Family-Friendly Vacation Rentals in Caine Woods, MD: Compare 10+ Sites & Save

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2309 Best Family Vacation Rentals in Caine Woods (Starting from $130)

Tiburon 10A
Tiburon 10A
Apartment
Ocean City, MD, USA
0.0k from Caine Woods center

Apartments, Cheap, Accommodations, Pools, Parking, Lodgings, Places to stay

2 Bedrooms8 Guests
6.5

Good

2 reviews

$130
Average price / night
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WHEN SIZE MATTERS THIS IS THE PLACE
WHEN SIZE MATTERS THIS IS THE PLACE
House
Ocean City, MD, 21842, United States
0.1k from Caine Woods center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet, Kitchen

6 Bedrooms18 Guests
9.8

Exceptional

73 reviews

$522
Average price / night
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Tiburon 1B
Tiburon 1B
Apartment
Ocean City, MD, USA
0.0k from Caine Woods center

Apartments, Cheap, Accommodations, Pools, Lodgings, Places to stay

2 Bedrooms4 Guests
10.0

Exceptional

1 reviews

$148
Average price / night
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Private 3 Bed 2 Bath Beach House. Remodeled, short walk to beach, wifi & laundry
Private 3 Bed 2 Bath Beach House. Remodeled, short walk to beach, wifi & laundry
House
Ocean City, MD, 21842, United States
0.1k from Caine Woods center

AC, Dryer, Extra Bed, Fireplace, Free Parking, Heater, Hot Tub, Internet, Kitchen

3 Bedrooms6 Guests
10.0

Exceptional

17 reviews

$511
Average price / night
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Near Beach Family-Friendly Home in Ocean City
Near Beach Family-Friendly Home in Ocean City
House
Ocean City, MD, USA
0.1k from Caine Woods center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay, Family

4 Bedrooms12 Guests
New to Booking
$644
Average price / night
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416 - 141st St
416 - 141st St
House
Ocean City, MD, USA
0.1k from Caine Woods center

Accommodations, Villas, Vacation homes, Cottages, Lodgings, Places to stay

3 Bedrooms8 Guests
New to Booking
$380
Average price / night
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Waterfront 2 Bedroom - 2 Blocks from the Beach - Premium Location
Waterfront 2 Bedroom - 2 Blocks from the Beach - Premium Location
Condo
Ocean City, MD, 21842, United States
0.2k from Caine Woods center

AC, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

3 Bedrooms7 Guests
9.4

Superb

42 reviews

$182
Average price / night
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Whispering Woods #26
Whispering Woods #26
Apartment
Ocean City, MD, USA
0.2k from Caine Woods center

Apartments, Cheap, Accommodations, Pools, Lodgings, Places to stay

2 Bedrooms6 Guests
9.8

Exceptional

6 reviews

$369
Average price / night
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Bayside Tiki Summary:
Bayside Tiki Summary:
House
Ocean City, MD, 21842, United States
0.3k from Caine Woods center

AC, Arcade, Balcony, Barbecue, Dryer, Extra Bed, Free Parking, Heater, Internet

3 Bedrooms8 Guests
New to Booking
$309
Average price / night
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Nanticoke Square 207B townhouse
Nanticoke Square 207B townhouse
House
Ocean City, MD, USA
0.2k from Caine Woods center

Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

2 Bedrooms7 Guests
10.0

Exceptional

1 reviews

$298
Average price / night
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SHORT WALK TO BEACH, QUIET RESIDENTIAL NEIGHBORHOOD
SHORT WALK TO BEACH, QUIET RESIDENTIAL NEIGHBORHOOD
House
Ocean City, MD, 21842, United States
0.3k from Caine Woods center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

3 Bedrooms8 Guests
8.8

Fabulous

3 reviews

$385
Average price / night
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Ocean City Townhome by Beach Bayside
Ocean City Townhome by Beach Bayside
Apartment
Ocean City, MD, USA
0.2k from Caine Woods center

Apartments, Cheap, Accommodations, Parking, Pet-friendly, Lodgings, Places to stay, Self-catering

2 Bedrooms4 Guests
9.0

Fabulous

27 reviews

$287
Average price / night
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Cozy 3BR Beach Home in Ocean City
Cozy 3BR Beach Home in Ocean City
Condo
Ocean City, MD, 21842, United States
0.3k from Caine Woods center

AC, Balcony, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms12 Guests
10.0

Exceptional

4 reviews

$459
Average price / night
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The Sea Captain's Sanctuary
The Sea Captain's Sanctuary
House
Ocean City, MD, USA
0.2k from Caine Woods center

Accommodations, Villas, Vacation homes, Cottages, Lodgings, Places to stay

3 Bedrooms8 Guests
New to Booking
$643
Average price / night
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Walk to the Beach! Firepit, Fully Fenced Yard, Grill, Bikes, N64, Pets/EV!
Walk to the Beach! Firepit, Fully Fenced Yard, Grill, Bikes, N64, Pets/EV!
Villa
Ocean City, MD, 21842, United States
0.3k from Caine Woods center

AC, Arcade, Balcony, Barbecue, Breakfast Available, Crib, Dryer, Fireplace, Fitness Equipment

1 Bedroom10 Guests
10.0

Exceptional

60 reviews

$718
Average price / night
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Walkable Condo with Pool Access in Ocean City!
Walkable Condo with Pool Access in Ocean City!
Apartment
Ocean City, MD, USA
0.2k from Caine Woods center

View, Fireplace/Heating, Accessibility, Security/Safety, Internet, Parking, Pool

2 Bedrooms6 Guests
New to Booking
$472
Average price / night
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2-story end-unit townhome near beach with deck, AC, outdoor pool & fast WiFi
2-story end-unit townhome near beach with deck, AC, outdoor pool & fast WiFi
House
Ocean City, MD, 21842, United States
0.3k from Caine Woods center

AC, Dryer, Extra Bed, Fireplace, Free Parking, Heater, Kitchen, Laundry, Living Area

3 Bedrooms8 Guests
9.2

Superb

20 reviews

$455
Average price / night
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Nautical North
Nautical North
House
Ocean City, MD, USA
0.2k from Caine Woods center

Cheap, Accommodations, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay, Family

3 Bedrooms8 Guests
9.0

Fabulous

8 reviews

$451
Average price / night
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2BR 2BA Quiet North OCMD Condo+Hot Tub+Beach+Pool
2BR 2BA Quiet North OCMD Condo+Hot Tub+Beach+Pool
Condo
Ocean City, MD, 21842, United States
0.4k from Caine Woods center

AC, Crib, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry

2 Bedrooms6 Guests
10.0

Exceptional

4 reviews

$354
Average price / night
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Serenity on Sailing Rd
Serenity on Sailing Rd
House
Caine Woods, Ocean City, Maryland, USA
0.2k from Caine Woods center

Balcony/Terrace, Laundry, Pet Friendly, Internet, Parking, Air Conditioner, Child Friendly

5 Bedrooms10 Guests
9.5

Superb

2 reviews

$598
Average price / night
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Fun w/ Family! Ocean City Condo - Stroll to Shore
Fun w/ Family! Ocean City Condo - Stroll to Shore
Condo
Ocean City, MD, 21842, United States
0.4k from Caine Woods center

AC, Dryer, Extra Bed, Free Parking, Heater, Kitchen, Laundry, Microwave, No Smoking

2 Bedrooms8 Guests
9.0

Fabulous

8 reviews

$394
Average price / night
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Coastal Beach Home | DogFriendly | Near Oceanfront
Coastal Beach Home | DogFriendly | Near Oceanfront
House
Ocean City, MD, 21842, United States
0.4k from Caine Woods center

AC, Balcony, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Kitchen

4 Bedrooms12 Guests
9.8

Exceptional

20 reviews

$560
Average price / night
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1 block to beach, arcade games, walk to restaurants water park, mini golf,&more!
1 block to beach, arcade games, walk to restaurants water park, mini golf,&more!
House
Ocean City, MD, 21842, United States
0.5k from Caine Woods center

AC, Arcade, Balcony, Crib, Dryer, Free Parking, Heater, Internet, Kitchen

3 Bedrooms12 Guests
10.0

Exceptional

3 reviews

$423
Average price / night
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Pool,Beach2Blocks,10%Sale! Pets,3 King Beds,Linens,Air Hockey
Pool,Beach2Blocks,10%Sale! Pets,3 King Beds,Linens,Air Hockey
House
Ocean City, MD, 21842, United States
0.5k from Caine Woods center

AC, Arcade, Balcony, Crib, Dryer, Free Parking, Heater, Internet, Kitchen

3 Bedrooms11 Guests
10.0

Exceptional

3 reviews

$598
Average price / night
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Walk to Beach: Condo w/ Pool Access in Ocean City
Walk to Beach: Condo w/ Pool Access in Ocean City
Condo
Ocean City, MD, 21842, United States
0.5k from Caine Woods center

AC, Balcony, Dryer, Extra Bed, Free Parking, Heater, Kitchen, Laundry, Microwave

2 Bedrooms8 Guests
9.0

Fabulous

4 reviews

$336
Average price / night
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New Luxe Home Steps to Ocean, Baby-Friendly, Pool, Garage, 2600 sq.ft -Sleeps 12
New Luxe Home Steps to Ocean, Baby-Friendly, Pool, Garage, 2600 sq.ft -Sleeps 12
House
Ocean City, MD, 21842, United States
0.6k from Caine Woods center

AC, Balcony, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

3 Bedrooms12 Guests
10.0

Exceptional

5 reviews

$424
Average price / night
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6 Bedroom Duplex in Ocean City, Maryland
6 Bedroom Duplex in Ocean City, Maryland
House
Ocean City, MD, 21842, United States
0.6k from Caine Woods center

AC, Arcade, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

6 Bedrooms20 Guests
10.0

Exceptional

2 reviews

$944
Average price / night
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Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Family Vacation Rentals in Caine Woods.

Stay Near Caine Woods's Top Attractions

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Caine Woods Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 2309 verified family-friendly vacation rentals in Caine Woods. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Caine Woods vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $130 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Caine Woods offer baby-friendly items such as high chairs, cribs, or pack-and-play options. Availability can vary, so it’s helpful to check the listing details before booking.

Yes, some rentals in Caine Woods are well suited for multi-generational stays, offering multiple bedrooms, separate living areas, and enough space for larger groups to stay comfortably together.

For busy travel periods such as school holidays or summer breaks, booking 90 to 120 days in advance is recommended to secure the best options. Availability may be more flexible during quieter times of the year.

Family-friendly rentals in Caine Woods often include amenities such as Child Friendly, Fireplace/Heating, and Laundry. These features help make stays more convenient and enjoyable for both adults and children.

You can use search filters to find rentals that offer features like game rooms, playgrounds, or entertainment areas. Checking property descriptions can also help you identify homes that are well suited for families with children.