
Holiday rentals with a pool in Osterville, Barnstable
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Top-rated rentals with a pool in Osterville, Barnstable
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Popular amenities for Osterville, Barnstable 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.

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!

Our families slice of heaven
This place was INCREDIBLE!! Marla and her family were so responsive and so welcoming!! This house was the cleanest I have ever stayed in. The furniture was so comfortable and cozy. I would HIGHLY recommend staying here! I hope to come back in the near future!! Thank you Marla and family for being such amazing hosts!!

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.

Mansion with Heated Pool Near Ocean
The place was nice and spacious. Great for large family gatherings. The pool was nice and although the water was not heated (which may partially have been due to the weather), Zachary and his team were very responsive and helped troubleshoot pool temperature. Overall we had a great stay!

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!

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!
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.

Ocean Edge: 2 bed/2 bath - Pools & Resort Access
Had a great weekend at Josh’s place! Smooth booking process, great communication, easy checkin. The space was clean and exactly as advertised. I’d definitely recommend both Josh as a host and this location as a Cape getaway!

Ocean Edge 2 Bed 2 Bath, Golf & Free Resort Access
Chris is an unbelievable 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!

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!
Quick stats about holiday rentals with a pool in Osterville, Barnstable
Total rentals
20 properties
Nightly prices starting at
$381 NZD 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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- Rentals with outdoor seating Osterville
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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
- Coast Guard Beach
- Owen Park Beach
- Onset Beach
- Nickerson State Park
- Inman Road Beach
- Pinehills Golf Club
- South Shore Beach
- Second Beach
- Oyster Harbors Beach
- White Horse Beach
- Island Park Beach
- Kalmus Park Beach
- Ridgevale Beach
- Chapin Memorial Beach
- The Breakers