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!

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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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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.

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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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$/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.

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Rental Price$2,850 to $3,100

Rental ID 113603

  • RTR Vacation Rental
  • Lease $2,850 to $3,100
  • Village Vineyard Haven
  • Bedrooms 2
  • Bathrooms 3

Beautifully appointed condominium in Tashmoo Wood. Bright and airy with cathedral ceilings, gourmet kitchen and central air. The den could be used as an extra bedroom. Association tennis and pool. A great family vacation spot.

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$/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.

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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.

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$/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.

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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.

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$/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.

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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.

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$/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.

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Rental Price$6,500 to $8,500

Rental ID 113579

  • RTR Vacation Rental
  • Lease $6,500 to $8,500
  • Village West Tisbury
  • Bedrooms 4
  • Bathrooms 4

Beautiful custom post and beam located in Deep Bottom Pond. Air-conditioned contemporary with cathedral ceilings and floor-to-ceiling windows facing the woods. Enjoy the spacious deck, hot tub and association tennis. Large, bright rooms and located close to the bike path. A basement sleeping room with sitting area, TV and private bath are perfect for extended family or nanny. New gunite pool and bluestone deck in a private wooded setting.

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$/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.

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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.

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$/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.

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Rental Price$2,000 to $4,750

Rental ID 116765

  • RTR Vacation Rental
  • Lease $2,000 to $4,750
  • Village West Tisbury
  • Bedrooms 5
  • Bathrooms 4

A beautiful 1.5 acre wooded property surrounded by state forest and wildlife preserve. Completely renovated in 2012 including all new kitchen, bathrooms, flooring throughout, appliances, 40-inch high definition flat screen TV, blu-ray player, ceiling fans, and a full sized washer & dryer. The house comfortably accommodates 10 guests in 5 bedrooms with 4 full bathrooms and 1 enclosed outdoor shower. The second floor has an en suite master bedroom with a balcony, a queen bedroom also with a balcony, a third bedroom with bunk beds (double and twin) and a share second full bath with a tub. The first floor has the fourth bedroom and the third full bath. Basement adds a 5th bedroom with a queen bed, and a full bath and TV/Media room. The backyard is beautiful & private with a bluestone patio and two cozy seating areas. There is an amazing wooden swing sets with 2 towers, keeping the kids happy while the adults relax on the lovely patio or hammock. The house includes wireless access and unlimited local and long distance phone service. Most rooms are equipped with ceiling fans. A neighborhood association pool and tennis court are available while open and West Tisbury private beaches (Lamberts Cove, Long point beach and Seth s Pond) passes may be purchased. Located on the bike path, just 4 miles from the town beach at Lambert s Cove, and includes use of the neighborhood pool and tennis club when open. Access is fully paved and less than 5 miles from the Vineyard Haven ferry.

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$
%
$/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.

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Rental Price$5,000 to $13,500

Rental ID 137839

  • RTR Vacation Rental
  • Lease $5,000 to $13,500
  • Village Oak Bluffs
  • Bedrooms 5
  • Bathrooms 4

$
$
%
$/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