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.

0 of 0 items showing

1 of 3 pages

Guest favourite

Home

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

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

Guest favourite

Apartment

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!

Guest favourite

Campervan/Motorhome

5 out of 5 average rating, 29 reviews

Seasonal 27’ Retro Glamping Steps From Bike Trail

A SECLUDED WELLFLEET LOCATION, STEPS FROM BIKE PATH WITH DELIGHTFUL AMENITIES. This 27’ Camper with upgrades, and shared HEATED POOL🔥* is located in a peaceful setting on private property (with Host’s Home set back ) just steps from the Cape Cod BikeTrail and Hiking Trails. Location will especially appeal to Avid Cyclists, as well as Beach Goers and people looking to enjoy activities in beautiful Wellfleet. Families welcome, Heated Pool* is great option when weather is cool, cloudy.

Guest favourite

Rental unit

4.97 out of 5 average rating, 70 reviews

Rock on Wellfleet!

A wonderful Wellfleet location! This second floor rental has a spacious bedroom with a queen bed, bathroom with a tub and living area with a well stocked kitchen. You would have the whole upstairs to yourself with a private door to come and go. You are also invited to use our pool at anytime! We're located very close to the Cape Cod Rail Trail for miles of bike riding, PB Boulangerie Bistro, Marconi Beach, the iconic Wellfleet drive-in and so much more. Bedding, towels and essentials provided.

Guest favourite

Home

5 out of 5 average rating, 15 reviews

Modern Beach House w/ Heated Pool & Game Room!

Relax at this peaceful newly renovated home with every amenity! Come to your very own private resort on Cape Cod, located on a quiet cul-de-sac in Eastham with tons to offer. Central A/C, heated pool, projector theater, game room, fire pit, outdoor grill w/ dining area and much more! Gimlet Getaway, as we have coined this oasis, is the perfect mix of relaxing Cape Cod and every ounce of a good time w/ all modern comforts and amenities. Message me for details! POOL IS SEASONAL (May-Oct).

Guest favourite

Apartment

4.92 out of 5 average rating, 39 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.

Guest favourite

Guest suite

5 out of 5 average rating, 40 reviews

The Port - #5

Come and stay at this classic cape cod oasis directly across the street from Allan Harbor. Tucked in a quiet, family friendly neighborhood. This space has a private entrance with a table for 2, where you can sit, relax and enjoy the fresh air off the comfort of your room. Enjoy easy access to popular shops, restaurants, beaches and a ferry to Nantucket from this cozy getaway. Easy self check in with free parking for 1 car. *Pack n' Play upon request

Guest favourite

Apartment

4.81 out of 5 average rating, 63 reviews

Designer Studio Condo with peeks of Cape Cod Bay.

See 'my property'. Beautiful, unique designer condo. Photos show what makes my place stand out from others. Please view and read captions ! 10 minute walk to Bay beach, 10 minute drive to Provincetown. Peeks of blue bay from private, spacious deck. Near Atlantic beaches, Truro vineyards, historic lighthouse & Wellfleet. Quiet in unit, 2nd floor, no one above. Guests 21+ welcome, 3 night minimum 5/20 to 6/27 check ins, 4 nights 6/28 to 9/1 check ins

Guest favourite

Apartment

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.

Guest favourite

Rental unit

5 out of 5 average rating, 36 reviews

Captains Quarters at Dune Crest Hotel

Panoramic views of Cape Cod Bay, Provincetown, Pilgrim Lake. Located on 12 acres in the National Seashore, this is the Owner's apartment at the Dune Crest Resort. 2 Ensuite bedrooms, open floor plan kitchen, dining, living room for gathering. Use of hotel amenities: Continental Breakfast, tennis court, swimming pool, hiking trails. Provincetown only a few miles away for dining, shopping, entertainment.

Superhost

Apartment

4.9 out of 5 average rating, 29 reviews

Spectacular Waterfront Condo

Enjoy direct water views of Cape Cod Bay in our beautiful 1st floor condo with central air. Our home is steps from the beach with an approx. 1 mile walk through the dunes to the Atlantic Ocean. We are perfectly situated on the East End with beach accessibility. Enjoy Provincetown’s great restaurants, many art galleries, shows and unique shops. Enjoy our home anytime of the year.

Holiday rentals for every style

Get the amount of space that is right for you

Popular amenities for Wellfleet rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

4.94 out of 5 average rating, 16 reviews

Room for multiple families!

5 out of 5 average rating, 71 reviews

Ocean Edge Resort/Pool access/2bedroom-2bath Condo

Show all

Quick stats about holiday rentals with a pool in Wellfleet

Total rentals
10 properties
Nightly prices starting at
€ 96 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

Holiday rentals with a pool in Wellfleet

Top-rated rentals with a pool in Wellfleet

Holiday rentals for every style

Houses

Cottages

Hotels

Popular amenities for Wellfleet rentals with a pool

House rentals with a pool

Home

Home

Home

Home

Home

Home

Home

Home

Apartment rentals with a pool

Apartment

Apartment

Apartment

Apartment

Apartment

Apartment

Apartment

Apartment

Quick stats about holiday rentals with a pool in Wellfleet

Total rentals

Nightly prices starting at

Total number of reviews

Wifi availability

Popular amenities

Local attractions

Destinations to explore