Ocean City Rentals - Flexible Vacation Rentals

Ocean City Flex Stay Rentals

OCMD Weekend & Short Stay Vacations

Here at Seaside Vacations, we understand how busy life is and that you can't always get away for a full week. That's what we LOVE about our Flex Stay Program ~ Arrive when you want, depart when you want, the world is your Oyster!

The homes in our Flex Stay Program have either a 2 or 3 night minimum all year long, not just the Off-Season! Take a weekend getaway to OCMD or stay a few days longer. Whatever your needs or requirements, we have the OCMD rental for you. As always, we're standing by ready to help you find just the right home for your next Beach Break!

Browse these amazing Ocean City Rentals with Flexible Stays so you can check-in on your schedule and not by a schedule set for you. Search and book online today!


Properties Available 151 properties available
Welcome to Newport Bay 5 - A little slice of heaven right in Ocean City! Have you been yearning for a little sun, a little sand, and some fabulous bay views? Perhaps a Beach Break that won’t break the bank? If you can make the time, we certainly have the place! Newport Bay 5 is a delightful Condo in the very heart of OCMD. With a great Uptown Locat
Hot HOT 10
Newport Bay 5
Condominium
$110 - $338 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 7 guests
Has the hustle and bustle of everyday life gotten to be a boring routine? Are you missing spending that ever important quality time with the ones that matter most? If you’re like the rest of us, it’s easy to fall into those routines and forget to take the time to appreciate what is truly important. Take time to enjoy what you work so hard for each
Hot HOT 8
Golden Sands 211
Condominium
$110 - $485 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 4 guests
San Remo 109 - Sky Above, Sand Below, Peace Within…..Ahhhhh, love the thought of Family Vacation, but think it's just a bit out of your reach? Not so at fabulous San Remo 109! Tucked away in a serene, quiet location on the Bay just off of 54th Street, this wonderful Community is very close to everywhere you want to be, yet still offers the peace an
Hot HOT 12
San Remo 109
Condominium
$115 - $593 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Escape the tedious daily routine and make time for what truly matters: quality moments with your loved ones. It's easy to get caught up in the grind and forget to appreciate life's most important things - that are not “things” at all. Now is the time to enjoy the rewards of your hard work. Nestled in a wonderful and timeless family Community right
Hot HOT 11
Golden Sands 108
Condominium
$119 - $492 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 4 guests
You work hard all year long. When the time is right, you’re looking for just the right place to slow down, and spend some hard earned quality time with the ones who matter most in your life. Well, look no further! We have the place you’ve been dreaming of! Nautical Lane 146 is an absolutely stunning 4 Bedroom/2.5 Bath home tucked back in Ocean City
Hot HOT 42
Nautical Lane 146
House Pet Friendly
$189 - $700 / per night
Bedrooms 4 bedrooms
Bathrooms 2 baths
Guests 10 guests
Capri 1805 is a phenomenal 2 Bedroom Condo in fabulous Ocean City, Maryland directly on the Beach and steps from dining, shopping and more!.Were you dazzled by your last Vacation Experience? If not, you clearly were not staying at fabulous Capri 1805. When you enter this breathtaking 18th Floor Condo, you’ll feel on top of the world with stunning V
Hot HOT 11
Capri 1805
Condominium
$125 - $616 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
You and your family work hard all year long. Don’t you think you all deserve some time to relax and rejuvenate with some fun in the sun? There’s no better place to connect than Ocean City, and no better place to stay than the fabulous Sea Watch 410 on 115th St.! The Sea Watch is one of the largest condominium buildings in Ocean City, and its amenit
Hot HOT 50
Sea Watch 410
Condominium
$160 - $729 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 8 guests
Have you been yearning for a Family vacation that doesn’t break the bank? Look no further, we have the place for you! Maresol 503 is a classic condo directly on the Bay in mid-town Ocean City. Comfort, great location and one of the best Open Bay Views anyone could dream of, all of that and a Seasonal outdoor community pool! Even better, Maresol 503
Hot HOT 27
Maresol 503
Condominium
$149 - $629 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Has the hustle and bustle of everyday life gotten you into a boring routine? Are you spending that ever important quality time with the ones that matter most? If you’re like the rest of us, it’s easy to fall into those routines and forget to take the time to appreciate what is truly important. Take time to enjoy what you work so hard for each year.
Hot HOT 7
Golden Sands 111
Condominium
$200 - $348 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 4 guests
Summer Beach 806 - Sky above, Sand below, Peace Within…..Have you been looking for just the right place - the perfect location - for your next family getaway? Look no further than fabulous Summer Beach 806 - a wonderful, secure, and timeless family community right on the beach, yet still close to everything Ocean City has to offer! This gorgeous Co
Hot HOT 11
Summer Beach 806
Condominium
$169 - $704 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 8 guests
Isn't it time to rediscover, relax, and rejuvenate with your family? There is no better place to do this than the fabulous Sea Watch 509 on 115th Street. The Sea Watch is one of the largest Condominium Buildings in Ocean City, and its Amenities are truly unrivaled. With 3 Swimming Pools, 3 Tennis Courts, a Basketball Court, a Game Room, a Playgroun
Hot HOT 14
Sea Watch 509
Condominium
$159 - $550 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 8 guests
Welcome to Reel Nauti at Ocean Village! A fabulous 2nd floor condo tucked in a quiet community in West Ocean City, close to OCMD, Assateague, and everywhere you want to be. The community of Ocean Village is centered around a large pond with a gazebo and relaxing fountain, and the community offers Pickleball, Basketball, Tennis, a kids Playground, a
Hot HOT 25
Reel Nauti at Ocean Village
Condominium Pet Friendly
$149 - $550 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests

Tell us what you're looking for and someone will contact you with available options.

I agree