Holiday rentals with a pool in Wellfleet

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Popular amenities for Wellfleet rentals with a pool

House rentals with a pool

Guest favourite
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
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
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!!
Guest favourite
Home in Falmouth
5 out of 5 average rating, 15 reviews

Home in Falmouth ~ 5 min drive to beach

AnnieRating, 5 stars8 months ago
This rental is exactly as described with accurate pictures. It was recently renovated with all new furnishings, new kitchen, appliances and baths. Our family enjoyed the brand new outdoor deck, picnic tables, gas grill, swing and s’mores by the fire pit. Unfortunately it was too chilly to use the pool. The kitchen had all supplies to make a large pasta meal. Our daughter ran the Falmouth Road race and so Sunday was a bit chaotic and the owner gave us flexibility to check out a bit later, which was a huge help!!. A wonderful family vacation!! Highly recommend.
Superhost
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 favourite
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!!
Top Guest favourite
Home in Hyannis Port
5 out of 5 average rating, 11 reviews

Home in Hyannis Port

RyanRating, 5 stars8 months ago
Chris' home was clean, bright and very well-stocked. He was timely in communication, and the area was perfect. Beaches, dining and shopping were all within walking distance or a quick drive. It's a great location for taking the ferry to either Martha's Vineyard or Nantucket. We certainly hope to return!
Guest favourite
Home in Provincetown
4.94 out of 5 average rating, 16 reviews

Glutton's Doom: Bright & Airy East End Delight

BillRating, 5 stars4 months ago
Wonderful wonderful! This was a great place for our family of four to spend a restorative Thanksgiving. The house is a gem, the neighborhood is quiet but still very walkable to everything, and the host is helpful and responsive. A+

Condo rentals with a pool

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

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

ChrisRating, 5 stars2 months 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 favourite
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 favourite
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 favourite
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 favourite
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
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
Condo in West Dennis
4.84 out of 5 average rating, 51 reviews

Hidden Hideaway

JennyRating, 5 stars6 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 favourite
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 holiday rentals with a pool in Wellfleet

  • Total rentals

    20 properties

  • Nightly prices starting at

    $156 AUD before taxes and fees

  • Total number of reviews

    750 reviews

  • Family-friendly rentals

    10 properties are a good fit for families

  • Wi-Fi availability

    20 properties include access to Wi-Fi

  • Popular amenities

    Kitchen, Wi-Fi and Pool

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