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Vacation rentals with a pool in Wellfleet

Find and book unique homes with a pool on Airbnb

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Popular amenities for Wellfleet rentals with a pool

House rentals with a pool

Guest favorite
A private backyard features a large swimming pool surrounded by a patio with stone paving. Lush greenery and low shrubs border the area, while a wooden table and chairs are positioned nearby. The house is visible in the background, framed by trees.
Home in Mashpee
4.9 out of 5 average rating, 20 reviews

Beautiful Mashpee Home with Pool

JudyRating, 5 stars8 months ago
The house was beautiful, better than expected! It was very spacious with lovely high ceilings in all the rooms. the bedrooms were all large and delightfully decorated, as were the two sitting rooms. In fact the layout worked really well for our family group: master bedroom with en suite for us grandparents, first floor bedrooms for one couple and their two kids with shared bathroom and extra sitting area with TV, and the garden room -with an enormous bed!- and ensuite bathroom for the other couple. The pool was a very good size with comfortable loungers and the large table on the terrace was perfect for mealtimes. The kitchen was fully equipped and there were an enormous range of dishes and utensils! The various beaches we visited were all within easy reach and Mashpee Commons was only a short drive away with a range of restaurants and shops. Nicole was very responsive and answered our questions quickly. We had a wonderful time and the house exceeded our expectations!
Superhost
A spacious bedroom features large glass sliding doors that provide access to a private deck. The room includes a comfortable bed with light bedding, two bedside lamps, and a desk positioned beside a window, allowing natural light to illuminate the space.
Home in New Seabury
5 out of 5 average rating, 7 reviews

Waterfront Home w/ Dock, Heated Pool, Kayaks & A/C

MadisonRating, 5 stars6 months ago
Prescott’s house is such a relaxing place to stay with a big group. The house has a very pretty view and is very clean and peaceful. We are very grateful for such a nice stay at this beautiful house. The BBQ outside didn’t work great but other than that we had a wonderful time! Thank you Prescott.
Superhost
An inground pool is surrounded by lush greenery, featuring vibrant flowering plants and bushes. The clear blue water reflects the sky, while stairs lead into the pool. A natural stone patio borders the pool area, enhancing the outdoor space.
Home in Orleans
4.92 out of 5 average rating, 25 reviews

5-bedroom Cape with a pool and yard games.

CatherineRating, 5 stars7 months ago
We enjoyed our stay very much ~ the house and large fenced yard w/deck (perfect for pup) are amazing & the hosts were very kind, accommodating & responsive. The location was great with a short ride to local beaches and/or Chatham for a fun day of shopping or night out. The host’s welcome basket with treats & seltzers were a great surprise after a long day of travel. We loved playing ping pong in the garage! I do suggest the listing bedroom descriptions & photos be updated as we were pleased to find a king bed in the master BR (vs the queen shown) and a full bed (vs the twin) in the downstairs guest-room. Perhaps renovations are underway so we were pleasantly surprised! The only improvements I would suggest are adding a screen door to the deck & heat for the pool, having more wine glasses (the kitchen was wonderfully stocked otherwise), & adding amenities like blankets, washcloths, a hair dryer, beach/pool towels & chairs (we brought our own). We hope to be back next year!!
Top guest favorite
Home in Sandwich
4.99 out of 5 average rating, 80 reviews

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

LaurenRating, 5 stars7 months ago
We stayed at the Cape Escape for 5 nights with 7 adults and two young children, and it was perfect. The setting and location of the house was private and serene. The house was well stocked including plenty of beach towels, chairs, baby gear, coolers, wagons, beach toys and more. We used the provided high chair as well. I especially loved the soaps and lotions and extra bath toiletries which made it feel like a hotel. There were multiple areas where our family could gather and eat. Dinners on the back porch st sunset were the best. We hope to be back next year!!
Top guest favorite
A saltwater pool is set within a stone patio area, surrounded by lush greenery. Lounge chairs and a shaded table with a red umbrella offer comfortable seating options. The serene view of Morey Pond is visible beyond the pool, framed by trees under a clear blue sky.
Home in Plymouth
4.96 out of 5 average rating, 55 reviews

Our families slice of heaven

MarkRating, 5 stars6 months ago
Marla's vacation home was very lovely. We liked the pictures of her place, but once we arrived we realized that she had remodeled a number of rooms. Each room was updated, very clean and cozy. Marla has made sure that her place is stocked with all of the large and small conveniences that guests would want in a home away from home. The location and the surroundings are stunning, especially with the Fall foliage. One can tell that Marla takes great pride in her beautiful rental. -Mark & Susan G
Superhost
A heated pool is surrounded by a spacious stone patio, featuring several lounge chairs with blue cushions. A black fence encloses the area, overlooking a lush green yard with trees in the background under a clear blue sky.
Home in Chatham
4.8 out of 5 average rating, 5 reviews

Family friendly luxury home with heated pool & spa

MartinRating, 5 stars8 months ago
This home is a gem. Clean and spacious for family and friends. The pool and hot tub make the entire property a private oasis. The location is perfect. A quiet neighborhood that is walkable to downtown Chatham. The host was equally fantastic: Very responsive via email and text for the few questions we had pre & post arrival. There are very clear, written instructions for everything in the house, pool & hot tub. We had a fantastic family vacation and would like to return!
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, 18 reviews

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

BryanRating, 5 stars7 months ago
Michael is a great host with a phenomenal property. The house was clean, the amenities are great, the pool was warm (we were there at the end of September when highs were in the mid-60s), kitchen is well equipped, and the location is great. We were a group of 3 families - 6 adults and 5 kids - and the layout of the house is perfect for multiple families. Each floor has its own main bedroom, it's own bathroom, plus ample extra space for a crib, pack n play, mattress, etc. We couldn't have asked for a better setup. Unfortunately for our stay the weather didn't cooperate with nearly non-stop rain, but we still had fun in the house (great spaces for movie watching, games, and ping pong), at the nearby children's museum, the beach, and Mashpee commons. We'll be back for sure!!
Superhost
An in-ground pool glistens under the sky, surrounded by a spacious patio. A two-story house with dark blue siding is visible in the background, along with lounge chairs arranged neatly. Lush green vegetation frames the scene, creating a secluded atmosphere.
Home in Bourne
4.75 out of 5 average rating, 4 reviews

Cozy Cape Cod House - Stroll or Bike the Canal

AlexandraRating, 5 stars12 months ago
Excellent accommodation, I was in winter but in summer it should be the maximum

Condo rentals with a pool

Guest favorite
Condo in Provincetown
4.97 out of 5 average rating, 211 reviews

P-Town Beach Beauty on the Bay. Water View!

ChrisRating, 5 stars1 month ago
We had a wonderful time at Rob's place in Provincetown this February. If you are looking for a quiet place on the East End in the off season this is an exceptional spot. Beautiful water views from the condo. A gorgeous beach with some of the best views in Provincetown is right across the street. Condo was perfectly cleaned upon arrival and exactly as described. Couldn't ask for more.
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 stars7 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
Condo in Brewster
4.97 out of 5 average rating, 178 reviews

Ocean Edge Resort-Pool Access-End Unit-2 bdr/2 bth

KathleenRating, 5 stars4 months ago
It is always comforting to stay at Anna’s condo. It feels like home with well thought out amenities, clean spaces, quiet surroundings and such a helpful host. It is a great space for families and has all you need to cook in. I highly recommend staying here.
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
4.89 out of 5 average rating, 28 reviews

1BR 2nd Floor Condo with pool

MarjorieRating, 5 stars6 months ago
Excellent location, clean, comfortable place to spend some time on the Cape. Perfect for my husband and I.
Guest favorite
A private deck is visible through sliding glass doors, featuring a set of bar-height chairs and a table. The view overlooks a grassy area, with the horizon suggesting proximity to the water. Natural light filters in, creating a welcoming space.
Condo in Provincetown
4.9 out of 5 average rating, 10 reviews

Luxury Waterfront Getaway

ThomasRating, 5 stars5 months ago
Michael's place is spacious, well-appointed, and very comfortable. The views from the living room are amazing, and the breeze from the bay is wonderful. I would definitely recommend staying here.
Superhost
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
4.84 out of 5 average rating, 58 reviews

Stylish & Modern Studio Condo - Steps to the Beach

RachelRating, 5 stars6 months ago
Great spot with just a 5 min walk to the beach. Cute and cozy which is just what I needed. Super clean and well maintained. Very much enjoyed my stay!
Superhost
A clear blue pool is surrounded by lounge chairs, offering a refreshing spot for relaxation. The two-story building in the background features balconies with umbrellas and well-maintained landscaping, creating a serene atmosphere for guests.
Condo in West Dennis
4.84 out of 5 average rating, 51 reviews

Hidden Hideaway

JennyRating, 5 stars5 months ago
The location is fabulous and very close to many amenities - coffee, groceries, restaurants and the beach. While it was a small space, it was well laid out, comfortable to be in, very clean and had a respectable kitchen for its small size (which I used). Devon was very proactive and friendly when I asked him about the microwave not working - I had missed that it wasn't plugged in! The condo was very quiet at night even though it is close to a road. I will definitely return to Devon's place should I need to travel there and it is available.
Guest favorite
Condo in Brewster
5 out of 5 average rating, 71 reviews

Ocean Edge Resort/Pool access/2bedroom-2bath Condo

KevinRating, 5 stars7 months ago
We had a great stay with Rob in his cottage at Ocean Edge! The place had clearly been recently updated and it utilized space well such that it lived much bigger then its footprint. While it rained the whole time we were there, we could see Ocean Edge being a fun community for active folks. We highly recommend you stay here!

Quick stats about vacation rentals with a pool in Wellfleet

  • Total rentals

    20 properties

  • Nightly prices starting at

    $100 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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