Holiday 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

Top Guest favourite
Home in Ocean City
5 out of 5 average rating, 47 reviews

Upscale Family Home, Community Pool, Grill

AnneRating, 5 stars3 weeks ago
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 :)
Guest favourite
Home in Ocean City
5 out of 5 average rating, 11 reviews

Beach House on the MD-DE Border of Ocean City!

JonRating, 5 stars9 months ago
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.
Guest favourite
Home in Ocean City
4.94 out of 5 average rating, 201 reviews

Right behind Alley Oops & Crab Bag. Walk to beach

KARARating, 5 stars2 weeks ago
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!
Top Guest favourite
Home in Lewes
5 out of 5 average rating, 23 reviews

Luxe Lewes Carriage House: Spa Hot Tub/Estate Pool

MaryRating, 5 stars4 days ago
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!
Guest favourite
Home in Ocean City
4.9 out of 5 average rating, 126 reviews

Beautiful Cottage W/ shared pool & close 2 beach

TerryRating, 5 stars2 weeks ago
Everything was as described. Jennifer was very responsive and left excellent instructions on everything. We will stay there again.
Guest favourite
Home in Rehoboth Beach
5 out of 5 average rating, 14 reviews

Gorgeous 5BR, 4.5BA, in town, pool, hot tub, beach

TammyRating, 5 stars2 weeks ago
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!
Guest favourite
Home in Ocean City
5 out of 5 average rating, 13 reviews

Charming Condo with pool and 2 bedrooms

AshleyRating, 5 stars3 weeks ago
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.
Guest favourite
Home in Ocean City
4.98 out of 5 average rating, 135 reviews

Stunning Bayview Home with Own Private Pool

EleniRating, 5 stars3 weeks ago
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

Guest favourite
Condo in Ocean City
4.82 out of 5 average rating, 154 reviews

Romantic Beachfront Penthouse Ocean City MD

PatriciaRating, 5 stars10 months ago
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 ❤️
Guest favourite
Condo in Ocean City
4.98 out of 5 average rating, 41 reviews

Charming Northside Park Condo w Pool, Walk 2 Beach

AndyRating, 5 stars4 weeks ago
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!
Superhost
Condo in Ocean City
4.75 out of 5 average rating, 4 reviews

*New*- North OC Oceanfront 1+BR with Pool

CortneyRating, 5 stars1 week ago
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!
Top Guest favourite
Condo in Ocean City
4.99 out of 5 average rating, 219 reviews

Cozy oceanfront condo with stunning ocean views

SamanthaRating, 5 stars1 week ago
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.
Superhost
Condo in Ocean City
4.94 out of 5 average rating, 18 reviews

Luxury 2BD Condo, Walk to Beach, Pool&Tennis Court

TracyRating, 5 stars2 weeks ago
We had an amazing stay the property was top tier the decor and design was very futuristic we loved everything about the stay!!!
Superhost
Condo in Ocean City
4.83 out of 5 average rating, 276 reviews

🏖 *Ocean *Ocean *Ocean* 🏖 Beautiful Condo!!

DanielleRating, 5 stars4 days ago
Our stay was amazing, and Adam was communicative and extremely helpful the entire stay! Beautiful place and great location.
Superhost
Condo in Ocean City
4.88 out of 5 average rating, 196 reviews

🌊Oceanfront studio w/ amazing views & amenities🏖

LawrenRating, 5 stars3 weeks ago
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!!!
Guest favourite
Condo in Ocean City
4.95 out of 5 average rating, 108 reviews

OCEAN FRONT Gem w/Pools, Movie Theater, Gameroom

BrittanyRating, 5 stars3 days ago
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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