
Holiday rentals with a pool in Dennis
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Dennis
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.
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Popular amenities for Dennis rentals with a pool
House rentals with a pool

Beautiful 5BR house with inground salt water pool
This place was big enough for my family and a very good experience from the time we arrived till we left. Maria was very polite and welcome to us. The pool was warm enough for us and she kept up with keeping it comfortable for my grandchikdren. I recommended this property as a place to stay for a week with your family. Perfect stay.

2 houses from Bay with hot tub, fully fenced in!
We had a lovely time at this bayfront home! The views from the balconies were amazing. The house was very very clean and had everything we needed. Host answered our questions and had helpful communications. We hope to visit again soon!

Comfortable Home in Millville with Private Pool
Jerrell was a wonderful host with a beautiful home. It was clean, easy to find, conveniently located near shops, and the pool was amazing. Would definitely stay again!

Tremendously Charming Get Away!
Very lovely and spacious place that made us feel right at home. The area is quiet and private, yet only 15 minutes away from downtown Cape May, making it a great location for what we were looking for. Gail was a superb host and made our first experience using Airbnb a very pleasant one. I definitely recommend!

Wilde Rose By The Bay - Salt water Inground pool
House was great and everything we expected. Rose responded very quickly and was very accommodating. Would recommend to anyone.

Mystical Cape May's Modern Farmhouse: The Widmore
Dave’s place was nothing short of phenomenal. I’ve stayed at many an Airbnb and have never had such a pristine experience along with a host that was bending over backwards. I don’t think I waited more than 10 minutes for a response from Dave when I had a question. The location is at the top of cape may with beautiful scenery in the front and total privacy in the back. I can’t encourage people enough to stay here! It was perfect.

Beautiful Beach House in Rehoboth
Had the absolute best time staying at this gem. The house is stunning and Autumn was a fantastic host! The house is spacious and open. It was exactly as described but better. We couldn’t have been happier. Will definitely be back!

Relaxing Getaway
I went with a group of friends to celebrate my bachelorette weekend. It was a amazing space! Everyone loved it and the house is extremely well maintained. Such a great spot to go have a relaxing weekend with family or friends. The house is super cute and well decorated. There are some great restaurants and bar near by. Rich was very responsive and professional. I had the best weekend with my girls!
Apartment rentals with a pool

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

Oceanfront Condo | NEW Retro Design | Beach + Pool
LOVED our stay at The Crest Beach House! We came a few years ago and knew this was the place to go when we wanted to return to the area. The new design is gorgeous. It perfectly captures that fun, nostalgic Wildwood vibe but feels so fresh, clean, and elevated. You can really tell how much thought went into every detail. The updated living area was one of our favorite parts — having a real sitting space made it feel like home. We could put the bedding away during the day and actually enjoy watching TV, playing games, and relaxing together. The location is still unbeatable — just steps from the beach and close to everything. Plus, all the amenities made packing super easy — from kitchen essentials to the little touches that make a vacation stress-free (like extra supplies for our toddler! - plates, utensils, beach toys, children books, sound machine, gated toddler pool section) Our favorite part is enjoying our morning coffee & tea on the balcony while listening to the waves 🌊 💗

Boardwalk side Cozy Family Condo w/ parking
We had an excellent stay! The space was on the smaller side as listed but it was thoughtfully set up and had everything our family needed for a comfortable visit. The location truly couldn’t be better — just steps from the beach and close to local restaurants and shops. It made it easy to enjoy our time together without having to travel far. Everything was clean, comfy, and convenient. Beach tags included and pool access were added bonuses! We’d definitely stay here again and hope to book again soon for an easy beach getaway. Book for yourself , You won’t be disappointed

Rarely Available Mid Century Modern Beach Front!
Out stay in Nick place was wonderful 😀 we love the location and the atmosphere of the place. The ocean view was phenomenal too ❤️ Thank you to Nick to let’s us stay here , We will definitely miss this place, and of course we will definitely come back again soon 🙃.

2b 2b condo! 2 master bedrooms! rehoboth beach
I had such a great experience staying at this Airbnb — one of the best I’ve ever booked! The space was super clean, well-organized, and felt really welcoming from the moment I arrived. There were extra blankets and pillows in the closet, which was a thoughtful touch, and I was greeted with a cute goodie basket full of snacks and essentials — such a nice surprise! The two bedrooms were spacious and cozy, perfect for relaxing after a long day. The entire place felt comfortable and well-kept, and the kitchen had everything I needed. The pool was definitely a highlight — clean, peaceful, and perfect for a quick dip or just lounging. Overall, this was an amazing stay. I’d absolutely come back and highly recommend it to anyone looking for a clean, cozy, and relaxing place!

Look Out the Window Ocean, Boardwalk, Beach
This Airbnb was everything we hoped for and more! The location is perfect—just steps away from the boardwalk and all the action in Atlantic City. Check-in and check-out were a breeze, making the whole experience stress-free. The views from the place were absolutely incredible—waking up to the ocean each morning was a dream. Highly recommend staying here if you’re looking for comfort, convenience, and a memorable getaway!

Modern 2BR/2BA – Beach Pass + Bikes, 5 Min Drive
We had a perfect stay at Jonathan’s place. Very clean & nicely decorated condo in a quiet, relaxed location which is an easy drive to Rehoboth. Comfortable beds. Convenient to the bike trail which we rode to Lewes & Cape Henlopen. I just found the single-gear bike was very hard to peddle so I’d recommend you plan on renting a newer one if you want to enjoy your ride (unless, of course, you want a challenging workout!)

Cozy condo in the Villages of Five Points, Lewes
This rental was really a great find for our stay in Lewes DE. Easy to find, keypad instructions were great, and very close to a lot of places! The hosts provided a clean and sanitized home for us for the week. The only issue was the low battery in the keypad in which the owner advised they would fix it—and we had zero trouble with it anyways! The hosts respond to any inquiry within a very reasonable time as well. They are very attentive to any questions and concerns you may have. My family and myself will definitely look into staying with these hosts again! Will also recommend to family and friends for their vacations as well. Thank you!
Quick stats about holiday rentals with a pool in Dennis
Total rentals
20 properties
Nightly prices starting at
₹6,923 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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- Brigantine Beach
- Broadkill Beach
- Fortescue Beach
- Cape May Beach NJ
- Mile Beach
- Public Beach
- Higbee Beach
- Poverty Beach
- Dewey Beach Access
- Cape Henlopen State Park
- Chicken Bone Beach
- Diggerland
- Willow Creek Winery & Farm
- Ocean City Beach
- Towers Beach
- Stone Harbor Beach
- Lucy the Elephant
- Poodle Beach
- Delaware Seashore State Park
- Pearl Beach
- Ventnor City Beach
- Wildwood Dog Park & Beach
- Peninsula Golf & Country Club
- Killens Pond State Park