Vacation rentals with a pool in Dennis

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Popular amenities for Dennis rentals with a pool

House rentals with a pool

Top guest favorite
Home in Ocean City
5 out of 5 average rating, 27 reviews

Ocean City home on the bay with pool!

DonaldRating, 5 stars7 months ago
Beautiful home,Better than described, super clean. I highly recommend! We rented the house for week to attend a wedding and couldn’t have been more pleased, from the boat slips/ docks for my jetskis, sea kayaks to the heated pool , all great features! Those were just a few things to mention, the entire home and property are drop dead gorgeous and well kept, every little thing you can think of was provided, these people go above and beyond to ensure you have a great vacation. I would highly recommend this property to friends and family members.
Top guest favorite
Home in North Wildwood
4.93 out of 5 average rating, 45 reviews

north wildwood beach block house pool use

CraigRating, 5 stars6 months ago
The whole process from reservations, to our stay then to check-out was easy and straightforward. This was to be a quiet weekend with my daughter and no (grand)kids. It was that and more. Great location. Very clean and well equipped. You can book this with confidence.
Top guest favorite
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.
Superhost
Home in Dover
4.67 out of 5 average rating, 12 reviews

Quiet Getaway with pool!

DarlineRating, 5 stars1 day ago
As we opened the door, there was that great, welcoming smell. The place was very clean, beds well made, ready for us. Our host even had snacks for us which were welcoming since we had a 3-hr trip to get there. We definitely recommend this place to a big family!
Guest favorite
Home in Cape May Court House
4.87 out of 5 average rating, 92 reviews

7 Bedroom| Beach| Pool| Walk to Bars & Restaurants

ErikaRating, 5 stars4 weeks ago
Jason was responsive and helpful. The only thing we were a bit disappointed with was the heated pool and hot tub. We were unable to use it because something was broken and his pool guy didn’t have the means to fix it over the weekend. While understandable, it was a bummer because that was one of the amenities we were really looking forward to. The house was spotless, rooms were comfortable and accommodating. If I could offer any tips for the homeowner, we would have liked to have seen instructions left for the heating/cooling split units as they were a bit weird to figure out having never used one. Overall, if I had another large party to accommodate, I would return here.
Top guest favorite
Home in Villas
4.99 out of 5 average rating, 126 reviews

Hot Tub Backyard Oasis, Private Beach, Local Pool

KaylaRating, 5 stars1 week ago
The house was even nicer than it appeared in the pictures. The living area is spacious and the bedrooms and bathrooms comfortable for our family's needs. The outdoor area was very enjoyable as well. It is evident that Heather has put a lot of care into creating a welcoming vacation home.
Top guest favorite
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.
Top guest favorite
Home in Rehoboth Beach
5 out of 5 average rating, 72 reviews

Spacious Living in Rehoboth, with a Pool

ClaireRating, 5 stars4 months ago
Lovely place to stay! My family and I had our Christmas here and it was the perfect space. It was comfortable, came well stocked, and had nice touches throughout the home.

Condo rentals with a pool

Guest favorite
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
Condo in Wildwood Crest
5 out of 5 average rating, 6 reviews

Ocean View Condo—Pool, Elevator, Linens, towels

PhyllisRating, 5 stars6 months ago
Three of us women friends spent a week in early October. Wonderful! Fun! Relaxing! The condo was bright and cheery, even nicer than the pictures. Comfy, close to beach, We loved eating on the patio, especially in the morning. Spotted a dolphin(s) from the porch with binoculars, spouting as he/she moved along. And a hawk low in the vegetation next to small boardwalk. Nice details that made us feel welcome, bottle of wine with a note, keurig coffee and hot chocolate, use of beach chairs. Lovely and set up thoughtfully for guests. Hope to visit again!
Guest favorite
Condo in North Wildwood
4.88 out of 5 average rating, 64 reviews

1 BED/1 BATH HEATED POOL BEACH CONDO FOR RENT

JaiseRating, 5 stars8 months ago
The accommodations were private and serene, providing a peaceful retreat. The location was convenient, with a short 15-minute walk to the vibrant boardwalk and sandy beaches. We appreciated the thoughtful gesture of welcome snacks, which were especially comforting after our long journey. The rocking chairs on the property offered a relaxing spot to unwind after our beach days. We enjoyed exploring the local dining scene, with standout meals at Vegas Diner and Russo’s Market. The sandwich I ordered at Russo’s Market was truly exceptional, the largest I’ve ever encountered. This was the perfect weekend getaway for my wife and me, offering a balance of relaxation, convenience, and local experiences.
Superhost
Condo in Wildwood
4.78 out of 5 average rating, 268 reviews

Cozy Wildwood Crest Beach - Poolside Condo

DianeRating, 5 stars7 months ago
Just returned from my 6th stay at Erica’s condo. Most of the units are owner occupied with only a few rentals. It’s perfect for those looking for a chill relaxing environment. Just a few blocks to the beach, Centennial Park (has live music series!), and Sunrise Park. Erica is an awesome host, the condo is perfect and well maintained. We’re already booked again for next year!
Top guest favorite
Condo in Rehoboth Beach
4.98 out of 5 average rating, 179 reviews

Renovated Condo Near Outlets, 3.5 Miles to Beach

PeterRating, 5 stars2 weeks ago
Perfect place for our stay. It was so clean and Zoltan and Noemy were so kind and gave us so much information. I'd give them more than 5 Stars if I could. I recommend their beautiful condo to anyone visiting Rehoboth! Thank you for a great stay!!
Guest favorite
Condo in North Wildwood
4.96 out of 5 average rating, 56 reviews

Surfside 2 Bedroom Condo with a Pool!

KristenRating, 5 stars1 week ago
I’ve stayed at this place multiple times. Great location and the perfect size. Would highly recommend!
Guest favorite
Condo in Milford
5 out of 5 average rating, 11 reviews

Cozy Condo

ArmandRating, 5 stars8 months ago
We really enjoyed our stay at the condo! Maria was helpful and responsive. All amenities were as described. We’d we happy to stay at this location again.
Guest favorite
Condo in Diamond Beach
4.92 out of 5 average rating, 26 reviews

Walkout Balcony to Pool Seapointe - Diamond Beach

MattRating, 5 stars1 week ago
My family and I enjoyed our stay which was off season. The indoor heated pool was great for my two small kids. The property looked nice and I’m sure in the late spring and summer it would be amazing. Right on the beach. Plenty to do and walk to. The unit is not huge but we did not feel cramped. I would recommend this place and the host.

Quick stats about vacation rentals with a pool in Dennis

  • Total rentals

    20 properties

  • Nightly prices starting at

    ﺩ.ﺇ294 before taxes and fees

  • Total number of reviews

    580 reviews

  • Family-friendly rentals

    10 properties are a good fit for families

  • Wifi availability

    20 properties include access to wifi

  • Popular amenities

    Kitchen, Wifi, and Pool

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