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

Harwich Haven: Pool & Fire Pit
We had a wonderful stay in Bryan’s house. We regularly visited Cape Cod from Scotland before our son was born, but this was our first visit with him (aged 7) and wanted to be sure we found the right place. The Harwich Haven was everything we could have wanted and more - spacious, clean, full of all the amenities we needed, and in a really fantastic location. Bryan was a tremendous host - always responsive, helpful and accommodating. We can’t recommend this home enough - the design and layout are thoughtful and we could easily imagine two families staying here without any problems (as it was, it was just the three of us enjoying the space immensely). Thanks Bryan - we dearly hope we can visit again soon!

Beautiful Mashpee Home with Pool
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!

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!!

Home in Falmouth ~ 5 min drive to beach
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.

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

Cozy Cape Cod House - Stroll or Bike the Canal
Excellent accommodation, I was in winter but in summer it should be the maximum

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

Cozy Studio Just Steps Away From the Beach!
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!

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.

Comfy Cape Escape! Spacious, Cozy, Close to Beach!
Wonderful beach location. We enjoyed the local walkable beaches and restaurants. Close to anywhere in the cape , we had a great trip.

Stylish & Modern Studio Condo - Steps to the Beach
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!

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.

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

Golf Course Views and Pools
My wife and I wanted a little end of summer get away and we couldn’t have been happier choosing Alexa’s condo at Ocean Edge! The condo was beautifully decorated, very clean, and everything we could have wanted for our short vacation. Alexa was always very responsive and friendly, we’ll certainly be keeping her in mind for our next cape vacation! Highly recommend for small families and couples!
Quick stats about vacation rentals with a pool in Brewster
Total rentals
60 properties
Nightly prices starting at
$130 before taxes and fees
Total number of reviews
1.6K reviews
Family-friendly rentals
50 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
30 properties have a dedicated workspace
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- Cape Cod
- Mayflower Beach
- West Dennis Beach
- East Sandwich Beach
- Cape Cod National Seashore
- Craigville Beach
- Duxbury Beach
- Sandwich Glass Museum
- Owen Park Beach
- Sagamore Beach
- New Silver Beach
- Onset Beach
- Lighthouse Beach
- Pinehills Golf Club
- Nickerson State Park
- Scusset Beach
- Grey's Beach
- Coast Guard Beach
- Oyster Harbors Beach
- Peggotty Beach
- Chapin Memorial Beach
- Corporation Beach
- Earle Road Beach
- Cahoon Hollow Beach
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