
Holiday rentals with beach access in Oak Bluffs
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Top-rated rentals with beach access in Oak Bluffs
Guests agree: these rentals with beach access are highly rated for location, cleanliness and more.

Studio Guest Suite in Modern Barn House
A beautiful guest suite on Martha’s Vineyard with a private entrance on the back wing of our newly renovated modern barn house. Surrounded by trees, beside a large meadow, this airy suite has vaulted wood ceilings with skylights. Enjoy the outdoor shower and new outdoor sitting area. The location is prime and centrally located, just off historic Music St, a short walk to our small town center which provides many amenities. Ask about our other private guest suite if you are traveling with others

Sea View Waterfront Beachfront Apartment
Prime location- right across the street from a sandy beach, a few minutes walk to the harbor, downtown, and transportation (boat, bus, etc). This beautiful street-level one-bedroom apartment sits across the street from the ocean, where you can take a dip and enjoy the beach. The apartment was recently redone and has a small bedroom with a queen size bed, small bathroom, full kitchen, and living room area with pull-out couch. Convenient to take the ferry into Oak Bluffs and walk to the apartment

Newly Renovated! Seconds to sand, fire pit, A/C
Recently Renovated! This Cape Cod Cottage is completely refreshed top to bottom. Less than 60 seconds to the sand. Cape cod vacations do not get any better than this! Located on idyllic Monomoscoy Island known for its gorgeous wildlife and stunning waterways, our home is the perfect choice to rent on Cape Cod. We are less than 10 Mins to Mashpee Commons and famous Mashpee Town Beach, Less than 5 mins to New Seabury and the Popponesset Inn, and only 15 mins to downtown Falmouth. Linens included!

Spectacular beach & pool combo; beautiful sunsets!
Close to airport, you’ll love backyard beach, water view, pool/grass yard, ambiance and outdoors space. Beach & Pool (POOL HEAT STARTS SUMMER, ENDS 9/1) is a hard to find combination!! Location is private, yet it's close to the 3 largest towns on Martha's Vineyard. Great for couples, families (with kids), and big groups. Enjoy dinner with the indoor/outdoor Sonos music system during a beautiful sunset! NOTE; Rate increase in high season, pool/spa is a combined unit & ONLY heated in summer!

Quaint Cape Cod Cottage on a Private Beach!
Create magical memories on the Cape at this sweet seaside cottage! A perfect place for a family-friendly getaway or a romantic retreat for two! The new contemporary coastal decor is cozy and comfortable and my place has all of the amenities you could want for your stay! Just steps to a beautiful beach with stunning sunsets and sunrises, cool ocean breeze, and the warm Nantucket Sound. Enjoy Popponesset Marketplace for food, shopping and fun or take a short drive to Mashpee Commons for more!

Sunny Studio Apartment on Martha's Vineyard
Our Sunny Studio is centrally located on Martha's Vineyard. A down-island location with an up-island feel. Open and airy studio with kitchenette and bath. The apartment has all the essentials. The apartment is located within walking distance of hiking and biking trails. A 10 to 15 minute car ride to any down-island town / beach. ***Please Note: Although conveniently located we are not within walking distance to Bars or Restaurants. We do recommend first time visitors rent or bring a car.

East Chop Cottage - walk to lighthouse & beach!
This quaint little cottage is located in the heart of East Chop, a neighborhood of Oak Bluffs. East Chop features the high, prominent bluffs that gave Oak Bluffs its name. A lighthouse, East Chop Light, stands at the north end of the chop on Telegraph Hill- only a five minute walk from the cottage. The cottage is a twelve minute walk to the harbor, and about a mile from the Oak Bluffs ferry! There is a public beach about 1/2 mile down the road. ***This space is not suitable for children

impeccable cottage STEPS to downtown OB & beach!
Unique opportunity to stay in an impeccable cottage in Downtown Oak Bluffs. With a front porch with rocking chairs, a back deck & grill, & an outdoor shower, and A/C! - this is the ideal oasis for your Vineyard Vacation. Turn right and find yourself steps from restaurants & shops on Circuit ave. Turn left and walk 5 mins to beautiful beaches. Everything you want out of vacation at your fingertips. Relax, and truly experience the Vineyard the way it was meant to be, at the @WeePackemInn

Waterview, Private, Walk to Beach, Mile to Town
Rustic barn-style home, waterview, spacious natural landscape, serenity, and privacy on 3 acres centrally located 1 mi from Oak Bluffs and Vineyard Haven centers. Walk to beach, bike path nearby, comfortable interiors, memory foam mattresses, cotton linens, 2 HDTVs, high-speed wifi, heat/AC, 2 ocean kayaks, and 2 bikes. Location, amenities and privacy surrounded by natural beauty make staying very easy and relaxing. Ask the host about ferry reservations if they appear to be sold out!

Beautiful 3 bedroom in Oak Bluffs, walk to beach
Located in Martha's Vineyard, close to beach, bike path, oak bluffs center, art and culture, parks,and the airport. You’ll love my place because of the outdoors space with a wrap around farmers porch, the proximity to the ferry, walking distance to neighborhood beach, less than 2 miles from ferry, screened in porch, central a/c, hardwood floors and an open floor plan. Real Cape Cod feel with modern amenities. Most of my guest come back year after year!

The Ideal Spot
The perfect getaway in Falmouth for all seasons! Our home is beautifully located overlooking Bourne’s Farm and we are steps away to the picturesque Shining Sea Bike Path. Enjoy a beautiful scenic 8.5 mile ride winding your way thru the Sippewisset marsh and along the coastline to the seaside village of Woods Hole. Where you can enjoy the local restaurants ,shops and science learning or jump on the ferry to Marta’s Vineyard.

Sleep 6 @ New Seabury w/ Pool Access, All Seasons!
Welcome to Your Coastal Getaway at The Mews, New Seabury – Mashpee, MA Tucked inside the beautiful New Seabury Country Club, our cozy Cape-style condo offers the perfect balance of relaxation and adventure on Cape Cod. Enjoy access to a private condo association pool just a 3-minute walk away, and a beach that is 5 min drive or 10 min bike ride or 30 min walk (walk cuts through golf course-ask host for directions).
Popular amenities for rentals with beach access in Oak Bluffs
Apartment rentals with beach access

In-law apt. with all the amenities of Home.

On Eel Pond: Woods Hole Waterfront Retreat

Shining Sea-Weekender-On the Bike Path

Sunny Private studio amazing deck kayaks & kitchen

Pet-Friendly Oak Bluffs 3BR | Deck & Fire Pit

Stylish retreat | walk to town | fire pit

The Mainstay at Menemsha Inn

Walking-distance to town, shops & ferry
House rentals with beach access

Martha's Vineyard Cottage: Walk to Town and Beach

Bayview on Seconsett Island

Newer const. Edgartown home A/C, car ferry tkts

The Lobster Pot: Lake Tashmoo, beachfront

Modern Marvel in Woods Hole - Walk to town & ferry

Entire home newly renovated- listed August 2025

Walk to Downtown Oak Bluffs - Modern Cottage

Stunning 4/2.5 Water View, Hot Tub, Dogs ok
Apartment rentals with beach access

Breezy Oak Bluffs Condo - Steps to Inkwell Beach!

Relax....You're on Island Time......

Serenity on Martha's Vineyard

Beachside Villiage-Oceanfront

LOCATION LOCATION!! Ocean- View TOP Floor Condo

Beach, Steps Away, * Reduced Seasonal Rental *

Cape Esacpe at New Seabury

Spectacular Martha's Vineyard Island Home!
When is the best time to visit Oak Bluffs?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $517 SGD | $546 SGD | $521 SGD | $478 SGD | $498 SGD | $630 SGD | $758 SGD | $939 SGD | $647 SGD | $504 SGD | $504 SGD | $513 SGD |
| Avg. temp | 0°C | 0°C | 3°C | 7°C | 12°C | 17°C | 21°C | 21°C | 18°C | 13°C | 8°C | 3°C |
Quick stats about holiday rentals with beach access in Oak Bluffs

Total holiday rentals
Explore 240 holiday rentals in Oak Bluffs

Nightly prices starting at
Oak Bluffs holiday rentals start at $38 SGD per night before taxes and fees

Verified guest reviews
Over 8,680 verified reviews to help you choose

Family-friendly holiday rentals
190 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 50 rentals that welcome pets

Rentals with dedicated workspaces
120 properties have a dedicated workspace

Wifi availability
240 of Oak Bluffs holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Oak Bluffs rentals

4.9 Average rating
Oak Bluffs stays are highly rated by guests – averaging 4.9 out of 5!
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- Rentals with beach access Dukes County
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- Rentals with beach access United States
- Cape Cod
- Mayflower Beach
- West Dennis Beach
- East Sandwich Beach
- Craigville Beach
- Duxbury Beach
- Easton Beach
- Onset Beach
- Roger Williams Park Zoo
- Second Beach
- Coast Guard Beach
- The Breakers
- Pinehills Golf Club
- South Shore Beach
- New Silver Beach
- Lighthouse Beach
- Bonnet Shores Beach
- Sandy Neck Beach
- East Matunuck State Beach
- Nickerson State Park
- Cahoon Hollow Beach
- Cape Cod Inflatable Park
- Fort Adams State Park
- Salty Brine State Beach




