Oak Bluffs Vacation Rentals

Discover our latest vacation rentals in the Martha's Vineyard town of Oak Bluffs. Look through a variety of listings including beautiful oceanfront homes, luxury estates, cottages, and more! You may also be interested in browsing all of our vacation rentals.

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Oak Bluffs, MA

Rental Price$5,103 to $9,000

Rental ID 130382

  • RTR Vacation Rental
  • Lease $5,103 to $9,000
  • Village Oak Bluffs
  • Bedrooms 5
  • Bathrooms 3

This home walking distance to downtown Oak Bluffs has been lovingly restored. With five bedrooms and three and half baths and three floors of living space this home is big enough for the whole family. The king sized master is the entire second floor and has an en-suite bath and private deck. The first floor has four bedrooms with 2 shared baths. In the living room, kitchen and dining area you will enjoy open living concept with a beautiful brick fireplace as the centerpiece. The basement is finished beautifully with a 50 inch flat screen. Perfect for rainy day games.

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$/month over payments
Federal 30-year interest rate: 3.49% last updated on Feb 20, 2020
* 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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Oak Bluffs, MA

Rental Price$3,000 to $4,000

Rental ID 125185

  • RTR Vacation Rental
  • Lease $3,000 to $4,000
  • Village Oak Bluffs
  • Bedrooms 4
  • Bathrooms 2

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$/month over payments
Federal 30-year interest rate: 3.49% last updated on Feb 20, 2020
* 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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Oak Bluffs, MA

Rental Price$8,825 to $10,600

Rental ID 132137

  • RTR Vacation Rental
  • Lease $8,825 to $10,600
  • Village Oak Bluffs
  • Bedrooms 4
  • Bathrooms 2

Waterfront custom Farmhouse overlooking Crystal Lake toward East Chop Drive. There is a large manicured lawn and garden with a path to the lake and a row boat for your enjoyment. Sit on the expansive deck and use the 8 x15 hot tub/ dip pool, outdoor shower and enjoy the view, or grill on your brick patio (ALL WITH INCREDIBLE VIEWS). A very peaceful location, yet a five minute drive to Circuit Ave, East Chop Light, and the beaches of Oak Bluffs. Vineyard Haven and Oak Bluffs ferries are also a five minute drive. A great area for the kids to play and FAMILIES to get around very easily. Also lovely walking paths nearby for birdwatchers. This well-maintained, well-equipped house offers linens and towels, bicycles, and is loaded with amenities. The first floor offers a large modern kitchen, breakfast bar open to the dining room and a large living room all with views of a lovely yard, Crystal Lake, and Vineyard Sound oceanfront beyond. There is also a sun room, 2 bedrooms, and 1.5 baths on this floor.

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$/month over payments
Federal 30-year interest rate: 3.49% last updated on Feb 20, 2020
* 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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Oak Bluffs, MA

Rental Price$1,500 to $3,750

Rental ID 132471

  • RTR Vacation Rental
  • Lease $1,500 to $3,750
  • Village Oak Bluffs
  • Bedrooms 2
  • Bathrooms 2

A peaceful retreat! Renovated cottage with modern furnishings on a large 1.99 acre landscaped lot in Fresh Pond Estates, an exclusive private community. The home is a two bedroom, two bath residence with a private sleeping den with a deluxe queen sleeper sofa allowing guests to convert into a three bedroom home. Convenient location off County Road Bike Path, equidistant to all Down Island Towns and a short bike ride to Farm Neck Golf & Tennis Club! This is a perfect rental for the active family. Beautiful Pastoral setting and a wonderful Screened Porch with plenty of seating for lounging and dining. There is a deck that wraps around the home with plenty of seating for outdoor dining or a family BBQ. A short drive to beaches and downtown shopping in Oak Bluffs, Vineyard Haven and Edgartown. Walking and biking trails are just steps away! The home is on a quiet, well-maintained private road and a perfect location for those seeking peace and quiet in a beautiful home!

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$/month over payments
Federal 30-year interest rate: 3.49% last updated on Feb 20, 2020
* 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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Oak Bluffs, MA

Rental Price$3,500 to $3,500

Rental ID 116966

  • RTR Vacation Rental
  • Lease $3,500 to $3,500
  • Village Oak Bluffs
  • Bedrooms 3
  • Bathrooms 2

Located in Meadow View Farms with association tennis available for your use, and across from Farm Neck Golf Course. This newly furnished and attractively decorated home with hardwood floors is set on an acre of land. Just two miles from the center of town shopping, restaurants and the beach. Spacious living area with finished basement entertainment room. Large deck with beautiful outdoor furniture and enclosed shower.

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$/month over payments
Federal 30-year interest rate: 3.49% last updated on Feb 20, 2020
* 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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Oak Bluffs, MA

Rental Price$3,500 to $5,040

Rental ID 138888

  • RTR Vacation Rental
  • Lease $3,500 to $5,040
  • Village Oak Bluffs
  • Bedrooms 4
  • Bathrooms 3

Set in a luxury community this modern 4 bedroom home is great for vacations. Located off the Edgartown-Vineyard Haven Road, the home is in a private community and is centrally located, only 5 miles from each of the down island’s 3 towns. There are private tennis courts and boat/kayak access to Sengekontacket pond. Scenic viewa abound and the private roads provide for safe bike riding, running and walking. Access to the island’s bicycle path network is just outside the entrance to Hidden Cove. The house sprawls over 3 levels. The recently modernized lower level contains 3 bedrooms, a full bathroom and washer/dryer. The main living level is a contiguous space of living room, media center, fireplace, full bathroom, dining area and kitchen. Brightly lit by 3 sliding glass doors that open out onto a deck facing Sengekontacket pond. The deck has a barbecue, lounges, plus table and chairs with umbrells for outdoor dining. The secluded upper level contains a master bedroom with ensuite bathroom. All in all a perfect base for a fantastic island vacation.

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%
$/month over payments
Federal 30-year interest rate: 3.49% last updated on Feb 20, 2020
* 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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Oak Bluffs, MA

Rental Price$3,500 to $8,200

Rental ID 127105

  • RTR Vacation Rental
  • Lease $3,500 to $8,200
  • Village Oak Bluffs
  • Bedrooms 4
  • Bathrooms 3

Beautifully appointed brand new four bedroom home. Steps to Niantic park, walk to Inkwell and downtown Oak Bluffs. Central air-conditioning and a lovely farmers porch to sit and watch the world go by.

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$/month over payments
Federal 30-year interest rate: 3.49% last updated on Feb 20, 2020
* 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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Oak Bluffs, MA

Rental Price$2,500 to $3,200

Rental ID 116387

  • RTR Vacation Rental
  • Lease $2,500 to $3,200
  • Village Oak Bluffs
  • Bedrooms 3
  • Bathrooms 2

Bright, spacious home located in a quiet neighborhood. Approx 0.5 mile from Oak Bluffs down town area. Walk or ride out of driveway directly onto the bike path. Professionally decorated throughout. Open space plan for maximum enjoyment. Large dining room for everyday or special gatherings. Abundant large windows throughout home for a light/airy feeling. Stone fireplace (gas powered) in the great room. Beautiful hardwood floors throughout living level. Master suite includes large private bathroom with ceramic floors and granite countertop. Ceiling fans in each bedroom as well as central air. The perfect home away from home.

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$
%
$/month over payments
Federal 30-year interest rate: 3.49% last updated on Feb 20, 2020
* 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

Oak Bluffs, MA

Rental Price$5,500 to $8,000

Rental ID 133995

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

This brand new construction located just minutes from downtown Oak Bluffs is well appointed and comfortable. A first floor master outfitted with a king bed and is ADA compliant is perfect for grandparents or the nanny. Upstairs you will find three more bedrooms. A generous sized master with sitting area and en suite bath. Two additional bedrooms that share a lovely bath with double vanity and walk in shower. The living area is open concept with a 65 inch flat screen television and comfortable furnishings for movie night. The kitchen is well appointed with high end pots and pans as well as a kitchen-Aid mixer.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.49% last updated on Feb 20, 2020
* 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

Oak Bluffs, MA

Rental Price$5,250 to $15,750

Rental ID 141578

  • RTR Vacation Rental
  • Lease $5,250 to $15,750
  • Village Oak Bluffs
  • Bedrooms 5
  • Bathrooms 3

Endless views of the ocean, directly across from the water, and steps away from a sandy beach excellent for swimming. Gorgeously remodeled last summer (2018) and designed with a sophisticated California-meets-MV feel inside, our welcoming, centrally-air-conditioned, 4 bedroom house sleeps 10 and is a rarity in this area. Blonde wood wide plank flooring, new kitchen, new doors & windows, mattresses, and appliances including dishwasher, gas range, French door refrigerator with ice maker and a king size bed in a larger than usual (for OB) master BR. The house is airy and uncluttered, with a wide 3-sided wraparound porch, perfect for watching the annual fireworks, dining outside or watching the world go by. 4 well appointed bedrooms -- one downstairs and three upstairs (including a larger bedroom with a queen & 2 twins which is perfect for sharing). Second-story deck off the master bedroom offers views of the ocean, as well as Farm Pond. A second porch off the second & third upstairs bedrooms also has ocean views. Two sets of French doors from the kitchen and dining area open out to a larger portion of the deck and stunning ocean views. Updated bathrooms (glass-door subway tile walk-in shower downstairs, a deep soaking tub upstairs), wide porches to relax and dine on, and an open and connected feeling downstairs (a wood topped bar/island connects guests to the dining area and the kitchen, open french doors connect it all to the deck and the outdoor seating/dining). The house is set back from the road by a generous lawn, and is a very short distance (a few houses) to the bike path that runs along the island s edge & State Beach and into Edgartown, and within easy walking distance of both the Oak Bluffs ferry docking and the shops and restaurants in town and along the harbor, so you ll never have to search for a parking space to dine in-town in the high season. There s a large dining table inside & barbecue and additional outdoor seating/dining table on the porch, TV (televisions in the living room and the master BR). 1 king bed, 2 queen beds, 1 full sized bed, and 2 twin beds. Additionally, upon request/discussion, there is a back guest cottage aka "The Nest". The Nest has a good size upstairs bedroom (offering what is then a 5th BR); queen bed and a twin bed (sharing the same room), a deck off the bedroom that has water views (ocean and Farm Pond), The guest house is air conditioned with mini split.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.49% last updated on Feb 20, 2020
* 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