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

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271 Best Vacation Rentals with Pool in Grand Cayman (Starting from $228)

Twin Palms by Grand Cayman Villas & Condos
Twin Palms by Grand Cayman Villas & Condos
House
Driftwood Village, Cayman Islands
2.9k from Grand Cayman center

Hot Tub, View, Pool, Oceanfront, Parking, Wellness Facilities, Security/Safety

7 Bedrooms14 Guests
New to Booking
$4049
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
1.6k from Grand Cayman 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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Parrot-ise 4 Bedroom Villa
Parrot-ise 4 Bedroom Villa
House
Brinkleys, Cayman Islands
3.0k from Grand Cayman center

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

4 Bedrooms8 Guests
New to Booking
$613
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
2.4k from Grand Cayman 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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Ocean Paradise
Ocean Paradise
Resort
Brinkleys, Cayman Islands
3.0k from Grand Cayman center

Accommodations, Pools, Resorts, Parking, 4-star, Lodgings, Beach, Places to stay, Family

15 Bedrooms40 Guests
9.5

Superb

2 reviews

$916
Average price / night
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Beach Front East End
Beach Front East End
Condo
East End, Cayman Islands
2.5k from Grand Cayman center

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

1 Bedroom4 Guests
New to Booking
$281
Average price / night
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Cayman Dream by Grand Cayman Villas & Condos
Cayman Dream by Grand Cayman Villas & Condos
House
Driftwood Village, Cayman Islands
3.1k from Grand Cayman center

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

2 Bedrooms6 Guests
New to Booking
$664
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
2.8k from Grand Cayman 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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Coconut Beach by Grand Cayman Villas & Condos
Coconut Beach by Grand Cayman Villas & Condos
House
Driftwood Village, Cayman Islands
3.2k from Grand Cayman center

Fireplace, Pool, Parking, Security/Safety, Guest Services, Internet, Air Conditioner

6 Bedrooms12 Guests
New to Booking
$1890
Average price / night
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Relax in Cayman Casual style. Modern convenience in a quiet beachfront setting.
Relax in Cayman Casual style. Modern convenience in a quiet beachfront setting.
Condo
Rum Point/Cayman Kai, Cayman Islands
2.8k from Grand Cayman center

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

2 Bedrooms4 Guests
10.0

Exceptional

73 reviews

$262
Average price / night
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Iggy Blue home
Iggy Blue home
House
Driftwood Village, Cayman Islands
3.3k from Grand Cayman center

Fireplace/Heating, Ocean View, Internet, Security/Safety, Hot Tub, Wellness Facilities, Air Conditioner

4 Bedrooms8 Guests
New to Booking
$1986
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
2.8k from Grand Cayman 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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Rip Kai Villa by Grand Cayman Villas & Condos
Rip Kai Villa by Grand Cayman Villas & Condos
House
Driftwood Village, Cayman Islands
3.5k from Grand Cayman center

Hot Tub, View, Fireplace, Pool, Oceanfront, Parking, Wellness Facilities

9 Bedrooms24 Guests
New to Booking
$5097
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
2.9k from Grand Cayman 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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Fischers Reef by Grand Cayman Villas & Condos
Fischers Reef by Grand Cayman Villas & Condos
House
Driftwood Village, Cayman Islands
3.6k from Grand Cayman center

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

8 Bedrooms20 Guests
New to Booking
$5090
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
2.9k from Grand Cayman 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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Olympus Villa by Grand Cayman Villas & Condos
Olympus Villa by Grand Cayman Villas & Condos
House
Driftwood Village, Cayman Islands
3.6k from Grand Cayman center

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

4 Bedrooms12 Guests
New to Booking
$2733
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
2.9k from Grand Cayman 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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Coral Kai home
Coral Kai home
House
Driftwood Village, Cayman Islands
3.8k from Grand Cayman center

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

5 Bedrooms10 Guests
New to Booking
$1772
Average price / night
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Paradise Found Oceanfront Condo - Flexible Cancellation
Paradise Found Oceanfront Condo - Flexible Cancellation
Condo
Grand Cayman, Cayman Islands
2.9k from Grand Cayman center

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

2 Bedrooms5 Guests
9.8

Exceptional

89 reviews

$228
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
2.9k from Grand Cayman 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
2.9k from Grand Cayman 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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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
2.9k from Grand Cayman 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
2.9k from Grand Cayman 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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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
2.9k from Grand Cayman 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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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
3.0k from Grand Cayman 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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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
3.0k from Grand Cayman center

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

2 Bedrooms6 Guests
10.0

Exceptional

10 reviews

$327
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 Grand Cayman.

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Grand Cayman Vacation Rentals with Pool on the Map

Frequently Asked Questions

You can explore 271 verified vacation rentals with a pool in Grand Cayman. 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 Grand Cayman vary depending on the season, property size, and whether the pool is private or shared. Rates typically start from around $228 per night, with private pool homes and peak travel periods often costing more.

Many rentals in Grand Cayman 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 Grand Cayman welcome pets. Currently, 4 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 Grand Cayman often include additional outdoor features such as Pool, View, and Ocean View. These amenities enhance comfort and make it easier to enjoy outdoor living during your stay.

Some vacation rentals in Grand Cayman 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.