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

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140 Best Vacation Rentals with Pool in Mastic Trail South Trailhead (Starting from $268)

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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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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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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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 & 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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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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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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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
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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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 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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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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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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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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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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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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On the Bay #103 Condo
On the Bay #103 Condo
House
Old Man Bay, Cayman Islands
4.0k from Mastic Trail South Trailhead center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Beach

1 Bedroom6 Guests
10.0

Exceptional

2 reviews

$473
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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On The Bay
On The Bay
Apartment
North Side, Cayman Islands
4.0k from Mastic Trail South Trailhead center

Apartments, Cheap, Accommodations, Pools, Parking, Lodgings, Vacation rentals, Places to stay, Self-catering

7 Bedrooms17 Guests
9.1

Superb

12 reviews

$268
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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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
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 Vacation Rentals with Pool in Mastic Trail South Trailhead.

Mastic Trail South Trailhead Vacation Rentals with Pool on the Map

Frequently Asked Questions

You can explore 140 verified vacation rentals with a pool in Mastic Trail South Trailhead. These include a wide range of private homes, villas, and condos that offer on-site swimming facilities for a more relaxing stay.

Prices for vacation rentals with a pool in Mastic Trail South Trailhead vary depending on the season, property size, and whether the pool is private or shared. Rates typically start from around $268 per night, with private pool homes and peak travel periods often costing more.

Many rentals in Mastic Trail South Trailhead offer private pools for exclusive use, while others provide access to shared or community pools. You can use filters to specifically find properties with private pools if that is your preference.

Yes, some vacation rentals with pools in Mastic Trail South Trailhead welcome pets. Currently, 1 listings allow pets, although policies may vary by property. It’s a good idea to review any rules related to pets around pool areas before booking.

Properties with pools are often in high demand, especially during warmer months and holidays, so booking 90 to 120 days in advance is recommended for the best selection. During off-peak seasons, you may still find availability closer to your travel dates.

Vacation rentals with pools in Mastic Trail South Trailhead often include additional outdoor features such as Pool, View, and Child Friendly. These amenities enhance comfort and make it easier to enjoy outdoor living during your stay.

Some vacation rentals in Mastic Trail South Trailhead offer heated pools, which can be especially useful during cooler months. In certain cases, pool heating may be available for an additional fee, so it’s best to check the property details before booking.