Martha’s Vineyard Vacation 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.

 

r=1-10

Rental Price$20,000 to $55,000

Rental ID 116620

  • RTR Vacation Rental
  • Lease $20,000 to $55,000
  • Village Edgartown
  • Bedrooms 5
  • Bathrooms 4

Exclusive seven acre waterfront property with spectacular waterviews from every room. Very private, located in desirable Herring Creek Farm, this home includes a Main house, Guest house as well as Pool House with heated gunnite pool and jacuzzi. NOTE: PLEASE CALL OUR RENTAL AGENT FOR WEEKLY RATES.

$
$
%
$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 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$20,000 to $45,000

Rental ID 116578

  • RTR Vacation Rental
  • Lease $20,000 to $45,000
  • 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.

$
$
%
$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 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$6,500 to $19,500

Rental ID 116542

  • RTR Vacation Rental
  • Lease $6,500 to $19,500
  • Village Edgartown
  • Bedrooms 4
  • Bathrooms 4

In-town Edgartown three bedroom with detached guesthouse and pool. Recently renovated, this home has it all! The main and guesthouse overlook the heated pool area with blue stone patio. Bright, airy, tastefully furnished with hardwood flooring throughout. Fully equipped gourmet kitchen with eat-in nook area. Includes media game room with wet bar in basement. Relax and enjoy sound system in living room, media room and pool patio. Private backyard area with two car garage. Great location just two blocks to town for shops and restaurants. The perfect in-town vacation home with pool.

$
$
%
$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 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$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.

$
$
%
$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 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 6
  • 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.

$
$
%
$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 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$5,900 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.

$
$
%
$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 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$1,500 to $5,590

Rental ID 116362

  • RTR Vacation Rental
  • Lease $1,500 to $5,590
  • Village Edgartown
  • Bedrooms 2
  • Bathrooms 2

A secluded island retreat situated on a three acre lot with meadow and wooded areas yet within easy reach to all six unique island villages and towns. Beautifully decorated, this home provides both indoor and outdoor living in a lovely setting. The stone patio, barbecue and wooded deck with hot tub and outdoor shower are the perfect answer for those marvelous vineyard days and nights. The sunroom/porch offers a bright and cheerful spaciousness regardless of the time of year or weather. An inground solar heated salt chlorinated pool is to be shared with guests from the Main house.

$
$
%
$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 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$3,880 to $5,882

Rental ID 125460

  • RTR Vacation Rental
  • Lease $3,880 to $5,882
  • Village Vineyard Haven
  • Bedrooms 4
  • Bathrooms 3

Charming house on over 2 landscaped acres in Mink Meadows Golf Community. With a private pool and walk to the beach it truly is perfect. This home is well appointed and the attention to detail is not to be missed. 4 bedrooms and 2 indoor living spaces and large deck it is ideal for large groups.

$
$
%
$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 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$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.

$
$
%
$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 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$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.

$
$
%
$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 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