Vacation Rentals with Private Pool in Mastic Trail South Trailhead, North Side: Compare 10+ Sites & Save

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57 Best Vacation Rentals with Private Pool in Mastic Trail South Trailhead (Starting from $291)

KiToCay by Grand Cayman Villas
KiToCay by Grand Cayman Villas
Apartment
Mastic Trail South Trailhead, North Side, Cayman Islands
3.7k from Mastic Trail South Trailhead center

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

1 Bedroom5 Guests
New to Booking
$620
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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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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The Mastic Cottage Collection on North Side
The Mastic Cottage Collection on North Side
Condo
North Side, KY1, Cayman Islands
2.9k from Mastic Trail South Trailhead center

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

7 Bedrooms14 Guests
10.0

Exceptional

2 reviews

$1507
Average price / night
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The Mastic Cana Cottage 2BR w/ Pool on North Side
The Mastic Cana Cottage 2BR w/ Pool on North Side
Condo
North Side, KY1, Cayman Islands
2.9k from Mastic Trail South Trailhead center

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

2 Bedrooms6 Guests
10.0

Exceptional

3 reviews

$477
Average price / night
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The Mastic Chapel Cottage 2BR w/ Pool on North Side
The Mastic Chapel Cottage 2BR w/ Pool on North Side
Condo
North Side, KY1, Cayman Islands
2.9k from Mastic Trail South Trailhead center

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

2 Bedrooms4 Guests
10.0

Exceptional

1 reviews

$538
Average price / night
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THE YELLOW HOUSE OF SEACLIFF RESORT HOMES
THE YELLOW HOUSE OF SEACLIFF RESORT HOMES
House
East End, Cayman Islands
3.3k from Mastic Trail South Trailhead center

AC, Balcony, Barbecue, Dryer, Extra Bed, Free Parking, Internet, Kitchen, Laundry

2 Bedrooms5 Guests
9.8

Exceptional

48 reviews

$375
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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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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Your Oceanside Retreat Awaits!
Your Oceanside Retreat Awaits!
Condo
Old Man Bay, Cayman Islands
3.7k from Mastic Trail South Trailhead center

AC, Balcony, Barbecue, Dryer, Elevator, Extra Bed, Free Parking, Hot Tub, Internet

2 Bedrooms6 Guests
10.0

Exceptional

56 reviews

$336
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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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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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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Cayman Sands: Secluded Beach Villa with Pool Atrium & Guest Cottage
Cayman Sands: Secluded Beach Villa with Pool Atrium & Guest Cottage
House
Grand Cayman, KY1-1202, Cayman Islands
4.2k from Mastic Trail South Trailhead center

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

5 Bedrooms14 Guests
9.8

Exceptional

46 reviews

$1368
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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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
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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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7BR Oceanfront Villa w/ 5 Master Suites, Bunk Room, Swim-Up Bar
7BR Oceanfront Villa w/ 5 Master Suites, Bunk Room, Swim-Up Bar
Villa
Breakers, Cayman Islands
4.5k from Mastic Trail South Trailhead center

AC, Dryer, Internet, Laundry, No Smoking, Pool, Washer

7 Bedrooms22 Guests
New to Booking
$12078
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
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SKY Luxurious Tranquility on a Private Beach In A Protected Marine Environment
SKY 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, Hot Tub, Internet

3 Bedrooms7 Guests
10.0

Exceptional

75 reviews

$466
Average price / night
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BeachPlumVilla - Snorkeler's Paradise
BeachPlumVilla - Snorkeler's Paradise
House
Grand Cayman, Cayman Islands
4.6k from Mastic Trail South Trailhead center

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

4 Bedrooms10 Guests
10.0

Exceptional

8 reviews

$1103
Average price / night
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Quiet, private nature retreat with pool and ocean views.
Quiet, private nature retreat with pool and ocean views.
House
Old Man Bay, KY1-1702, Cayman Islands
4.6k from Mastic Trail South Trailhead center

AC, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Microwave, No Smoking

4 Bedrooms8 Guests
10.0

Exceptional

9 reviews

$688
Average price / night
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Coco Kai Beach Front Villa with Heated Pool and Private Dock
Coco Kai Beach Front Villa with Heated Pool and Private Dock
House
North Side, Cayman Islands
4.7k from Mastic Trail South Trailhead center

AC, Arcade, Balcony, Barbecue, Breakfast Available, Crib, Dryer, Free Parking, Internet

6 Bedrooms15 Guests
10.0

Exceptional

95 reviews

$959
Average price / night
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Calypso Blue  Luxury 6BR Oceanfront Villa  Private Pool & Reef  Grand Cayman
Calypso Blue Luxury 6BR Oceanfront Villa Private Pool & Reef Grand Cayman
Villa
North Side, Cayman Islands
4.7k from Mastic Trail South Trailhead center

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

6 Bedrooms12 Guests
10.0

Exceptional

108 reviews

$1291
Average price / night
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Far Tortuga: 20 Adults Single Level Beach Villa w/ Heated Pool and Private Dock
Far Tortuga: 20 Adults Single Level Beach Villa w/ Heated Pool and Private Dock
House
North Side, KY 1-1702, Cayman Islands
4.8k from Mastic Trail South Trailhead center

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

8 Bedrooms20 Guests
10.0

Exceptional

19 reviews

$1357
Average price / night
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BEACHFRONT w/ Private Dock-50 ft Pool-Theatre
BEACHFRONT w/ Private Dock-50 ft Pool-Theatre
House
Northside, KY1-1601, Cayman Islands
4.8k from Mastic Trail South Trailhead center

AC, Barbecue, Crib, Dryer, Extra Bed, Free Parking, Internet, Kitchen, Laundry

5 Bedrooms14 Guests
9.8

Exceptional

77 reviews

$724
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 Vacation Rentals with Private Pool in Mastic Trail South Trailhead.

Mastic Trail South Trailhead Vacation Rentals with Private Pool on the Map

Frequently Asked Questions

You can explore 57 verified vacation rentals with a private pool in Mastic Trail South Trailhead. These include standalone villas and private homes where the pool is reserved exclusively for your group.

Prices for rentals with a private pool in Mastic Trail South Trailhead vary depending on the property size, location, and travel season. Rates typically start from around $291 per night, with higher prices for larger homes, prime locations, or peak travel periods.

Yes, properties listed with private pools are intended for the exclusive use of guests staying at that home. You can review listing photos and descriptions to better understand the layout and level of privacy offered.

Yes, some vacation rentals with private pools in Mastic Trail South Trailhead also welcome pets. Currently, 3 listings allow pets, although policies may vary. It’s a good idea to review any rules related to pets and outdoor areas before booking.

Private pool properties are often in high demand, especially during holidays and warmer months, so booking 90 to 120 days in advance is recommended. During quieter periods, you may still find availability closer to your travel dates.

Vacation rentals with private pools in Mastic Trail South Trailhead often include additional features such as Private Pool, Pool, and Balcony/Terrace. These amenities enhance comfort and create a more relaxing, self-contained stay.

Some family-friendly vacation rentals in Mastic Trail South Trailhead include safety features such as pool fences, covers, or screened enclosures. It’s recommended to check the property details to confirm whether a specific rental meets your safety preferences.