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

Total holiday rentals
Explore 20 holiday rentals in Wellfleet

Nightly prices starting at
Wellfleet holiday rentals start at ₹13,442 per night before taxes and fees

Verified guest reviews
Over 840 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space & child-friendly amenities

Wifi availability
20 of Wellfleet holiday rentals include wifi 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/2bedroom-2bath Condo
Recently renovated end unit townhouse located in the heart of The OE Villages. Beautiful views towards the golf course, and southern exposure with lots of natural light, A/C, W/D and private patio with Weber grill and outdoor furniture. Sports Membership so Guest passes are available for purchase at Linx for use of pools, hot tubs and gyms. Additional costs for use of courts may apply. Bike rail trail, Ice cream store, great restaurants, coffee, beaches and Kayak/Bike rentals are all close by.
5.0 out of 5 average rating, 105 reviews
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.
4.98 out of 5 average rating, 54 reviews
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.
4.93 out of 5 average rating, 134 reviews
"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!
4.99 out of 5 average rating, 103 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 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.
4.9 out of 5 average rating, 40 reviews
Townhouse at Ocean Edge 2B/2B + Loft
Experience resort-style living at its finest! Tucked away just a 10-minute drive to the beach, this delightful townhouse offers the perfect blend of comfort and convenience. With two bedrooms, two baths, and an additional cozy loft space, there's ample room for relaxation. Enjoy lounging on the patio, take a refreshing dip in one of the resort pools (for an additional fee paid directly to Ocean Edge) or head to the beach for some sun and surf. Your ultimate getaway awaits!
5.0 out of 5 average rating, 37 reviews
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.
4.91 out of 5 average rating, 11 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.
4.97 out of 5 average rating, 264 reviews
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!
4.87 out of 5 average rating, 67 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.
4.87 out of 5 average rating, 46 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.
4.87 out of 5 average rating, 125 reviews
Game Room- Movie Projector Room- Fire Pit
Nestled in the heart of the Cape, our cozy and beautifully styled retreat becomes a magical group getaway, why we coined it "Gimlet Getaway". While many envision Cape Cod as a summer playground, it can become the best spring sanctuary for you and your large group! (Pool closes Sept 21, 2026, will reopen end of May 2027, please reach out for further details)
5.0 out of 5 average rating, 12 reviewsPopular amenities for Wellfleet rentals with a pool
House rentals with a pool

Private Pool, near beaches, 3 BR/3 BA, Central Air
4.96 out of 5 average rating, 145 reviews
Charming Cape Escape with Pool, Hot Tub & Fire Pit
5.0 out of 5 average rating, 11 reviews
Pool. Hot Tub. Game Room. Walk to Beach. Luxury!
5.0 out of 5 average rating, 15 reviews
Jolly Captain Lighthouse
4.85 out of 5 average rating, 26 reviews
Heated Pool | 5 Min Walk to Beach | Dog-Friendly
5.0 out of 5 average rating, 7 reviews
Amazing Chatham Pool/patio/deck, 5 BR 4 1/2 Bath
4.95 out of 5 average rating, 62 reviews
Walk 2Beach, Pool, Hot Tub, GameRoom, PetsOK
4.92 out of 5 average rating, 51 reviews
Winslow Acres [heated] Pool Escape; pool May-Oct
4.92 out of 5 average rating, 53 reviewsApartment rentals with a pool

Ocean Edge Resort-Pool Access-CentralAC-2 bdr/2bth
5.0 out of 5 average rating, 112 reviews
New Seabury Cape Condo | Pool & Beach Escape
4.97 out of 5 average rating, 183 reviews
Resort Pools & Golf Views · Walk to Bay Beaches
4.87 out of 5 average rating, 77 reviews
Designer Studio Condo with peeks of Cape Cod Bay.
4.8 out of 5 average rating, 82 reviews
Bright Cape Condo in Ocean Edge
4.92 out of 5 average rating, 25 reviews
Steps from Bass River Marina · Private Balcony
4.96 out of 5 average rating, 83 reviews
Newly Updated Condo w/ Pool - Steps to Boatslip!
4.94 out of 5 average rating, 52 reviews
Ocean Edge 2 Bed 2 Bath, Golf & Free Resort Access
4.96 out of 5 average rating, 99 reviewsOther holiday rentals with a pool

Dennis Deluxe King Room | Full Studio w/ Kitchenet
4.89 out of 5 average rating, 19 reviews
Bright and Lovely Cottage With Community Pool
4.9 out of 5 average rating, 93 reviews
Breezy Pool Retreat Near Mayflower Beach
4.9 out of 5 average rating, 70 reviews
Family Cape Cod Oasis-Pool-Hot Tub-Game&Kids Room
5.0 out of 5 average rating, 30 reviews
King Bed Suite (Pet Friendly) in a Great Location
4.82 out of 5 average rating, 39 reviews
Large Home Heated Swimming Pool Private Beach
4.95 out of 5 average rating, 92 reviews
Cottage at the Escape Inn
4.97 out of 5 average rating, 37 reviews
The Captain's Quarters Suite - #10
4.97 out of 5 average rating, 78 reviewsDestinations to explore
- Apartment rentals Wellfleet
- Pet-friendly rentals Wellfleet
- Beachfront rentals Wellfleet
- Rentals with beach access Wellfleet
- House rentals Wellfleet
- Waterfront rentals Wellfleet
- Cottage rentals Wellfleet
- Family-friendly rentals Wellfleet
- Rentals with lake access Wellfleet
- Flat rentals Wellfleet
- Rentals with pools Barnstable County
- Rentals with pools Massachusetts
- Rentals with pools United States
- Cape Cod
- Mayflower Beach
- West Dennis Beach
- Craigville Beach
- Onset Beach
- East Sandwich Beach
- Duxbury Beach
- Sandy Neck Beach
- Saquish Beach
- Nauset Beach
- New Silver Beach
- Skaket Beach
- Popponesset Peninsula
- Cape Cod Canal
- Falmouth Heights Beach
- Pinehills Golf Club
- Race Point Beach
- Inkwell Beach
- Coast Guard Beach
- Cape Cod Inflatable Park
- Cahoon Hollow Beach
- Nickerson State Park
- Sea Gull Beach
- Marconi Beach





