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

Cody's Place Boston Airport Pool/Beaches ParkFree
Retreat, relax, & refresh in your own private entry basement in law apartment of our well bunkered Beach House. BEST LOCATION across from the mighty Atlantic & Iconic Winthrop Arms Hotel/Restaurant. Take in the salty air & breathtaking sunrises. Steps from Ocean Sunrise & Sandy Beach Surf. Walking distance to public transport, restaurants, parks, or Uber/Walk to the center bars & other attractions. Vacation living. Ferry minutes to downtown Boston. 1 of 3 officially licensed AirBnB's in town.

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!

Peaceful suite in Boston with city views
Enjoy Boston in an elegant 2 bedroom/bath with sleek interior furnishing for long and short stays. Just a 5 min walk from the T and close to Boston College/Harvard, you can tastefully engage with all of Boston. Unit Features -> Blazing Fast WiFi -> 65” Roku TV Living Room -> 50” (x2) Roku TV Bedroom -> Fully Stocked Kitchen -> Washer & Dryer -> 2 Queen Bed -> 1 Twin Bed -> 1 Sleeper Sofa Ideal for business travelers, couples, nurses, and everyone looking to experience Boston in style!

Large groups. Private Retreat. Entire home
Get ready to soak up the sun and enjoy some fun at this Somerset vacation rental! This family and PET-friendly house features 5 bedrooms, 2 bathrooms, and a beautiful backyard you won't want to leave! Near the Rhode Island Border!! Fire up the grill and enjoy dinner al fresco before gathering around the fire pit or relaxing in the hot tub. The spacious kitchen has everything you need to prepare meals before a day of exploring Pierce Beach, hiking in Colt State Park, or Lizzie Borden history!

Cozy Private Suite halfway between Cape & Boston
Large private room located in the Basement of a single family home. The home is conveniently located less than one minute from route 3 half way between Boston and Cape Cod. The room has a full size bed, and a euro lounger that can be used to relax and watch TV or reclyned for sleeping. There is a kitchenette located in the room which has a Fridge with top freezer, a microwave and a Keurig . The private bath is located inside the bedroom. Cool off in the pool during summer months.

Spacious vacation unit in premium suburban town
Weston is one of Boston area's most desirable towns. <30 min to downtown Boston with a lot of open space. Centrally located with easy access to highways, train stations, etc. Next to a park with hiking trails, this is a secondary unit (Duplex units) with its own separate entry/exit. 3 bedrooms (one on lower level, two on 2nd level), kitchen, 2 baths (both on lower level). ~2000 square feet of space. Some seasons (including some winters) we have hens in the backyard...

The Holly Cottage
Welcome to Centerville, enjoy this fully equipped 1 bedroom 1 bath home with an easy walk or ride to just about everything. Enjoy the nearby ocean and beaches, or take a ride downtown to Main Street for dining and entertainment. Only a short distance to the ferries for a day trip to the islands and you can be back in time to catch a concert at the Melody Tent. Enjoy your days by the pool and your evenings grilling out on the large deck or chatting with the koi fish.

Great Location. Near Beach & Main Street. Unit M1
Our home-away-from-home accommodations include this charming studio with lawn space, a private deck with outdoor furniture and a gas grill. The cottage is comfortably furnished and features a small kitchen. This cottage has a queen bed and a table with sitting area. The kitchen is nicely updated with updated with beautiful granite countertops and stainless steel appliances including an stove/oven, microwave, mini-fridge, toaster, coffee maker. Keurig, and kettle.

The Secret Garden 4 Bedroom, 7 Bed 3 Baths
This beautiful 2.5 acre fully fenced in private property has gardens, an in-ground pool & pool house with an outdoor heated shower. Our home offers 2 kitchens, dining room seating 12, a great room, 3 bedrooms with private sitting areas & lower level with 2 bunk beds (bottoms are full beds) & exercise area. Outside are 2 grills & a fire pit. We are 3 miles from the beach, shopping/cafes, 45 minutes from Boston (on a train route) and 20 minutes to Cape Cod.

P-Town Beach Beauty on the Bay. Water View!
Beautiful Water View East End 2 bedroom condo across the street from the beach on the bay. Just cross the road and take the association maintained steps down to the beach. This beach boasts a nice tidal swing where you can walk out in the shallows during low tide. The condo is in the perfect East End location, combining closeness to the center of town, with your own beach and not having the noise and parking issues of downtown Provincetown.

Historic 1 Bed/In Town/Best Location/Hot tub/deck
Please do not book weekends, holidays, or summer dates in advance. This 1-bedroom is only offered to fill midweek gaps when the full home isn’t booked. Beautifully restored historic home in the heart of town—steps from the Pilgrims' first settlement, ocean, restaurants, shops, and more. Located on Town Brook near the Gristmill, with a deck, firepit, hot tub, grill, cozy bed, and working wood stove. Clean, comfortable, and full of charm.

Seaview Summit | Ocean Views, Indoor Pool, Beach
Perched above the coastline with panoramic Atlantic views, Seaview Summit House is Plymouth's premier oceanfront retreat. Designed for discerning travelers seeking serenity, space, and sophistication. With a heated indoor pool, expansive outdoor living areas, and direct beach access just moments away, this stunning property delivers a five-star experience in every season. Book your stay today. You'll be glad you did.
Popular amenities for Plymouth rentals with a pool
House rentals with a pool

Secluded Oasis w/ Heated Salt Pool - 10 to Newport

In-Ground Pool Oasis | 5 Min to Cape Cod Beaches!

Modern Home w/ Pool & Game Room | Mins to Newport

Sunny Cape w/Private Pool, Steps to Private Lake

STEPS to Private Beach-7 Beds, Pool, Fenced Yard

Coastal Retreat in Sandwich -Pool Access, Dogs OK!

Winslow Acres [heated] Pool Escape; pool May-Oct

Jolly Captain Lighthouse
Condo rentals with a pool

Cozy Studio Just Steps Away From the Beach!

1BR 2nd Floor Condo with pool

Stylish & Modern Studio Condo - Steps to the Beach

Hidden Hideaway

Spectacular Waterfront Condo

Mary's Cape Escape

Bright Beach Condo • Walk to Sand & Shops

Newly Updated Condo w/ Pool - Steps to Boatslip!
Other vacation rentals with a pool

Serenity - 36’ Aft Cabin Carver

Chic Pool Condo Near Mayflower Beach

Townhouse Close to Downtown Newport & Beaches

Salt Winds

Bass Rocks Upper Decks, special winter rates

Dog Friendly Cape Oasis | Pool+Beach |Tennis Court

Home w/ golf view, salted heat pool, mins to beach

Oceanfront 5BR with amazing views & private pool
When is the best time to visit Plymouth?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ951 | ﺩ.ﺇ940 | ﺩ.ﺇ1,010 | ﺩ.ﺇ984 | ﺩ.ﺇ1,091 | ﺩ.ﺇ1,733 | ﺩ.ﺇ1,833 | ﺩ.ﺇ1,715 | ﺩ.ﺇ1,377 | ﺩ.ﺇ1,172 | ﺩ.ﺇ1,036 | ﺩ.ﺇ1,285 |
| Avg. temp | -3°C | -2°C | 2°C | 8°C | 14°C | 19°C | 22°C | 22°C | 18°C | 11°C | 6°C | 0°C |
Quick stats about vacation rentals with a pool in Plymouth

Total vacation rentals
Explore 30 vacation rentals in Plymouth

Nightly prices starting at
Plymouth vacation rentals start at ﺩ.ﺇ294 per night before taxes and fees

Verified guest reviews
Over 2,080 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
30 of Plymouth vacation rentals include wi-fi access

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

4.7 Average rating
Plymouth stays receive an average rating of 4.7 out of 5 from guests
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