
Vacation rentals with a pool in Maryland Beach
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Top-rated rentals with a pool in Maryland Beach
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Mad Men Beach House*DogFriendly*7 Min Walk 2 Sea*OUTDOOR MOVIE EXPERIENCE*Private Dock*WORK SPACE*New CRIB
After relaxing at the beach (just a 7 min walk away), unwind on our deck "watchin' the tide rollin' away!" Get the best of the bay & the beach with this dog-friendly hidden gem! Imagine evenings enjoying the bay breeze as you crack crabs on the deck! Relax inside our open-concept great room that allows everyone to be together. Fish on our private dock or use it for your own boat or jet-ski to dock there. Witness spectacular sunsets with our Kayaks. Enjoy a well lit, private work space to virtual work w/ high speed internet! A new wood CRIB now in master suite for restful sleep! The pools and tennis/pickleball courts are only a few blocks away for your enjoyment! Plus, a truly unique OUTDOOR MOVIE EXPERIENCE for all our guests to make for the best Vacay EVER!
FamilyLocationView
4.93 out of 5 average rating, 290 reviews
Beautiful waterview 2B condo w/Dock&Close to Beach
Welcome to the Canal Bungalow! A stylish 1000 sq. foot retreat to enjoy all the fun & relaxation of the coastal lifestyle in North Oc. Bring your boat with you and dock alongside your back porch, enjoy pool access in a private gated community, or bring your sports gear for Northside Park. We are tucked away on the quiet bayside of OC & only a few minutes walk to the beach. Unwind on our beautiful balcony while watching the boats go by & finally understand the true meaning of a coastal lifestyle!
LocationFamilyHeating
5.0 out of 5 average rating, 123 reviews
3 BR Waterfront Home, Minutes to the Beach
Recently updated waterfront house located in the family-friendly Montego Bay community. Enjoy beautiful sunsets on the back deck or hop in one of the kayaks for a paddle around the wide-open canal. Try your hand at crabbing or fishing off the dock to catch your dinner. Within easy walking distance of the beach and Northside Park (about 10 minutes walk to both). Beach chairs, toys, boogie boards, and umbrellas are yours to use for fun in the sand and surf. The dock is available for boat tie-ups.
FamilyLocationLayout
4.93 out of 5 average rating, 152 reviews
Direct Oceanfront Newly Renovated W/ Pool 2 Bd
A slice of paradise on the 18th floor! This fully renovated beachfront condo boasts breathtaking views of the glistening ocean. With two bedrooms and two modern baths, this haven offers the perfect blend of luxury and comfort. Imagine waking up to the sound of waves crashing and sipping your morning coffee overlooking the endless horizon. Whether you're lounging by the shimmering pool or strolling along the pristine shoreline, every moment here is infused with the tranquility of coastal living.
LocationFamilyCheckout
4.99 out of 5 average rating, 107 reviews
Cozy 3 BR Pet Friendly Beach, Bay & Pond nearby.
Relax with the family in this comfortable and charming home. There is room for 8 to sleep comfortably. The dining room and breakfast nook offer plenty of seating for all with a spacious kitchen. Our corner lot offers the option for outdoor fun like slip and slide, corn hole, frisbee, and more! Nearby: Beach, Bay, Wildlife sanctuary surrounded by a walking trail, Pool, Tennis, restaurants & Eventful Northside Park! Quiet and peaceful location to make family or romantic memories of a lifetime.
ValueLocationKitchen
4.97 out of 5 average rating, 162 reviews
Luxury Oceanfront Getaway!
Welcome to Marigot Beach, one of the most coveted buildings in OC. This newly renovated condo features a spacious one-bedroom with its own private 1/2 bath. Full bathroom located in the hallway. Sleeping arrangements can comfortably accommodate up to 4 guests, 2 can rest in the bedroom while 2 can enjoy the queen-size sofa in the living room. Included: free WiFi, smart TVs, fully equipped kitchen, washer/dryer, elevator. PLUS, a designated parking spot! Pool/hot tub closed are now OPEN!
FamilyValuePool
4.96 out of 5 average rating, 104 reviews
Cozy oceanfront condo with stunning ocean views
Fully updated 1 bed/1 bath oceanfront condo in a quiet, mid-rise building with a beachfront pool in uptown OC. The perfect unit for a quick romantic getaway, long weekend, or family vacation. We are happy to accommodate the dates and timeframes that meet the needs of our guests. If possible, please consider these recommended timeframes for your booking: Memorial Day - Labor Day -7 Nights, Fri-Fri or Mon-Mon -3 Nights, Fri-Mon -4 Nights, Mon-Fri Labor Day - Memorial Day -Any 2 Nights
ValueLocationBiking
4.98 out of 5 average rating, 271 reviews
Oceanfront 1 Bedroom, Balcony, Sitting Room, Pool
Opal Osprey: This OVERSIZE one-bedroom condo has been completely remodeled... giant oceanfront balcony PLUS a large patio room on the bayside! Expansive ocean views from every angle, super easy beach access, wonderful atmosphere in the quiet north end of OC. Linens included! Property Amenities - King size bed & queen sleeper - Large outdoor pool - Elevators - Dedicated high-speed WiFi and router w/ ethernet (Xfinity 100Mbps) - 2 Smart TVS with Xfinity, Roku - Keyless check-in 24/7
ValueLocationGetting around
4.95 out of 5 average rating, 191 reviews
Oceanfront Condo w/ Resort Amenities 3BDR &3pools
Sea Watch Condo's is an ideal family location with tons of amenities. The until is a recently updated 3 bedroom 2 bathroom condo that sleeps 6 people in 2 queen beds, 2 twin beds . The unit is ocean front with a large oceanfront balcony. The amenities Include, basketball court, tennis courts, playground, arcade, movie theater, billiard room, indoor pool and outdoor pool as well as a restaurant. The condo has 24 hour security and plenty of parking. Pools closed in off season
ValueLocationCheck-in
4.88 out of 5 average rating, 147 reviews
Direct Oceanfront with a View and Amenities Galore
Note: Must be 25 or older to rent our home. Beautifully renovated 2 bedroom beach front condo with views of both the beach and bay. Enjoy watching the waves roll in or a stunning sunrise through floor to ceiling windows without ever getting out of your king size bed. In the evening, open your front door to witness breathtaking sunsets over the bay. Or just relax with a drink on the beachfront balcony and listen to the waves with full 100% view of the beach and ocean.
LocationFamilyAccess
4.94 out of 5 average rating, 339 reviews
Nice 2 BR Oceanfront, Year Round Fun & Amenities!
Gorgeous kitchen & main areas renovated March ‘22. 2 bedroom, 1.5 bath, direct oceanfront condo on 7th floor of Golden Sands building in OC. It’s clean, comfy, stylish, full of amenities & in a great location. Great WiFi, 3 TVs with cable, DVD, well stocked kitchen & stunning ocean view with large balcony. Top floor has indoor pool, fitness room, sauna & game room. Outdoor pool, tiki bar, gift shop, market & deli open weather permitting in May, then daily by Memorial Day.
FamilyValueBathroom
4.91 out of 5 average rating, 331 reviews
Water Front Condo w/Pool Short Walk to Beach
FIRST FLOOR UNIT Bayside Condominium Sleeps 4 - 6 max Walking Distance to Northside Park Walk to the Ocean , don't worry about beach parking NON SMOKING 1 Bedroom 1 Bath condo, First floor unit with an outside deck This Air Conditioned, One Bedroom Condo has a fully equipped kitchen, washer/dryer, full refrigerator. There is a Queen bed and a full bed along with 1 Queen Sleep sofa in the living room *MUST BE 21 OR OVER* No Pets!
ValueFamilyAccuracy
4.89 out of 5 average rating, 187 reviewsPopular amenities for Maryland Beach rentals with a pool
House rentals with a pool

Ocean Pines Retreat with Beach Club
LocationValuePool
4.99 out of 5 average rating, 140 reviews
Spacious waterfront home & boat access!
FamilyLocationBackyard
4.95 out of 5 average rating, 108 reviews
Beautiful Waterfront Home-Private, Clean, Relaxing
LocationFamilyGetting around
4.99 out of 5 average rating, 238 reviews
The Big Chill at Bethany Beach
ValueLocationSleep quality
4.98 out of 5 average rating, 105 reviews
A Bethany Beach Gem 1.5 miles to Ocean Pickle Ball
ValueFamilyHospitality
4.94 out of 5 average rating, 218 reviews
Beachy Sunset Island Townhouse!
FamilyValueBathroom
4.91 out of 5 average rating, 102 reviews
Coastal Home - Outdoor Shower & 2 Pools
FamilyLocationHospitality
4.98 out of 5 average rating, 122 reviews
Lighthouse Bay Luxury Townhome | Arcade Loft
ValueLocationWalkability
5.0 out of 5 average rating, 14 reviewsCondo rentals with a pool

Ocean Front Condo
FamilyValueBathroom
4.97 out of 5 average rating, 102 reviews
1st Floor Canal Front POOL 2 Blocks 2 Beach/Park
FamilyValueIndoor spaces
4.97 out of 5 average rating, 116 reviews
Oceanview Oasis with 2 private balconies
FamilyLocationKitchen
4.86 out of 5 average rating, 127 reviews
Gone Coastal | Bay Views, Pool | Top Floor
ValueFamilyAccuracy
4.97 out of 5 average rating, 124 reviews
Designer Oceanfront Condo | Pool, Hot Tub & Deck
LocationFamilyLayout
4.94 out of 5 average rating, 106 reviews
Entire beautifully updated Condo with Ocean Views!
FamilyValueCheckout
4.93 out of 5 average rating, 107 reviews
Oceanfront Family Oasis: Pool, Beach & Parking!
FamilyLocationLaundry
4.9 out of 5 average rating, 366 reviews
DirectOceanFront on Boardwalk/Newly Remodeled/Pool
FamilyValueLong stay
4.78 out of 5 average rating, 244 reviewsOther vacation rentals with a pool

Oceanfront•Pool • Private Balcony w/Sunrise Views
ValueFamilyDecor
4.85 out of 5 average rating, 39 reviews
Little Paradise
FamilyValueCondition
5.0 out of 5 average rating, 33 reviews
Amenity Rich Carousel Buillding
FamilyValueOutdoor spaces
4.9 out of 5 average rating, 69 reviews
NEW: Oceanfront End-Unit Condo w/ 100ft Balcony
FamilyLocationComfort
5.0 out of 5 average rating, 11 reviews
Pool,Beach 2 Blocks,Pets,Air Hockey,Arcades,Garage
LocationFamilyCheck-in
5.0 out of 5 average rating, 34 reviews
2 BR 2BA North Ocean City Condo
LocationFamilyLaundry
4.93 out of 5 average rating, 59 reviews
Beachside Luxe: Pool, Ensuite & Family Favorite
LocationFamilyBeach
5.0 out of 5 average rating, 33 reviews
Beautiful Ocean City Escape w/ pool
FamilyLocationCleanliness
4.94 out of 5 average rating, 62 reviewsDestinations to explore
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