Vacation rentals with a pool in Eastham

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Top-rated rentals with a pool in Eastham

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

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Guest favorite

Home in Yarmouth Port

4.9 out of 5 average rating, 42 reviews

Winslow Acres [heated] Pool Escape; pool May 15

Pool Open 5/15 Escape to the Cape at this beautifully maintained home with lovely seasonal heated pool (heated spring/fall). Hot tub available all year. Make s'mores and memories year-round at the fire pit table. 4 bedrooms and 2.5 baths (2 showers) plus an outside shower May through October. Plenty of room for up to 8 people - sorry, no parties - (plus pets - fee applies)! Only 3 miles to beaches. The ferry to Nantucket and Martha's Vineyard is not far, and a great addition to any Cape trip!

Top guest favorite

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!

Superhost

Home in Dennis

4.63 out of 5 average rating, 30 reviews

House on Cape Cod with pool close to beach

This single family house is located at the end of a cul de sac in a quite neighborhood in walking distance to Mayflower and Bayview beaches. You enter through the bright and open kitchen, looking out over the patio and the pool. The open living and dining room open up to a sun room where you can relax after a fun day at the beach. The two smaller bedrooms share a big bathroom with tub and double sink, whereas the master bedroom has its own bathroom. A big dining table can host up to 8 people.

Top guest favorite

Home in Plymouth

4.97 out of 5 average rating, 32 reviews

Getaway with pool

Look no further! This stunning beach house offers everything you need. Situated on a quiet street on Cape Cod Bay, it is very close to area beaches and ponds. The outdoor space is perfect for entertaining and includes lap pool, three decks, patio and fire pit. The downstairs includes living room, family room, bedroom, full bath, eat-in kitchen, and enclosed porch overlooking the backyard. The second floor features 4 more bedrooms, 2 baths, laundry room, and en suite primary bedroom with deck.

Guest favorite

Home in Popponesset

5 out of 5 average rating, 12 reviews

18 Menemsha Rd., Popponesset, Pool, 3-Beds, 4 bath

This home was custom built in 2022, and is designed to provide comfort, luxury and loads of charm for the discerning vacationer. New construction with a nod to the Nantucket Sea Captain's houses of yesteryear. Professionally decorated and landscaped, offering every amenity you could possibly desire; from an in-ground, heated, saltwater pool (with electric cover), hot tub, outdoor shower, fire-pit, and even a cabana with a sink, refrigerator, and smart TV. Just a 3 min walk to private beach.

Superhost

Guest suite in Barnstable

4.92 out of 5 average rating, 25 reviews

Cozy 1-bedroom cottage with pool and beach access

Cozy apartment within short walking distance of a gorgeous private beach on the bayside of Cape Cod. The gentle bay is perfect for families. Walk the flats during low tide or float in the gentle bay waters. Later relax by the outdoor pool. Or take a walk on the Mass Audubon Long Pasture Wildlife Sanctuary trails. Note: this private apartment is attached to owner's residence but has its own private entrance and parking spot. IN SEASON RENTAL: SATURDAY TO SATURDAY unless approved by host

Guest favorite

Home in Brewster

4.97 out of 5 average rating, 31 reviews

Modern Cape, Private Salt Water Pool, Beaches-Golf

Welcome to your perfect Cape Cod vacation! Nestled in the center of the Cape. Min. to 3 golf courses, 5 ocean beaches, lakes, bike trail etc. Vast serene private 1.5 acres adjacent to conservation land. Lighted Private heated salt water pool, Bocce Court, Putting green, corn hole, hammock, outdoor shower etc. Expansive double deck with awning . Chef’s kitchen & all essential amenities provided. Spacious Beautiful indoor/outdoor dining/entertaining. Pool heat 05/15 to 10/01

Guest favorite

Home in New Seabury

5 out of 5 average rating, 11 reviews

Cape Gem in New Seabury with private heated pool

Our Pristine, Newly Renovated, Patio home with Private heated Pool, located in the Mews of New Seabury, offers the privacy and peacefulness for the perfect vacation. The sandy local beaches—South Cape Beach and Popponesett—are both very short drive away (5-10 minutes)! Highlights of the seashore resort community of New Seabury: Mashpee Commons (fine dining, shops, movie cinema), golf courses, boating, walking trails, close proximity to ferries to Nantucket and Martha’s Vineyard.

Superhost

Home in Forestdale

4.64 out of 5 average rating, 11 reviews

New Cape Escape for 10 People With Heated Pool

This spacious 4-bed, 3-bath newly renovated retreat with a two-car garage and ample parking is designed for the ultimate getaway. Entertainment options abound with a dedicated poker room, complete with a stylish bar, and a delightful kids playroom on the lower level. Step into the backyard oasis with a salted heated pool, fenced for privacy, creating a perfect space for outdoor enjoyment. This dog-friendly haven is tailor-made for large families or multi-family vacations.

Guest favorite

Condo in Provincetown

4.93 out of 5 average rating, 41 reviews

Newly Updated Condo w/ Pool - Steps to Boatslip!

This newly updated 2-bed, 1-bath condo, which sleeps 4, is the perfect escape for your Ptown vacation. This first floor condo is only a short walk from Commercial Street and steps to the beach and embodies the best of the Ptown experience! You will love spending time lounging around the lovely pool and exploring all that Commercial Street has to offer! As this property is only steps from the beach, you won't have to venture far to breathe in that relaxing ocean breeze.

Superhost

Home in East Falmouth

5 out of 5 average rating, 3 reviews

Spacious home with Pool! Close to Beaches & Town!

Escape to a stunning 4-bedroom vacation rental house in East Falmouth and enjoy a private pool, game room, and charming back patio with an outdoor dining table and gas grill. This light-filled coastal getaway is located just over a mile from Menauhant Beach and a short drive from Main Street in Falmouth. With its perfect location and easy access to the ferry to Nantucket or Martha's Vineyard, this is the perfect place to call home during your Cape Cod adventure.

Superhost

Townhouse in Brewster

4.81 out of 5 average rating, 16 reviews

Ocean Edge Townhouse/Pool Access

End unit townhouse located in heart of OE Villages with private patio, A/C & W/D. There’s no better way to experience all that Brewster has to offer than taking your family to stay at the Ocean Edge Resort. Just minutes off the property you will find yourself at the beach, on the golf course, or at one of the many excellent local restaurants. Unit has pool & fitness access for additional fees.