Family-Friendly Vacation Rentals in Grand Cayman, Cayman Islands: Compare 10+ Sites & Save

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247 Best Family Vacation Rentals in Grand Cayman (Starting from $228)

Castaway Cove by Grand Cayman Villas & Condos
Castaway Cove by Grand Cayman Villas & Condos
House
Driftwood Village, Cayman Islands
2.8k from Grand Cayman center

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

4 Bedrooms10 Guests
New to Booking
$917
Average price / night
Check Availability
Seafire Residence N703
Seafire Residence N703
Condo
Grand Cayman, KY1 KY, Cayman Islands
0.7k from Grand Cayman center

AC, Balcony, Dryer, Fitness Equipment, Internet, Kitchen, Laundry, No Smoking, TV

1 Bedroom4 Guests
New to Booking
$2383
Average price / night
Check Availability
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
Check Availability
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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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
Check Availability
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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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
Check Availability
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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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
Check Availability
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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Northside Grand Cayman Getaway with Private Beach!
Northside Grand Cayman Getaway with Private Beach!
House
North Side, Cayman Islands
3.4k from Grand Cayman center

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

4 Bedrooms10 Guests
8.0

Good

1 reviews

$931
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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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
Check Availability
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
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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
Check Availability
Kozy Kai - Sealodge 17 - Romantic Beachfront cottage by Cayman Villas!
Kozy Kai - Sealodge 17 - Romantic Beachfront cottage by Cayman Villas!
Condo
Cayman Kai, KY1-1202, Cayman Islands
3.1k from Grand Cayman center

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

1 Bedroom2 Guests
9.8

Exceptional

74 reviews

$246
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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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
3.3k from Grand Cayman 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
3.5k from Grand Cayman 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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Oceanfront Resort Villa w/ Stunning Views, Pool, Spa & Onsite Staff
Oceanfront Resort Villa w/ Stunning Views, Pool, Spa & Onsite Staff
Villa
Breakers, Cayman Islands
4.1k from Grand Cayman center

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

6 Bedrooms18 Guests
10.0

Exceptional

1 reviews

$9289
Average price / night
Check Availability
Coral Loft 4BR + 1 BR Oceanfront Villa w/ Private Pool & Beach in Grand Cayman
Coral Loft 4BR + 1 BR Oceanfront Villa w/ Private Pool & Beach in Grand Cayman
Villa
Rum Point, KY1 1503, Cayman Islands
4.3k from Grand Cayman center

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

5 Bedrooms12 Guests
10.0

Exceptional

6 reviews

$1433
Average price / night
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Charming 2-bedroom condo with AC in Bodden Town
Charming 2-bedroom condo with AC in Bodden Town
Condo
Bodden Town, Cayman Islands
4.3k from Grand Cayman center

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

2 Bedrooms6 Guests
10.0

Exceptional

5 reviews

$257
Average price / night
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Relax in coastal luxury - renovated oceanfront condo Kaibo  phase 2 - B13
Relax in coastal luxury - renovated oceanfront condo Kaibo phase 2 - B13
Condo
Grand Cayman, KY1-1007, Cayman Islands
4.3k from Grand Cayman center

AC, Barbecue, Dryer, Free Parking, Hot Tub, Internet, Kitchen, Laundry, Living Area

2 Bedrooms6 Guests
10.0

Exceptional

107 reviews

$364
Average price / night
Check Availability
Oceanfront Ground Floor 2 Bedroom Condo 30 Unit Complex Close to all Amenities
Oceanfront Ground Floor 2 Bedroom Condo 30 Unit Complex Close to all Amenities
Condo
Rum Point, Cayman Islands
4.3k from Grand Cayman center

AC, Barbecue, Dryer, Extra Bed, Free Parking, Hot Tub, Internet, Kitchen, Laundry

2 Bedrooms4 Guests
9.8

Exceptional

29 reviews

$461
Average price / night
Check Availability
Cayman Kai - U-Kai-Lele2 Bed/ 2 Bath Beach Front Condo
Cayman Kai - U-Kai-Lele2 Bed/ 2 Bath Beach Front Condo
Condo
Rum Point, KY1-1201, Cayman Islands
4.3k from Grand Cayman center

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

2 Bedrooms6 Guests
10.0

Exceptional

61 reviews

$275
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 Grand Cayman.

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Grand Cayman Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 247 verified family-friendly vacation rentals in Grand Cayman. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Grand Cayman vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $228 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Grand Cayman 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 Grand Cayman 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 Grand Cayman often include amenities such as Child Friendly, Ocean View, and 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.