Family-Friendly Vacation Rentals in Montego Bay, MD: Compare 10+ Sites & Save

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2129 Best Family Vacation Rentals in Montego Bay (Starting from $112)

Montego Bay-106 Sea Lane home
Montego Bay-106 Sea Lane home
House
MD, USA
0.1k from Montego Bay center

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

3 Bedrooms7 Guests
New to Booking
$251
Average price / night
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Relax Here in this quiet Beach house!
Relax Here in this quiet Beach house!
House
Ocean City, MD, 21842, United States
0.1k from Montego Bay center

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

2 Bedrooms7 Guests
9.6

Exceptional

19 reviews

$331
Average price / night
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Montego Bay-Bayside Blues on Beachcomber
Montego Bay-Bayside Blues on Beachcomber
House
Ocean City, MD, USA
0.1k from Montego Bay center

Accommodations, Pools, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals, Places to stay

1 Bedroom8 Guests
6.8

Good

8 reviews

$538
Average price / night
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Spacious waterfront home, Walk to beach, restaurants and more.
Spacious waterfront home, Walk to beach, restaurants and more.
House
Ocean City, MD, 21842, United States
0.2k from Montego Bay center

AC, Balcony, Barbecue, Dryer, Fitness Equipment, Free Parking, Heater, Internet, Kitchen

3 Bedrooms13 Guests
10.0

Exceptional

59 reviews

$462
Average price / night
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Holly Point B5
Holly Point B5
House
Ocean City, MD, USA
0.2k from Montego Bay center

Accommodations, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay, Accessible hotels

2 Bedrooms6 Guests
New to Booking
$386
Average price / night
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3 BR 2 BA Home in Montego Bay - Community Pool
3 BR 2 BA Home in Montego Bay - Community Pool
House
Ocean City, MD, 21842, United States
0.3k from Montego Bay center

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

3 Bedrooms6 Guests
9.8

Exceptional

36 reviews

$394
Average price / night
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Montego Bay - Sea Lane
Montego Bay - Sea Lane
House
Ocean City, MD, USA
0.2k from Montego Bay center

Accommodations, Pools, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals, Places to stay

3 Bedrooms6 Guests
New to Booking
$112
Average price / night
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Walk to Maryland Beach: Canal-Front Escape w/ Dock
Walk to Maryland Beach: Canal-Front Escape w/ Dock
House
Ocean City, MD, 21842-5892, United States
0.3k from Montego Bay center

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

2 Bedrooms5 Guests
9.8

Exceptional

7 reviews

$326
Average price / night
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Oyster Lane Hideout
Oyster Lane Hideout
House
Ocean City, MD, USA
0.3k from Montego Bay center

Cheap, Accommodations, Pools, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals

2 Bedrooms6 Guests
8.0

Good

2 reviews

$448
Average price / night
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Spacious home w/ community pools, tennis, & docks - ADA compliant
Spacious home w/ community pools, tennis, & docks - ADA compliant
House
Ocean City, MD, 21842, United States
0.4k from Montego Bay center

AC, Dryer, Free Parking, Heater, Kitchen, Laundry, Living Area, Microwave, No Smoking

3 Bedrooms6 Guests
8.6

Fabulous

39 reviews

$277
Average price / night
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Walk to Maryland Beach Canal-Front Escape with Dock
Walk to Maryland Beach Canal-Front Escape with Dock
House
Ocean City, MD, USA
0.3k from Montego Bay center

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

2 Bedrooms5 Guests
7.6

Good

8 reviews

$349
Average price / night
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Ideal for a family getaway, newly furnished home in Montego Bay waiting for you!
Ideal for a family getaway, newly furnished home in Montego Bay waiting for you!
House
Ocean City, MD, 21842, United States
0.4k from Montego Bay center

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

3 Bedrooms11 Guests
10.0

Exceptional

25 reviews

$377
Average price / night
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Montego Bay - Lola B's Bayside Beach Bungalow
Montego Bay - Lola B's Bayside Beach Bungalow
House
Ocean City, MD, USA
0.3k from Montego Bay center

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

2 Bedrooms6 Guests
New to Booking
$258
Average price / night
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Beautiful Bay Views *  2 Kayaks To Explore The Bay * Private Dock For Boat!* NEW MASTER BATH in 2022
Beautiful Bay Views * 2 Kayaks To Explore The Bay * Private Dock For Boat!* NEW MASTER BATH in 2022
House
Ocean City, MD, 21842, United States
0.5k from Montego Bay center

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

3 Bedrooms8 Guests
10.0

Exceptional

70 reviews

$619
Average price / night
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Twin Tree Road 511 home
Twin Tree Road 511 home
House
Ocean City, MD, USA
0.4k from Montego Bay center

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

3 Bedrooms8 Guests
New to Booking
$439
Average price / night
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Beautiful Bay Views *  2 Kayaks To Explore The Bay * Private Dock For Your Boat!
Beautiful Bay Views * 2 Kayaks To Explore The Bay * Private Dock For Your Boat!
House
Ocean City, MD, 21842, United States
0.5k from Montego Bay center

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

1 Bedroom3 Guests
10.0

Exceptional

2 reviews

$894
Average price / night
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Montego Bay - South Ocean Drive 203
Montego Bay - South Ocean Drive 203
House
Ocean City, MD, USA
0.4k from Montego Bay center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals

3 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$136
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
0.5k from Montego Bay 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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Montego Bay
Montego Bay
House
Montego Bay, Ocean City, Maryland, USA
0.4k from Montego Bay center

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

3 Bedrooms5 Guests
9.4

Superb

7 reviews

$453
Average price / night
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On The Water * Private Dock * Sunset Porch Views
On The Water * Private Dock * Sunset Porch Views
House
Ocean City, MD, 21842, United States
0.5k from Montego Bay center

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

3 Bedrooms6 Guests
9.8

Exceptional

46 reviews

$515
Average price / night
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Pop Pop's Place in Montego Bay
Pop Pop's Place in Montego Bay
House
Ocean City, MD, 21842, United States
0.6k from Montego Bay center

AC, Dryer, Heater, Internet, Kitchen, Microwave, No Smoking, Pool, Tennis Court

3 Bedrooms5 Guests
New to Booking
$397
Average price / night
Check Availability
Luxe Family Home, Sleeps 10, Community Pool
Luxe Family Home, Sleeps 10, Community Pool
House
Ocean City, MD, 21842, United States
0.6k from Montego Bay center

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

3 Bedrooms10 Guests
10.0

Exceptional

18 reviews

$645
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
0.6k from Montego Bay 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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Bayside Tiki Summary:
Bayside Tiki Summary:
House
Ocean City, MD, 21842, United States
0.7k from Montego Bay center

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

3 Bedrooms8 Guests
New to Booking
$309
Average price / night
Check Availability
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
0.7k from Montego Bay center

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

3 Bedrooms7 Guests
9.4

Superb

42 reviews

$182
Average price / night
Check Availability
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
0.7k from Montego Bay 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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SHORT WALK TO BEACH, QUIET RESIDENTIAL NEIGHBORHOOD
SHORT WALK TO BEACH, QUIET RESIDENTIAL NEIGHBORHOOD
House
Ocean City, MD, 21842, United States
0.8k from Montego Bay center

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

3 Bedrooms8 Guests
8.8

Fabulous

3 reviews

$385
Average price / night
Check Availability

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 Montego Bay.

Stay Near Montego Bay's Top Attractions

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Montego Bay Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 2129 verified family-friendly vacation rentals in Montego Bay. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Montego Bay vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $112 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Montego Bay 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 Montego Bay 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 Montego Bay often include amenities such as Child Friendly, Fireplace/Heating, and Balcony/Terrace. 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.