
Vacation rentals with a pool in Wellfleet
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Top-rated rentals with a pool in Wellfleet
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Popular amenities for Wellfleet rentals with a pool
House rentals with a pool

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

5-bedroom Cape with a pool and yard games.
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!!

Our families slice of heaven
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

Family friendly luxury home with heated pool & spa
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!

Cape Oasis with large pool + lots of privacy.
The house was exactly as described and pictured. Located in a quiet neighborhood—enjoyed taking morning and evening walks for exercise. It was exceptionally clean, kitchen was well-equipped, spacious bedrooms with comfortable beds, plenty of towels and linens, roomy enough for everyone to enjoy private time. The pool was a big plus for family fun and there was plenty of space on the patio/deck to enjoy a meal cooked on the grill. Cortney was very responsive and provided helpful info on restaurants, shopping, and nearby beaches. We had everything we needed for a relaxing and comfortable stay in Sandwich.

Cape House with Pool by Canal
This home was great for our family. The pool and backyard are beautiful, and the house was clean and welcoming. There are a lot of activities in the area. I would stay here again!

Spacious Upper Cape Retreat with Private Pool
We had a lovely stay as a mixed group of kids and adults in this quiet house with a great pool, outdoor space, and common areas. You can walk to the bike path easily from the house and the next door neighbors sell veggies and eggs. Makes it easy to get back and forth to the cape for activities without staying on the other side of the bridge!

Home in Hyannis Port
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!
Condo rentals with a pool

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

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

1BR 2nd Floor Condo with pool
Excellent location, clean, comfortable place to spend some time on the Cape. Perfect for my husband and I.

Luxury Waterfront Getaway
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.

Private 3bdrm Condo Tashmoo Woods
What a relaxing and wonderful stay! Barbara’s place was welcoming and even better than the pictures. The house has everything you need and the addition of the community pool was the cherry on top. The host was extremely responsive and helpful. We look forward to returning to Barbara‘s place the next time my family and I visit MV.

Hidden Hideaway
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.

Modern, clean waterviews
This was my second stay at Garrett’s and the place was just as nice as I remembered (plus a a few upgrades). Garrett’s always quick to respond to inquiries, unit had just about everything we needed including beach towels and location is great as it’s a short bike ride from center town and peaceful/quiet if you’re looking for a balanced vacation.

Martha’s Vineyard Condo * Near Ferry
Great location and a nice quaint spot for one or two ! Great value for the area as well
Quick stats about vacation rentals with a pool in Wellfleet
Total rentals
20 properties
Nightly prices starting at
$157 CAD 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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- Cape Cod National Seashore
- Sandwich Glass Museum
- Owen Park Beach
- Sagamore Beach
- New Silver Beach
- Lighthouse Beach
- Onset Beach
- Scusset Beach
- Corn Hill Beach
- Nickerson State Park
- Brant Beach
- Barlows Landing Beach
- White Horse Beach
- Pilgrim Beach
- Surfside Beach
- South Cape Beach
- Oyster Harbors Beach
- Kalmus Park Beach
- Inman Road Beach
- Madequecham Beach
- Ridgevale Beach
- Forest Beach
- Grey's Beach
- Cahoon Hollow Beach