
Vacation rentals with a pool in Oak Bluffs
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Oak Bluffs
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Exclusive New Seabury Home w/ Heated Pool ⛳️🏖🦞☀️🐠
~~ You Have Arrived! Welcome to "The Fore Seasons" in desirable New Seabury on Cape Cod. ⛳️🏖🌸☀️ You will be sure to fall in love with old Cape Cod in this 4,500 sqft private home located on the 10th hole fairway of the championship golf course. With its 4 bedrooms, 4 bathrooms, Heated Inground Pool, Outdoor Shower, Putting Green, Ping Pong table and Ctrl Air there is enough room for the largest families. Pool open from Mid-May until through Columbus Day! Available year round for all gathering

Private Pool, near beaches, 3 BR/3 BA, Central Air
Enjoy the Barnstable historic seaside village of Cotuit in this sprawling house with central air, nestled in the pines on a quiet street with private gated (unheated) pool, lg. backyard, firepit, ample parking, just blocks from Main St, Ropes Beach, scenic ocean views, fort playground, and Kettleer baseball. Each bedroom has a TV and ensuite bathroom! Relax in the seasonal sunroom overlooking the pool; grill burgers on the patio. Max. 9 (6 adults). Pool open 6/20-9/15/24. The reviews tell all!

New Seabury Oasis with Pool!
Relax with the whole family at this peaceful New Seabury retreat. 5 bedrooms, 3 bathrooms with separate living rooms on each floor. Newly updated backyard and heated pool. Backs up to 10th/11th hole of the Ocean Course at New Seabury. Great for a large family or two families to share. Master bedroom has built in desk space to allow to work from home, as needed. Walk to Popponessett marketplace and all the beautiful outdoor space New Seabury has to offer. Short drive to South Cape beach.

Renovated ranch with pool access
Renovated home in E. Falmouth offers endless relaxation and recreation: swim, bike, fish, kayak, walk, lounge. Short walk to Assoc beach or to the Seashores Clubhouse pool (seasonal). Bring your kayak: explore Washburn Island & Waquoit Bay. Sleeps 6 with 1-floor living, AC, laundry, large back deck, and outdoor shower. Nearby, you'll find dining/shopping areas, wineries/breweries, & more. A short drive to Woods Hole offers fast boats to Martha's Vineyard. Book now and enjoy Sandy Feet Retreat.

1.2 Acre Estate | Pool | Close to Beaches | Games
A beautifully maintained 1900s historic estate on expansive grounds with over 3,300 sq. ft. of living space, this 6-bed, 3-bath sanctuary blends historical elegance with Cape Cod charm! •Private Pool •2 miles to beach •Comfortably sleeps 12- perfect for groups & families •Family friendly (Pack N Play, toys, high chair) •Fully stocked kitchen •Two gas fireplaces •Ample outdoor & indoor games •Dedicated workspace •Outdoor dining & fire pit •Peloton and gym equipment •Poker table •Smart TV's

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!

Private 3bdrm Condo Tashmoo Woods
This 3 bedroom (3 king) 2 1/2 baths newly renovated condo is in a private setting with screened in porch. New kitchen, gas grill on deck, outdoor shower. -Access to the Tashmoo Woods Association pool, tennis courts and play ground. -Close to West Chop beaches. -Two miles from downtown Vineyard Haven. On bus route, but best to have a car. -The primary bedroom (king bed) is downstairs and the 2 upstairs bedrooms share a bath (shower only). Minimum rental 5 days, 1 week in summer.

Falmouth/Woods Hole Charming Cottage By the Sea
Welcome to our Cottage By The Sea Rental located only minutes from the quaint village of Woods Hole, Falmouth and the Martha's Vineyard Ferry. We are located in the perfect setting to relax and enjoy all the area has to offer. Come enjoy The Shining Sea Bike path which is 10.7 miles , Sandy beaches, lively restaurants & local music scene, shopping on historic Main Street, Farmers Markets & more. Your sure to fall in Love with " Ole Cape Cod " when you visit our home and area

Home w/ golf view, salted heat pool, mins to beach
Newly renovated home in the heart of New Seabury! You'll love the breathtaking golf course view from our backyard, where you can enjoy a heated saltwater pool, a large deck, and a patio with a fire pit. Our spacious home offers a fully equipped kitche, a coffee bar and plenty of open space for family gatherings. 5 minutes from the stunning South Cape beach, and surrounded by attractions like the Children's Museum and Mashpee Commons.

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).

Quaint North Falmouth near Old Silver Beach
Located in the Quaint village of North Falmouth, yet close to beaches, this one-bedroom Apartment is a great place to relax. It has a tiled walk-in shower and heated floor in the bathroom. The kitchen includes a microwave, toaster oven, cook top stove, and a Keurig coffee maker. The pool is not heated and is open seasonally (July 1 - Labor Day) Very private location. Close to Old Silver Beach!

Beautiful Edgartown Colonial with heated pool.
Stunning 5 bedroom, 10 room, 3500 square foot colonial in beautiful area. Gourmet kitchen, dining room, living room, den, family room with ping pong. Huge deck, private yard with fire pit and outdoor shower. 30 x 16 x 4 heated in ground pool. Central air. Kayaks, bikes. Seven passenger Toyota Highlander available to rent May- October.
Popular amenities for Oak Bluffs rentals with a pool
House rentals with a pool

Waterfront Home w/ Dock, Heated Pool, Kayaks & A/C

Beautiful Mashpee Home with Pool

Home in Falmouth ~ 5 min drive to beach

Mashpee Manor Pool House

Spacious 5 bedroom with pool!

Sunny Cape w/Private Pool, Steps to Private Lake

Sippewissett Forest Magic by the Sea

Dog Friendly Cape Oasis | Pool+Beach |Tennis Court
Condo rentals with a pool

Surfside Resort Cape Cod, Falmouth MA

2BR Condo in Cape Cod w/ Patio & Laundry

Falmouth MA, Cape Cod Getaway

Lovely lakefront studio/condo with pool

Beachside Villiage-Oceanfront

Island Inn - Two Bedroom Suite - 1A - Oak Bluffs,

Two bedroom condo .on the water Falmouth, ma

5 Mi to Mashpee Commons: Coastal Mashpee Condo
Other vacation rentals with a pool

Serene East Falmouth Retreat

New Seabury pool/hot tub near beach,Popponesett

Beautiful Cape Cod Retreat w/Pool

Summer 2026 Open! Walk to Great Pond, central a/c

New Seabury Home with Pool and Golf Course View

Quaint, relaxing Cape Cod condo

Private POOL*New Seabury* 3 bedroom

WestTisbury Charm, Carroll House
When is the best time to visit Oak Bluffs?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | € 1,120 | € 710 | € 1,120 | € 919 | € 567 | € 1,079 | € 967 | € 1,293 | € 840 | € 1,041 | € 606 | € 1,185 |
| 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 vacation rentals with a pool in Oak Bluffs

Total vacation rentals
Explore 30 vacation rentals in Oak Bluffs

Nightly prices starting at
Oak Bluffs vacation rentals start at € 129 per night before taxes and fees

Verified guest reviews
Over 770 verified reviews to help you choose

Family-friendly vacation rentals
30 properties offer extra space & kid-friendly amenities

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
30 of Oak Bluffs vacation rentals include wi-fi 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!
Destinations to explore
- Plainview Vacation rentals
- New York Vacation rentals
- Long Island Vacation rentals
- Boston Vacation rentals
- East River Vacation rentals
- Hudson Valley Vacation rentals
- Jersey Shore Vacation rentals
- Philadelphia Vacation rentals
- South Jersey Vacation rentals
- Pocono Mountains Vacation rentals
- The Hamptons Vacation rentals
- Capital District, New York Vacation rentals
- House rentals Oak Bluffs
- Condo rentals Oak Bluffs
- Private suite rentals Oak Bluffs
- Rentals with lake access Oak Bluffs
- Rentals with a hot tub Oak Bluffs
- Pet-friendly rentals Oak Bluffs
- Rentals with a fireplace Oak Bluffs
- Apartment rentals Oak Bluffs
- Waterfront rentals Oak Bluffs
- Rentals with outdoor seating Oak Bluffs
- Rentals with a kayak Oak Bluffs
- Rentals with a washer and dryer Oak Bluffs
- Rentals with a patio Oak Bluffs
- Rentals with beach access Oak Bluffs
- Bed and breakfasts Oak Bluffs
- Family-friendly rentals Oak Bluffs
- Boutique hotels Oak Bluffs
- Rentals with a fire pit Oak Bluffs
- Hotel rooms Oak Bluffs
- Beachfront rentals Oak Bluffs
- Rentals with breakfast Oak Bluffs
- Rentals with pools Dukes County
- Rentals with pools Massachusetts
- Rentals with pools 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
- Town Neck Beach
- Lighthouse Beach
- New Silver Beach
- Nickerson State Park
- Cape Cod Inflatable Park
- Cahoon Hollow Beach
- Sandy Neck Beach
- Salty Brine State Beach
- Sea Gull Beach
- Martha's Vineyard Museum




