Cayman Islands Vacation Rentals with Pools
Condo
10.0(284 Reviews)
2 Bedrooms
2 Baths
6 Guests
1100 ft²
Oceanfront
Hot Tub
Pool
Ocean View
US $509/Night
7 Nights - US $3,560
Resort
10.0(15 Reviews)
8 Baths
18 Guests
1078.54 ft²
- Oceanfront
- Hot Tub
Fireplace/Heating- Pool
US $329/Night
7 Nights - US $2,302
Apartment
10.0(17 Reviews)
3 Bedrooms
1 Bath
8 Guests
- Pool
- Ocean View
Balcony/Terrace
View
US $1,150/Night
7 Nights - US $8,050
Villa
10.0(205 Reviews)
3 Bedrooms
3 Baths
8 Guests
3000 ft²
Private Pool- Hot Tub
- Pool
- Ocean View
US $525/Night
7 Nights - US $3,677
Apartment
10.0(13 Reviews)
3 Bedrooms
3 Baths
6 Guests
1700.7 ft²
- Oceanfront
- Hot Tub
- Pool
- Ocean View
US $864/Night
7 Nights - US $6,047
Condo
10.0(202 Reviews)
2 Bedrooms
2 Baths
6 Guests
1182 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Ocean View
US $462/Night
7 Nights - US $3,233
House
10.0(5 Reviews)
1 Bedroom
2 Baths
6 Guests
1248.61 ft²
- Fireplace/Heating
- Pool
- View
Parking
US $459/Night
7 Nights - US $3,214
Condo
10.0(153 Reviews)
2 Bedrooms
2 Baths
6 Guests
1300 ft²
- Hot Tub
- Pool
- Ocean View
- Balcony/Terrace
US $649/Night
7 Nights - US $4,543
Villa
10.0(4 Reviews)
3 Bedrooms
3 Baths
8 Guests
1001.04 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
US $629/Night
7 Nights - US $4,401
Condo
10.0(150 Reviews)
3 Bedrooms
3 Baths
8 Guests
2400 ft²
- Oceanfront
- Hot Tub
- Pool
- Ocean View
US $977/Night
7 Nights - US $6,836
Apartment
10.0(3 Reviews)
1 Bedroom
2 Baths
6 Guests
1001.04 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $978/Night
7 Nights - US $6,846
Condo
10.0(149 Reviews)
2 Bedrooms
2 Baths
6 Guests
950 ft²
- Hot Tub
- Pool
- Ocean View
- Balcony/Terrace
US $249/Night
7 Nights - US $1,742
Why Choose Rent By Owner for your Cayman Islands Vacation Rentals with Pools?
What makes our Vacation Rentals with Pools special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Weekly Weather Forecast for Cayman Islands
How to Book Your Cayman Islands Vacation Rentals with Pools
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals with pools. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Cayman Islands
Common Vacation Rentals with Pools Amenities
What amenities can you expect?
Our Vacation Rentals with Pools are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Other Places to Stay in Cayman Islands
Grand Cayman
Seven Mile Beach
North Sound
North Side
Grand Cayman Beaches
Rum Point
West Bay
Brinkleys
George Town
Northwest Point
East End
Bodden Town
Frequently Asked Questions About Cayman Islands Rentals with Pools
1. What are the top Rentals With Pools in Cayman Islands?
There are a lot of options in Cayman Islands. If you plan on staying in the Cayman Islands area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Rentals With Pools in Cayman Islands:
- Palm Heights
- Cayman Reef Resort 1 - Beach Haven
- Calypso Blue Luxury 6BR Oceanfront Villa Private Pool & Reef Grand Cayman
- #14 Oceanfront Discovery Point Club -Fall Spec. Stay 6 & Get the 7th Night FREE!
- Sunset Cove Your Dream Vacation is Affordable on Seven Mile Beach Grand Cayman.
- Relax in coastal luxury - renovated oceanfront condo Kaibo phase 2 - B13
- Cayman White Sand Beach + Quiet Pool = Relaxation
- Stunning 4 Bedroom Condo located directly on 7 MILE BEACH. Location! Location!
- Luxury Condo on 7 Mile Beach - Discovery Point #10 - May to November Specials!
- Spectacular Condo on 7 Mile Beach. Discovery Point #11. Specials: May - November
2. How many Rentals With Pools are available in Cayman Islands?
Currently, the total number of properties listed by RBO in 2026 is over 2028 in the Cayman Islands area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Rentals With Pools in Cayman Islands.
More Rentals You May Like Near Cayman Islands
House
10.0(3 Reviews)
1 Bedroom
2 Baths
4 Guests
1194.79 ft²
- Fireplace/Heating
- Pool
- View
- Parking
US $611/Night
7 Nights - US $4,277
House
10.0(148 Reviews)
2 Bedrooms
2 Baths
6 Guests
1900 ft²
- Pool
- Ocean View
- Balcony/Terrace
- View
US $352/Night
7 Nights - US $2,463
Condo
10.0(147 Reviews)
1 Bedroom
1 Bath
4 Guests
754 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
US $427/Night
7 Nights - US $2,989
Condo
10.0(141 Reviews)
2 Bedrooms
2 Baths
6 Guests
1100 ft²
- Oceanfront
- Hot Tub
- Pool
- Ocean View
US $464/Night
7 Nights - US $3,249
Condo
10.0(140 Reviews)
1 Bedroom
1 Bath
4 Guests
754 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
US $279/Night
7 Nights - US $1,950
Condo
10.0(139 Reviews)
2 Bedrooms
2 Baths
5 Guests
1767 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $449/Night
7 Nights - US $3,141
Condo
10.0(124 Reviews)
3 Bedrooms
2 Baths
6 Guests
1229 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
US $506/Night
7 Nights - US $3,539
Condo
10.0(123 Reviews)
3 Bedrooms
3 Baths
8 Guests
2400 ft²
- Hot Tub
- Pool
- Ocean View
- Balcony/Terrace
US $998/Night
7 Nights - US $6,987
Condo
10.0(122 Reviews)
4 Bedrooms
4 Baths
10 Guests
2800 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $1,384/Night
7 Nights - US $9,689
Condo
10.0(116 Reviews)
1 Bedroom
1 Bath
4 Guests
754 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
US $364/Night
7 Nights - US $2,545
Apartment
10.0(116 Reviews)
1 Bedroom
1 Bath
4 Guests
- Private Pool
- Hot Tub
- Pool
- Ocean View
US $226/Night
7 Nights - US $1,582
Condo
10.0(113 Reviews)
3 Bedrooms
3 Baths
8 Guests
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
US $815/Night
7 Nights - US $5,704
