Family-friendly holiday rentals in Wellfleet

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Popular amenities for Wellfleet family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favourite
Home in Chatham
4.95 out of 5 average rating, 271 reviews

Slate House - a modern waterfront getaway

CourtneyRating, 5 stars1 month ago
Six of us celebrated our 10th annual Girls Weekend at Slate House and we loved it! The view was incredible and so calming! The house is beautifully decorated and clutter-free. We used the lovely kitchen and also ordered in dinner and ate at the dining room table. The beds were super cozy with great linens. We loved using the hot tub, even with temps below freezing! We walked the nature trail that starts a few feet from the driveway, which was about a mile loop and also spent time shopping in Chatham. It was relaxing, fun, restorative and the house was just perfect!
Guest favourite
Home in Eastham
4.99 out of 5 average rating, 80 reviews

The Penney House Retreat/Hot Tub Gardens Peace

KathleenRating, 5 stars6 months ago
The Penny's House is close to all the beaches, great restaurants and the bike path is accessible via the back of the property which we loved. Her house is beautiful and the kitchen was fully stocked with all cookware you needed to make family dinners together. My family was very comfortable with out stay here! Thanks, Kathleen,Jack and family
Superhost
Home in West Dennis
4.8 out of 5 average rating, 162 reviews

Walk2Beach, HotTub, FirePit, PetsOk

AndreaRating, 5 stars1 week ago
Great school vacation getaway for our group of 8! Home was clean and comfortable. Kids loved the game room. We enjoyed our walk to beach (0.8 miles) which took us about 12 minutes as a group to get to. The hot tub was perfect for the cold/frigid temps. Its minutes away to great restaurants and the well known little Cuffy's shop. The Cape Cod Mall was about a 15 minite drive without traffic. James provided great customer service and follow-up throughout our stay by messaging prior to arrival, during stay and exiting. Highly recommend to anyone looking for a great place to vacation!
Superhost
Townhouse in Mashpee
5 out of 5 average rating, 3 reviews

4th July week! Cape Cod Townhome

DmitryRating, 5 stars81 months ago
The place is great if you don't mind having to drive to a beach or to town. It's spacious and clean. And Ruth is a great host. She was very responsive.
Guest favourite
Home in Dennis
4.92 out of 5 average rating, 50 reviews

Cape Cod Lakefront Home

JustinRating, 5 stars6 months ago
Nice private house with lots of bedrooms, a pool and nice grounds. House was very clean. We had a great time with our family. Can walk to a few places in town, but need to get into the car for most. The Dennis beaches were great and just a short drive away. Would recommend this place for families. The house has access to Scargo Lake, which is nice, but it is a bit of a hike down a good-sized hill. Host was nice and responsive to questions.
Guest favourite
Home in Centerville, Barnstable
4.97 out of 5 average rating, 151 reviews

Luxury House 0.25 mi from Craigville Beach

MeganRating, 5 stars3 months ago
We had the best holiday spent at beyond the beach. This house has everything we could have needed, toys for kiddos which we appreciated and organized and clear instructions for every step of the way. Cannot wait to return!
Guest favourite
Apartment in Oak Bluffs
4.93 out of 5 average rating, 135 reviews

Victorian Oasis: Driveway, hot tub, grill & more

EmilyRating, 5 stars5 months ago
This was our second time renting this property. We had a lovely adults weekend, and really enjoyed our stay.
Guest favourite
Home in Orleans
4.94 out of 5 average rating, 50 reviews

2-Acre Oasis Near Water, Hot Tub, 9 Mins to Nauset

KaitlinRating, 5 stars6 months ago
Amazing location - our family had an amazing stay at David's home. We spent early mornings sipping coffee on the beautiful big porch, took morning and evening walks around the cute neighborhood and found several walking paths with beautiful scenery. After spending the day at the beach (a 5-7 minute drive) we would come back and walk to the nearby lake for a fresh water swim or float. On the cooler evenings we enjoyed the hot tub and played lots of ping pong and other games in the barn. David was responsive and accomodating - and his recommendations of restaurants and things to do did not disappoint! We will definitely be back - it was an amazing and relaxing trip made even better by our stay in this beautiful home! Thank you David!

Family- and pet-friendly home rentals

Guest favourite
Guest suite in West Dennis
4.93 out of 5 average rating, 137 reviews

*Bass River Victorian Escape* Central A/C*WiFi

ErikaRating, 5 stars6 months ago
We had a wonderful week staying at Melissa and George’s Airbnb. The place was the perfect size for our family, a great place to hang out in between activities and had everything we needed. The screened in porch was heavenly and perfect for drying wet stuff from the beach. Lots of great amenities (chairs, boogie boards, etc) to use as well for our many trips to the beach and nearby lakes. Plenty of games to choose from too. The foosball table in the basement was a nice bonus. The hosts gave helpful recommendations and there was plenty of fun things to do within a short drive. Would highly recommended this place!
Guest favourite
Townhouse in Provincetown
4.85 out of 5 average rating, 133 reviews

Minutes to Town with Great ViEWS

AliciaRating, 5 stars4 months ago
This was our second time to stay at Glenn’s townhome. He is an excellent host, responsive, and friendly making for a wonderful experience every time! We absolutely love his property! Great space, great location, and just as described! It’s in walking distance to all the great restaurants and shops in Ptown. We look forward to our next stay!
Superhost
Home in Brewster
4.86 out of 5 average rating, 126 reviews

Sun filled single level retreat, outdoor shower

AlexandraRating, 5 stars5 months ago
We had a really great stay and it was perfect for our group of friends to enjoy a wedding that was nearby. The home is comfortable and perfect for cooking and hanging out. Loved the backyard. The bed (at least the one in the master bedroom) was super comfortable for my bad back. Be sure to bring shampoo etc and you’ll have a wonderful time.
Guest favourite
Home in North Truro
4.97 out of 5 average rating, 191 reviews

Escape to N. Truro 3BR Pet Friendly

ChelseaRating, 5 stars2 weeks ago
This home is amazing. It’s close to so many things to do. Within a few minutes drive of the beach and Provencetown. The yard is large and spacious for pups and there are so many board games and places to sit. The kitchen is amazing and the location feels private despite being in a small neighborhood. Would highly recommend this as the perfect get away!
Guest favourite
Home in Dennis Port
4.92 out of 5 average rating, 377 reviews

★ 0.4mi Beach &Village ★Firepit & Fireplace★ Bikes

JordanaRating, 5 stars1 week ago
We stay here often when visiting the Cape. Aruna is an amazing host and her home is lovely! I would definitely recommend staying here!
Guest favourite
Home in Dennis, Cape Cod
4.99 out of 5 average rating, 270 reviews

Stunning Waterfront! 3bdr/2bth/GasFireplace/kayaks

MonaRating, 5 stars3 weeks ago
The Sunrise Cottage is a beautiful and cozy place to stay at, even in the winter. We all kept saying we could imagine living here! Meg was a perfect host - kind, communicative and willing to be flexible. I would 100% recommend to anyone who is looking for a great place to stay on the Cape.
Guest favourite
Home in Dennis Port
4.98 out of 5 average rating, 269 reviews

Shirley's Place - Pet Friendly Sleeps Six!

MeghanRating, 5 stars4 months ago
We loved our weekend at Karen's place! The house was cozy and clean, and had everything we needed for a comfortable stay (including treats for our pup)! The yard and deck were nice and private, and the house was conveniently located to many restaurants, shops, and not far from the water. Karen made us feel right at home!
Guest favourite
Home in Brewster
4.98 out of 5 average rating, 187 reviews

SeaPeace Cottage-East Brewster Deck,Firepit,W/D AC

PaulRating, 5 stars5 months ago
We attended a wedding at the Ocean Edge Resort and we found Paige's home to be convenient to the venue and activities and a great alternative to staying on property. The home was clean and neat and had everything we needed. The weather turned out beautiful so we took full advantage of the outdoor space. I would highly recommend Paige's home to anyone who likes to be close to the beach, restaurants and golf, but far enough away to be quiet and peaceful.

Family-friendly home rentals with a pool

Guest favourite
Condo in Provincetown
4.97 out of 5 average rating, 211 reviews

P-Town Beach Beauty on the Bay. Water View!

ChrisRating, 5 stars1 week ago
We had a wonderful time at Rob's place in Provincetown this February. If you are looking for a quiet place on the East End in the off season this is an exceptional spot. Beautiful water views from the condo. A gorgeous beach with some of the best views in Provincetown is right across the street. Condo was perfectly cleaned upon arrival and exactly as described. Couldn't ask for more.
Superhost
Home in East Falmouth
4.93 out of 5 average rating, 15 reviews

Gorgeous Cape Cod Property!

ManiRating, 5 stars45 months ago
This place is everything you see in the pictures and more! Location is perfect - in a quiet enough neighborhood but a short walk from scenic falmouth ocean views and beaches and a short drive from downtown Falmouth for shops and restaurants. The pool is in excellent condition, clean and even though the weather didnt cooperate during our visit, the water was warm enough to enjoy even in 50 degree weather. The bedrooms are roomy and there are lots of unique cozy places to socialize for mid to large families or groups. The house is immaculately clean and Susan is perfect as a host - super responsive, prompt and flexible.
Guest favourite
Home in Plymouth
4.96 out of 5 average rating, 55 reviews

Our families slice of heaven

MarkRating, 5 stars4 months ago
Marla's vacation home was very lovely. We liked the pictures of her place, but once we arrived we realized that she had remodeled a number of rooms. Each room was updated, very clean and cozy. Marla has made sure that her place is stocked with all of the large and small conveniences that guests would want in a home away from home. The location and the surroundings are stunning, especially with the Fall foliage. One can tell that Marla takes great pride in her beautiful rental. -Mark & Susan G
Guest favourite
Home in Mashpee
5 out of 5 average rating, 8 reviews

Beautiful Home w/ Pool, Fire pit and Game Room!

KimRating, 5 stars6 months ago
This was our family's first visit to the Cape, and the first time that mom had been back in decades. We had a wonderful stay! Mashpee was a great location - there was local access to good beaches and restaurants; but also a great location to access Sandwich and the Canal, Falmouth, Woods Hole and the Islands, all the way to Provincetown and everything in between. And we took advantage of it all over the week we stayed. Ed was a wonderful host! From booking until we checked out, he was very communicative, friendly, and had great information about local attractions and specialties. The property was very comfortable, and big enough for our family to relax and recharge. And our son loved the heated pool! We would definitely rent this or any of Ed's properties again!
Guest favourite
Home in Cotuit
4.94 out of 5 average rating, 18 reviews

ShoestringBayHouse, waterfront & pool in Cotuit

ZackRating, 5 stars4 months ago
Perfect stay - just be sure to bring or order sheets and towels!
Guest favourite
Home in New Seabury
4.91 out of 5 average rating, 54 reviews

Private POOL*New Seabury*3 Bedroom

Jean PaulRating, 5 stars6 months ago
The home was pristine, more than what we could have asked for. Shelly was an amazing host, again, more than we could have asked for. You want a gorgeous home, with a stellar host, in the cape, with a private pool, amazing amenities, on a golf course and very close to the beaches, fun spots for kids, and shops, go to this place.
Superhost
Apartment in West Yarmouth
4.85 out of 5 average rating, 48 reviews

Ocean View 2-Bedroom Private Suite

LouisRating, 5 stars6 months ago
Good location ! Plenty to do and friendly service. I’d use them again
Guest favourite
Condo in Provincetown
4.93 out of 5 average rating, 100 reviews

Modern, clean waterviews

JacobRating, 5 stars8 months ago
This was my second stay at Garrett’s and the place was just as nice as I remembered (plus a a few upgrades). Garrett’s always quick to respond to inquiries, unit had just about everything we needed including beach towels and location is great as it’s a short bike ride from center town and peaceful/quiet if you’re looking for a balanced vacation.

Quick stats about holiday rentals that are family-friendly in Wellfleet

  • Total rentals

    260 properties

  • Nightly prices starting at

    $129 AUD before taxes and fees

  • Total number of reviews

    7.1K reviews

  • Pet-friendly rentals

    80 properties allow pets

  • Rentals with a pool

    10 properties have a pool

  • Rentals with dedicated workspaces

    80 properties have a dedicated workspace

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