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Vacation rentals with a pool in Wellfleet

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Wellfleet

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

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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!

Guest favourite

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!

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.

Guest favourite

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 favourite

Villa in New Seabury

5 out of 5 average rating, 42 reviews

Heated Indoor Pool & Spa - Golf Course View

CHERRY BLOSSOM RETREAT Cold days, raining days, power outage won't be an issue if you can steal away to this home, with an indoor heated salt water pool and hot tub fully equipped with a backup generator, with a view of the famous 13-Hole Championship Golf Course Cape Cod. Our ultimate luxury home is filled with arcades, air hockey, foosball and other indoor entertainments for guests to enjoy, comfortably sleeps 6-8 and just a few minute drive to all of the amenities New Seabury has to offer.

Guest favourite

Home in Popponesset

5 out of 5 average rating, 11 reviews

Popponesset-Pool, hot tub, fire pit; 3-Bds, 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.

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 favourite

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

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 favourite

Condo in Provincetown

4.93 out of 5 average rating, 40 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.

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.

Guest favourite

Townhouse in Brewster

4.86 out of 5 average rating, 103 reviews

Ocean Edge Cape House with Beach, Pool, and AC

Your dream Cape Cod getaway awaits! This classic Cape Cod cottage is nestled in the heart of Brewster, offering a perfect blend of comfort, relaxation, and outdoor adventure. With access to a private beach, resort-style amenities, and iconic local attractions, this is the ultimate retreat for families, couples, or groups looking to experience the best of the Cape.

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Popular amenities for Wellfleet rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Guest favourite

Home in Mashpee

4.9 out of 5 average rating, 20 reviews

Beautiful Mashpee Home with Pool

Home in New Seabury

5 out of 5 average rating, 7 reviews

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

Home in Orleans

4.92 out of 5 average rating, 25 reviews

5-bedroom Cape with a pool and yard games.

Guest favourite

Home in Sandwich

4.99 out of 5 average rating, 80 reviews

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

Guest favourite

Home in Plymouth

4.96 out of 5 average rating, 55 reviews

Our families slice of heaven

Home in Barnstable

4.88 out of 5 average rating, 34 reviews

Paradise home in centerville

Home in Bourne

4.75 out of 5 average rating, 4 reviews

Cozy Cape Cod House - Stroll or Bike the Canal

Guest favourite

Home in Sandwich

5 out of 5 average rating, 8 reviews

Cape Oasis with pool + privacy. New Summer 2024

Condo rentals with a pool

Guest favourite

Condo in Provincetown

4.97 out of 5 average rating, 208 reviews

P-Town Beach Beauty on the Bay. Water View!

Condo in Dennis Port

4.8 out of 5 average rating, 5 reviews

2BR Presidential Cape Cod Resort Ocean Front

Guest favourite

Condo in Dennis Port

4.78 out of 5 average rating, 58 reviews

Cozy Studio Just Steps Away From the Beach!

Guest favourite

Condo in Brewster

4.97 out of 5 average rating, 178 reviews

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

Guest favourite

Condo in West Dennis

4.89 out of 5 average rating, 28 reviews

1BR 2nd Floor Condo with pool

Guest favourite

Condo in Provincetown

4.9 out of 5 average rating, 10 reviews

Luxury Waterfront Getaway

Guest favourite

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

Quick stats about vacation rentals with a pool in Wellfleet

Total rentals
10 properties
Nightly prices starting at
$144 CAD before taxes and fees
Total number of reviews
740 reviews
Wifi availability
10 properties include access to wifi
Popular amenities
Kitchen, Wifi, and Pool
Local attractions
Cape Cod National Seashore, Moby Dick's Restaurant, and The Beachcomber of Wellfleet

Destinations to explore