Family-friendly vacation rentals in Dennis

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Dennis family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favorite
The exterior of the two-level condo is depicted, featuring a light green facade with white railings and balconies. The entrance, with a white door and copper awning, is shown along with two garage doors below. A landscaped area with minimal shrubs is visible next to the driveway.
Condo in North Wildwood
4.96 out of 5 average rating, 105 reviews

Beach block condo, pool/spa, 2 parking, 4 bdrms

MichelleRating, 5 stars1 month ago
The house was very spacious and accommodating. Great location near the beach and boardwalk. The host always responded quickly and was very easy going. We would definitely stay here again.
Guest favorite
Home in Dewey Beach
4.96 out of 5 average rating, 164 reviews

McAvoy B & B

JaimeeRating, 5 stars2 weeks ago
Great spot, responsive host, overall great experience!
Superhost
A view of the shared backyard reveals a hot tub surrounded by greenery and patio furniture. Colorful chairs are positioned on the lawn, inviting relaxation. The fenced area provides a sense of privacy. Nearby structures are visible, contributing to the neighborhood's atmosphere.
Apartment in Wildwood Crest
4.91 out of 5 average rating, 102 reviews

Nice and perfect for two. Hot Tub open for Use!

MattRating, 5 stars7 months ago
This is my 4th time staying and every year new improvements are made. I enjoy my time at this location
Top guest favorite
A dining area is visible, featuring a wooden table surrounded by black chairs with red seat cushions. A pendant light hangs above, illuminating the space. Adjacent to the dining area, a kitchen with light-colored cabinetry and modern appliances is suggested, creating a welcoming atmosphere.
Condo in Rehoboth Beach
4.96 out of 5 average rating, 160 reviews

Classy Beach Getaway

BrianRating, 5 stars2 weeks ago
Adair was very communicative and the condo was amazing! The decorations were a standout and made the unit feel like home.
Guest favorite
A view from the balcony showcases a sunny street lined with multi-story residential buildings. The horizon features distant structures, with the vibrant blue sky above scattered with wispy clouds, providing a sense of open space and proximity to the beach.
Condo in North Wildwood
4.91 out of 5 average rating, 213 reviews

North Wildwood 3 bedroom condo. Nice 18th street

NatashaRating, 5 stars1 month ago
This is the 2nd time my family and I stayed at Chris’s lovely humble abode. It is so pristine and comfortable in a quiet neighborhood. It’s close to the beach and restaurants (maybe 5 minutes by car). Thank you Chris for your prompt responses to a couple of our minor issues and/or questions. We really appreciate it!
Superhost
A jacuzzi is situated in a serene backyard setting, surrounded by trees. The cover is slightly raised, revealing a clear, reflective water surface. In the background, a house and a wooden fence are partially visible, enhancing the private atmosphere.
Home in Rehoboth Beach
4.68 out of 5 average rating, 72 reviews

Great Family Home in Rehoboth! Walk to the Beach!

KevinRating, 5 stars8 months ago
Our time spent in Reho was fantastic and so happy we had a great Airbnb to return to after all our excursions!
Superhost
Home in Atlantic City
4.86 out of 5 average rating, 322 reviews

AC Beach House / Hot Tub / 4 Blocks to Beach

TeleshaRating, 5 stars2 weeks ago
My stay was great! They responded as quickly as they could when needed. They were so kind to us overall. I loved their place! It was huge, spacious and I felt right at home. I loved the games they had for us too, the Nintendo was so cool!! We did try to use the hot tub, but we didn’t see it. I definitely should have asked where it was but everything else was great! Thank you so much!
Superhost
Home in Rehoboth Beach
4.95 out of 5 average rating, 105 reviews

Amazing Bay Vista Beauty with Private Pool!

RobertRating, 5 stars8 months ago
We have stayed here many times & wouldn't consider any place else. The home is very well furnished. The kitchen is very well supplied. It is minutes from Lewes, Rehoboth Beach, and Delaware State Parks and provides a very large swimming pool + hot tub. And you can't beat it for privacy which is very important to our large family. I'd give then place more stars if they were available.

Family- and pet-friendly home rentals

Guest favorite
A cozy living area features a comfortable dark sofa and a wooden dining table with matching chairs. A television is mounted on the wall opposite a sliding glass door, which opens to a deck with outdoor seating. Natural light fills the space.
Home in Brigantine
4.86 out of 5 average rating, 250 reviews

Gorgeous Beach House! Great Location. Low Pet Fee.

JohnRating, 5 stars6 days ago
Everything was super smooth and extremely cozy and clean. You have an amazing place! We loved it Looking forward to staying again soon!
Guest favorite
A cozy cottage is framed by vibrant green trees and shrubs, with a wooden deck featuring railings at the front. A patch of colorful flowers is visible near the base of the structure, enhancing the welcoming atmosphere of the home.
Cottage in Lewes
4.87 out of 5 average rating, 200 reviews

BnB’s Dog-Friendly Cottage

SharronRating, 5 stars1 week ago
Jacki’s place was very homey and comfortable. The place was very clean, quiet and had all the amenities one would need. She was also very responsive to any questions. I would highly recommend a stay in her little cottage.
Guest favorite
A sandy path leads through lush green grass toward the calm bay waters under a partly cloudy sky. The scenery captures the serene transition from land to water, inviting exploration just steps from the beach.
Cottage in Cape May
4.92 out of 5 average rating, 599 reviews

Charming Bayfront Tranquility

ShwetaRating, 5 stars3 days ago
I had a truly wonderful stay at Thomas’s place. The home is nestled in a peaceful, quiet neighborhood right by the ocean, offering stunning sunsets each evening right from the backyard. The house is well-equipped with everything you might need, but what stood out most was the positive energy throughout the space, it feels warm and welcoming. Thomas himself is a lovely host: kind, responsive, and thoughtful. I wholeheartedly recommend his place!
Guest favorite
A cheerful sunroom is filled with colorful toys and books, offering an inviting play space for children. A blue chair sits beside a lamp, while a television is positioned on a white shelf. Bright light enters through the windows adorned with white shutters.
Bungalow in Wildwood
4.94 out of 5 average rating, 106 reviews

One Level Beach Retreat by the Boardwalk and Beach

AdamRating, 5 stars6 months ago
Easy walk to the beach, great place if you have younger kids! Communication was great as well. Overall really happy with the stay, and my 6 year old stated it was one of his favorite places when we were leaving. If we return to the area in the future we'll see if it's still available to rent!
Guest favorite
A charming two-story farmhouse is situated under a large tree, surrounded by open green meadows. The house features a wraparound porch and large windows, blending with the natural environment. Sunlight filters through the trees, highlighting the vibrant greenery and wildflowers in the yard.
Cottage in Millville
4.89 out of 5 average rating, 230 reviews

Grandpa's House

JulianneRating, 5 stars1 month ago
We came back to this Airbnb a second time. It was just as lovely, beautiful, and serene to be in as the first time around. Thank you Kathleen and team for such a a wonderful stay and for being so great with communication and accommodations. 10/10 recommend this hidden gem! The entrance to the house may be hard to find at first, but once you do find the trail to drive in, it’s like driving through the enchanted forest into a private oasis. Thank you again!
Guest favorite
A charming house with blue siding and a welcoming front porch is surrounded by lush greenery. The porch features white railings and seating areas, while a mailbox stands at the edge of the front yard, contributing to a peaceful, country setting.
Cottage in Cape May
4.9 out of 5 average rating, 247 reviews

House on the Hill- Dog Friendly Near Cape May

SandraRating, 5 stars4 weeks ago
A lovely charming dog friendly home. It was a short drive to beaches, shops and restaurants. Ellen and Michael are wonderful hosts. The dogs enjoyed resting on the back porch and playing in the fenced in yard. We could not have asked for a more comfortable place for our stay in Cape May. An absolute gem.
Top guest favorite
A wooden deck is featured with white Adirondack chairs facing a small garden area. A dog walks across the deck towards a quaint shed with a circular window. Lush greenery surrounds the space, highlighting the natural setting.
Guesthouse in West Cape May
4.96 out of 5 average rating, 175 reviews

Dog Friendly Cape May Cottage

SarahRating, 5 stars3 months ago
We had a wonderful weekend. The space was clean and just like the photos. The neighborhood was quiet-but close to restaurants& shopping. Mike was super responsive&friendly& the space was great for our dog.
Guest favorite
A fenced backyard features a small tree with budding leaves, bordered by well-maintained lawn. Potted plants are arranged near a stone patio, which holds a set of black iron furniture beneath a screened porch, providing a serene outdoor dining space.
Home in Rehoboth Beach
4.9 out of 5 average rating, 117 reviews

Luxury Carriage House in Rehoboth Beach

TerryRating, 5 stars7 months ago
Beautiful home in beautiful neighborhood! Kitchen was well-equipped. Convenient location was an easy walk to the town of Rehoboth. Linda was very responsive to our questions and at check-in she walked us through how to use the appliances.

Family-friendly home rentals with a pool

Top guest favorite
Townhouse in Rehoboth Beach
4.94 out of 5 average rating, 175 reviews

Modern Beach Vibe - Rehoboth Beach

JonahRating, 5 stars2 weeks ago
great location close to everything we wanted to do..clean, well equipped and we'll maintained
Superhost
A shaded park area is presented, featuring a wooden gazebo and a playground. The playground includes blue slides and climbing structures set among lush green grass and trees. Picnic tables are located nearby, inviting outdoor gatherings.
Condo in Rehoboth Beach
4.79 out of 5 average rating, 285 reviews

Right on Silver Lake walk to beach!

NancyRating, 5 stars3 months ago
This was our third stay in this cozy little place and it was as clean and comfortable as always. Enjoyed beautiful snowy views of the frozen lake. We really appreciate the fireplace this time of year. Looking forward to visiting again!
Guest favorite
Home in Cape May
4.82 out of 5 average rating, 131 reviews

Beautiful 5BR house with inground salt water pool

JanitaRating, 5 stars7 months ago
We loved our stay! We had a great time as a family. one thing we thought of was we were very thankful our children were at the ages (5,3,2, 7 months) they were since there was lots and lots of glass stuff sitting around.
Guest favorite
The living area is furnished with a couch, loveseat, and chair, arranged around a coffee table on a colorful area rug. A flat-screen TV is mounted on the wall, and natural light is provided by windows with sheer curtains. Decorative lamps and art pieces enhance the space.
Condo in Rehoboth Beach
4.88 out of 5 average rating, 115 reviews

Coastal Beach Retreat: 3BR | Pool | Patio | W/D

TaylorRating, 5 stars7 months ago
Loved the place! Would be happy to visit again during the summer.. very close to the beach just a short drive, located on a one way highway just to note. Had the best time! Thank you!
Guest favorite
A colorful playground features multiple slides, climbing structures, and swings under a clear blue sky. The area is bordered by green grass and stone elements, providing a playful and inviting space for families to enjoy.
Condo in Rehoboth Beach
4.94 out of 5 average rating, 113 reviews

Cozy Condo on Silver Lake - Walk to the beach!

SarahRating, 5 stars7 months ago
Sue's place was absolutely perfect for our five night stay! Great location and an easy walk to the beach and town. The condo was so comfortable and had everything we could ever want. We were greeted with beautiful view of the lake every morning. It was everything we wanted and more. Sue and Don were the perfects hosts, so friendly and helpful! Can't wait to come back!
Top guest favorite
A refreshing saltwater inground pool is highlighted, featuring a unique shape with blue illumination surrounding the water. The pool is enclosed by a white fence, offering privacy and a serene environment for relaxation.
Home in Wildwood Villas
4.92 out of 5 average rating, 113 reviews

Wilde Rose By The Bay - Salt water Inground pool

NatashaRating, 5 stars7 months ago
This is a lovely home in a peaceful and safe neighborhood, perfect for families. We would stay again! It really is just steps to the beach. The kitchen was well stocked with spices and supplies to prepare meals. Everything was in working condition. The pool is beautiful! I loved the lights at night. The entire pool area is gated and locked, good to know for little ones. The shower had great water pressure. The outdoor shower has hot water too! The TV was very easy to use and had many options. Of note, the entire upstairs could accommodate a second family with a mini fridge, half bathroom, two beds, separate entrance, sofa/tv/table/patio - the photos really don’t do this home justice. I was very impressed when I walked inside. My kids LOVED the adorable spiral staircase to get upstairs! We had no problems with it, but it would be hard to keep little climbers off of it. The master bedroom is downstairs, something to consider with littles that wake up in the night and need to get down.
Top guest favorite
Home in Cape May
4.99 out of 5 average rating, 103 reviews

Bright, Airy 3 BR on 2 acres w/ POOL-West Cape May

MichaelRating, 5 stars5 months ago
Once again, we had a great time at Cara's home! Our third year here and we continue to be very happy with the location, amenities, and charm of the house. Thank you so much for your flexibity and for the wonderful note and delightful bottle of wine. Andrea & Michael
Top guest favorite
The private pool is surrounded by a spacious wooden deck. Two lounge chairs and a small side table are positioned adjacent to the pool, along with additional seating in the background. Clear water can be seen invitingly reflecting the daylight.
Home in Rehoboth Beach
5 out of 5 average rating, 192 reviews

Beautiful Beach House in Rehoboth

JenniferRating, 5 stars1 day ago
We had a wonderful stay at Autumn's house. The house itself was really lovely - clean, spacious, comfortable, and beautifully decorated. And the location was unbeatable: near enough to the beach and restaurants in town to walk everywhere, but in an adorable and quiet neighborhood. (We were visiting in the off season, so probably things are more hectic in the summer, but I would absolutely pick this house over other options in the future). Autumn was also very communicative and responsive. A great find all around.

Quick stats about vacation rentals that are family-friendly in Dennis

  • Total rentals

    110 properties

  • Nightly prices starting at

    ﺩ.ﺇ294 before taxes and fees

  • Total number of reviews

    1.8K reviews

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with a pool

    10 properties have a pool

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

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