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Oak Bluffs, MA vacation rentals
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Best Vacation rentals and Airbnb offers in Oak Bluffs, MA

Best Oak Bluffs, MA vacation rentals with a balcony

4 Mi To Bristol Beach! Coastal Retreat W/ Pond - Oak Bluffs, MA
8.0 2 reviews
Oak Bluffs, MA
08/08 – 08/10
$466/nighttotal: $932 (2 )

4 Mi To Bristol Beach! Coastal Retreat W/ Pond

2 4
house , Falmouth
This East Falmouth Cape Cod cottage, a 4-mile drive from Bristol Beach and near South Cape Beach State Park, offers easy access to local attractions.
The 700-square-foot house features two bedrooms, one bathroom, sleeps seven, and includes a fully equipped kitchen with a dishwasher, air conditioning, Wi-Fi, a private patio, and parking (extra charge).
Bella Luna - Oak Bluffs, MA
8.8 104 reviews
Oak Bluffs, MA
08/08 – 08/10
$1054/nighttotal: $2108 (2 )

Bella Luna

2 4
house , Falmouth
This Falmouth vacation rental is located just 1.3 miles from Bristol Beach and within a 20-mile radius of attractions like the Sandwich Glass Museum, Heritage Museums & Gardens, and John F Kennedy Hyannis Museum. The house has received excellent ratings for user experience, location, and cleanliness.
This 2-bedroom, 2-bathroom home is perfect for families or groups of up to 6 guests and offers 1120 square feet of living space. Enjoy features like air conditioning, a fully equipped kitchen, a balcony with sea views, free Wi-Fi, cable TV, and a private garden with parking.
Seabreeze Escape - Oak Bluffs, MA
Oak Bluffs, MA
08/05 – 08/11
$929/nighttotal: $5574 (6 )

Seabreeze Escape

4 2
house , Falmouth
Seabreeze Escape, a four-bedroom Falmouth house rental, is located near Bristol Beach (1.3 miles) and South Cape Beach State Park (10 miles), offering easy access to Falmouth's attractions.
This 1150-square-foot home features a fully equipped kitchen, air conditioning, a patio, garden, and accommodates up to 15 guests, perfect for family getaways or group trips near Falmouth beaches.

Browse Family-Friendly Vacation Rentals in Oak Bluffs, MA

Family beach vacations in Oak Bluffs, MA are better in spacious rentals that offer plenty of room to spread out near the shore.

Cozy Retreat Near Beaches With Washer/dryer, Ac, Games, Patio & Yard - Oak Bluffs, MA
9.2 5 reviews
Oak Bluffs, MA
08/05 – 08/11
$859/nighttotal: $5154 (6 )

Cozy Retreat Near Beaches With Washer/dryer, Ac, Games, Patio & Yard

4 2
apartment , Falmouth
This recently renovated apartment is centrally located in East Falmouth, providing easy access to local dining, Inkwell Beach, and the Woods Hole Ferry Terminal, all within 2 miles.
This 1150 square foot home accommodates up to 8 guests with 4 bedrooms, a full kitchen, air conditioning, and a private backyard with a patio and gas grill, offering on-site entertainment like board games and yard games.
Storybook Cottage, Shining Sea Bikeway, Dogs Okay! - Oak Bluffs, MA
Oak Bluffs, MA
08/08 – 08/10
$614/nighttotal: $1228 (2 )

Storybook Cottage, Shining Sea Bikeway, Dogs Okay!

1 4
apartment , Falmouth
This West Falmouth apartment is located just off Route 28, offering a 2-minute walk to the Shining Sea Bikeway and a short drive to downtown Falmouth's shops and restaurants.
This family-friendly vacation rental accommodates up to four guests in two bedrooms and features a full kitchen with a dishwasher, air conditioning, and access to a garden.
The Seashell Cove - Martha's Vineyard - Oak Bluffs, MA
9.8 26 reviews
Oak Bluffs, MA
08/21 – 08/22
$1508/nightfor 1 night

The Seashell Cove - Martha's Vineyard

4 8
apartment , Edgartown
This Katama vacation home, located within two miles of Edgartown's Old Whaling Church, Vincent House Museum, and Edgartown Public Library, and three miles from Katama Plains Natural Heritage Area and Lighthouse Beach, offers convenient access to historic sites and natural beauty.
This four-bedroom, four-bathroom house sleeps eight guests and features a fully equipped kitchen, a private patio, a garden, and a spa, providing ample space and amenities for a relaxing Edgartown getaway.
Winnetu Oceanside Resort At South Beach - Oak Bluffs, MA
8.0 2 reviews
Oak Bluffs, MA
08/08 – 08/10
$4217/nighttotal: $8434 (2 )

Winnetu Oceanside Resort At South Beach

1 4
resort , Edgartown
Winnetu Oceanside Resort at South Beach is located near South Beach, a three-minute walk away, and 3.2 miles from Edgartown's Main Street, offering easy access to both beach and town.
This Edgartown resort boasts seasonal heated pools, a fitness center, complimentary children's programs, tennis courts, and The Dunes restaurant with ocean views; various accommodations, including studios, cottages, and up to four-bedroom suites, are available.

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Best Oak Bluffs, MA vacation rentals with parking

Partial Ocean View Above Restaurant (203) - Oak Bluffs, MA
8.4 5 reviews
Oak Bluffs, MA
08/05 – 08/11
$348/nighttotal: $2088 (6 )

Partial Ocean View Above Restaurant (203)

1 2
apartment , Falmouth
This Falmouth apartment rental is situated above a bar, a short walk from the beach.
The one-bedroom, one-bathroom unit sleeps two guests and features a king-size bed, air conditioning, parking, and internet access.
Stay 1 Block From Ocean At 7-bed Retreat With Yard, Deck And Game Room, Host Up To 22 Across 16 Beds, Gas Fireplace, Gas Grill, Ample Parking, Walk To Menauhant Beach, Perfect For Family Getaway, 24 Hr Hospitality - Oak Bluffs, MA
Oak Bluffs, MA
08/05 – 08/11
$3792/nighttotal: $22752 (6 )

Stay 1 Block From Ocean At 7-bed Retreat With Yard, Deck And Game Room, Host Up To 22 Across 16 Beds, Gas Fireplace, Gas Grill, Ample Parking, Walk To Menauhant Beach, Perfect For Family Getaway, 24 Hr Hospitality

7 2
house , Falmouth
This seven-bedroom Falmouth mansion, a four-minute walk from Menauhant Beach and within a 10-19 mile radius of Heritage Museums & Gardens, Sandwich Glass Museum, and South Cape Beach State Park, offers luxurious accommodations for large groups.
The 4,890-square-foot home boasts five bathrooms, a fully equipped kitchen with dishwasher, a fireplace, air conditioning, free Wi-Fi, parking, and a garden, comfortably sleeping up to 39 guests.
Beautiful Estate With Salt Water Pool  & Pond With Kayaks - Oak Bluffs, MA
Oak Bluffs, MA
08/21 – 08/22
$7512/nightfor 1 night

Beautiful Estate With Salt Water Pool & Pond With Kayaks

5 8
apartment , Oak Bluffs
This estate is located in Prestigious Fresh Pond Estates, Oak Bluffs, offering a private, wooded setting with a freshwater pond just 2 miles from Oak Bluffs center and 500 feet from a bike path.
This 4500 square foot house accommodates up to 12 guests with 5 bedrooms and 3 bathrooms, featuring a heated saltwater pool, Jacuzzi, outdoor kitchen, and private 2-bedroom living quarters, ideal for multi-family stays.
Saltwind Cottage | Beach Walk • Cozy Fireplace - Oak Bluffs, MA
10 51 reviews
Oak Bluffs, MA
08/05 – 08/11
$976/nighttotal: $5856 (6 )

Saltwind Cottage | Beach Walk • Cozy Fireplace

1 2
apartment , Falmouth
This Falmouth, Cape Cod vacation home is situated near Green Pond, a short drive from Menauhant Beach, Surf Drive Beach, and Old Silver Beach.
The 7,405-square-foot lot houses a two-bedroom, one-bathroom cottage sleeping four, featuring a fully equipped kitchen, in-unit laundry, outdoor shower, fire pit with TV, BBQ grill, and two TVs, plus a gas fireplace; enjoy nearby Main Street shops and restaurants.

Choose the Right Vacation Rentals with a Pool in Oak Bluffs, MA

Complement your time by the water with a dip in the pool at these Oak Bluffs, MA vacation rentals with on-site swimming facilities.

Falmouth/woods Hole 
Charming Cottage By The Sea - Oak Bluffs, MA
10 64 reviews
Oak Bluffs, MA
08/05 – 08/11
$604/nighttotal: $3624 (6 )

Falmouth/woods Hole Charming Cottage By The Sea

1 2
house , Falmouth
This Falmouth cottage, near Woods Hole and minutes from the Martha's Vineyard ferry, offers convenient access to the Shining Sea Bike Path and Falmouth's Main Street.
The one-bedroom, one-bathroom unit sleeps two guests and features a full kitchen with dishwasher, a king-size bed, private parking, and access to a shared saltwater pool (June-September), along with a private Jacuzzi.

Top-Rated Oceanfront Vacation Rentals in Oak Bluffs, MA

Enjoy a relaxing beach getaway with these coastal and seaside vacation rentals in Oak Bluffs, MA. Book your next shoreside stay today.

Maushop With Scenic Views - Oak Bluffs, MA
8.7 3 reviews
Oak Bluffs, MA
08/08 – 08/10
$1141/nighttotal: $2282 (2 )

Maushop With Scenic Views

1 4
cabin , Mashpee

Traveler-Approved Luxury Vacation Rentals in Oak Bluffs, MA

Indulge in a luxury vacation rental in Oak Bluffs, MA, where high-end design meets world-class 5-star comfort.

Sailor’s Lantern - Oak Bluffs, MA
Oak Bluffs, MA
08/05 – 08/11
$799/nighttotal: $4794 (6 )

Sailor’s Lantern

3 2
house , Falmouth
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