Holiday rentals with a pool in Tisbury

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Popular amenities for Tisbury rentals with a pool

House rentals with a pool

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!
Superhost
Home in Teaticket
4.83 out of 5 average rating, 6 reviews

Charming Home-Pool, Game Room, walk to quiet beach

TedRating, 5 stars10 months ago
We had a wonderful time at this home. The pool was clean and warm; we used it every day. The house was well stocked- dishes, spices, utensils, pots and pans… and plenty of chairs out by the pool for outdoor meals. The neighborhood was quiet and safe to take nice morning walks down to the little beach 1/4 miles away. Great quality seafood at Falmouth Fish Market, and many grocery/household store options less than 2 miles from the house. We paid extra for the linens; good choice for us since we had a full house.
Top guest favourite
Home in Edgartown
4.92 out of 5 average rating, 49 reviews

Beautiful Edgartown Colonial with heated pool.

DavidRating, 5 stars3 weeks ago
We had such a fantastic stay at Sue’s beautiful Edgartown home! The house was charming, spotless, and well-stocked with everything we needed—from kids’ toys and extra keys to cozy spaces for the whole family. Even with some chilly weather, we made great memories thanks to Sue’s warmth and hospitality. One huge highlight was the car rental—what a convenient bonus! It was clean, reliable, and made exploring the island a breeze. Sue was responsive and thoughtful throughout our stay, checking in with helpful suggestions and going above and beyond. She truly made us feel at home. From shell picking at Felix Neck to relaxing in the playroom and enjoying everything the Vineyard has to offer, our family had a wonderful time. We’re already talking about our next trip back—and hoping Sue’s hot tub addition is ready by then! Highly recommend!
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!
Guest favourite
Home in Plymouth
4.91 out of 5 average rating, 35 reviews

Getaway with pool

KatharineRating, 5 stars1 week ago
We loved Laura’s place! Super easy to check in and Laura was quick to respond to any questions we had! Would 100% stay here again
Top guest favourite
Home in Hyannis Port
5 out of 5 average rating, 13 reviews

Home in Hyannis Port

Ryan & LindsayRating, 5 stars2 weeks ago
Our family of five had a wonderful stay! We picked the location because it was in the middle of the Cape and easy for us to explore the coast. The house is newly renovated and in pristine condition. The beds were comfortable and the bathrooms were fresh and new. We had plenty of space and felt right at home. The host was very responsive. We highly recommend!
Guest favourite
Home in North Falmouth
5 out of 5 average rating, 16 reviews

New Construction Home with Pool in N. Falmouth

KeriRating, 5 stars1 week ago
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!
Superhost
Home in Plymouth
4.85 out of 5 average rating, 27 reviews

The Plymouth Pool House

ColleenRating, 5 stars1 week ago
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.

Apartment rentals with a pool

Guest favourite
Apartment 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
Apartment 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
Apartment in Dennis Port
4.84 out of 5 average rating, 76 reviews

Comfy Cape Escape! Spacious, Cozy, Close to Beach!

ChrisRating, 5 stars9 months ago
Wonderful beach location. We enjoyed the local walkable beaches and restaurants. Close to anywhere in the cape , we had a great trip.
Guest favourite
Apartment in Dennis Port
4.86 out of 5 average rating, 63 reviews

Stylish & Modern Studio Condo - Steps to the Beach

JadenRating, 5 stars5 days ago
Everything was clean and the location is great! Peaceful walk to the beach!
Superhost
Apartment in West Dennis
4.84 out of 5 average rating, 51 reviews

Hidden Hideaway

JennyRating, 5 stars7 months ago
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.
Superhost
Apartment 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
Apartment in South Yarmouth
4.75 out of 5 average rating, 4 reviews

Cape Cod, South Yarmouth July 19-26. Sleeps 8

RickyRating, 5 stars35 months ago
Loved the location and the apartment was facing the water, which meant a light cool breeze most of the time all day and night. The 2 bedroom apt was very clean and spacious and the 5 of us did not get in each of our ways. While inside, we did not hear any noise from our next door neighbors and sliding doors silenced any outdoor noise. The AC was cold and very comfortable. Amenities including additional outdoor access to a peaceful water area with picnic tables, Adirondack chairs was a huge plus. Indoor pool helped too with two little ones. Beach parking passes at a discount. Staff was very nice and accommodating. Parking was easy and plenty of spaces. Would recommend and we would stay again.
Superhost
Apartment 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 .

Quick stats about holiday rentals with a pool in Tisbury

  • Total rentals

    50 properties

  • Nightly prices starting at

    ₹11,250 before taxes and fees

  • Total number of reviews

    830 reviews

  • Family-friendly rentals

    40 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

Destinations to explore