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.

 

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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.

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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: 4.62% last updated on Jun 14, 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$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.

{$office->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: 4.62% last updated on Jun 14, 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$7,500 to $19,500

Rental ID 134281

  • RTR Vacation Rental
  • Lease $7,500 to $19,500
  • Village Edgartown
  • Bedrooms 5
  • Bathrooms 4

New construction just finished summer 2017! Coastal-inspired Gambrel with open layout and integrated outdoor living spaces, including a screened porch and farmer s porch, plus heated gunite pool with hot tub, and a large stone patio, redwood glider and hammock in the yard. The first floor includes open Living, Dining, and Kitchen Areas. The Living Area has vaulted ceilings and is anchored by a 16-foot tall, stone fireplace. There are built-in media center, plus French doors. The Dining area features see through gas fireplace. There are 9-foot ceilings a wall of glass windows, and a large dining table with high back comfortable chairs. The fully-equipped kitchen features large center prep bar, granite counters, high-end appliances. One end of the Kitchen opens to the Screened porch with Brazilian wood ceiling and floor to ceiling wood burning fireplace that overlooks the pool area. One of three Master Bedrooms Suites is on the first floor. It has a deluxe master bath with double granite vanity, soaking tub, double walk-in shower. The other two en suite Masters, are upstairs. The second floor has one other Bedroom, a shared bath, and a large, open TV/Family area with media center. There is a fully built-out, deluxe Lower Level with high ceilings, windows, and French doors that let in lots of light. The space features a Game/Media Area with pool table, ping pong, media center, plus gym are, and Kitchenette, casual Dining Area, a 4th king bedroom and a half bath. The outdoor space is centered around the 38x18-foot, heated gunite pool and hot tub for 6 and chaise lounge for 8. The pool is outfitted with swim jet and swim current system. The pool is surrounded by 1400 sq foot stone patio that has ample lounging, dining and seating areas for outdoor entertaining. A big bonus to the property is a garage outfitted with a universal electrical car charger. The property has professionally landscaped grounds and gardens, with trees providing privacy and luxurious outdoor setting. The is in a quiet residential neighborhood in Katama, a mile away from Edgartown Village and mile and a half from South Beach.

{$office->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: 4.62% last updated on Jun 14, 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$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.

{$office->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: 4.62% last updated on Jun 14, 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$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.

{$office->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: 4.62% last updated on Jun 14, 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$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.

{$office->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: 4.62% last updated on Jun 14, 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$3,500 to $8,000

Rental ID 116630

  • RTR Vacation Rental
  • Lease $3,500 to $8,000
  • Village West Tisbury
  • Bedrooms 5
  • Bathrooms 4

Charming, shingle home decorated with comfortable New England antiques. Freshly painted throughout and new carpeting in bedrooms. Large wooded lot with professional landscaping and heated pool with heated waterfall spa. Quiet, paved road near Alley s general store and art galleries.

{$office->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: 4.62% last updated on Jun 14, 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$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.

{$office->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: 4.62% last updated on Jun 14, 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$15,000 to $15,000

Rental ID 113896

  • RTR Vacation Rental
  • Lease $15,000 to $15,000
  • Village Oak Bluffs
  • Bedrooms 5
  • Bathrooms 4

The stresses of life will melt away as you enjoy the peace and tranquility of this acre and a half property. Nestled in a forest, you will enjoy the spectacular landscape with easy access to down-island towns. Sip your morning coffee an a porch rocker overlooking two ponds, work out in the private gym or roast marshmallows at the fire pit. Serenity has everything you will want for the perfect vacation.

{$office->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: 4.62% last updated on Jun 14, 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.

{$office->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: 4.62% last updated on Jun 14, 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