
Holiday rentals with a pool in Maryland Beach
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Top-rated rentals with a pool in Maryland Beach
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Popular amenities for Maryland Beach rentals with a pool
House rentals with a pool

Upscale Family Home, Community Pool, Grill
This place was amazing! It was so clean, well-stocked, and comfortable. Rob had all of the little touches including books and games for our kids, white noise machines, and lots of kitchen supplies like spices. The beds were super comfortable and we had even more space than we needed. Thanks so much for a wonderful weekend :)

Beach House on the MD-DE Border of Ocean City!
We had a great time at Karan’s place. It was clean and beautiful, in the perfect location. Unfortunately, the previous guest misplaced the pool key but Karan was apologetic and worked hard to get us access to the pool when we needed it. We had a great time and would definitely visit again.

Right behind Alley Oops & Crab Bag. Walk to beach
We had a great stay! The home was spotless and had everything we needed for a comfortable visit. The covered porch was a lovely spot to relax, rain or shine. Best of all, it’s in an ideal location—just a short walk to the beach, restaurants, and local shops. Highly recommend!

Luxe Lewes Carriage House: Spa Hot Tub/Estate Pool
Let's see...if Martha Stewart had a rental cottage, it would look just like Lisa and Jay's carriage house. Everything from the splendid charcuterie board and Prosecco on ice that awaited us upon our arrival to the beautifully designed cottage and wonderful gardens helped create an amazing vacation that we will not forget anytime soon. Jay and Lisa truly paid attention to every detail right down to the perfectly placed English antiques, fresh cut flowers and towels so thick you could drown in them. Nothing was missing and their hospitality made you feel right at home. We had smiles on our face the entire time! This is now my new Happy place. The gold standard by which every rental will be judged....perfect hosts, perfect place..like I said...Martha Stewart. Thank you Lisa and Jay for making our stay a wonderful experience!! We will definitely be back to your Lewes Carriage House whenever possible!

Beautiful Cottage W/ shared pool & close 2 beach
Everything was as described. Jennifer was very responsive and left excellent instructions on everything. We will stay there again.

Gorgeous 5BR, 4.5BA, in town, pool, hot tub, beach
We had a wonderful stay during our first visit to Rohoboth. The house was beautiful, spacious, and clean. The host was quick to respond to any question or need. The kitchen had everything we needed to cook and the dining area was great for playing our group games. We loved the pool and hot tub area as well. We would definitely come back!

Charming Condo with pool and 2 bedrooms
Our stay was wonderful. Beach and many restaurants/bars within walking distance. The host was extremely accommodating, kindly offering us the flexibility to check in a day early and check out late—an option we ultimately didn’t use, but greatly appreciated. The property was clean, comfortable, and exactly as described. I would gladly choose to stay here again.

Stunning Bayview Home with Own Private Pool
Thank you for hosting us! We had a blast. The house was perfect to host a bachelorette weekend with friends! There was enough space for everyone to sleep comfortably. We appreciated all of the additions in the kitchen and the grill. Made it easy to cook. Would recommend!
Condo rentals with a pool

Romantic Beachfront Penthouse Ocean City MD
This is the second year we stayed at this beautiful condo! Views of both ocean and the bay are spectacular!! Condo was clean and easy to access. Love the pool and beach! Close to great restaurants!! Margaret is a fantastic host!! Highly recommend this condo! We will definitely be back next year ❤️

Charming Northside Park Condo w Pool, Walk 2 Beach
Julie's condo is very cozy and welcoming. It's a wonderful place for a weekend or a longer vacation. Julie was very responsive and proactive anytime my wife and I had any questions. Plenty of recommendations were provided to us so we could better plan our time in Ocean. Thank you so much, Julie! We'll be back again!

*New*- North OC Oceanfront 1+BR with Pool
We had an absolutely amazing time, your house is beautiful and makes you feel right at home. We Loved the balcony, we sat out every morning and night to over see the beach! We would absolutely rebook this home again in the near future! You guys are doing a great job & makes us want to buy a condo now! Thank you!

Cozy oceanfront condo with stunning ocean views
Joe and Kristi were so nice, the condo was beautiful! The view of the beach was amazing, you can see the beach from the deck and even from inside through the glass, if you’re having a couple hours of relaxing time between activities, the view and sound of the beach makes it still fun to be inside on vacation. Great space to sleep. It was an amazing place to stay for vacation.

Luxury 2BD Condo, Walk to Beach, Pool&Tennis Court
We had an amazing stay the property was top tier the decor and design was very futuristic we loved everything about the stay!!!

🏖 *Ocean *Ocean *Ocean* 🏖 Beautiful Condo!!
Our stay was amazing, and Adam was communicative and extremely helpful the entire stay! Beautiful place and great location.

🌊Oceanfront studio w/ amazing views & amenities🏖
Lisa’s place was awesome and exactly how she described it! We loved waking up to the sounds of the ocean and the beautiful views of the bay and ocean. Everything you need is in this condo!!! Thanks again Lisa!!!

OCEAN FRONT Gem w/Pools, Movie Theater, Gameroom
I would 100% recommend Rodrigo’s condo! Such a quick walk to the beach and the amenities were great especially with a toddler. I liked how it wasn’t directly on the boardwalk, it made it feel like an area guided more towards families. The private laundry room was a great bonus too as well as being a corner unit to leave your beach items outside as well. I liked how there were items for children in the condo such as a pack and play and children’s plates etc. we didn’t need these items, but it was nice to see that it was included for those with children that may have forgotten certain items. Rodrigo was a great host as he was very quick to respond and was very helpful as well as just checking in to see that everything went smoothly and if we needed anything. I would definitely book here again for the next time we visit Ocean City, Maryland!!!!!
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- Ocean City Beach
- Broadkill Beach
- Assateague Island National Seashore
- Cape May Beach NJ
- Mile Beach
- Higbee Beach
- Poverty Beach
- Ocean City Boardwalk
- Dewey Beach Access
- Cape Henlopen State Park
- Jolly Roger Amusement Park
- Willow Creek Winery & Farm
- Northside Park
- Towers Beach
- Stone Harbor Beach
- Assateague Beach
- Jolly Roger at the Pier
- Bayside Resort Golf Club
- Poodle Beach
- Pearl Beach
- Delaware Seashore State Park
- Wildwood Dog Park & Beach
- Peninsula Golf & Country Club
- Plantation Lakes Golf and Country Club