Ocean Pines holiday rentals
We found 7,390 holiday rentals — enter your dates for availability
Discover a selection of 122 homes and other holiday rentals in Ocean Pines that are perfect for your trip. Whether you’re staying in a holiday home with your children or with friends, you'll have the best amenities for spending time at your home away from home, which might include parking and a garden. At the end of the day, you'll find a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.
Holiday rentals with weekly discounts – Ocean Pines
Showing deals for:4 Dec - 11 Dec
Exceptional
(73 reviews)
FAIRWAY TO HEAVEN: GOLF course views and BEACH parking pass
Berlin
S$2,028
for 7 nights, 1 apartment
S$290 per night
includes taxes & fees
Exceptional
(127 reviews)
Pet Friendly Near Berlin, Assateague Island Beaches and Ocean City
Berlin
S$1,694
for 7 nights, 1 home
S$242 per night
includes taxes & fees
Exceptional
(10 reviews)
Ocean Pines Chalet
Berlin
S$2,611
for 7 nights, 1 home
S$373 per night
includes taxes & fees
Exceptional
(44 reviews)
Ocean Pines Retreat with Beach Club
Berlin
S$2,461
for 7 nights, 1 home
S$352 per night
includes taxes & fees
Exceptional
(29 reviews)
Private and pet-friendly, with game room and upgraded kitchen
Berlin
S$2,248
for 7 nights, 1 home
S$321 per night
includes taxes & fees
Exceptional
(18 reviews)
Summer Breeze - Waterfront Cottage For Rent
Berlin
S$3,819
for 7 nights, 1 home
S$546 per night
includes taxes & fees
Exceptional
(30 reviews)
Newley Renovated Beach Home, Min. to Ocean City,1st FL. Master Suite, walk in
Berlin
S$2,743
for 7 nights, 1 home
S$392 per night
includes taxes & fees
Exceptional
(105 reviews)
Huge Direct Oceanfront Townhouse with Beautiful Sunrises
Ocean City
S$3,039
for 7 nights, 1 home
S$434 per night
includes taxes & fees
Exceptional
(111 reviews)
Direct Oceanfront 3 bedroom condo perfect for family and friends with pools
Ocean City
S$2,001
for 7 nights, 1 apartment
S$286 per night
includes taxes & fees
Exceptional
(147 reviews)
BEAUTIFUL & CLEAN! Waterfront condo with epic sunsets and a POOL!
Ocean City
S$1,820
for 7 nights, 1 apartment
S$260 per night
includes taxes & fees
Exceptional
(5 reviews)
Cozy house in Ocean pines, only 10 mins away from Ocean City.
Berlin
S$3,489
for 7 nights, 1 home
S$498 per night
includes taxes & fees
Exceptional
(57 reviews)
Beautiful Beachfront 2 Level Penthouse w 2 balconies! Full Ocean Views SLEEPS 7!
Ocean City
S$7,048
for 7 nights, 1 apartment
S$1,007 per night
includes taxes & fees
Exceptional
(53 reviews)
10 minute walk to the beach! Family- size condo
Ocean City
S$1,902
for 7 nights, 1 apartment
S$272 per night
includes taxes & fees
Exceptional
(61 reviews)
Bear Trap Dunes: Spacious and Sparkling 3 Bedroom with All the Amenities!
Ocean View
S$2,053
for 7 nights, 1 home
S$293 per night
includes taxes & fees
Exceptional
(30 reviews)
SERENE WATER VIEWS-Relaxing family beach house
Ocean City
S$4,724
for 7 nights, 1 home
S$675 per night
includes taxes & fees
Exceptional
(101 reviews)
Stay at Heron Cove located in popular Mallard Lakes!
Selbyville
S$847
for 7 nights, 1 apartment
S$121 per night
includes taxes & fees
Exceptional
(9 reviews)
Broad Marsh Beach Home | Pool + Balcony Views
Ocean City
S$3,058
for 7 nights, 1 apartment
S$437 per night
includes taxes & fees
Exceptional
(94 reviews)
ADAGIO#207 BEAUTIFUL 3 BED/3 BATH OCEAN BLOCK CONDO W/INDOOR POOL STEPS TO BEACH
Ocean City
S$3,011
for 7 nights, 1 apartment
S$430 per night
includes taxes & fees
Exceptional
(105 reviews)
Direct Oceanfront Condo on 11th Floor with Amazing views of Ocean and Bay
Ocean City
S$1,608
for 7 nights, 1 apartment
S$230 per night
includes taxes & fees
Exceptional
(111 reviews)
Delightful Escape, Oceanfront 2BDR , Awesome Views, Pool, Clean!
Ocean City
S$1,956
for 7 nights, 1 apartment
S$279 per night
includes taxes & fees
Exceptional
(101 reviews)
Escape to The Ocean! , Ocean Front, Beautiful View, Pool!
Ocean City
S$1,956
for 7 nights, 1 apartment
S$279 per night
includes taxes & fees
Exceptional
(13 reviews)
Private Pool Steps From the Beach
Ocean City
S$1,645
for 7 nights, 1 apartment
S$235 per night
includes taxes & fees
Exceptional
(65 reviews)
Beachfront living near Seacrets! Don't let this memorable getaway pass you by.
Ocean City
S$2,436
for 7 nights, 1 apartment
S$348 per night
includes taxes & fees
Exceptional
(90 reviews)
Great Location for your vacation. Very Pet Friendly!. Close to Boardwalk/Beach.
Ocean City
S$3,275
for 7 nights, 1 apartment
S$468 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find properties near top attractions in Ocean Pines
Ocean Pines Golf and Country Club
More information about Ocean Pines Golf and Country Club. Opens in a new window.Find the best place to stay - Ocean Pines
Patio, Pool Access! Coastal Ocean Pines Cottage
Sleeps 3 · 3 bedrooms · 1 bathroom
Dog Friendly! Ocean Pines 'Crabby Cottage'
Sleeps 3 · 2 bedrooms · 1 bathroom
Spacious Home, With Dock, Sleeps 9, Access To Beach Club & Pool
Sleeps 9 · 3 bedrooms · 2 bathrooms
White Horse Park-Spinnaker Lane 96 - Free WIFI,Pool,AC
Sleeps 4 · 3 bedrooms · 1 bathroom
White Horse Park-Skipjack Court 120
Sleeps 4 · 2 bedrooms · 1 bathroom
Pet friendly-Waterfront Home- Pools-Self Check-In- Beach Club Parking Included.
Sleeps 8 · 3 bedrooms · 2 bathrooms
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value
Frequently asked questions
What is the most popular type of holiday rental accommodation in Ocean Pines?
Based on our research, houses are the most desirable type of holiday rental in Ocean Pines. But of course, everyone's idea of the perfect stay differs. Vrbo has holiday rentals of all sizes and shapes, and we'll help you to find the perfect match.
How much does it cost to rent a holiday rental in Ocean Pines?
Property type, length of stay and season are some of the conditions that can influence the price of a holiday home. Simply click on your travel dates to find your perfect fit. From comfy cottages to expansive luxury villas, all Vrbo holiday rentals provide unbeatable value.
How much does it cost to rent a beach house in Ocean Pines?
Prices for beach houses in Ocean Pines vary depending on the style and size of the property and time of year you're travelling. Simply enter your dates of travel into Vrbo and the number of guests to view holiday rental options and prices. From there you can use our filters to refine your search results by nearby activities, ratings, amenities and more.
Are there pet-friendly holiday rentals in Ocean Pines?
Pack up a suitcase for the pooch in your life because Ocean Pines has 173 stays that welcome pets with open arms. Let your four-legged pal join in on the family trip at one of our pet-friendly holiday rentals on Vrbo. Simply enter your travel dates then check the "Pets allowed" filter box.
Can I rent a house with a pool in Ocean Pines?
Grab your swimsuit and pool noodle, because there are 128 houses with a private pool in Ocean Pines. Stay at one of these superb holiday rentals and you'll enjoy pool days every day. Simply enter your dates into Vrbo, then check the "pool" filter to find a place to make a splash!
What are popular rental amenities in Ocean Pines?
A nearby waterfront, a lake view and a swimming pool are the most popular rental amenities in Ocean Pines. Whether you're taking a trip by yourself, with your other half or a bunch of friends, Vrbo can help you find a holiday home that suits your style with all the features you'll enjoy.
Are there large group holiday rentals in Ocean Pines?
You can choose from 44 holiday rentals in Ocean Pines that can host a group of 10 or more people. Whether you're organising a holiday with extended family or a celebration like an anniversary, there's ample space to get your favourite people together under the same roof.
Are there holiday rentals in Ocean Pines that welcome kids?
With 173 family-friendly holiday homes to choose from in Ocean Pines, now is the perfect time to introduce your little ones to the pleasures of travel. Simply click on our "Properties good for families" filter to look for stays that feature conveniences perfect for families on the move, such as multiple bedrooms, pools, hot tubs and bunk beds.
What are the top attractions for families in Ocean Pines?
Keeping the kids entertained during your stay in Ocean Pines is simple with these top family-friendly attractions:
- Frontier Town Water Park and Golf
- GlenRiddle Golf Club
- River Run Golf Club
Are there one-bedroom holiday rentals in Ocean Pines?
Yes, there are two one-bedroom properties in Ocean Pines to pick from. A one-bedroom holiday rental is a great option if it's only two of you or if you're holidaying alone. Add in more convenience, space and privacy compared to a hotel, and you've got the makings of an unforgettable trip.
Can I find two-bedroom holiday rentals in Ocean Pines?
Choose from 14 two-bedroom homes in Ocean Pines. Settle the kids into the second room or fill it with a couple of your nearest and dearest friends. There's a spot for whoever's lucky enough to be joining your journey.
Are there holiday rentals with WiFi in Ocean Pines?
Whether you want to keep up with the headlines, make a video call or update your social media accounts, there are 41 holiday homes with WiFi in Ocean Pines. Check the "WiFi" box when searching on Vrbo and stay connected on your getaway.
How can I find holiday rentals with air conditioning in Ocean Pines?
Ocean Pines has 166 holiday rentals where you'll be able to spend your days in air-conditioned comfort. To find a stay on Vrbo that features this amenity, enter your desired travel dates and use the convenient filters to select the "air conditioning" box.
How old do you have to be to rent a holiday rental in Ocean Pines?
The minimum age requirements can differ across properties on Vrbo, so be sure to check the rules of the holiday rental in Ocean Pines you want to book. But typically, it's 16, 18 or 21.
How long can I rent a holiday rental in Ocean Pines for?
The amount of time you can rent an Ocean Pines holiday home for is down to each property. Just put in your dates of travel to see available options offering longer term stays. They come with all the things you need to make your extended break more enjoyable and convenient, such as kitchens and air conditioning. Some holiday homes may also offer weekly or monthly discounts, so you can stick around for longer for less.
More holiday ideas
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- 4100 Ocean City Holiday Rentals
- Coconut Malorie Resort Holiday Rentals
- Severn I Holiday Rentals
- Makai Condominiums Holiday Rentals
- Time-N-Tide Holiday Rentals
- Summersea Holiday Rentals
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- Caine Woods Holiday Rentals
- Oceans Edge Holiday Rentals
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- Ocean Rise Holiday Rentals
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- Jocelyn Manor Holiday Rentals
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- West Winds Holiday Rentals
- Sea Watch Holiday Rentals
- Sandy Lane Estates Condominium Holiday Rentals
- Sea Breeze Holiday Rentals
- Seaside Escape Holiday Rentals
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