
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 ₹13,418 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, 104 reviews
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
5.0 out of 5 average rating, 112 reviews
Modern Oasis, Heated Saltwater Pool, Beach, Golf
Welcome to an exceptional modern Cape Oasis on a private & quiet cul-de-sac Mins. to Golf, beaches, lakes, bike path Bright airy, spacious, central AC, modern/new furnishing,enjoyable year-round Expansive deck, pool lounge & yard Fenced in w/full privacy Thoughtfully curated for multi families/groups Resort style retreat w/tranquility & fun games Location is virtually close to everything Pool heat: Memorial day weekend -last Sun. of Sept. All essentials provided 6+ free parking
5.0 out of 5 average rating, 13 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
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.
4.94 out of 5 average rating, 52 reviews
Charming Cape Escape with Pool, Hot Tub & Fire Pit
Welcome to Searside Retreat, your ultimate Cape Cod escape in South Dennis! This charming home offers a private pool, open layout, and modern comforts just minutes from top beaches, restaurants, and shops. Relax in a quiet neighborhood in the heart of the Cape. Mayflower Beach - 10min Chapin Beach - 6 min Cape Cod Rail Trail – 10min The Marshside Restaurant – 2min Sesuit Harbor Cafe - 5 min Scargo Cafe - 5 min Smugglers Ice Cream - 5 min Learn more below!
5.0 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, 45 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, 124 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
Winslow Acres [heated] Pool Escape; pool May-Oct
4.92 out of 5 average rating, 52 reviews
Harwich Haven: Pool & Fire Pit
5.0 out of 5 average rating, 42 reviews
Jolly Captain Lighthouse
4.85 out of 5 average rating, 26 reviews
Amazing Chatham Pool/patio/deck, 5 BR 4 1/2 Bath
4.95 out of 5 average rating, 62 reviews
Coastal Luxury Oasis - Ag2 Luxury Home
5.0 out of 5 average rating, 5 reviews
Popponesset, Exclusive, 3-Bdrm, 4-Bths, Sleeps 6,
5.0 out of 5 average rating, 23 reviews
In-Ground Pool Oasis | 5 Min to Cape Cod Beaches!
4.8 out of 5 average rating, 49 reviewsApartment rentals with a pool

Sea Salt Studio - Steps to Glendon Rd Beach
4.93 out of 5 average rating, 134 reviews
New Seabury Cape Condo | Pool & Beach Escape
4.97 out of 5 average rating, 182 reviews
Bright Cape Condo in Ocean Edge
4.92 out of 5 average rating, 25 reviews
Resort Pools & Golf Views · Walk to Bay Beaches
4.87 out of 5 average rating, 76 reviews
Luxury Waterfront Getaway
4.91 out of 5 average rating, 22 reviews
Ocean Edge 2 Bed 2 Bath, Golf & Free Resort Access
4.96 out of 5 average rating, 99 reviews
Steps from Bass River Marina · Private Balcony
4.96 out of 5 average rating, 83 reviews
Designer Studio Condo with peeks of Cape Cod Bay.
4.8 out of 5 average rating, 82 reviewsOther holiday rentals with a pool

Breezy Pool Retreat Near Mayflower Beach
4.9 out of 5 average rating, 69 reviews
Two Bedroom Condo in Ocean Edge Resort
5.0 out of 5 average rating, 11 reviews
Waterfront Bass River Jolly Captain
4.87 out of 5 average rating, 39 reviews
Deluxe Double Room | Full Studio w/ Kitchenette
4.91 out of 5 average rating, 11 reviews
Luxury retreat, in-ground pool, 10-person hot tub
5.0 out of 5 average rating, 42 reviews
Heated Pool | 5 Min Walk to Beach | Dog-Friendly
5.0 out of 5 average rating, 6 reviews
Coastal Charm New Seabury: 5BRs with Private Pool
4.94 out of 5 average rating, 53 reviews
Relaxing Ptown Retreat • Pool • Beach Access
4.89 out of 5 average rating, 114 reviewsDestinations to explore
- Apartment rentals Wellfleet
- Pet-friendly rentals Wellfleet
- House 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





