Vacation Rentals with Private Pool in Grand Cayman Beaches, Cayman Islands: Compare 10+ Sites & Save

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87 Best Vacation Rentals with Private Pool in Grand Cayman Beaches (Starting from $254)

Pools of the Kai 11 by Grand Cayman Villas & Condos
Pools of the Kai 11 by Grand Cayman Villas & Condos
House
Driftwood Village, Cayman Islands
5.3k from Grand Cayman Beaches center

View, Fireplace/Heating, Pool, Oceanfront, Parking, Security/Safety, Guest Services

2 Bedrooms4 Guests
New to Booking
$507
Average price / night
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Rum Reef, 6 bedroom house in North Side, pool, private beach, kayaks, bikes.
Rum Reef, 6 bedroom house in North Side, pool, private beach, kayaks, bikes.
House
North Side, Cayman Islands
2.2k from Grand Cayman Beaches center

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

6 Bedrooms14 Guests
9.8

Exceptional

7 reviews

$994
Average price / night
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Pools of the Kai 3 by Grand Cayman Villas & Condos
Pools of the Kai 3 by Grand Cayman Villas & Condos
House
Driftwood Village, Cayman Islands
5.3k from Grand Cayman Beaches center

Ocean View, Kitchen, Air Conditioner, Parking, Internet, Private Pool, View

2 Bedrooms4 Guests
New to Booking
$869
Average price / night
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The Pools #1- the Luxury Beachfront Hideaway with Private Pool
The Pools #1- the Luxury Beachfront Hideaway with Private Pool
Condo
North Side, Cayman Kai,, no zip code, Cayman Islands
2.4k from Grand Cayman Beaches center

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

1 Bedroom4 Guests
9.6

Exceptional

93 reviews

$299
Average price / night
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Pools of the Kai 10 by Grand Cayman Villas & Condos
Pools of the Kai 10 by Grand Cayman Villas & Condos
House
Driftwood Village, Cayman Islands
5.3k from Grand Cayman Beaches center

Security/Safety, Ocean View, Private Pool, Parking, Internet, View, Guest Services

2 Bedrooms4 Guests
New to Booking
$521
Average price / night
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Rum& Little Barron Villa: Your North Side Haven-Beach, Ocean, Garden Views!
Rum& Little Barron Villa: Your North Side Haven-Beach, Ocean, Garden Views!
House
North Side, KY1-1102, Cayman Islands
2.5k from Grand Cayman Beaches center

AC, Balcony, Barbecue, Crib, Dryer, Free Parking, Heater, Hot Tub, Internet

4 Bedrooms8 Guests
9.2

Superb

5 reviews

$947
Average price / night
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KiToCay by Grand Cayman Villas
KiToCay by Grand Cayman Villas
Apartment
Grand Cayman Beaches, Cayman Islands
6.1k from Grand Cayman Beaches center

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

1 Bedroom5 Guests
New to Booking
$620
Average price / night
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The Pink Beach House - Private House and Pool directly on the Beach, Rum Point
The Pink Beach House - Private House and Pool directly on the Beach, Rum Point
House
Rum Point, KY1, Cayman Islands
2.7k from Grand Cayman Beaches center

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

3 Bedrooms6 Guests
9.8

Exceptional

184 reviews

$657
Average price / night
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Timeless Paradise: Ultra-Luxe Ocean Estate w/ Elevated Pool, Arcade Room, and Home Cinema
Timeless Paradise: Ultra-Luxe Ocean Estate w/ Elevated Pool, Arcade Room, and Home Cinema
House
Rum Point, KY1-1202, Cayman Islands
2.7k from Grand Cayman Beaches center

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

11 Bedrooms28 Guests
10.0

Exceptional

2 reviews

$4723
Average price / night
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Twin Palms: Beach House w/ 60-ft Pool + Heated Spa in Rum Point
Twin Palms: Beach House w/ 60-ft Pool + Heated Spa in Rum Point
House
Rum Point, KY1-1202, Cayman Islands
3.0k from Grand Cayman Beaches center

AC, Arcade, Balcony, Dryer, Fitness Equipment, Free Parking, Hot Tub, Internet, Kitchen

7 Bedrooms14 Guests
10.0

Exceptional

20 reviews

$2973
Average price / night
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Steps to Sand & Sea - Oceanfront Condo with Pool in Quiet Cayman Kai/Rum Point
Steps to Sand & Sea - Oceanfront Condo with Pool in Quiet Cayman Kai/Rum Point
Condo
Cayman Kai, Rum Point, Grand Cayman Island, Cayman Islands
3.0k from Grand Cayman Beaches center

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

2 Bedrooms6 Guests
9.8

Exceptional

59 reviews

$276
Average price / night
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Tranquil beach retreat - The Nest @ North Pointe Condos, Rum Point, Grand Cayman
Tranquil beach retreat - The Nest @ North Pointe Condos, Rum Point, Grand Cayman
Condo
North Side, 11702, Cayman Islands
3.0k from Grand Cayman Beaches center

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

2 Bedrooms4 Guests
10.0

Exceptional

29 reviews

$324
Average price / night
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SAVE 10% – Coco Sands – 2 bed, 2 bath beachfront condo with sea view, Rum Point
SAVE 10% – Coco Sands – 2 bed, 2 bath beachfront condo with sea view, Rum Point
Condo
North Side, KY1-1207, Cayman Islands
3.0k from Grand Cayman Beaches center

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

3 Bedrooms6 Guests
10.0

Exceptional

22 reviews

$301
Average price / night
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Parrot-ise 4 Bedroom Oceanfront Villa in Cayman Kai
Parrot-ise 4 Bedroom Oceanfront Villa in Cayman Kai
House
Rum Point, KY1, Cayman Islands
3.1k from Grand Cayman Beaches center

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

4 Bedrooms8 Guests
9.8

Exceptional

56 reviews

$742
Average price / night
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\"Cayman Breeze\" - 2BR Oceanfront Condo w/ Quiet Setting near Rum Point
\"Cayman Breeze\" - 2BR Oceanfront Condo w/ Quiet Setting near Rum Point
Condo
Rum Point, KY1-1701, Cayman Islands
3.1k from Grand Cayman Beaches center

AC, Balcony, Barbecue, Business Services, Crib, Dryer, Free Parking, Internet, Kitchen

2 Bedrooms6 Guests
9.8

Exceptional

143 reviews

$254
Average price / night
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Caymanian Style Home\nw/ Pool, Pickle Ball Court, Optional Private Bar\n
Caymanian Style Home\nw/ Pool, Pickle Ball Court, Optional Private Bar\n
House
Rumpoint, 00000, Cayman Islands
3.1k from Grand Cayman Beaches center

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

5 Bedrooms10 Guests
9.8

Exceptional

59 reviews

$711
Average price / night
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Beachfront Peace!  Awesome top floor condo on Caribbean plus military discount!
Beachfront Peace! Awesome top floor condo on Caribbean plus military discount!
Condo
North Side, Cayman Islands
3.1k from Grand Cayman Beaches center

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

2 Bedrooms6 Guests
9.8

Exceptional

14 reviews

$415
Average price / night
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BEACH and POOL at Rum Point - North Side in most secluded and tranquil area
BEACH and POOL at Rum Point - North Side in most secluded and tranquil area
Condo
North Side, KY1–1700, Cayman Islands
3.2k from Grand Cayman Beaches center

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

2 Bedrooms6 Guests
10.0

Exceptional

10 reviews

$327
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
3.5k from Grand Cayman Beaches 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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Reef Romance, Rum Point Oceanfront Villa with Private Pool and Gorgeous Beach!
Reef Romance, Rum Point Oceanfront Villa with Private Pool and Gorgeous Beach!
House
Cayman Islands, Cayman Islands
3.6k from Grand Cayman Beaches center

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

5 Bedrooms10 Guests
9.6

Exceptional

54 reviews

$1156
Average price / night
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Rip Kai by Grand Cayman Villas
Rip Kai by Grand Cayman Villas
Villa
Rum Point, KY1-1202, Cayman Islands
3.8k from Grand Cayman Beaches center

AC, Balcony, Barbecue, Dryer, Elevator, Extra Bed, Fitness Equipment, Free Parking, Heater

9 Bedrooms24 Guests
10.0

Exceptional

1 reviews

$6339
Average price / night
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CORAL VISTA - Infinity Pool, Arcade, Theater, Private Cabana
CORAL VISTA - Infinity Pool, Arcade, Theater, Private Cabana
House
North Side, KY1-1701, Cayman Islands
3.9k from Grand Cayman Beaches center

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

10 Bedrooms26 Guests
10.0

Exceptional

57 reviews

$3296
Average price / night
Check Availability
Pease Bay House Cayman Islands
Pease Bay House Cayman Islands
House
Grand Cayman, KY1-1701, Cayman Islands
4.0k from Grand Cayman Beaches 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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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
4.0k from Grand Cayman Beaches 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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Grand Cayman Private Beach Cottage Without The High Price
Grand Cayman Private Beach Cottage Without The High Price
Cottage
Pease Bay, Cayman Islands
4.0k from Grand Cayman Beaches center

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

1 Bedroom4 Guests
10.0

Exceptional

39 reviews

$558
Average price / night
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Luxurious Beachfront 6-bed House with Guest House- Sleeps up to 21 Guests!
Luxurious Beachfront 6-bed House with Guest House- Sleeps up to 21 Guests!
House
Bodden Town, KY1-1600, Cayman Islands
4.0k from Grand Cayman Beaches center

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

6 Bedrooms16 Guests
10.0

Exceptional

4 reviews

$2098
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
4.0k from Grand Cayman Beaches center

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

7 Bedrooms22 Guests
New to Booking
$12078
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 Private Pool in Grand Cayman Beaches.

Where to stay in Grand Cayman Beaches? Best neighborhoods & areas

Grand Cayman Beaches Vacation Rentals with Private Pool on the Map

Frequently Asked Questions

You can explore 87 verified vacation rentals with a private pool in Grand Cayman Beaches. These include standalone villas and private homes where the pool is reserved exclusively for your group.

Prices for rentals with a private pool in Grand Cayman Beaches vary depending on the property size, location, and travel season. Rates typically start from around $254 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 Grand Cayman Beaches also welcome pets. Currently, 2 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 Grand Cayman Beaches often include additional features such as Pool, Private Pool, and View. These amenities enhance comfort and create a more relaxing, self-contained stay.

Some family-friendly vacation rentals in Grand Cayman Beaches 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.