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Holiday 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!

Guest favourite

Cottage in Provincetown

4.92 out of 5 average rating, 24 reviews

Beachside cottage with pool in Provincetown

Relax with family or friends at this cottage at Beach Point Club. Enjoy a BBQ on the large deck or walk to the beach on the private boardwalk, which is steps away from the cottage. Take in the water view from the side of the deck, hop on the shuttle to downtown Provincetown, or relax by the community pool. Bedrooms contain queen beds, and there are mini splits in the living room and bedrooms. Open-concept kitchen contains cooking basics and a Keurig. Linens provided. Pool open July - September

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 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

Home in Brewster

5 out of 5 average rating, 10 reviews

Cape Cod Beach Retreat w/ Pool

Our summer retreat is quintessential Cape Cod charm. A great place to spend a relaxing and fun summer vacation. Great for large, multigenerational or multiple families it has room to spread out. The pool area is a gem, serene and surrounded by a breathtaking garden and waterfall - a place where you can feel the stress go. The home is equipped with comfort in mind. Located minutes to popular Cape Cod attractions including various beach choices, hiking, shopping and dining.

Guest favourite

Apartment 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

Guest favourite

Home in Falmouth

5 out of 5 average rating, 15 reviews

Home in Falmouth ~ 5 min drive to beach

Guest favourite

Home in New Seabury

5 out of 5 average rating, 18 reviews

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

Guest favourite

Home in Cotuit

4.94 out of 5 average rating, 18 reviews

ShoestringBayHouse, waterfront & pool in Cotuit

Home in West Yarmouth

5 out of 5 average rating, 4 reviews

4 - Bedroom 2 - Bath Cottage with Private Beach

Guest favourite

Home in Hyannis Port

5 out of 5 average rating, 11 reviews

Home in Hyannis Port

Home in Mashpee

4.69 out of 5 average rating, 48 reviews

The Wakeby esCAPE ~ Pool & Walk to Beach!

Guest favourite

Home in Barnstable

5 out of 5 average rating, 19 reviews

Luxury retreat, in-ground pool, 10-person hot tub

Apartment rentals with a pool

Guest favourite

Apartment in Provincetown

4.97 out of 5 average rating, 208 reviews

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

Apartment in Dennis Port

4.8 out of 5 average rating, 5 reviews

2BR Presidential Cape Cod Resort Ocean Front

Guest favourite

Apartment in Dennis Port

4.78 out of 5 average rating, 58 reviews

Cozy Studio Just Steps Away From the Beach!

Guest favourite

Apartment in Brewster

4.97 out of 5 average rating, 178 reviews

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

Guest favourite

Apartment in West Dennis

4.89 out of 5 average rating, 28 reviews

1BR 2nd Floor Condo with pool

Guest favourite

Apartment in Provincetown

4.9 out of 5 average rating, 10 reviews

Luxury Waterfront Getaway

Guest favourite

Apartment in Dennis Port

4.84 out of 5 average rating, 58 reviews

Stylish & Modern Studio Condo - Steps to the Beach

Apartment in West Dennis

4.84 out of 5 average rating, 51 reviews

Hidden Hideaway

Quick stats about holiday rentals with a pool in Wellfleet

Total rentals
10 properties
Nightly prices starting at
₹8,496 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