
Vacation rentals with a pool in Maryland
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Maryland
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Maryland rentals with a pool
House rentals with a pool

4BR, 4BA, Amazing Indoor Pool, EV charger, ~10 acr
Gorgeous private property, surrounded by nature. Welcoming home with wonderful amenities. Instantly aware a great deal of thought was put into all aspects of this home, providing a seamless transition to vacation mode. Host was very communicative and helpful. Would highly recommend.

Sophia’s victorian
Perfect place for our stay in Germantown. Very cozy and the kitchen was fully stocked with cookware. Plenty of rooms for everyone to have their own space and also the family room was big enough for everyone to hang out together.

Amazing Large 4 Bedroom West OC Town House, Pool!
My family and I enjoyed our stay. We didn’t want to leave. The location was excellent. It was close to boardwalk, restaurants and the outlet mall. I loved not having to drive far to places. We will be back.

The Bury Oasis: Pool◈Hot Tub◈Master Suite◈PingPong
The Oasis was perfect for our needs . We will definitely book it again in the future!

Modern Bay Dream
Rick was very supportive and his communication was superb. Great host with a beautiful cozy home. 5 star all across the board.

Large Home with Pool & 7 bedrooms; sleeps 21
Staying here made our family wedding stay away from home, a very memorable and fun weekend for the whole family. Muvh better than being stuck in a hotel with lots of kids!!

Gunpowder Retreat
We had a great weekend! The host was incredibly kind and accommodating, making check-in and communication smooth from start to finish. The house itself was well-stocked, clean, and thoughtfully organized—perfect for relaxing with a small family group. We especially enjoyed winding down in the cozy living room and falling asleep to a movie after a fun day out. Would absolutely stay here again!

Luxury Home with Pool for 20
This was a great place for our family of 13 to stay during the weekend of our niece's wedding in Baltimore. The home has plenty of large common areas, dining space, and super comfortable beds - even the queen-size bunk beds on the lower level had high-end mattresses. The kitchen is well-equipped. We had 4 additional family members drop in for dinner on our last night there, and it was no problem preparing food for, and serving, 17 people. Everyone was happy with this choice for our accommodations.
Condo rentals with a pool

Bayside Boaters' Paradise | Pool | Family Fun
Beautiful view on the bay. Ally was very thorough & communicative throughout the process. Only thing that is kind of a bummer is that linens are not included. But other than that, I highly recommend Ally's condo.

Ocean Front 802 Midtown Oasis Pool & Parking
Katherine’s place is a great stay! The view from the balcony is lovely and the photos online are accurate. The bed was also probably the most comfortable bed we’ve ever had at an Airbnb. The location is just a few blocks from the start of the boardwalk and there are many restaurants within quick walking distance. It is very closer to one of the Jolly Roger locations that has a water park and a go kart section. It is however a longer walk (over 30 blocks) from the busiest part of the boardwalk. Because of this though it makes the are much quieter so it all depends on what you are looking for. We loved our stay and would absolutely stay again! In addition Kathryne was very responsive and even ordered and extra fire stick for one of the rooms so we could try and get Disney+ in there for our kids - above and beyond. Thank you for a great stay.

2BR Waterfront | 1st Floor | Patio | Pool | W/D
The place was optimum for our mini vacay. We absolutely loved the area, it was peaceful and relaxing and the amenities were just right. Jaqueline remained open and available for communication and was very clear in her expectations of us as guest. Definitely 5 Stars!

Ocean View Condo W/ Indoor and Outdoor Pool
Awesome place and great location for all OC activities!

Time N Tide Condo - 2 BR w/Pool, Boardwalk/Beach
The Time-n-Tide condo was great! Very well furnished, great decor, excellent amenities and great location. We felt very relaxed and comfortable during our stay, super cozy. Tina & Daryl we're very helpful with information and responsive to any questions we had. We hope to stay here again - great choice and value.

OC's Only Private Resort
Great place in a great spot! We enjoyed quiet mornings on the porch and being able to walk to nearby shops and restaurants with ease.

Paradise At Sunset Island In OC
We love staying at Sunset Island. This is the first time in a condo and it was perfect!

Family Friendly Two BR OCMD Condo Bay Side
It was a great place with lots of space! Diane even had a helpful manual with local stores, restaurants, hospitals, and pharmacies around the area. Very easy check in and check out process.
Destinations to explore
- Rentals with a patio Maryland
- Fitness-friendly rentals Maryland
- Private suite rentals Maryland
- Pet-friendly rentals Maryland
- Rentals with a fire pit Maryland
- Aparthotel rentals Maryland
- Ski-in/ski-out rentals Maryland
- Beachfront rentals Maryland
- Mansion rentals Maryland
- Beach house rentals Maryland
- Cabin rentals Maryland
- Rentals with a sauna Maryland
- Rentals with beach access Maryland
- Hotel rentals Maryland
- Chalet rentals Maryland
- Apartment rentals Maryland
- Cottage rentals Maryland
- Rentals with breakfast Maryland
- Beach condo rentals Maryland
- House rentals Maryland
- Rentals with outdoor seating Maryland
- Rentals with a fireplace Maryland
- Boutique hotel rentals Maryland
- Rentals with a home theater Maryland
- Rentals with a washer and dryer Maryland
- Townhouse rentals Maryland
- Rentals with lake access Maryland
- Smoking-friendly rentals Maryland
- Condo rentals Maryland
- Boat rentals Maryland
- Guesthouse rentals Maryland
- Tiny house rentals Maryland
- Kid-friendly rentals Maryland
- Rentals with an EV charger Maryland
- Rentals with an accessible height bed Maryland
- Bed and breakfasts Maryland
- Family-friendly rentals Maryland
- Lakehouse rentals Maryland
- Rentals with a hot tub Maryland
- Waterfront rentals Maryland
- Rentals with a kayak Maryland
- Rentals with an accessible height toilet Maryland
- Bungalow rentals Maryland
- Farmstay rentals Maryland
- Villa rentals Maryland
- Rentals with pools United States
- Cabins United States
- Treehouses United States
- Glamping United States
- Tiny Houses United States
- Beach Houses United States
- Campers and RVs United States
- Lakehouses United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Things to do Maryland
- Tours Maryland
- Nature and outdoors Maryland
- Sports activities Maryland
- Food and drink Maryland
- Art and culture Maryland
- Sightseeing Maryland
- Things to do United States
- Wellness United States
- Tours United States
- Sports activities United States
- Nature and outdoors United States
- Sightseeing United States
- Food and drink United States
- Entertainment United States
- Art and culture United States
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes