Vacation Rentals with Pool in Vineyard Playhouse, MA: Compare 10+ Sites & Save

AirbnbBooking.comVrboExpediaKayakTripadvisorHotels.comAgoda.com
  1. VBOR
  2. Vacation Rentals with Pool
  3.  USA

  4.  Massachusetts

  5.  Vineyard Haven
  6.  Vineyard Playhouse

Refine your search

Price per night

Amenity Filter

Rating

56 Best Vacation Rentals with Pool in Vineyard Playhouse (Starting from $223)

#OB Pool House
#OB Pool House
House
Oak Bluffs, MA, USA
4.8k from Vineyard Playhouse center

Accommodations, Pools, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay, Family

5 Bedrooms10 Guests
1.0

Review score

1 reviews

$1516
Average price / night
Check Availability
Bright condo w Pool, walking distance to town!
Bright condo w Pool, walking distance to town!
Condo
Tisbury, MA, 02568, United States
0.4k from Vineyard Playhouse center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking

1 Bedroom2 Guests
9.4

Superb

3 reviews

$223
Average price / night
Check Availability
Luxe 4 Bed/4 Ensuite Bath, A/C In-Town Vineyard Haven, Gunite Pool and Spa
Luxe 4 Bed/4 Ensuite Bath, A/C In-Town Vineyard Haven, Gunite Pool and Spa
House
Vineyard Haven, MA, 02568, United States
0.5k from Vineyard Playhouse center

AC, Barbecue, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry

4 Bedrooms9 Guests
10.0

Exceptional

24 reviews

$1664
Average price / night
Check Availability
Tisbury - Airy 4-bedroom with Peaceful Pool
Tisbury - Airy 4-bedroom with Peaceful Pool
House
Tisbury, MA, 02568, United States
0.8k from Vineyard Playhouse center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms8 Guests
New to Booking
$1024
Average price / night
Check Availability
Spacious 6-bedroom house sleeps 12+ with pool, close to Tashmoo and pet friendly
Spacious 6-bedroom house sleeps 12+ with pool, close to Tashmoo and pet friendly
House
Tisbury, MA, 02568, United States
1.0k from Vineyard Playhouse center

AC, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Internet, Kitchen, Laundry

6 Bedrooms14 Guests
New to Booking
$3956
Average price / night
Check Availability
Serene 6-bedroom Vineyard Haven Retreat
Serene 6-bedroom Vineyard Haven Retreat
House
Tisbury, MA, 02568, United States
1.1k from Vineyard Playhouse center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, No Smoking, Outdoor Space

6 Bedrooms12 Guests
New to Booking
$3877
Average price / night
Check Availability
Stunning Tisbury Retreat with Pool
Stunning Tisbury Retreat with Pool
House
Tisbury, MA, 02568, United States
1.4k from Vineyard Playhouse center

AC, Barbecue, Crib, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Internet

5 Bedrooms10 Guests
10.0

Exceptional

4 reviews

$2752
Average price / night
Check Availability
West Chop Tashmoo Beach Townhouse w/Pool Pickleball & Tennis borders Golf Course
West Chop Tashmoo Beach Townhouse w/Pool Pickleball & Tennis borders Golf Course
House
Tisbury, MA, 02568, United States
1.4k from Vineyard Playhouse center

AC, Barbecue, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Internet, Kitchen

3 Bedrooms5 Guests
New to Booking
$422
Average price / night
Check Availability
Mink Meadows Luxury Getaway With Pool
Mink Meadows Luxury Getaway With Pool
House
Vineyard Haven, MA, 02568, United States
2.0k from Vineyard Playhouse center

AC, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Kitchen, Laundry

5 Bedrooms10 Guests
10.0

Exceptional

5 reviews

$2627
Average price / night
Check Availability
PRIVACY & RELAXATION ON MARTHA'S VINEYARD
PRIVACY & RELAXATION ON MARTHA'S VINEYARD
House
Tisbury, MA, 02568, United States
2.0k from Vineyard Playhouse center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

6 Bedrooms12 Guests
10.0

Exceptional

8 reviews

$1785
Average price / night
Check Availability
Modern 4 bed/3.5 bath Farmhouse, private HEATED POOL and AC on bike path
Modern 4 bed/3.5 bath Farmhouse, private HEATED POOL and AC on bike path
House
Oak Bluffs, MA, 02568, United States
2.4k from Vineyard Playhouse center

AC, Arcade, Balcony, Barbecue, Crib, Dryer, Free Parking, Heater, Internet

6 Bedrooms10 Guests
10.0

Exceptional

71 reviews

$1206
Average price / night
Check Availability
Beautiful home with pool in great location- close to everything!
Beautiful home with pool in great location- close to everything!
House
Oak Bluffs, MA, 02568, United States
2.5k from Vineyard Playhouse center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms6 Guests
10.0

Exceptional

22 reviews

$709
Average price / night
Check Availability
Retreat to Martha's Vineyard with a Private Pool & Outdoor Living in Oak Bluffs\n
Retreat to Martha's Vineyard with a Private Pool & Outdoor Living in Oak Bluffs\n
House
Oak Bluffs, MA, 02557, United States
2.5k from Vineyard Playhouse center

AC, Barbecue, Dryer, Fitness Equipment, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms9 Guests
10.0

Exceptional

7 reviews

$1326
Average price / night
Check Availability
 Relax & Renew at Luxury Villa with Heated Pool & Hot Tub,Tennis,Bikes,Firepit!
Relax & Renew at Luxury Villa with Heated Pool & Hot Tub,Tennis,Bikes,Firepit!
House
Oak Bluffs, MA, 02557, United States
2.6k from Vineyard Playhouse center

AC, Balcony, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Hot Tub

5 Bedrooms10 Guests
9.4

Superb

13 reviews

$1592
Average price / night
Check Availability
East Chop Beach House w/Pool
East Chop Beach House w/Pool
House
Oak Bluffs, MA, 02568, United States
3.1k from Vineyard Playhouse center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

5 Bedrooms10 Guests
10.0

Exceptional

3 reviews

$2479
Average price / night
Check Availability
Grand Coastal-Style Estate In The Preserve
Grand Coastal-Style Estate In The Preserve
House
Oak Bluffs, MA, 02557, United States
3.2k from Vineyard Playhouse center

AC, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet

5 Bedrooms12 Guests
10.0

Exceptional

4 reviews

$2315
Average price / night
Check Availability
4-BR, Hot tub, Wifi, AC, Fire pit. No Pets.
4-BR, Hot tub, Wifi, AC, Fire pit. No Pets.
House
Oak Bluffs, MA, 02557, United States
3.4k from Vineyard Playhouse center

AC, Arcade, Balcony, Barbecue, Dryer, Free Parking, Heater, Hot Tub, Internet

5 Bedrooms12 Guests
New to Booking
$1508
Average price / night
Check Availability
THE PARK ESTATE! Your Martha's Vineyard Getaway!
THE PARK ESTATE! Your Martha's Vineyard Getaway!
House
Oak Bluffs, MA, 02557, United States
3.8k from Vineyard Playhouse center

AC, Arcade, Balcony, Barbecue, Crib, Dryer, Extra Bed, Fireplace, Free Parking

6 Bedrooms16 Guests
9.8

Exceptional

17 reviews

$7810
Average price / night
Check Availability
Oak Bluffs Retreat. NEW PRIVATE POOL
Oak Bluffs Retreat. NEW PRIVATE POOL
House
Oak Bluffs, MA, 02568, United States
4.2k from Vineyard Playhouse center

AC, Balcony, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area

3 Bedrooms6 Guests
10.0

Exceptional

14 reviews

$3725
Average price / night
Check Availability
Carriage House, Swimming, Boating, Kayaking, just steps from your door...
Carriage House, Swimming, Boating, Kayaking, just steps from your door...
House
Oak Bluffs, MA, 02557, United States
4.3k from Vineyard Playhouse center

AC, Barbecue, Breakfast Available, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms5 Guests
9.8

Exceptional

63 reviews

$921
Average price / night
Check Availability
Beautiful Estate with salt water pool  & pond with kayaks
Beautiful Estate with salt water pool & pond with kayaks
House
Oak Bluffs, MA, 02557, United States
4.4k from Vineyard Playhouse center

AC, Barbecue, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet

5 Bedrooms12 Guests
New to Booking
$4877
Average price / night
Check Availability
Luxury 4-Bedroom Property with Private Beach on Seaview Ave in Oak Bluffs
Luxury 4-Bedroom Property with Private Beach on Seaview Ave in Oak Bluffs
House
Oak Bluffs, MA, 02557, United States
4.5k from Vineyard Playhouse center

AC, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry, No Smoking

4 Bedrooms9 Guests
New to Booking
$2585
Average price / night
Check Availability
Oak Bluffs Renovated Retreat With Pool, Tennis, and Sengekontacket Pond Access!
Oak Bluffs Renovated Retreat With Pool, Tennis, and Sengekontacket Pond Access!
House
Edgartown, MA, 02539, United States
4.6k from Vineyard Playhouse center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Laundry, Microwave, No Smoking

3 Bedrooms8 Guests
New to Booking
$1669
Average price / night
Check Availability
Lovely spacious MV 3-bdr, 3 bath island home, sleeps 12,  air and comm. pool.
Lovely spacious MV 3-bdr, 3 bath island home, sleeps 12, air and comm. pool.
House
West Tisbury, MA, 02575, United States
4.7k from Vineyard Playhouse center

AC, Balcony, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, No Smoking

3 Bedrooms12 Guests
New to Booking
$879
Average price / night
Check Availability
Airy, Quiet Vacation Rental Home, assn. pool on MV.  Car ferry tix available.
Airy, Quiet Vacation Rental Home, assn. pool on MV. Car ferry tix available.
House
West Tisbury, MA, 02575, United States
4.7k from Vineyard Playhouse center

Barbecue, Dryer, Extra Bed, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms8 Guests
10.0

Exceptional

22 reviews

$816
Average price / night
Check Availability
Relax & Unwind: Poolside Martha’s Vineyard Stay
Relax & Unwind: Poolside Martha’s Vineyard Stay
House
Oak Bluffs, MA, 02568, United States
4.9k from Vineyard Playhouse center

AC, Balcony, Barbecue, Dryer, Fireplace, Heater, Internet, Kitchen, Microwave

5 Bedrooms10 Guests
New to Booking
$1374
Average price / night
Check Availability
Spectacular Martha's Vineyard Island Home!
Spectacular Martha's Vineyard Island Home!
House
Oak Bluffs, MA, 02557, United States
5.0k from Vineyard Playhouse center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms12 Guests
9.2

Superb

9 reviews

$483
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals with Pool in Vineyard Playhouse.

Where to stay in Vineyard Playhouse? Best neighborhoods & areas

Vineyard Playhouse Vacation Rentals with Pool on the Map

Frequently Asked Questions

You can explore 56 verified vacation rentals with a pool in Vineyard Playhouse. These include a wide range of private homes, villas, and condos that offer on-site swimming facilities for a more relaxing stay.

Prices for vacation rentals with a pool in Vineyard Playhouse vary depending on the season, property size, and whether the pool is private or shared. Rates typically start from around $223 per night, with private pool homes and peak travel periods often costing more.

Many rentals in Vineyard Playhouse offer private pools for exclusive use, while others provide access to shared or community pools. You can use filters to specifically find properties with private pools if that is your preference.

Yes, some vacation rentals with pools in Vineyard Playhouse welcome pets. Currently, 12 listings allow pets, although policies may vary by property. It’s a good idea to review any rules related to pets around pool areas before booking.

Properties with pools are often in high demand, especially during warmer months and holidays, so booking 90 to 120 days in advance is recommended for the best selection. During off-peak seasons, you may still find availability closer to your travel dates.

Vacation rentals with pools in Vineyard Playhouse often include additional outdoor features such as Pool, Laundry, and Balcony/Terrace. These amenities enhance comfort and make it easier to enjoy outdoor living during your stay.

Some vacation rentals in Vineyard Playhouse offer heated pools, which can be especially useful during cooler months. In certain cases, pool heating may be available for an additional fee, so it’s best to check the property details before booking.