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.

Owners are currently updating 2025 rates from 2024 and are subject to change. Please call 508.696.9999 or email us to confirm.
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Search Pool Vacation Rentals

329 results
Waterfront Edgartown
 
$35,000 - $60,000/wk
Rental #115161
7 Bed
| 6+ Bath
Details
Waterview Chilmark
 
$30,000 - $60,000/wk
Rental #158635
6 Bed
| 5+ Bath
Details
Waterfront Chilmark
 
$55,000 - $55,000/wk
Rental #127429
6 Bed
| 5+ Bath
Details
Waterview Chilmark
 
$30,000 - $45,000/wk
Rental #115781
5 Bed
| 5 Bath
Details
In-Town Edgartown
 
$45,000 - $45,000/wk
Rental #143614
6 Bed
| 6+ Bath
Details
Waterview Chilmark
 
$45,000 - $45,000/wk
Rental #115401
6 Bed
| 5+ Bath
Details
Down-Island Edgartown
 
$38,000 - $42,000/wk
Rental #154379
6 Bed
| 6+ Bath
Details
Waterview Chilmark
 
$25,000 - $40,000/wk
Rental #115167
5 Bed
| 3+ Bath
Details
Down-Island Edgartown
 
$20,000 - $40,000/wk
Rental #158700
5 Bed
| 4+ Bath
Details
Waterfront Aquinnah
 
$40,000 - $40,000/wk
Rental #127760
4 Bed
| 3+ Bath
Details
Waterview West Tisbury
 
$39,500 - $39,500/wk
Rental #150846
6 Bed
| 5+ Bath
Details
Waterview Chilmark
 
$36,000 - $36,000/wk
Rental #149051
4 Bed
| 0 Bath
Details
In-Town Edgartown
 
$12,000 - $35,000/wk
Rental #144698
5 Bed
| 5+ Bath
Details
Waterfront Chilmark
 
$35,000 - $35,000/wk
Rental #115463
5 Bed
| 3 Bath
Details
Waterview Chilmark
 
$35,000 - $35,000/wk
Rental #115677
5 Bed
| 3+ Bath
Details
Up-Island Chilmark
 
$25,000 - $35,000/wk
Rental #139208
4 Bed
| 4+ Bath
Details
Walk to Beach Edgartown
 
$20,000 - $34,000/wk
Rental #151516
4 Bed
| 4+ Bath
Details
Down-Island Edgartown
 
$20,000 - $30,500/wk
Rental #139359
5 Bed
| 4+ Bath
Details
Waterfront Edgartown
 
$7,500 - $30,000/wk
Rental #149285
4 Bed
| 4 Bath
Details
Waterview Chilmark
 
$20,000 - $30,000/wk
Rental #144841
5 Bed
| 4+ Bath
Details
Waterfront Chilmark
 
$14,000 - $30,000/wk
Rental #154815
6 Bed
| 6+ Bath
Details
Waterview Chilmark
 
$30,000 - $30,000/wk
Rental #115085
4 Bed
| 3+ Bath
Details
Waterfront Edgartown
 
$6,000 - $30,000/wk
Rental #154412
3 Bed
| 3 Bath
Details
Up-Island Chilmark
 
$30,000 - $30,000/wk
Rental #127953
6 Bed
| 6+ Bath
Details
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