Holiday rentals with a pool in Wellfleet

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Top-rated rentals with a pool in Wellfleet

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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

Guest favourite

Apartment 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!

Guest favourite

Campervan/Motorhome in Wellfleet

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 in Wellfleet

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 in North Truro

4.92 out of 5 average rating, 109 reviews

Heated Pool, Beach, Pets, ADA, EV Charg, 4 ensuite

25X42 heated pool(April 1st-Dec 8th) SEASON- June 15th-Sept 7th (7) night min. SAT.-SAT. ONLY OFF SEASON- Sept 7th-June 17th (2) night min. NO BALLOONS, PARTY, EVENTS, GATHERINGS, BRIDAL, WEDDING RECEPTIONS, MAX 12 for pool/dinners. Extra guests=immediate eviction. Before booking we encourage you to compare our home to others offering all amenities in Truro, to understand market rates/values of homes in Truro, MA. If you find an equal home of lesser value we will adjust accordingly.

Guest favourite

Home in North Eastham

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 in Brewster

4.91 out of 5 average rating, 43 reviews

Stylish Ocean Edge Condo #TheCouplesNest

Experience Cape Cod from our stylish 2nd floor condo in Fletcher Village at Ocean Edge, Brewster. Centrally located, it offers easy access to beaches, the Rail Trail, and local dining. Enjoy amenities like pools, tennis, and golf. The modern condo features a fully equipped kitchen and a balcony, perfect for relaxation or adventure throughout the year. Whether you're biking on scenic trails or relaxing by the pool, our condo provides the ideal setting for a memorable Cape Cod experience.

Guest favourite

Apartment in New Seabury

4.98 out of 5 average rating, 130 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

Guest favourite

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.

Guest favourite

Guest suite in Harwich Port

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 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.

Holiday rentals for every style

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Popular amenities for Wellfleet rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

Superhost

Home in Barnstable

4.67 out of 5 average rating, 12 reviews

Stunning Cape Home - Inground Pool, 5 Min To Beach

Superhost

Home in Dennis

4.63 out of 5 average rating, 30 reviews

House on Cape Cod with pool close to beach

Guest favourite

Home in Dennis

4.92 out of 5 average rating, 50 reviews

Cape Cod Lakefront Home

Guest favourite

Home in Hyannis Port

5 out of 5 average rating, 11 reviews

Home in Hyannis Port

Superhost

Home in Yarmouth Port

4.9 out of 5 average rating, 42 reviews

Winslow Acres [heated] Pool Escape; pool May 15

Guest favourite

Home in Yarmouth Port

5 out of 5 average rating, 6 reviews

Luxury heated Pool hot tub near mayflower beach

Guest favourite

Home in Yarmouth

4.94 out of 5 average rating, 16 reviews

Room for multiple families!

Guest favourite

Home in Hyannis Port

5 out of 5 average rating, 5 reviews

Townhouse on the beach, pool, walk to Main St.

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Apartment rentals with a pool

Superhost

Apartment in Dennis Port

5 out of 5 average rating, 4 reviews

Cape Cod 1BR Condo on lovely Ocean Front Resort

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 West Dennis

4.89 out of 5 average rating, 28 reviews

1BR 2nd Floor Condo with pool

Guest favourite

Apartment in Brewster

4.9 out of 5 average rating, 39 reviews

Ocean Edge: 2 bed/2 bath - Indoor Pools/Gym!

Guest favourite

Apartment in Brewster

4.98 out of 5 average rating, 57 reviews

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

Guest favourite

Apartment in Dennis Port

4.84 out of 5 average rating, 58 reviews

Stylish & Modern Studio Condo - Steps to the Beach

Superhost

Apartment in Provincetown

4.9 out of 5 average rating, 29 reviews

Spectacular Waterfront Condo

Guest favourite

Apartment in Provincetown

4.92 out of 5 average rating, 39 reviews

Newly Updated Condo w/ Pool - Steps to Boatslip!

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Quick stats about holiday rentals with a pool in Wellfleet

Total rentals
10 properties
Nightly prices starting at
$134 SGD 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

Cottages

Houses

Hotels

Popular amenities for Wellfleet rentals with a pool

House rentals with a pool

Home in Barnstable

Home in Dennis

Home in Dennis

Home in Hyannis Port

Home in Yarmouth Port

Home in Yarmouth Port

Home in Yarmouth

Home in Hyannis Port

Apartment rentals with a pool

Apartment in Dennis Port

Apartment in Dennis Port

Apartment in West Dennis

Apartment in Brewster

Apartment in Brewster

Apartment in Dennis Port

Apartment in Provincetown

Apartment in Provincetown

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