Rentals with Pools

Across the entire island of Martha’s Vineyard, there are a myriad of rental homes with pools that may be of interest to you and your family. From beautiful oceanfront properties located on paramount shores of Oaks Bluffs, to luxurious inland estates atop the hills of Tisbury, we at Coldwell Banker Landmarks Real Estate are here to help you find the dream rental with a pool that is ideal for you and your loved ones. No matter what your reason for venturing to this heavenly area is, there truly is something to do for those of all ages. Popular activities include shopping in Edgartown’s authentic downtown district, eating at one of Oak Bluff’s renowned restaurants, sailing smooth ocean waters, and visiting some of the nude beaches - if you’re daring enough!. Don’t wait before these grand openings become occupied. Start browsing our list of rental properties with pools, today!

If you would like to view one of these listings, please contact us or call 508-693-6866. To stay up to date on your favorite listings and searches, register with our site.

 

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Rental Price$6,000 to $23,500

Rental ID 116541

  • RTR Vacation Rental
  • Lease $6,000 to $23,500
  • Village Edgartown
  • Bedrooms 4
  • Bathrooms 4

Located just two blocks from Edgartown Village this newly constructed sophisticated luxury retreat offers gracious style and comforts throughout. This 5200 square foot home features casual elegance and all of the finest amenities as well as a heated pool and blue stone patio for outdoor entertaining and enjoyment. There are four bedrooms, each with en-suite baths, the master separated by French doors for privacy and a den on the first floor which upon request can be converted into the fifth bedroom with a queen bed. You will find the media/game room hard to beat, with a large-screen TV and a pool table that has a Ping-Pong option. Perfect home for the family who wishes to have it all. Finishing touches are currently being completed and more photos to be posted soon.

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Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

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$
$
%
$/month over payments
Federal 30-year interest rate: 4.32% last updated on Feb 8, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Rental Price$25,000 to $30,000

Rental ID 133977

  • RTR Vacation Rental
  • Lease $25,000 to $30,000
  • Village Chilmark
  • Bedrooms 5
  • Bathrooms 3

The house itself is spacious with elegant details, state of the art systems, and an attractive floor plan. Craftsmanship quality in this 5,400 square foot home is everywhere, from the kitchen, with its granite counters, center island with copper counter, custom cabinetry, and tile floors & backsplash. To the living areas and bedrooms, that include heart pine flooring, high-ceilings with exposed wood beams, wainscoting and moldings. And, the bathrooms, with their high-end fixtures, tile flooring and custom elements. The kitchen includes a Sub-Zero refrigerator, eight-burner, gas, Viking, stovetop, and two Bosch dishwashers. Heating/AC system includes a Viessmann boiler, forced hot air heat and air conditioning, and radiant heat in the lower level. Floor plan includes a number of bonus areas, table tennis room, media/TV room, wine cellar with brick floor and cedar paneling; two master suites, and an open main level that centers on the living room, which includes cathedral ceilings, fieldstone fireplace, and egress to exterior decking. Many rooms with water views. This beautiful home features all of the finest amenities as well as a heated pool for outdoor entertaining and enjoyment and just recently put tennis court.

{$agent->Name}

Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.32% last updated on Feb 8, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Rental Price$7,000 to $8,800

Rental ID 116995

  • RTR Vacation Rental
  • Lease $7,000 to $8,800
  • Village West Tisbury
  • Bedrooms 4
  • Bathrooms 3

Relax and enjoy this private retreat set on two acres in a quiet neighborhood off of Lamberts Cove Road. This is the ultimate entertainer indoors as well as outdoors. Step out back onto a beautifully landscaped yard with in-ground pool and a pergola shaded mahogany deck, fire pit and outdoor shower. Deluxe pool house offers full guest house accomodations - two twin beds with private half bath/shower. Open and spacious Main house with fully equipped gourmet kitchen. Includes three comfortably furnished bedrooms on second floor. Step down to lower level basement for a fully furnished entertainment room with media system, exercise gym, half bath, laundry room and queen sleeper sofa. Secluded yeard is fully fenced. A short walk through the woods will take you to a private pond.

{$agent->Name}

Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.32% last updated on Feb 8, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Rental Price$12,500 to $13,500

Rental ID 116973

  • RTR Vacation Rental
  • Lease $12,500 to $13,500
  • Village West Tisbury
  • Bedrooms 3
  • Bathrooms 4

Located in desirable Upper Makonikey, this spectacular home enjoys delightful distant views overlooking Vineyard Sound, the Elizabeth Islands, and Woods Hole beyond. This ten room home contains 4,000 sq ft of living area, state-of-the-art systems, three fireplaces, step-down library with vaulted ceiling, dining room opens to the porch and grounds. A fully-equipped chef s kitchen with 2 refrigerators and 2 ranges. the breakfast room leads to a deck with picturesque vistas. Relax and enjoy afternoons lounging by the lovely Gunite swimming pool. Just a short walk to a private association beach.

{$agent->Name}

Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.32% last updated on Feb 8, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Rental Price$35,000 to $45,000

Rental ID 116963

  • RTR Vacation Rental
  • Lease $35,000 to $45,000
  • Village Edgartown
  • Bedrooms 5
  • Bathrooms 6

Luxurious Edgartown waterfront estate with award-winning infinity pool surrounded by 150 acres of conservation land. This quintessential summer escape offers views, location and lifestyle. Deluxe amenities abound in this 8,000 sq ft custom built compound, the main house includes four bedrooms and five baths. A fully equipped gourmet kitchen with top of the line appliances and beautiful stone fireplace with sitting area add the perfect touch. Private guest quarters located above the garage includes separate bath, kitchen and living area. Elegant craftsmanship and attention to detail throughout the design of this home, everything state of the art. The bluestone patio, custom built stone gas grill, entertainment bar and sink and professionally landscaped grounds add to your summer outdoor entertaining. It s everything that you and your family could possible need for a spectacular Vineyard experience.

{$agent->Name}

Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.32% last updated on Feb 8, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Rental Price$2,500 to $2,950

Rental ID 116923

  • RTR Vacation Rental
  • Lease $2,500 to $2,950
  • Village Vineyard Haven
  • Bedrooms 2
  • Bathrooms 3

Spacious Tashmoo Woods condo with association pool and tennis courts. Bright, open main living, dining, kitchen area, comfortably furnished throughout. Sliding doors to outdoor deck, perfect for outdoor dining and relaxing. Additional sleeping area in den (full size sofa bed). Great location, close to ferry, public beach and center of town.

{$agent->Name}

Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.32% last updated on Feb 8, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Rental ID 116852

  • RTR Vacation Rental
  • Village West Tisbury
  • Bedrooms 3
  • Bathrooms 2
  • Half Baths 1

Our sunny, spacious home is tastefully furnished and decorated with Island arts and crafts. High ceilings, open-plan living/dining area as well as a loft area is as appealing as it is comfortable. Back deck is perfect for relaxing after the beach, having a BBQ or watching the sun set through the native pine and oak forest. Located on a quiet lane in charming West Tisbury promises peace and tranquility while still being centrally located to all island towns. It is a short walking distance to the State Forest, bike path and numerous walking trails. Fully equipped home with kitchenware, linens, towels and beach gear - just bring clothes!

{$agent->Name}

Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.32% last updated on Feb 8, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Rental Price$2,150 to $2,800

Rental ID 116849

  • RTR Vacation Rental
  • Lease $2,150 to $2,800
  • Village Vineyard Haven
  • Bedrooms 3
  • Bathrooms 3

Striking contemporary townhouse, located in Tashmoo Woods. Nice solid oak floors. Association tennis courts and pool.

{$agent->Name}

Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.32% last updated on Feb 8, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Rental Price$13,500 to $25,000

Rental ID 116806

  • RTR Vacation Rental
  • Lease $13,500 to $25,000
  • Village West Tisbury
  • Bedrooms 4
  • Bathrooms 4

One of the most breathtaking spots on the island, stunning panoramic views of the South Shore! This recently renovated one-of-a-kind home sits on a dune overlooking the ocean with an inground pool and private har-tru tennis court. Each of the four bedrooms has its own private deck and bathroom. The kitchen offers great space for hanging out, or entertaining. Large stretch of private, sandy beach provides for an unforgettable island retreat.

{$agent->Name}

Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.32% last updated on Feb 8, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Rental Price$5,000 to $20,000

Rental ID 116755

  • RTR Vacation Rental
  • Lease $5,000 to $20,000
  • Village Edgartown
  • Bedrooms 5
  • Bathrooms 4

Masterfully renovated 1850’s Sea Captain’s home situated on a quiet tree lined street. Designer decorated Grecian Revival is within walking distance to the harbor, restaurants and beaches. Main level includes a large gourmet kitchen adjacent to a bright family with working fireplace. A living room, dining room (each with its own fireplace), wood paneled media room and office completes the first floor. There are four bedrooms and three baths on the second floor (two of these bedrooms have french doors that lead to a second floor balcony. On the third floor you will find a large sunny bedroom/play area along and bathroom. Separate from the main house is a detached one bedroom studio with full bath. This private compound located in the heart of Edgartown village is professionally landscaped with a heated pool and hot tub.

{$agent->Name}

Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.32% last updated on Feb 8, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule A VisitAsk A QuestionMore Details