk to Beach West Tisbury
 
$6,500 - $9,300/wk
Rental #116419
5 Bed
| 3+ Bath
Details
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