Holiday rentals in Isle of Wight Bay

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Top-rated holiday rentals in Isle of Wight Bay

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Guest favourite

Apartment in Ocean City

4.9 out of 5 average rating, 176 reviews

**Beautiful newly renovated OC MD water view home*

Beautiful Bay view ground floor unit steps away from the water, 1 free parking spot available for guests and tons of street parking comfortable for 2 people for a long stay and 4 for a weekend getaway Located in the middle of all Ocean city major attractions Walking distance to the beach and Jolly Roger Amusement water Park and tons of other activities and restaurants. 6 min away from famous Seacrets, Macky’s & Fish Tales 8 min drive to OC famous board walk & downtown 15 min to Shopping Outlets

2–9 May

$193 SGD per night

Guest favourite

Apartment in Ocean City

4.82 out of 5 average rating, 124 reviews

1 BR Ocean Block (Unit 17) 40th St Midtown OC

Renovated ocean block condo with vintage charm & modern amenities. Second floor walk-up. Wonderful covered balcony for enjoying the sea breeze. Only 75 yards away from the beach. The Mid-Town OC location offers the best of everything...close to the boardwalk but far from the noise, great restaurants & bars within walking distance. Enjoy live music & a drink on the beach at Coconuts, only 9 blocks to Jolly Roger or Secrets. Walk to the OC Convention Center just across Coastal Hwy on the bayside.

29 Oct – 5 Nov

$141 SGD per night

Guest favourite

Apartment in Ocean City

4.97 out of 5 average rating, 123 reviews

Mid-Town OC! Ocean Block... Steps to the Beach!

OCEAN VIEW and STEPS to the BEACH... Newly remodeled in 2023! 2 bed/2 bath condo with ocean & bay views is located in desirable mid-town Ocean City. Walk to dining, shopping, convention center, amusements & nightlife. Be in the middle of everything, but still have a quiet place to relax. **Summer Months - check-ins on Mon & Fri ONLY Memorial Day to Labor Day. Book Weeks or Mini-weeks. (Weeks: Fri - Fri OR Mon - Mon) (Mini-Weeks: Mon to Fri OR Fri to Mon). *Other months check-in any night

15–22 Nov

$169 SGD per night

Guest favourite

Apartment in Ocean Pines

4.96 out of 5 average rating, 106 reviews

Quiet Water View Condo

Steps to 2 pools, 2 marinas, tiki bar and OP Yacht Club. Live music Thursday-Sunday evenings from 6-10pm, (in season). Beach day? Ocean City 15 min drive or walk to the marina and hop on a boat with friends and head across the bay into OC. Assateague Island is a 20 min drive. Crabbing? Fishing? Walk to one of the many Ocean Pines canals or ponds. Golfing? The links are just across the Parkway. Wedding party? Be footsteps away from make lasting memories. Free beach parking on 49th included

9–16 Nov

$189 SGD per night

Guest favourite

Townhouse in Ocean City

4.91 out of 5 average rating, 221 reviews

SunburstParadise: OceanView Boardwalk Luxury w/2🚘G

Relax and enjoy our newly updated, beautifully decorated 3 Br/ 3 Ba luxury ocean block Townhouse, (2014) which has a 2 car garage on 16th street. The end unit luxury townhouse is less than a 2 minutes walk from the beach and the boardwalk in a prime Downtown location. Enjoy beautiful sunrises Ocean View from two private balconies and drink coffee from Starbucks Coffee across street. Within walking distance are great restaurants/bars, mini-golf, shopping, amusements, and nightlife.

22–29 Jan

$141 SGD per night

Guest favourite

Apartment in Ocean City

4.93 out of 5 average rating, 167 reviews

Coastal and Bright Oceanfront Condo

Relax and find your inner peace at our oceanfront condo. Enjoy breathtaking unobstructed ocean views from the private balcony. Wake up to a beautiful sunrise each morning and enjoy a peaceful moon-lit view in the evening. Our condo is filled with coastal and bright decor sure to make you feel right at home. Located in North Ocean City, you will find plenty of shops and restaurants within walking distance. Park your car, bury your feet in the sand, and forget about your worries.

8–15 Nov

$191 SGD per night

Guest favourite

Apartment in Ocean City

4.97 out of 5 average rating, 222 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.

8–15 Nov

$150 SGD per night

Guest favourite

Guest suite in Berlin

4.99 out of 5 average rating, 148 reviews

Berlin/Ocean City Suite- Relax/Refresh near beach!

A remodeled, above garage guest suite separate from the main house in America's Coolest Small Town, Berlin Md! You will benefit from a separate entrance to your above garage suite which will allow you to enjoy your own quiet space to relax and embrace the small, quaint town of Berlin, all while a mere 15 minutes to the beaches of OCEAN CITY and Assateague! Multiple dining experiences and tons of shopping await you in either historic Berlin or world famous Ocean City!

30 Jan – 6 Feb

$155 SGD per night

Guest favourite

Flat in Frankford

4.98 out of 5 average rating, 122 reviews

Cozy Cottage Getaway

Enjoy this newly remolded 1 bedroom apartment tucked away on 2+ acres 3 miles from Bethany beach. Close to Rehobeth beach for outlet tax free shopping or Ocean City MD just 13 miles. You’ll be minutes away from lots of restaurants, stores, mini golf, arcade, night life etc. Property includes a 1/4 mile walking/running trail, fire pit and basket ball court. This is the perfect place to escape away from the busy Beach life but close enough to enjoy everything fully.

8–15 Oct

$169 SGD per night

Guest favourite

Apartment in Ocean City

4.99 out of 5 average rating, 173 reviews

Direct Oceanfront close to Northside Park!

Location, location, location! 2 bed, 2 bath direct oceanfront condo, with incredible ocean sunrise views from your private enclosed patio. Master bedroom features unbelievable views of the ocean, glass slider out to the patio & in suite full bath! Walking distance to Northside Park, restaurants & shopping. 2 assigned parking spaces. Elevator or steps - you pick. Washer/dryer in unit.

26 Jan – 2 Feb

$165 SGD per night

Guest favourite

Apartment in Ocean City

5.0 out of 5 average rating, 127 reviews

The Search For Surf-Ocean Block Sleeps 4

The Search for Surf is an ocean block retreat on 121st Street. Whether you love sunrises or want to sleep in, this is the perfect place for you. Top floor living assures no noise from above. Walking distance to Starbucks and over 20 different restaurants, as well as Ocean City's only ice rink. The Search for Surf is about the endless search for that perfect, fun vacation experience.

21–28 Apr

$146 SGD per night

Guest favourite

Apartment in Ocean City

4.87 out of 5 average rating, 139 reviews

Unit 7 on 41 St Ocean Side 50 steps to beach

Dominica Beach is a 2-story condo, close to the ocean on 41st Street Only 50 paces to the sand dunes and you'll have your toes in the sand! There are no streets to cross to get the beach. Complementary linen service based on the number of guests, Within walking distance of the Convention Center, restaurants, amusement parks, mini-golf, & more.

16–23 Oct

$105 SGD per night