
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 ₹13,440 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.

Pool. Hot Tub. Game Room. Walk to Beach. Luxury!
Welcome to The Tide Watch - our luxurious retreat, perfect for families or a group of friends! This stunning home features high-end furniture, a pool, hot tub & games including ping pong & air hockey. With kid-friendly amenities, everyone will feel at home. Relax, play & create unforgettable memories in this upscale oasis designed for fun & relaxation! Walk to small neighborhood beach 3 min drive to Jacknife Beach 6 min drive to downtown Chatham Experience Chatham with us & Learn More Below!

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.

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.

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.

Ocean Edge Resort-Pool Access-Golf View-2 bdr/2bth
Newly renovated 2nd floor 2bed/2 full baths condo located within Ocean Edge Resort, with balcony overlooking the golf course. Access to OE resort amenities (additional fees apply) and restaurants. Easy access to Cape Cod Rail Trail . Scenic route 6A offers arts & crafts galleries, coffee/tea spots and local shops. A 10 minute car ride to a 36 hole Captains Golf course. Short ride to 10 Brewster bay beaches famous for their tidal flats. 15 minute walk to Ellis Landing Beach, great sunsets!

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.

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!

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.

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.

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!

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.

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.
Popular amenities for Wellfleet rentals with a pool
House rentals with a pool

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

Amazing Chatham Pool/patio/deck, 5 BR 4 1/2 Bath

Charming Cape Escape with Pool, Hot Tub & Fire Pit

Coastal Luxury Oasis - Ag2 Luxury Home

Jolly Captain Lighthouse

Winslow Acres [heated] Pool Escape; pool May-Oct

ShoestringBayHouse, waterfront & pool in Cotuit

Large Home Heated Swimming Pool Private Beach
Apartment rentals with a pool

New Seabury Cape Condo | Pool & Beach Escape

Newly Updated Condo w/ Pool - Steps to Boatslip!

Bright Cape Condo in Ocean Edge

Designer Studio Condo with peeks of Cape Cod Bay.

Luxury Waterfront Getaway

Resort Pools & Golf Views · Walk to Bay Beaches

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

Steps from Bass River Marina · Private Balcony
Other holiday rentals with a pool

Dennis Deluxe King Room | Full Studio w/ Kitchenet

Cottage at the Escape Inn

Two Bedroom Condo in Ocean Edge Resort

Breezy Pool Retreat Near Mayflower Beach

King Bed Suite (Pet Friendly) in a Great Location

Walk to the beach or sit poolside! Updated studio!

The Captain's Quarters Suite - #10

Relaxing Ptown Retreat • Pool • Beach Access
Destinations to explore
- House rentals Wellfleet
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- Pet-friendly rentals Wellfleet
- Beachfront rentals Wellfleet
- Rentals with beach access 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





