Guest favoriteHuge 5 Bedroom/Ocean Views/ Pool/ Now Accepting Bookings for 2024
5.00House in Ocean City
5 Bedrooms · 3 Bathrooms · Sleeps 14
$335/night
Stays with Pool in Maryland
25 stays availableStatewideAmenity
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Guest favorite
Top rated6 Bedroom/3.5 Bath Direct Bayfront Home Near the Beach in Downtown Ocean City
5.00House in Ocean City
6 Bedrooms · 3 Bathrooms · Sleeps 16
$900/night
Top ratedYear Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28
5.00Estate in Cambridge
7 Bedrooms · 7 Bathrooms · Sleeps 28
$1,800/night
Top ratedFabulous Large Ocean Front Condo located on the OC boardwalk
5.00Condo in Ocean City
3 Bedrooms · 3 Bathrooms · Sleeps 11
$217/night
Top ratedOceanfront, Jacuzzi (overlooks ocean), Fireplace, 2 Heated Pools, Game rooms
5.00Condo in Ocean City
3 Bedrooms · 2 Bathrooms · Sleeps 13
$195/night
Top ratedFabulous Views from this Spacious Ocean Front 4 BR Condo Sleeps 12 Indoor Pool not open 2020
5.00Condo in Ocean City
4 Bedrooms · 3 Bathrooms · Sleeps 12
$293/night
Top ratedGeorgous Large Ocean Front Condo on Boardwalk w/ Extended Balcony Roof Top Pool
5.00Condo in Ocean City
3 Bedrooms · 3 Bathrooms · Sleeps 11
$207/night
Top ratedLarge Bayfront Condo Private Balcony Fantastic Views of Bay and Sunsets Rooftop Pool/Sundeck
5.00Condo in Ocean City
3 Bedrooms · 3 Bathrooms · Sleeps 10
$157/night
Top ratedSpacious West Ocean City Town Home - Close to Attractions - Great Community
5.00House in Ocean City
5 Bedrooms · 4 Bathrooms · Sleeps 14
$500/night
Top ratedCedar Point 6.5 Acre Waterfront Family Retreat With Pool And Sandy Beach!
5.00Cottage in Cambridge
3 Bedrooms · 2 Bathrooms · Sleeps 9
$550/night
Kingsbay Waterside Cottage | Crisfield Vacation Rental
Cottage in Crisfield
1 Bedroom · 1 Bathroom · Sleeps 4
$400/night
Top ratedNew! Bayfront Condo w/ Fantastic Views Small building with Great Bay Front Pool
5.00Condo in Ocean City
4 Bedrooms · 3 Bathrooms · Sleeps 12
$224/night
Top ratedKingsbay Mansion Bayhouse | Crisfield Vacation Home
5.00House in Crisfield
5 Bedrooms · 3 Bathrooms · Sleeps 10
$750/night
Top ratedKingsbay Waterside Retreat House
5.00House in Crisfield
5 Bedrooms · 3 Bathrooms · Sleeps 10
$895/night
Top ratedKingsbay Dockside Waterfront House
5.00House in Crisfield
4 Bedrooms · 3 Bathrooms · Sleeps 8
$795/night
Top ratedSpectacular Ocean Views! Large Penthouse Level Condo on Boardwalk w/60' Balcony
5.00Condo in Ocean City
3 Bedrooms · 3 Bathrooms · Sleeps 10
$205/night
Top ratedBeautiful Totally Refinished Penthouse with Great Views and 1 blk to
5.00Condo in Ocean City
5 Bedrooms · 3 Bathrooms · Sleeps 14
$268/night
Top ratedGreat Large Ocean Front Condo Directly on Boardwalk Elevated Pool 70" HD
5.00Condo in Ocean City
3 Bedrooms · 3 Bathrooms · Sleeps 12
$445/night
Top rated3 Bed, 2 Bath 30th Street Condo, 100 yards to the beach
5.00Condo in Ocean City
3 Bedrooms · 2 Bathrooms · Sleeps 10
$300/night
Top rated30th St Great Location 150 Yards to the Beach
5.00Condo in Ocean City
3 Bedrooms · 2 Bathrooms · Sleeps 10
$340/night
Top rated18th Street- Great Location 400 Ft to the Beach and Boardwalk
5.00Condo in Ocean City
3 Bedrooms · 2 Bathrooms · Sleeps 10
$350/night
Top ratedThe Atlantic at Your Doorstep
5.00Condo in Ocean City
2 Bedrooms · 2 Bathrooms · Sleeps 8
$145/night
Top ratedOutstanding View of the Atlantic from Your Living Room
5.00Condo in Ocean City
1 Bedroom · 1 Bathroom · Sleeps 6
$136/night
Top ratedCommanding View From Direct Oceanfront Condo
5.00Condo in Ocean City
1 Bedroom · 1 Bathroom · Sleeps 6
$134/night
Top ratedDiamond Head - Ocean View Condo w/Pool, Elevator And Just Steps To The Beach!!
5.00Condo in Ocean City
1 Bedroom · 1 Bathroom · Sleeps 6
$100/night
About Stays with Pool in Maryland
Guest reviews for Stays with Pool in Maryland: 5.0 average from 90 reviews across 24 of 25 stays
Stays with Pool in Maryland — 25 vacation rentals booked directly with their owners and managers.