Vacation rentals with a pool in Wellfleet

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Popular amenities for Wellfleet rentals with a pool

House rentals with a pool

Top guest favorite
Home in Sandwich
4.99 out of 5 average rating, 82 reviews

"Cape Escape" luxury home w/pool & beach access.

JanelleRating, 5 stars3 weeks ago
We have stayed in multiple houses / penthouses throughout the U.S. , however, this home surpassed them all. Jennifer was amazing from the beginning of the booking with answering my questions and went above and beyond to make this special occasion memorable. The house is well equipped! The sounds of birds chirping in the morning , the breeze, and the view of the pond when drinking coffee was so serene. The space in the house was more than I expected with everyone having lots of space to enjoy all the designated areas for playing board games, Video game room( so cool) , reading , watching tv - there was a room for everyone’s enjoyment from our 12 year old, 17, 25, to my 78 year old parents. The well thought out toiletries in every bathroom, spa slippers and robes in each bedroom, ear plugs located by the bedside, laundry room that has labeled racks of beach items and games , kitchen with all its wonderful amenities- I can do on and on. We WILL be back !
Guest favorite
An outdoor pool area showcases a heated inground pool with clear water, surrounded by a wooden deck. Sun loungers are placed nearby, and patio umbrellas provide shade. Lush greenery and trees line the background, offering a serene environment. A beach ball floats in the water.
Home in New Seabury
5 out of 5 average rating, 20 reviews

Exclusive New Seabury Home w/ Heated Pool ⛳️🏖🦞☀️🐠

AriannaRating, 5 stars2 weeks ago
We had a wonderful stay here in New Seabury! The house is beautiful, spacious and just as described. The heated pool was an added bonus! Michael provided prompt and clear communication when needed. I would absolutely stay here again!
Superhost
An outdoor area showcases a heated pool surrounded by lounge chairs and a shaded seating arrangement. The back of a large two-story home is visible, with multiple windows indicating spacious interiors. Green trees line the background, adding a natural element to the setting.
Home in Plymouth
4.82 out of 5 average rating, 17 reviews

Mansion with Heated Pool Near Ocean

AnayRating, 5 stars2 weeks ago
The place was nice and spacious. Great for large family gatherings. The pool was nice and although the water was not heated (which may partially have been due to the weather), Zachary and his team were very responsive and helped troubleshoot pool temperature. Overall we had a great stay!
Superhost
A light-filled living area features comfortable seating with blue and white accents. A natural wood coffee table sits in the center, surrounded by a cozy area rug. A separate dining space is visible through an open archway, showcasing a charming dining table and decorative elements.
Home in Plymouth
4.74 out of 5 average rating, 61 reviews

Tranquil Family Retreat in Plymouth

ImaniRating, 5 stars1 month ago
Overall, the home was beautiful, and my friends and I truly enjoyed our stay. The only minor challenges were getting in through the front door and not having a chance to use the arcade. The kitchen area was absolutely stunning, and I personally loved the master suite. We all agreed that we could definitely see ourselves coming back. Apologies for our late-night conversation getting a bit too lively—the gentle reminder was appreciated. Thank you for being such wonderful hosts!
Guest favorite
The exterior of the house is framed by lush greenery, showcasing a wooden entryway leading to a spacious deck. The building features a rustic shingle design, with large windows allowing natural light to reach the interior.
Home in Provincetown
4.95 out of 5 average rating, 19 reviews

Glutton's Doom: Bright & Airy East End Delight

VirginiaRating, 5 stars2 weeks ago
Great location and lovely space! We loved our stay here. We were a 15-20 minute very pleasant walk to the main commerce and there’s an adorable little market right next door to the house for any groceries and baked goods. The house has everything you’d need and is surrounded by trees. Very peaceful.
Superhost
The outdoor area features a heated fiberglass pool with a curved design, surrounded by a concrete patio. Sun loungers and a shaded seating area under an umbrella are visible, along with a grassy section and the home's exterior, showcasing large windows and a door leading inside.
Home in East Sandwich
4.92 out of 5 average rating, 65 reviews

Large Home Heated Swimming Pool Private Beach

SahilRating, 5 stars2 weeks ago
We had a great stay at this place! The house was exactly as described—clean, comfortable, and well-stocked with everything we needed. Check-in was smooth, and the host provided clear instructions throughout. The neighborhood was quiet and convenient, with easy access to local attractions and restaurants. Would definitely recommend this spot to anyone visiting the area!
Top guest favorite
A classic colonial home is set on a large green lawn, surrounded by trees. The expansive front porch features white railings and multiple seating areas. An American flag gently flutters to the side, while colorful flowers add a touch of vibrancy to the landscape.
Home in Chatham
4.97 out of 5 average rating, 39 reviews

Oceanview/pool&spa/private beach! 5 bedrms, 4 bath

BarbaraRating, 5 stars8 months ago
We loved our stay in Justin’s home. The house is well-stocked, beds are comfortable, and our family had plenty of room. Justin was very responsive and helpful with any questions. Renting towels and sheets was new for us, but it was easy and all set up for us when we arrived. We loved the huge front porch and enjoyed coffee and the quiet neighborhood outdoors each morning. We would definitely return if we make another trip that way.
Top guest favorite
A private, gated pool is surrounded by a concrete deck and bordered by lush greenery. The sparkling blue water is enhanced by a bright yellow floating ring. In the background, a spacious sunroom and outdoor seating areas are visible, offering convenience and leisure options.
Home in Cotuit
4.95 out of 5 average rating, 114 reviews

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

ZackRating, 5 stars8 months ago
Awesome stay! Great house/location and Sandy is an awesome host. Highly recommend

Condo rentals with a pool

Guest favorite
A spacious sleeping area features a large bed with neutral bedding and colorful accent pillows. A TV is mounted on the wall. Natural light filters through a sliding glass door, which opens to an outdoor area with a small table and chairs.
Condo in Dennis Port
4.78 out of 5 average rating, 58 reviews

Cozy Studio Just Steps Away From the Beach!

NupurRating, 5 stars9 months ago
Perfect little studio for two people! Great location - close to beaches and restaurants and there’s even a pool! Michael was super responsive and the place was exactly like the pictures!
Guest favorite
A clean outdoor pool is framed by a spacious concrete deck with lounge chairs positioned nearby. Lush greenery and landscaped areas are visible around the pool, contributing to a serene environment. The sky above is clear, enhancing the bright atmosphere of the setting.
Condo in West Dennis
4.9 out of 5 average rating, 30 reviews

1BR 2nd Floor Condo with pool

DougRating, 5 stars2 days ago
The unit was secure and in a nice area. Close to shopping, sightseeing, and beaches. The unit was bright and cheery and clean. Keith is a good host.
Guest favorite
A charming, single-story building is visible from the road, featuring a gray exterior and a white picket fence that encloses a well-kept yard. Leafy trees provide shade, and clear blue skies are overhead, creating a welcoming ambiance for guests.
Condo in Dennis Port
4.84 out of 5 average rating, 76 reviews

Comfy Cape Escape! Spacious, Cozy, Close to Beach!

ChrisRating, 5 stars9 months ago
Wonderful beach location. We enjoyed the local walkable beaches and restaurants. Close to anywhere in the cape , we had a great trip.
Guest favorite
The living room features two comfortable sofas adorned with colorful cushions, situated around a wooden coffee table on a vibrant area rug. Natural light fills the space, highlighting the dining area and fully equipped kitchen visible in the background.
Condo in Brewster
4.88 out of 5 average rating, 40 reviews

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

JasonRating, 5 stars8 months ago
Had a great weekend at Josh’s place! Smooth booking process, great communication, easy checkin. The space was clean and exactly as advertised. I’d definitely recommend both Josh as a host and this location as a Cape getaway!
Guest favorite
A clear blue pool is surrounded by a spacious patio area. Several lounge chairs are positioned nearby under the sun. The pool is accessed via a white gated area, with a clean, inviting atmosphere represented by the well-maintained surroundings.
Condo in Dennis Port
4.85 out of 5 average rating, 62 reviews

Stylish & Modern Studio Condo - Steps to the Beach

DavidRating, 5 stars2 weeks ago
I had a fantastic experience during my stay! The place was exactly as described—clean, cozy, and well-equipped. The host was incredibly welcoming and responsive, making the check-in process a breeze. The location was perfect, with easy access to local attractions and restaurants. It truly felt like a home away from home. I would definitely recommend this place to anyone looking for a great stay. I can't wait to come back!
Guest favorite
An unheated communal pool is framed by a tan patio and white fencing. Surrounding the pool, blue lounge chairs and umbrellas provide seating options. The two-story building in the background features a deck with stairs leading to the second floor, bordered by green trees.
Condo in Tisbury
4.9 out of 5 average rating, 73 reviews

Sunny 2bedroom condo w pool, walk to town

ShayRating, 5 stars7 months ago
We had a great time at Leah’s place. She is a terrific communicator, immediate responses. She also reached out to share about local fun events that were happening during our stay. So nice! We would definitely stay there again.
Guest favorite
A shared pool area features a clear blue pool surrounded by lounge chairs in yellow and green hues. The pool is enclosed by a wooden fence, with the condo visible in the background, displaying gray shingle siding and a small porch.
Condo in Provincetown
4.93 out of 5 average rating, 41 reviews

Newly Updated Condo w/ Pool - Steps to Boatslip!

KenRating, 5 stars5 months ago
Amy and Julie were wonderful hosts! The home was comfortable, clean and had all the amenities we needed for our 6 night stay. The location was great, just a block from the beach and close to all the restaurants and shops. It was the perfect place for us and our Boston Terrier to ring in the new year. We enjoyed our stay and would certainly return again!
Superhost
The entrance of the condominium is shown, featuring a wooden exterior with shingles. A pathway leads to the door, surrounded by neatly trimmed shrubs and grass. Bright sunlight highlights the clear sky and the inviting pathway.
Condo in Falmouth
4.72 out of 5 average rating, 18 reviews

Condo in Falmouth MA

MarkRating, 5 stars1 month ago
The Condo was clean & comfortable. Having two bedrooms with queen beds was perfect for us, and sharing the 1 bathroom worked fine. The price was better than most other options. It was peaceful, and very quiet during our stay (in early May). Having the pool available would be very nice in summer months.

Quick stats about vacation rentals with a pool in Wellfleet

  • Total rentals

    20 properties

  • Nightly prices starting at

    ﺩ.ﺇ367 before taxes and fees

  • Total number of reviews

    750 reviews

  • Family-friendly rentals

    10 properties are a good fit for families

  • Wifi availability

    20 properties include access to wifi

  • Popular amenities

    Kitchen, Wifi, and Pool

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