Family-Friendly Vacation Rentals in Mastic Trail South Trailhead, North Side: Compare 10+ Sites & Save

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123 Best Family Vacation Rentals in Mastic Trail South Trailhead (Starting from $291)

Sea Beauty by Grand Cayman Villas & Condos
Sea Beauty by Grand Cayman Villas & Condos
House
Breakers, Cayman Islands
1.7k from Mastic Trail South Trailhead center

Parking, Guest Services, Air Conditioner, Security/Safety, Internet, Fireplace/Heating, Child Friendly

2 Bedrooms6 Guests
New to Booking
$499
Average price / night
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The peace and tranquility of this cottage Works Wonders on the soul....
The peace and tranquility of this cottage Works Wonders on the soul....
House
Grand Cayman, KY1, Cayman Islands
1.8k from Mastic Trail South Trailhead center

AC, Balcony, Barbecue, Breakfast Available, Dryer, Free Parking, Internet, Kitchen, Laundry

4 Bedrooms10 Guests
10.0

Exceptional

79 reviews

$757
Average price / night
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Sea Beauty - Charming Cottage with Pool and Private Beach Lot
Sea Beauty - Charming Cottage with Pool and Private Beach Lot
House
Mastic Trail South Trailhead, North Side, Cayman Islands
1.7k from Mastic Trail South Trailhead center

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

2 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$677
Average price / night
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Casa Tortuga - private beachfront villa with pool - Call Cayman Villas!
Casa Tortuga - private beachfront villa with pool - Call Cayman Villas!
Villa
Frank Sound, KY1-2000, Cayman Islands
2.2k from Mastic Trail South Trailhead center

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

3 Bedrooms6 Guests
9.4

Superb

51 reviews

$681
Average price / night
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HIdden Treasure by Grand Cayman Villas & Condos
HIdden Treasure by Grand Cayman Villas & Condos
House
Half Moon Bay, Cayman Islands
2.1k from Mastic Trail South Trailhead center

View, Fireplace/Heating, Pool, Oceanfront, Parking, Wellness Facilities, Security/Safety

5 Bedrooms14 Guests
New to Booking
$2070
Average price / night
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Blue Serenity: Beach House w/Pool, Pickleball Courts + Backyard Snorkeling
Blue Serenity: Beach House w/Pool, Pickleball Courts + Backyard Snorkeling
House
Grand Cayman, KY1-1202, Cayman Islands
3.4k from Mastic Trail South Trailhead center

AC, Dryer, Extra Bed, Fitness Equipment, Free Parking, Internet, Kitchen, Laundry, Living Area

4 Bedrooms10 Guests
9.6

Exceptional

26 reviews

$1332
Average price / night
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Hidden Treasure & Guesthouse by Grand Cayman Villas & Condos
Hidden Treasure & Guesthouse by Grand Cayman Villas & Condos
House
Half Moon Bay, Cayman Islands
2.1k from Mastic Trail South Trailhead center

View, Fireplace/Heating, Pool, Oceanfront, Parking, Wellness Facilities, Security/Safety

6 Bedrooms18 Guests
New to Booking
$1258
Average price / night
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Villa Esprit – Stunning 3 Bedroom Beachfront Villa in North Side with pool!
Villa Esprit – Stunning 3 Bedroom Beachfront Villa in North Side with pool!
House
North Side, KY1-1001, Cayman Islands
3.7k from Mastic Trail South Trailhead center

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

3 Bedrooms6 Guests
10.0

Exceptional

95 reviews

$941
Average price / night
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White Cottage by Grand Cayman Villas & Condos
White Cottage by Grand Cayman Villas & Condos
House
East End, Cayman Islands
2.4k from Mastic Trail South Trailhead center

View, Fireplace/Heating, Pool, Oceanfront, Parking, Wellness Facilities, Security/Safety

5 Bedrooms11 Guests
New to Booking
$2775
Average price / night
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Silver Reef 10-Luxury beachfront unit with rooftop terrace & outdoor kitchen!
Silver Reef 10-Luxury beachfront unit with rooftop terrace & outdoor kitchen!
Condo
Northside, KY1-0000, Cayman Islands
3.8k from Mastic Trail South Trailhead center

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

2 Bedrooms4 Guests
9.4

Superb

6 reviews

$459
Average price / night
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The Mastic Sunnyhill Cottage
The Mastic Sunnyhill Cottage
House
North Side, Cayman Islands
2.9k from Mastic Trail South Trailhead center

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

1 Bedroom6 Guests
New to Booking
$441
Average price / night
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4BR Suite at Black Urchin Boutique Resort
4BR Suite at Black Urchin Boutique Resort
Condo
Breakers, Cayman Islands
3.8k from Mastic Trail South Trailhead center

AC, Balcony, Breakfast Available, Dryer, Elevator, Internet, Laundry, No Smoking, Pool

4 Bedrooms12 Guests
New to Booking
$4857
Average price / night
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The Mastic Chapel Cottage
The Mastic Chapel Cottage
House
North Side, Cayman Islands
3.0k from Mastic Trail South Trailhead center

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

1 Bedroom4 Guests
New to Booking
$529
Average price / night
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Beach House and Cottage with 2 Full Kitchens, Sleeps 16.
Beach House and Cottage with 2 Full Kitchens, Sleeps 16.
Villa
Old Man Bay, Cayman Islands
4.0k from Mastic Trail South Trailhead center

AC, Arcade, Barbecue, Crib, Dryer, Fireplace, Fitness Equipment, Free Parking, Internet

5 Bedrooms17 Guests
10.0

Exceptional

6 reviews

$1115
Average price / night
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The Mastic Cana Luxury Cottage
The Mastic Cana Luxury Cottage
House
North Side, Cayman Islands
3.0k from Mastic Trail South Trailhead center

Luxury, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals

1 Bedroom6 Guests
New to Booking
$441
Average price / night
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YOU'VE Arrived! Beachfront 3BR condo w/ Pool-Relax... North Side near Rum Point
YOU'VE Arrived! Beachfront 3BR condo w/ Pool-Relax... North Side near Rum Point
Condo
Old Man Bay, KY1-1001, Cayman Islands
4.0k from Mastic Trail South Trailhead center

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

3 Bedrooms6 Guests
10.0

Exceptional

82 reviews

$507
Average price / night
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The Mastic Cottage Collection
The Mastic Cottage Collection
House
North Side, Cayman Islands
3.0k from Mastic Trail South Trailhead center

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

7 Bedrooms14 Guests
New to Booking
$1316
Average price / night
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Oceanfront 5 Bedroom Pool Home - Blue Vista Villa
Oceanfront 5 Bedroom Pool Home - Blue Vista Villa
House
Old Man Bay, KY1, Cayman Islands
4.1k from Mastic Trail South Trailhead center

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

5 Bedrooms16 Guests
9.6

Exceptional

23 reviews

$1245
Average price / night
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Blue Serenity by Grand Cayman Villas & Condos
Blue Serenity by Grand Cayman Villas & Condos
House
Half Moon Bay, Cayman Islands
3.4k from Mastic Trail South Trailhead center

Ocean View, Kitchen, Air Conditioner, Parking, Internet, View, Oceanfront

4 Bedrooms10 Guests
New to Booking
$1896
Average price / night
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Oceanfront Resort Villa w/ Stunning Views, Pool, Spa & Onsite Staff
Oceanfront Resort Villa w/ Stunning Views, Pool, Spa & Onsite Staff
Villa
Breakers, Cayman Islands
4.2k from Mastic Trail South Trailhead center

AC, Balcony, Barbecue, Breakfast Included, Crib, Dryer, Hot Tub, Internet, Kitchen

6 Bedrooms18 Guests
10.0

Exceptional

1 reviews

$9289
Average price / night
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BEAUTIFUL 3 BEDROOM VILLA LOCATED DIRECTLY ON THE BEACH, EXCELLENT SNORKELING
BEAUTIFUL 3 BEDROOM VILLA LOCATED DIRECTLY ON THE BEACH, EXCELLENT SNORKELING
Villa
Grand Cayman, Cayman Islands
4.3k from Mastic Trail South Trailhead center

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

3 Bedrooms6 Guests
10.0

Exceptional

73 reviews

$357
Average price / night
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Pease Bay House Cayman Islands
Pease Bay House Cayman Islands
House
Grand Cayman, KY1-1701, Cayman Islands
4.4k from Mastic Trail South Trailhead center

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

6 Bedrooms12 Guests
10.0

Exceptional

1 reviews

$5095
Average price / night
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The Harvey Nicole: Modern Caribbean Ocean Front Condo Grand Cayman.
The Harvey Nicole: Modern Caribbean Ocean Front Condo Grand Cayman.
Condo
Grand Cayman, BWI, Cayman Islands
4.4k from Mastic Trail South Trailhead center

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

2 Bedrooms5 Guests
10.0

Exceptional

94 reviews

$291
Average price / night
Check Availability
Villa at the Sea Front
Villa at the Sea Front
Villa
North Side, Cayman Islands
4.4k from Mastic Trail South Trailhead center

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

3 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$318
Average price / night
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Pease Bay Manor is a private, secluded beachfront villa - call Cayman Villas
Pease Bay Manor is a private, secluded beachfront villa - call Cayman Villas
House
Bodden Town, KY1-1601, Cayman Islands
4.4k from Mastic Trail South Trailhead center

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

6 Bedrooms12 Guests
10.0

Exceptional

15 reviews

$984
Average price / night
Check Availability
Secluded Waterfront Single Family Villa with Private Pool – 3,000 Sq of Luxury
Secluded Waterfront Single Family Villa with Private Pool – 3,000 Sq of Luxury
Villa
East End - Half Moon Bay, Cayman Islands
4.5k from Mastic Trail South Trailhead center

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

3 Bedrooms8 Guests
10.0

Exceptional

204 reviews

$623
Average price / night
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SAND Luxurious Tranquility on a Private Beach In A Protected Marine Environment
SAND Luxurious Tranquility on a Private Beach In A Protected Marine Environment
Apartment
Half Moon Bay, East End, KY1-1501, Cayman Islands
4.6k from Mastic Trail South Trailhead center

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

3 Bedrooms7 Guests
10.0

Exceptional

86 reviews

$464
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 Mastic Trail South Trailhead.

Mastic Trail South Trailhead Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 123 verified family-friendly vacation rentals in Mastic Trail South Trailhead. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Mastic Trail South Trailhead vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $291 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Mastic Trail South Trailhead 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 Mastic Trail South Trailhead 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 Mastic Trail South Trailhead often include amenities such as Child Friendly, View, and Ocean View. 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.