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$3,500 to $8,500

Rental ID 121396

  • RTR Vacation Rental
  • Lease $3,500 to $8,500
  • Village Vineyard Haven
  • Bedrooms 5
  • Bathrooms 3

Contemporary split level home located on a cul-de-sac in a pleasant neighborhood. This home features 5 bedrooms, 3.5 baths, and an updated kitchen with 2 Viking ovens, granite counters and large island. The family room, 2 bedrooms and bath on the lower level is a great space for the kids or extended family and has a separate entrance to side yard. Outside the heated gunite swimming pool is surrounded by lovely landscaping, patio, and deck; a perfect escape if you do not want to spend time at the beach. Great for BBQ’s too. Come enjoy this little piece of heaven for your Vineyard vacation. A perfect place for fun in the sun!

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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: 3.78% last updated on Sep 14, 2017
* 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: 3.78% last updated on Sep 14, 2017
* 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: 3.78% last updated on Sep 14, 2017
* 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: 3.78% last updated on Sep 14, 2017
* 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: 3.78% last updated on Sep 14, 2017
* 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$7,500 to $7,500

Rental ID 116729

  • RTR Vacation Rental
  • Lease $7,500 to $7,500
  • Village Chilmark
  • Bedrooms 4
  • Bathrooms 3

Breathtaking south shore ocean views from this pastoral setting await you. This striking contemporary has great spaces for everyone. Lovely furnishings and decor. All this and Chilmark beaches too.

{$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: 3.78% last updated on Sep 14, 2017
* 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$2,000 to $2,600

Rental ID 116689

  • RTR Vacation Rental
  • Lease $2,000 to $2,600
  • Village Vineyard Haven
  • Bedrooms 2
  • Bathrooms 4

A beautiful, dramatic staircase is the architectural focal point of this upscale condominium located in the Tashmoo Woods Association. There are two bedrooms with en suite baths, a den/study with a first floor full bath, and a finished basement with a sleeper sofa and private bath for additional sleeping space. Many desirable features including oak floors, fireplace, AC, and a deck with an expansive backyard. Association amenities include a pool, four tennis courts, dock on Tashmoo for canoes and kayaks, and beach on Vineyard Sound.

{$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: 3.78% last updated on Sep 14, 2017
* 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$20,000 to $40,000

Rental ID 116578

  • RTR Vacation Rental
  • Lease $20,000 to $40,000
  • Village Edgartown
  • Bedrooms 6
  • Bathrooms 5

Elegant waterfront home on Eel Pond with private pool and carriage house suite. Spacious open interior with great attention to detail and full of amenities. Beautiful grounds and large patio area for outdoor entertaining. Located in desirable Edgartown, convenient to downtown area - boutique shopping, restaurants, galleries, cinema and harbor stroll.

{$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: 3.78% last updated on Sep 14, 2017
* 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$14,500 to $14,500

Rental ID 116373

  • RTR Vacation Rental
  • Lease $14,500 to $14,500
  • Village Oak Bluffs
  • Bedrooms 4
  • Bathrooms 3

Spectacular views, over 500 feet of private beach on the Lagoon. Recently renovated home, exterior transformed from contemporary to cottage-shingle style. Houses largest triceratops skull ever found. Caution must be taken with children due to high decks.

{$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: 3.78% last updated on Sep 14, 2017
* 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$5,900 to $8,830

Rental ID 116363

  • RTR Vacation Rental
  • Lease $5,900 to $8,830
  • Village Edgartown
  • Bedrooms 3
  • Bathrooms 3

This award winning design home is set in a beautiful meadow on the outskirts of Edgartown. Luxurious 3200 sq ft home features 10-12 ft ceilings, a spacious living room, a sun/family room with surround sound entertainment center. Fully equipped kitchen with top of the line appliances. Includes a rec room with exercise equipment. A lovely country porch with blue stone patio with hot tub provide great outdoor living. An inground solar heated, salt chlorinated pool is shared with guests from the guesthouse.

{$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: 3.78% last updated on Sep 14, 2017
* 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