
Vacation rentals with a pool in Wellfleet
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Wellfleet
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Chic Pool Condo Near Mayflower Beach
Escape to your stylish Cape Cod retreat! This beautifully renovated pool condo is just a 4-min drive from Mayflower Beach. Enjoy serene pool access, free parking, a state-of-the-art kitchen, and a cozy electric fireplace. With a queen bed, sofa bed and pack n' play, it's the perfect getaway for couples or small families of up to 4. Fast WiFi at 500 Mbps, makes this perfect for remote workers. Experience the best eateries & drinking establishments of Dennis Village in this modern, coastal haven.

Ocean Edge 2 Bed 2 Bath, Golf & Free Resort Access
Enjoy this 1,000 SF, 2 bed, 2 full new marle tile bathrooms, 2 showers, at Ocean Edge, right in the middle of the golf course. This Airbnb is a full member of the Ocean Edge Resort and allows you access to Ocean Edge golf, and free resort access included up to 6 guests to swimming pools, tennis, gym & pickleball. No one lives here, it is absent of personal items. From the moment you enter, you will know that you have made a great choice and that your time here will be above your expectations.

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!

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.

Designer Studio Condo with peeks of Cape Cod Bay.
Beautiful, unique designer condo with custom built ins. Photos show what makes my place stand out from others. Please view and read captions!! 10 minute walk to Bay beach, 10 minute drive to Provincetown. Peeks of blue bay from very large private deck. Near Atlantic beaches, Truro vineyards, historic lighthouse & Wellfleet. Quiet in unit, 2nd floor, no one above. Guests 21+ welcome. 4 night minimum. 10% discount for 7 nights, 15% discount for 10 nights. Please read more details in 'The Space'

The Sea Salt Studio - Steps to the Beach!
Gorgeous studio (Unit #1) only 175 yards from white sand Glendon Road beach. 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.

Heated Pool, Game Room, Projector Room, Private
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-Sept)

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.

Hidden Hideaway
Welcome to Mid Cape Cod. Location, Location, Location. Wake up in the morning and have coffee on your private patio. The view overlooks the well manicured back yard bordered by tress and bunnies running around. After coffee, walk down main street for breakfast and more coffee at 3 Fins. Now that you are hyped, walk across the street and rent a Kayak or SUP for the day. Paddle out the Bass river down to the Nantucket sound. Have lunch next door at Sundancers.

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.

Bright Beach Condo • Walk to Sand & Shops
Soak in ocean views from this sun-filled, stylish condo just steps from the beach and a short walk to town. Enjoy brand-new beds, an open layout, and a peaceful, breezy vibe perfect for relaxing. Ideal for couples, solo adventurers, business travelers, or families with kids. Whether you're here to unwind or explore, this light-filled retreat is the perfect home base. We can’t wait to welcome you!

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

Harwich Haven: Pool & Fire Pit

Harwich House: Private Pool, Game Room & Putt-Putt

5-bedroom Cape with a pool and yard games.

Family Fun- Games, Pool & HotTub, Dogs ok! Slps 10

18 Menemsha Rd., Popponesset, Pool, 3-Beds, 4 bath

Heated Pool. Hot Tub. Game Room. Beach Nearby!

Modern Cape, Private Heated Pool, Beach, Golf

Cape Cod Lakefront Home
Condo rentals with a pool

Cozy Studio Just Steps Away From the Beach!

1BR 2nd Floor Condo with pool

Ocean Edge: 2 bed/2 bath - Pools & Resort Access

Stylish & Modern Studio Condo - Steps to the Beach

Mary's Cape Escape

Spectacular Waterfront Condo

Newly Updated Condo w/ Pool - Steps to Boatslip!

Ocean Edge Resort/Pool access/2bedroom-2bath Condo
Other vacation rentals with a pool

15 Cottage St; Pool, Parking, AC; Walkable; W. End

Spacious, newly updated condo

Lovely townhouse at Cape Cod's Ocean Edge

Cape Cod Family Vacation

15 Cottage #2 Top floor

A Beautiful Es-Cape

Oceanview Condo w/ Fireplace & Patio

Modern East End Loft - Private Beach & Pool Access
Quick stats about vacation rentals with a pool in Wellfleet

Total vacation rentals
Explore 10 vacation rentals in Wellfleet

Nightly prices starting at
Wellfleet vacation rentals start at ﺩ.ﺇ404 per night before taxes and fees

Verified guest reviews
Over 750 verified reviews to help you choose

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

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

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

4.7 Average rating
Wellfleet stays receive an average rating of 4.7 out of 5 from guests
Destinations to explore
- Plainview Vacation rentals
- New York Vacation rentals
- Long Island Vacation rentals
- Boston Vacation rentals
- East River Vacation rentals
- Hudson Valley Vacation rentals
- Jersey Shore Vacation rentals
- South Jersey Vacation rentals
- Pocono Mountains Vacation rentals
- The Hamptons Vacation rentals
- Capital District, New York Vacation rentals
- Jersey City Vacation rentals
- Rentals with a fire pit Wellfleet
- Condo rentals Wellfleet
- Pet-friendly rentals Wellfleet
- House rentals Wellfleet
- Rentals with a fireplace Wellfleet
- Rentals with a washer and dryer Wellfleet
- Rentals with beach access Wellfleet
- Beachfront rentals Wellfleet
- Cottage rentals Wellfleet
- Rentals with a patio Wellfleet
- Rentals with lake access Wellfleet
- Waterfront rentals Wellfleet
- Family-friendly rentals Wellfleet
- Rentals with outdoor seating Wellfleet
- Rentals with pools Barnstable County
- Rentals with pools Massachusetts
- Rentals with pools United States
- Cape Cod
- Mayflower Beach
- West Dennis Beach
- East Sandwich Beach
- Craigville Beach
- Duxbury Beach
- Onset Beach
- Coast Guard Beach
- Pinehills Golf Club
- Lighthouse Beach
- New Silver Beach
- Nickerson State Park
- Sandy Neck Beach
- Cape Cod Inflatable Park
- Cahoon Hollow Beach
- Martha's Vineyard Museum
- Sea Gull Beach
- Scusset Beach State Reservation
- Popponesset Peninsula
- Race Point Beach
- Skaket Beach
- Sandwich Glass Museum
- Bass River Beach
- Saquish Beach




