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

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  2. Vacation Rentals with Private Pool
  3.  USA

  4.  Massachusetts

  5.  Vineyard Haven

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39 Best Vacation Rentals with Private Pool in Vineyard Haven (Starting from $709)

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
0.6k from Vineyard Haven center

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

4 Bedrooms9 Guests
10.0

Exceptional

24 reviews

$1664
Average price / night
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Tisbury - Airy 4-bedroom with Peaceful Pool
Tisbury - Airy 4-bedroom with Peaceful Pool
House
Tisbury, MA, 02568, United States
0.7k from Vineyard Haven center

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

4 Bedrooms8 Guests
New to Booking
$1024
Average price / night
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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
1.1k from Vineyard Haven center

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

6 Bedrooms14 Guests
New to Booking
$3956
Average price / night
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Stunning Tisbury Retreat with Pool
Stunning Tisbury Retreat with Pool
House
Tisbury, MA, 02568, United States
1.6k from Vineyard Haven center

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

5 Bedrooms10 Guests
10.0

Exceptional

4 reviews

$2752
Average price / night
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PRIVACY & RELAXATION ON MARTHA'S VINEYARD
PRIVACY & RELAXATION ON MARTHA'S VINEYARD
House
Tisbury, MA, 02568, United States
2.1k from Vineyard Haven center

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

6 Bedrooms12 Guests
10.0

Exceptional

8 reviews

$1785
Average price / night
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Mink Meadows Luxury Getaway With Pool
Mink Meadows Luxury Getaway With Pool
House
Vineyard Haven, MA, 02568, United States
2.2k from Vineyard Haven center

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

5 Bedrooms10 Guests
10.0

Exceptional

5 reviews

$2627
Average price / night
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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
2.3k from Vineyard Haven center

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

6 Bedrooms10 Guests
10.0

Exceptional

71 reviews

$1206
Average price / night
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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
2.4k from Vineyard Haven center

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

2 Bedrooms6 Guests
10.0

Exceptional

22 reviews

$709
Average price / night
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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
2.4k from Vineyard Haven center

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

4 Bedrooms9 Guests
10.0

Exceptional

7 reviews

$1326
Average price / night
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 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
2.5k from Vineyard Haven center

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

5 Bedrooms10 Guests
9.4

Superb

13 reviews

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

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

5 Bedrooms10 Guests
10.0

Exceptional

3 reviews

$2479
Average price / night
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Grand Coastal-Style Estate In The Preserve
Grand Coastal-Style Estate In The Preserve
House
Oak Bluffs, MA, 02557, United States
3.1k from Vineyard Haven center

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

5 Bedrooms12 Guests
10.0

Exceptional

4 reviews

$2315
Average price / night
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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
3.2k from Vineyard Haven center

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

5 Bedrooms12 Guests
New to Booking
$1508
Average price / night
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THE PARK ESTATE! Your Martha's Vineyard Getaway!
THE PARK ESTATE! Your Martha's Vineyard Getaway!
House
Oak Bluffs, MA, 02557, United States
3.7k from Vineyard Haven center

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

6 Bedrooms16 Guests
9.8

Exceptional

17 reviews

$7810
Average price / night
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Oak Bluffs Retreat. NEW PRIVATE POOL
Oak Bluffs Retreat. NEW PRIVATE POOL
House
Oak Bluffs, MA, 02568, United States
4.0k from Vineyard Haven center

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

3 Bedrooms6 Guests
10.0

Exceptional

14 reviews

$3725
Average price / night
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Relax & Unwind: Poolside Martha’s Vineyard Stay
Relax & Unwind: Poolside Martha’s Vineyard Stay
House
Oak Bluffs, MA, 02568, United States
4.7k from Vineyard Haven center

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

5 Bedrooms10 Guests
New to Booking
$1374
Average price / night
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Peaceful Island Getaway with Pool and Exclusive Beach Pass
Peaceful Island Getaway with Pool and Exclusive Beach Pass
House
West Tisbury, MA, 02568, United States
5.4k from Vineyard Haven center

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

3 Bedrooms6 Guests
New to Booking
$856
Average price / night
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Main house and a separate apartment with saltwater pool, spa, outdoor cooking!
Main house and a separate apartment with saltwater pool, spa, outdoor cooking!
House
West Tisbury, MA, 02568, United States
5.7k from Vineyard Haven center

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

7 Bedrooms12 Guests
10.0

Exceptional

5 reviews

$4116
Average price / night
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Sengekontacket Contemporary With Pool, Hot Tub And Water Views
Sengekontacket Contemporary With Pool, Hot Tub And Water Views
House
Edgartown, MA, 02539, United States
6.3k from Vineyard Haven center

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

4 Bedrooms10 Guests
New to Booking
$1872
Average price / night
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Gorgeous Edgartown Colonial with Heated Pool, Central Air, Car
Gorgeous Edgartown Colonial with Heated Pool, Central Air, Car
House
Edgartown, MA, 02539, United States
6.5k from Vineyard Haven center

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

5 Bedrooms10 Guests
10.0

Exceptional

61 reviews

$889
Average price / night
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Modern West Tisbury Retreat  3BR/2BA  Pool & Outdoor Shower
Modern West Tisbury Retreat 3BR/2BA Pool & Outdoor Shower
House
West Tisbury, MA, 02575, United States
6.6k from Vineyard Haven center

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

3 Bedrooms6 Guests
New to Booking
$992
Average price / night
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5BR Family Retreat | Pool, Fire Pit & Two Living Areas
5BR Family Retreat | Pool, Fire Pit & Two Living Areas
House
Edgartown, MA, 02539, United States
6.7k from Vineyard Haven center

AC, Heater, Internet, Kitchen, Microwave, No Smoking, Pool, TV

5 Bedrooms10 Guests
New to Booking
$2756
Average price / night
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Spacious 5BR Home w/ Pool & Two Living Areas
Spacious 5BR Home w/ Pool & Two Living Areas
House
Edgartown, MA, 02539, United States
6.7k from Vineyard Haven center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave, No Smoking

5 Bedrooms10 Guests
New to Booking
$1604
Average price / night
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Modern & Spacious Edgartown Home with Pool
Modern & Spacious Edgartown Home with Pool
House
Edgartown, MA, 02539, United States
6.7k from Vineyard Haven center

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

3 Bedrooms8 Guests
10.0

Exceptional

14 reviews

$1029
Average price / night
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Beautiful property and home
Beautiful property and home
House
Edgartown, MA, 02539, United States
7.8k from Vineyard Haven center

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

6 Bedrooms12 Guests
10.0

Exceptional

24 reviews

$1538
Average price / night
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Charming home with heated pool near bike path - sleeps 10
Charming home with heated pool near bike path - sleeps 10
House
Edgartown, MA, 02539, United States
8.1k from Vineyard Haven center

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

3 Bedrooms10 Guests
New to Booking
$845
Average price / night
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Beautifully Renovated Edgartown Home with Pool in Quiet Location Close to Town.
Beautifully Renovated Edgartown Home with Pool in Quiet Location Close to Town.
House
Edgartown, MA, 02539, United States
8.2k from Vineyard Haven center

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

3 Bedrooms6 Guests
10.0

Exceptional

16 reviews

$1156
Average price / night
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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 Private Pool in Vineyard Haven.

Stay Near Vineyard Haven's Top Attractions

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Vineyard Haven Vacation Rentals with Private Pool on the Map

Frequently Asked Questions

You can explore 39 verified vacation rentals with a private pool in Vineyard Haven. These include standalone villas and private homes where the pool is reserved exclusively for your group.

Prices for rentals with a private pool in Vineyard Haven vary depending on the property size, location, and travel season. Rates typically start from around $709 per night, with higher prices for larger homes, prime locations, or peak travel periods.

Yes, properties listed with private pools are intended for the exclusive use of guests staying at that home. You can review listing photos and descriptions to better understand the layout and level of privacy offered.

Yes, some vacation rentals with private pools in Vineyard Haven also welcome pets. Currently, 9 listings allow pets, although policies may vary. It’s a good idea to review any rules related to pets and outdoor areas before booking.

Private pool properties are often in high demand, especially during holidays and warmer months, so booking 90 to 120 days in advance is recommended. During quieter periods, you may still find availability closer to your travel dates.

Vacation rentals with private pools in Vineyard Haven often include additional features such as Pool, Private Pool, and Fireplace/Heating. These amenities enhance comfort and create a more relaxing, self-contained stay.

Some family-friendly vacation rentals in Vineyard Haven include safety features such as pool fences, covers, or screened enclosures. It’s recommended to check the property details to confirm whether a specific rental meets your safety preferences.