Holiday 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

Superhost
Home in New Seabury
5 out of 5 average rating, 7 reviews

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

MadisonRating, 5 stars8 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.
Guest favourite
Home in Mashpee
4.9 out of 5 average rating, 20 reviews

Beautiful Mashpee Home with Pool

JudyRating, 5 stars9 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 Dennis
4.63 out of 5 average rating, 30 reviews

House on Cape Cod with pool close to beach

KeelyRating, 5 stars10 months ago
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!
Top Guest favourite
Home in Plymouth
4.96 out of 5 average rating, 56 reviews

Our families slice of heaven

EmilyRating, 5 stars7 months ago
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!!
Guest favourite
Home in Falmouth
5 out of 5 average rating, 15 reviews

Home in Falmouth ~ 5 min drive to beach

AnnieRating, 5 stars10 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 Plymouth
4.82 out of 5 average rating, 17 reviews

Mansion with Heated Pool Near Ocean

AnayRating, 5 stars3 weeks ago
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!
Superhost
Home in Plymouth
4.74 out of 5 average rating, 62 reviews

Tranquil Family Retreat in Plymouth

KristenRating, 5 stars1 week ago
Isabeau and Shaun were incredibly accommodating and responsive, and we found the entire experience so seamless. Would definitely rent from them again!
Top Guest favourite
Home in Buzzards Bay
5 out of 5 average rating, 27 reviews

Cape House with Pool by Canal

SamanthaRating, 5 stars9 months ago
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

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 stars9 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 West Dennis
4.9 out of 5 average rating, 30 reviews

1BR 2nd Floor Condo with pool

DougRating, 5 stars1 week ago
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.
Guest favourite
Condo in Brewster
4.88 out of 5 average rating, 40 reviews

Ocean Edge: 2 bed/2 bath - Pools & Resort Access

JasonRating, 5 stars8 months ago
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!
Top Guest favourite
Condo in Brewster
4.97 out of 5 average rating, 72 reviews

Ocean Edge 2 Bed 2 Bath, Golf & Free Resort Access

LucasRating, 5 stars5 days ago
Chris is an unbelievable host.
Guest favourite
Condo in Dennis Port
4.85 out of 5 average rating, 62 reviews

Stylish & Modern Studio Condo - Steps to the Beach

DavidRating, 5 stars3 weeks ago
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!
Superhost
Condo in Falmouth
4.72 out of 5 average rating, 18 reviews

Condo in Falmouth MA

MarkRating, 5 stars1 month ago
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.
Superhost
Condo in Hyannis Port
4.82 out of 5 average rating, 17 reviews

Beachfront Complex in Hyannis

ErinRating, 5 stars10 months ago
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 .
Guest favourite
Condo in Brewster
5 out of 5 average rating, 72 reviews

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

DonnyRating, 5 stars8 months ago
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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