Family-friendly holiday rentals in Westport

What a gorgeous location! Pet friendly, peaceful and convenient.

Resort vibes with a chef's kitchen and stunning views! ***** Our stay at Larry's house was fantastic! The kitchen was absolutely amazing - spacious, modern, and fully equipped with everything we needed. We enjoyed cooking and gathering there. The real highlight was the outdoor space. The view was breathtaking! The pool and hot tub made it feel like we were staying in a private resort. Michael was helpful and responsive, making everything easy from check in to check out. We would love to come back.

My husband and I and our small dog had a fantastic stay. Sharon accommodated a (very!) early morning checkin time and was very responsive and clear throughout our stay. The unit suited our needs well and we absolutely loved spending time in the back patio/garden area.

Our family stayed here after graduation and it was perfect

We stayed at this home with a group of five people and the home fit everyone great. The view from the home of the marsh is beautiful and we spent Saturday hanging out on the dock. It is really peaceful and we had an amazing time. Michele was a pleasure to work with and was very accommodating with being flexible for check in and check out times. Thank you again!

We visited Island Grace for a long weekend and enjoyed the many perks of this beautiful home! It was a perfect spot to visit Edgartown, Oak Bluffs, and beaches and just a short drive to other areas and towns. We enjoyed biking, the hot tub, and the well-appointed kitchen. The beds were so comfortable! We truly had everything we needed and thought it was so fun to watch their HGTV episode!

Beautiful home! David gave perfect instructions for everything about the house and was very responsive. We all had a fantastic weekend, and will definitely be booking again! Thank you David!

Beautiful setting with ocean views and pretty landscaping and gardens view out every window. Easily accommodated six people in our party. Home was equipped with everything we needed. Outside seating, hot tub and grill area are lovely. We had a nor’easter arrive so didn’t get to enjoy outside too much but the little that we did was incredible! Gas fireplace in living room kept dampness at bay and was just lovely. Two inside eating areas were perfect! Would come back in a heartbeat!

We loved our stay. The cottage was adorable, clean, and had everything needed. The outside yard and waterfront was precious. We couldn’t have enjoyed our stay more and will absolutely stay again!

Great location with off street parking!

We had a wonderful time here! What a perfect location. John was so accommodating. Definitely would rent again from him!

This home is gorgeous and filled with timeless artifacts and family heirlooms. Beautiful spots to sit outside with a morning coffee. My partner and I made a point of staying in and cooking one night because we felt right at home and wanted to appreciate the ambiance. We enjoyed the privacy and proximity to Newport very much as well. Well outside any potential chaos of downtown yet only a couple minute drive to Easton Beach. Thank you so much!

Fran's house is lovely, everything one needs for a fabulous stay. She is a very good host - responsive and informative. She lives on the prpoerty but we never saw her. We had a really great stay!!!

First time traveling to this area and it was perfect. Our family of 7 had an amazing time and was very comfortable. Areas were spacious, beautiful yard, two bathrooms (a definite plus) centrally located to everything, very clean, comfortable sleeping, everything you need when traveling. I can't say enough about this home. Was on a busy street but that did not have any negative impact at all. Roland gave great recommendations and he was spot on! The French bakery, seafood restaurants and beaches were a stone's throw away. Great location and spectacular accommodations. We also took advantage of the fire pit 😋 thank you so much Roland, this was a short getaway that my family and I needed. Definitely recommend!

I went with a group of girls and it was perfect for what we needed! It was so cute and spacious. It was too cold for us to utilize the roof top deck area but on a warm sunny day it would be perfect! There was plenty of room for all of us to get ready. All the bedrooms were big as well. The location was walkable to everything! Parking was great as well and easy. The host responded to all my questions very quickly. This was one of the best Airbnb’s I’ve ever stayed at. I would definitely recommend!!!

The house is amazing! It has everything that you would need and is so comfortable. The property is peaceful, and it feels like you’re on your own little island while still being minutes from stores and restaurants. We had a perfect weekend celebrating some milestone birthdays in our family.

Lovely home and well outfitted for our stay. Conveniently located on well maintained grounds.

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!!

Kristin went above and beyond in making sure me and my guests were well taken care of. She was extremely responsive and even let me come 7 hours before my check in to drop off my birthday cake in the fridge so it didn’t have to sit in a cooler all day at the beach. She gave me local recommendations and was just a really lovely host. I really appreciated her accommodations. My friends and I enjoyed swimming in the pool after the beach and sitting on the deck. Highly recommend!

This was our second time staying at Paul’s home, and once again had a wonderful experience! Paul and Meredith are welcoming, kind, and friendly. The house is spacious, and has plenty of room for our family to enjoy a week together - relaxing, cooking and playing games. The views are beautiful, and we enjoyed lots of time bird watching and soaking it in. We enjoyed easy access to our favorite Cape restaurants and shopping. This home is perfect for a Cape getaway, and Paul is a fantastic host!

Barbara’s condo was roomy and comfortable. We fell in love with the screened in porch. Lovely room for a cup of coffee in the mornings and a glass of wine in the late afternoon. We took a short ride through the woods to the town beach which led us to beautiful views of Tashmoo. We had a great time!

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.

This place was beautiful! The kitchen was spacious and accommodated our larger group nicely. Hosts left clear instructions and proactively checked in. They were even nice enough to open their pool a little earlier so we could enjoy it. Highly recommend staying here if you are planning a girls’ weekend. Bedrooms were comfy, and everyone in my group had a lovely time. Thank you!

Beautiful house. Kid friendly Really close to the beach Amazing hosts