We noticed that you're using an unsupported browser. The Tripadvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Ocean Pines Holiday Rentals

List your property
Owner log in
Check-in
— / — / —
Check-out
— / — / —
Guests
0 rooms, 2+ guests
Bedrooms
Any
Bathrooms
Any
Amenities
Show more
Suitability
Show more
Property type
Show more
Distinctive Features
Show more
Distance from
1 mi
59 rentals in Ocean Pines.
Sort by:
Tripadvisor Sort

Million Dollar View! Waterfront oasis with Ocean City skyline view!

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

CANAL FRONT - GREAT VIEWS - 5 BDRM, 3&1/2 BATHS, 2 KINGS, GOLF, RELAX...

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Newly Renovated Home With Impressive Views Of The 7Th Green!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Beautiful Quiet Beach Home in the Pines Close to Everything

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Recently Painted and Furnished Ocean Pines Cottage

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Quaint waterfront bungalow just minutes from the beaches of Ocean City, MD

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Ocean City, MD Area Luxury Big Water View, 6+ BR/5.5 BA Decks/Views/Perfect!

Holiday Rental House
6 bedrooms
7 bathrooms
Sleeps 14
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Spacious, charming house close to beach. 5 bdrs, 3bth w/ screened in porch.

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Spacious, well maintained, 4br 3bath home overlooking Golf Course. LINEN OPTION

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

White Horse Park. Quiet Community. Close to Ocean City. Sleeps 7. Pet Friendly!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Save time - get the best Ocean Pines rentals sent straight to your email!

Gorgeous wired waterfront home with magnificent sunset views. Kayaks included.

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

waterfront beach retreat with boat dock

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Superb Direct Waterfront on St. Martin River in Ocean Pines With 2 Dock Slips

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Home Away From Home, pet friendly retreat!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Beautiful Handycap accessible home in Ocean Pines with Beach Parking permit.

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Water front secluded house with pier and view of the bay overlooking OC

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Golf course front home - 4 Bedrooms/3 full baths - 8 separate beds

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Cozy Ocean Pines / Ocean City Cottage

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Bring Your Boat to this Relaxing Ocean Pines Home & Enjoy the OC Waterways!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Dog-Friendly Berlin Home w/ Pool & Water Access!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

OFF SEASON DISCOUNTS AVAILABLE! Beautiful single story home in Ocean Pines.

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Ocean Pines House w/ Screened-In Deck & Grill!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

One Level Waterfront Home- Pet Friendly- 5 Pools- Sleeps 11- Self Check-In !

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Enjoy Beautiful Views From This 3 BR 2 BA Home on Quiet Canal in Ocean Pines.

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Spacious Home, With Dock, Sleeps 9, Access To Beach Club & Pool

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Family-friendly home on a wooded lot w/ a loft, deck, & fire pit

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Cozy, family friendly cottage, 2 BR 1 Bath, 10m to Ocean City, pool & clubhouse

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Coastal Cottage - Charm, Comfort and Spectacular Water Front near OC Beaches

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Spacious, two-story home w/full kitchen, balcony & outdoor fire pit

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Unique waterfront home w/ shared pools, a furnished deck, & a full kitchen

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Waterfront townhome w/deck, sunroom, amazing bay view & shared pool

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Salty Air Serenity * 728 Ocean Parkway in Ocean Pines, Maryland

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Reasonably Priced Family- Friendly Home, Sleeps 7

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Spacious home w/ shared pool and tennis court! Great home for families!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Large 4 BR 2.5 BA Home in Ocean Pines- Spacious, Airy & Peeks of the River

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Family-friendly home on canal w/entertainment, dock & free WiFi

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Super & Charming Clean Ocean Pines Home with Beach Club Parking Included!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Ocean Pines House w/ Private Hot Tub 2 Mi to Golf!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

This newly decorated, 4 bedroom 2 ½ bath home is nestled in the woods in North O

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Dog-friendly condo with shared pool plus lake, canal, and golf course views

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Berlin Resort Comm Home - 15 Mins from Ocean City!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

14 Hickory Way

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Payment Protection

New Listing! Charming Eastern Shore Retreat w/ Access to 5 Pools - Near Beach

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Family-Friendly Duplex Close to Ocean City Beach w/Shared Pool, WiFI, AC, W/D!

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

790 Ocean Parkway

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
More info
Check-in
Check-out
Payment Protection

NEW! Cozy Ocean Pines Cottage: Swim, Shop & Golf!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Family Home w/Shared Pool, Private Washer/Dryer, AC, Free WiFi - Close to Beach

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Waterfront getaway in a quiet neighborhood w/ free WiFi, dock, & furnished deck

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Charming Waterfront Beach home near Ocean City

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection

Endless Summer, water front oasis

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
PreviousNext
12
Frequently Asked Questions about Ocean Pines