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Search results; 362 places

Guest favorite
Home in Edgartown
Modern 4-bedroom House with Private Swimming Pool
7 beds
Apr 20 – 25
5.0 out of 5 average rating, 18 reviews
Home in Edgartown
Edgartown Home with Heated Pool
7 beds
Apr 21 – 26
Apartment in Oak Bluffs
Charming Studio Close to Beach | Pool | Tennis
1 king bed
Apr 26 – May 1
4.85 out of 5 average rating, 41 reviews
Townhouse in Oak Bluffs
Lovely 2BR Island Inn | Pool | Deck | Firepit
4 beds
Apr 19 – 24
4.63 out of 5 average rating, 24 reviews
Apartment in Oak Bluffs
Coastal Studio Island Inn | Patio | Pool
2 beds
Apr 18 – 23
4.47 out of 5 average rating, 15 reviews
Guest favorite
Home in Oak Bluffs
Spectacular beach & pool combo; beautiful sunsets!
5 beds
Apr 18 – 23
4.93 out of 5 average rating, 168 reviews
Guest favorite
Condo in Tisbury
Sunny 2bedroom condo w pool, walk to town
3 beds
May 19 – 24
4.91 out of 5 average rating, 45 reviews
Home in Edgartown
Harper House ( Edgartown)
Apr 20 – 25
New place to stay
Home in Tisbury
Airy 4-bedroom with peaceful pool
6 beds
May 25 – 30
5.0 out of 5 average rating, 8 reviews
Guest favorite
Home in Edgartown
Summer Liv'in with Pool, Spa & Sauna
10 beds
May 18 – 23
5.0 out of 5 average rating, 15 reviews
Condo in Oak Bluffs
Dog-friendly 1st-Floor 1BR Near Beach/Park | Pool
2 beds
Apr 21 – 26
4.84 out of 5 average rating, 32 reviews
Guest favorite
Home in Edgartown
Edgartown Designer Retreat With Pool For 2024!
5 beds
Apr 23 – 28
5.0 out of 5 average rating, 6 reviews
Home in Tisbury
A Piece of Serenity
5 beds
Jun 1 – 8
4.84 out of 5 average rating, 32 reviews
Townhouse in Oak Bluffs
Charming 2BR Waterview Island Inn | Pool | Deck
4 beds
Apr 19 – 24
4.5 out of 5 average rating, 10 reviews
Condo in Oak Bluffs
Perfect 2BR Island Inn | Patio | Pool
3 beds
Apr 22 – 27
4.66 out of 5 average rating, 38 reviews
Guest favorite
Cottage in Edgartown
Lovely two - story private cottage.
1 queen bed
May 5 – 10
4.98 out of 5 average rating, 86 reviews
Superhost
Home in Edgartown
Katama gem.
4 beds
Apr 18 – 23
4.79 out of 5 average rating, 99 reviews
Guest favorite
Home in Oak Bluffs
Oak Bluffs with Pool! Perfect for Entertaining!
9 beds
May 23 – 28
4.81 out of 5 average rating, 36 reviews