
Vacation rentals with a pool in Osterville, Barnstable
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Top-rated rentals with a pool in Osterville, Barnstable
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.
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Popular amenities for Osterville, Barnstable rentals with a pool
House rentals with a pool

Canal Retreat: Easy Cape Access with Seasonal Pool
This house was very clean and adorable. The hosts were very responsive. There was what i believed to be a significant issue on the part of airb&b. They had the wrong adress listed for the house. Again this was not the hosts fault. It was listed as a house in Plymouth but was actually in Bourne, which I was very upset about after driving around for an hour and literally alomost trying to get into a strangers house at night in the dark. Airb&b refused to do anything for me to make this right and blamed it on google maps which is laughable. So for the house and the hosts (residentually) I give 5 stars. For airb&b I give 0 stars.

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.

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!

House on Cape Cod with pool close to beach
Alena's place had everything we needed for a lovely week on the Cape. Great pool and location between Mayflower and Dennis Village. My daughter loved the home's bright airy playroom and it kept us sane and entertained on a couple of rainy days. Would definitely visit again!

Tranquil Family Retreat in Plymouth
Isabeau and Shaun were incredibly accommodating and responsive, and we found the entire experience so seamless. Would definitely rent from them again!

Modern Cape, Private Salt Water Pool, Beaches-Golf
Our stay with Walt was incredible! The place came exactly as described and matched all of the photos. It also had all of the necessary ammenities when hosting large group of 11 people. Plenty of places to sleep, plenty of blankets and towels. Walt was extremely responsive and easy to communicate with when I had questions while we were in his residence. 10/10 would recommend!!

New Construction Home with Pool in N. Falmouth
We had an amazing stay at Stephanie’s place in Falmouth! The home was immaculate, spotlessly clean and even better than we expected. The photos were beautiful, but somehow the house exceeded them. Stephanie and Ellen were wonderful hosts, very responsive and helpful with anything we needed. The layout was perfect for our family, giving everyone their own private space while still feeling cozy and connected. The pool and hot tub were huge hits and made our time extra relaxing and fun. We would absolutely stay here again. Highly recommend!

The Plymouth Pool House
This property had everything you wanted! The pool, the grill, the fire pit, and if it rains you have your own personal movie theater. Anything you need is all right there. I was sad when we had to leave! The host Jared is very responsive and friendly, I couldn’t recommend this property more.
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!

1BR 2nd Floor Condo with pool
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.

Stylish & Modern Studio Condo - Steps to the Beach
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!

Sunny 2bedroom condo w pool, walk to town
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.

Condo in Falmouth MA
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.

Beachfront Complex in Hyannis
I loved our stay . The place inside was bigger than I was expecting. They have so many dishes, glasses, towels, blankets, chairs, etc to use. The place was great, just wish our weather was better. Thank you for being so helpful before and during our stay . Hope to return next year .

Ocean Edge Resort/Pool access/2bedroom-2bath Condo
We really enjoyed our stay. Great condition, really clean, easy parking, and great location right at the Ocean Edge resort. Rob was an excellent host, super communicative and responsive. Would stay again!

A Beautiful Es-Cape
Jean Pierre provided us with a great place to stay in a location with a lot to offer. Everything was very neat and clean, and he was very responsive to any questions we had. Thanks again!
Quick stats about vacation rentals with a pool in Osterville, Barnstable
Total rentals
20 properties
Nightly prices starting at
G$48,104 GYD before taxes and fees
Total number of reviews
160 reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
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- Cape Cod
- Mayflower Beach
- West Dennis Beach
- East Sandwich Beach
- Craigville Beach
- Duxbury Beach
- Easton Beach
- Sagamore Beach
- Sandwich Glass Museum
- Owen Park Beach
- Coast Guard Beach
- Onset Beach
- Inman Road Beach
- South Shore Beach
- Nickerson State Park
- Second Beach
- Oyster Harbors Beach
- Pinehills Golf Club
- Scusset Beach
- Cahoon Hollow Beach
- Island Park Beach
- Kalmus Park Beach
- White Horse Beach
- Peggotty Beach