
Vacation rentals with a pool in Wellfleet
Find and book unique homes with a pool on Airbnb
Quick stats about vacation rentals with a pool in Wellfleet

Total vacation rentals
Explore 20 vacation rentals in Wellfleet

Nightly prices starting at
Wellfleet vacation rentals start at ﺩ.ﺇ 514 per night before taxes and fees

Verified guest reviews
Over 840 verified reviews to help you choose

Family-friendly vacation rentals
10 properties offer extra space & kid-friendly amenities

Wi-Fi availability
20 of Wellfleet vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Wellfleet rentals

4.6 Average rating
Wellfleet stays receive an average rating of 4.6 out of 5 from guests
Top-rated rentals with a pool in Wellfleet
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Ocean Edge Resort-Pool Access-CentralAC-2 bdr/2bth
Modern 2nd floor 2 bed/2 full bath Ocean Edge condo located in the heart of Brewster with balcony overlooking the resort golf course. Access to OE resort amenities (additional fees apply). Easy access to Cape Cod Rail Trail. Scenic route 6A offers arts & crafts galleries, coffee places 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. 15 minute walk to Ellis Landing Beach, great sunsets! Central A/C and heat
ValueFamilyCondition

Modern Cape, Private Heated Pool, Beach, Golf
Welcome to your perfect vacation/reunion in the center of the Cape. Min. to 3 golf courses, 5 ocean beaches, lakes, park, trails. Bright modern quality home, AC, enjoyable year-round. Vast serene private 1.5 acres adjacent to conservation land. Pool heated Memorial day weekend- last Sunday of Sept. Bocce Court, Putting green, Corn hole, Hammock, Outdoor shower, AC. Expansive double deck with awning. Beautiful indoor/outdoor dining/entertaining. All essentials provided. 7+ free parking.
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Sea Salt Studio - Steps to Glendon Rd Beach
Funky studio (Unit #1) only 175 yards from a white sand beach on Nantucket Sound. Soak up the sun at the beach, relax by the pool or enjoy a relaxing cocktail on your own private patio. This studio is equipped with a fridge, microwave and gas stove as well as a fully stocked kitchenette and cable/Roku TV. A futon couch offers extra sleeping space, if needed. Outside, enjoy a natural gas grill. Walk or bike to multiple restaurants, ice cream shops and all the amenities Dennis Port has to offer.
FamilyLocationComfort

"Cape Escape" luxury home w/pool & beach access.
Welcome to the Cape Escape! Enjoy views of Spectacle Pond from the 70 ft. deck of this recently renovated 5 bed/3 bath spacious home meeting all your needs! Relax by the in-ground pool in the private enclosed yard. Enjoy nights around the fire-pit. Directly across the driveway you can enjoy kayaking, sunbathing & swimming at the neighborhood beach. Within 6 miles of the home you will find the historic Sandwich boardwalk, Ocean beaches, Cape Cod Canal and more! Perfect for family gatherings!
ValueLocationQuiet

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 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 pool. Bedrooms contain queen beds. There are mini splits in the living room and bedrooms. Open-concept kitchen contains cooking basics and a Keurig. Linens provided. Pool open July to Sept. No smoking & no pets.
LocationFamilyParking

5-bedroom Cape with a pool and yard games.
Five-bedroom and three-bath Cape style home with large fenced backyard and an inground pool. Various yard games are available - outdoor ping pong table and corn toss. Short distance to Pleasant Bay, freshwater ponds, and the ocean. Approximately five miles from downtown Chatham and Orleans Center. A variety of local shops, and restaurants, and catch the Cape Cod Baseball under the lights just minutes away. (Our pool is not heated - the opening and closing is weather dependent).
FamilyLocationGetting around

The Cottages at Even'tide Resort - Seagull
Seagull cottage is one of 8 cottages located at the Even'tide Resort. Where else on Cape Cod can you rent a private cottage and enjoy a huge heated indoor pool and direct access to a 22 mile paved bike path? A 1 mile hike through the woods takes you to Marconi National Seashore beach. You have access to all the amenities at the motel including ping pong, billiards, 5 hole mini golf, shuffleboard, corn hole, fitness room, playground, basketball court, and coin op laundry.
LocationFamilyAccuracy

The Holly Cottage
Welcome to Centerville, enjoy this fully equipped 1 bedroom 1 bath home with an easy walk or ride to just about everything. Enjoy the nearby ocean and beaches, or take a ride downtown to Main Street for dining and entertainment. Only a short distance to the ferries for a day trip to the islands and you can be back in time to catch a concert at the Melody Tent. Enjoy your days by the pool and your evenings grilling out on the large deck or chatting with the koi fish.
LocationFamilyHospitality

Great Location. Near Beach & Main Street. Unit M1
Our home-away-from-home accommodations include this charming studio with lawn space, a private deck with outdoor furniture and a gas grill. The cottage is comfortably furnished and features a small kitchen. This cottage has a queen bed and a table with sitting area. The kitchen is nicely updated with updated with beautiful granite countertops and stainless steel appliances including an stove/oven, microwave, mini-fridge, toaster, coffee maker. Keurig, and kettle.
FamilyValueDecor

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.
ValueFamilyLong stay

Wellfleet~Beautiful One Day Perfect The Next
Are you looking for the perfect getaway in charming Wellfleet? This two-bedroom cottage is located in a private, detached cottage village. Enjoy the beautiful SEASONAL in-ground pool (OPENS July 4th & CLOSES LABOR DAY) and a welcoming family-friendly atmosphere. The cottage is centrally located with a five-minute drive to both bay and ocean side beaches, freshwater kettle ponds, Wellfleet center, and the rail trail!
ValueLocationLaundry

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
House rentals with a pool

Private Pool, near beaches, 3 BR/3 BA, Central Air
ValueFamilyParks

ShoestringBayHouse, waterfront & pool in Cotuit
LocationFamilyGetting around

Pool. Hot Tub. Game Room. Walk to Beach. Luxury!
FamilyLocationOutdoor spaces

Beach Pass Included! Brand New Spa! Central AC!
LocationFamilyAir conditioning

Jolly Captain Lighthouse
FamilyLocationBeach

In-Ground Pool Oasis | 5 Min to Cape Cod Beaches!
FamilyLocationView

Coastal Charm New Seabury: 5BRs with Private Pool
ValueFamilyGrill

House on Cape Cod with pool close to beach
LocationFamilyGrill
Condo rentals with a pool

New Seabury Cape Condo | Pool & Beach Escape
LocationValueNearby

Luxury Waterfront Getaway
FamilyValueBiking

Designer Studio Condo with peeks of Cape Cod Bay.
FamilyLocationAccess

Bright Cape Condo in Ocean Edge
FamilyLocationQuiet

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

Steps from Bass River Marina · Private Balcony
LocationFamilyParking

Newly Updated Condo w/ Pool - Steps to Boatslip!
LocationFamilyHiking

Resort Pools & Golf Views · Walk to Bay Beaches
FamilyValueBiking
Other vacation rentals with a pool

Townhouse at Ocean Edge 2B/2B + Loft
LocationFamilyNearby

Two Bedroom Condo in Ocean Edge Resort
FamilyLocationCleanliness

Ocean Edge Townhouse/Pool Access
FamilyValuePets

Dennis Deluxe King Room | Full Studio w/ Kitchenet
ValueFamilyIndoor spaces

The Captain's Quarters Suite - #10
FamilyLocationBeach

King Bed Suite (Pet Friendly) in a Great Location
FamilyLocationComfort

Breezy Pool Retreat Near Mayflower Beach
FamilyLocationLong stay

Beachwalk cozy studio with pool!
LocationBackyardWalkability
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- Cape Cod
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