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Vacation rentals with a pool in Sandwich

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Sandwich

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Home in East Sandwich

4.92 out of 5 average rating, 64 reviews

Large Home Heated Swimming Pool Private Beach

Perfect for extended-family fun in this stunningly built home (3300 sqft) with 5 bedrooms and 4 bathrooms. First-floor shower. Walk 1000 feet to a private beach with full access rights. Along the beach, you can stroll further east to Sandy Neck Beach. Open kitchen, dining and great rooms are perfect for entertaining! Swim in the ocean or jump right into a beautiful 16x40 heated fiberglass pool with pool lights! Hosted by an extremely experienced host who's committed to making your stay perfect.

Home in Cotuit

4.95 out of 5 average rating, 113 reviews

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!

Condo in Brewster

4.97 out of 5 average rating, 177 reviews

Ocean Edge Resort-Pool Access-End Unit-2 bdr/2 bth

2nd floor Ocean Edge end unit condo located in the heart of Brewster with access to OE resort amenities: pools, gyms, tennis courts, as well as access to resort activities (fees apply). Easy access to Cape Cod Rail Trail for bicycles. Scenic route 6A offers arts & crafts galleries and local shops. A 10 minute car ride to a 36 hole Captains Golf course. Short ride to 10 Brewster bay beaches famous for tidal flats. A 30 minute ride to Cape Cod National Sea Shore. Welcome to your Happy Place!

Rental unit in Dennis

4.9 out of 5 average rating, 29 reviews

Cozy condo in Dennis Village. Welcome home!

Cozy up & relax in this calm, stylish, new, fully equipped 1 BR condo (sofa bed in 2025). Cape Storia d’ Amore is 4 mins from Mayflower in the heart of Dennis Village. Less than 5 minutes from all the great dining options in Dennis Village. 12 mins from Cape Cod Inflatable Park. Large, fenced in pool is just steps away. new: - kitchen w/ new range, DW, fridge, Keurig/drip coffee maker, cookware. New bath w/walk in shower, washer & dryer. Smart TV, Roku, internet, fireplace, AC in summer.

Home in Oak Bluffs

4.94 out of 5 average rating, 191 reviews

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!

Home in Plymouth

4.9 out of 5 average rating, 184 reviews

Thanksgiving House Dining Table seats 12-14

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 & chiminea. We are 3 miles from the beach, shopping/cafes, 45 minutes from Boston (on a train route) and 20 minutes to Cape Cod. POOL can be HEATED for $500.00/Visit.

Home in Sandwich

4.99 out of 5 average rating, 80 reviews

"Cape Escape" luxury home w/pool & beach access.

Welcome to the Cape Escape! Enjoy views of Spectacle Pond from the 70 ft. deck of this recently renovated 5 bed/3 bath spacious home meeting all your needs! Relax by the in-ground pool in the private enclosed yard. Enjoy nights around the fire-pit. Directly across the driveway you can enjoy kayaking, sunbathing & swimming at the neighborhood beach. Within 6 miles of the home you will find the historic Sandwich boardwalk, Ocean beaches, Cape Cod Canal and more! Perfect for family gatherings!

Home in Plymouth

4.9 out of 5 average rating, 242 reviews

Ocean Side, Amazing View, close to town/beach, Spa

PRICING IS FOR 2 GUESTS, 1 BEDROOM, 1 BATH ONLY, can add additional bed/bath for a fee, YOU WILL HAVE THE HOUSE TO YOURSELF. We only use this listing to fill gaps when the larger listing isn't rented & will decline ALL WEEKENDS, HOLIDAYS, PEAK times and will only accept mid-week, non summer/holidays. Please read additional info. OCEAN FRONT, HISTORIC SUMMER COTTAGE, AMAZING VIEWS, GREAT LOCATION, less than 1 mile walk to town and beach. Hot tub, fireplace, stocked kitchen, fresh linens.

Home in Edgartown

4.78 out of 5 average rating, 111 reviews

Katama gem.

Select Dog friendly, - mile from downtown, mile from south beach, steps to bike path, fenced in yard.. Gorgeous pool, w/a seperate pool house with flatscreen, mini fridge, and fold out queen. Downstairs the "cave", there is bar, pool/ping pong, flatscreen, pull out queen. Basic gym w/flatcreen.. Four bedrooms- one with private deck, and an upstairs office, five using very private pool house . The pool is sublime, hot tub is new, large yard, upstairs bathrooms with heated floors,

Condo in New Seabury

4.98 out of 5 average rating, 128 reviews

Sleep 6 @ New Seabury w/ Pool Access, All Seasons!

Welcome to our beautiful Cape Condo located in The Mews at New Seabury Country Club in Mashpee, MA. Our unit provides access to a private condo association pool a 3 min walk from the unit. Also, we have: -5 min bike/car ride to beach -Central air, wifi, cable, gas grill -Located on Championship Golf Course -Beach chairs, beach towels/toys -New Seabury Village restaurants, mini-golf, bowling, museums -20 min drive to Hy-Line Ferry to Nantucket/Martha's Vineyard

Townhouse in Brewster

4.86 out of 5 average rating, 103 reviews

Ocean Edge Cape House with Beach, Pool, and AC

Classic Cape Cod Cottage with air conditioning in the heart of The Cape with access to a private beach, swimming pool, and tennis courts. Walk to the store, restaurants and easy access to the Cape Cod Rail Trail. Walk, bike or drive to Nickerson State Park for hiking trails, fresh water swimming, paddle boarding, and fishing. This is a perfect setting for families with plenty of green space and a gated community. The house has a grill and 2 balconies to enjoy.

Condo in Provincetown

4.97 out of 5 average rating, 207 reviews

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.

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Popular amenities for Sandwich rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Home in Barnstable

4.67 out of 5 average rating, 12 reviews

Stunning Cape Home - Inground Pool, 5 Min To Beach

Home in Dennis

4.63 out of 5 average rating, 30 reviews

House on Cape Cod with pool close to beach

Home in Plymouth

4.96 out of 5 average rating, 55 reviews

Our families slice of heaven

Home in New Seabury

5 out of 5 average rating, 18 reviews

Exclusive New Seabury Home w/ Heated Pool ⛳️🏖🦞☀️🐠

Home in Plymouth

4.77 out of 5 average rating, 13 reviews

Mansion with Heated Pool Near Ocean

Home in Plymouth

4.75 out of 5 average rating, 55 reviews

The Poppy: Tranquil Family Home With Arcade

Home in Mashpee

4.81 out of 5 average rating, 54 reviews

Sunny Cape w/Private Pool, Steps to Private Lake

Home in Yarmouth Port

4.9 out of 5 average rating, 42 reviews

Winslow Acres [heated] Pool Escape; pool May 15

Condo rentals with a pool

Condo in Dennis Port

4.78 out of 5 average rating, 58 reviews

Cozy Studio Just Steps Away From the Beach!

Condo in West Dennis

4.89 out of 5 average rating, 28 reviews

1BR 2nd Floor Condo with pool

Condo in Brewster

4.98 out of 5 average rating, 56 reviews

Ocean Edge 2 Bed 2 Bath, Golf & Free Resort Access

Condo in Dennis Port

4.84 out of 5 average rating, 58 reviews

Stylish & Modern Studio Condo - Steps to the Beach

Condo in West Dennis

4.84 out of 5 average rating, 51 reviews

Hidden Hideaway

Condo in Provincetown

4.9 out of 5 average rating, 29 reviews

Spectacular Waterfront Condo

Condo in Provincetown

4.93 out of 5 average rating, 100 reviews

Modern, clean waterviews

Condo in Falmouth

5 out of 5 average rating, 4 reviews

InnSeason Resorts Captains Quarter's

Quick stats about vacation rentals with a pool in Sandwich

Total rentals
40 properties
Nightly prices starting at
$60 before taxes and fees
Total number of reviews
670 reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace

Destinations to explore