North Side Holiday Rentals
House
- Cayman Islands
- ·
- Rum Point
- 0.53 mi to center
10.0Exceptional
(152 Reviews)
2 Bedrooms
2 Baths
6 Guests
1900 ft²
Parking
Pool
Ocean View
Balcony/Terrace
US $364/Night
7 Nights - US $2,545
Apartment
- Cayman Islands
- ·
- Rum Point
- 0.59 mi to center
10.0Exceptional
(3 Reviews)
2 Bedrooms
3 Baths
6 Guests
1496.18 ft²
Oceanfront- Parking
- Pool
- Ocean View
US $353/Night
7 Nights - US $2,471
Apartment
- Cayman Islands
- ·
- Old Man Bay
- 0.13 mi to center
10.0Exceptional
(13 Reviews)
1 Bedroom
1 Bath
4 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $354/Night
7 Nights - US $2,477
Villa
- Cayman Islands
- ·
- North Side
- 0.71 mi to center
10.0Exceptional
(113 Reviews)
6 Bedrooms
4 Baths
12 Guests
3600 ft²
Private Pool
Breakfast- Parking
- Pool
US $1,309/Night
7 Nights - US $9,163
House
- Cayman Islands
- ·
- Rum Point
- 0.75 mi to center
10.0Exceptional
(3 Reviews)
1 Bedroom
1 Bath
2 Guests
796.53 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $316/Night
7 Nights - US $2,212
Condo
- Cayman Islands
- ·
- Rum Point
- 0.44 mi to center
10.0Exceptional
(113 Reviews)
2 Bedrooms
2 Baths
6 Guests
1150 ft²
- Oceanfront
Hot Tub- Parking
- Pool
US $342/Night
7 Nights - US $2,396
Villa
- Cayman Islands
- ·
- North Side
- 1.13 mi to center
10.0Exceptional
(111 Reviews)
3 Bedrooms
2 Baths
6 Guests
1400 ft²
- Parking
- Ocean View
- Balcony/Terrace
View
US $505/Night
7 Nights - US $3,536
New
Condo
- Cayman Islands
- ·
- Rum Point
- 0.45 mi to center
10.0Exceptional
(111 Reviews)
2 Bedrooms
2 Baths
6 Guests
1200 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
US $277/Night
7 Nights - US $1,936
Villa
- Cayman Islands
- ·
- North Side
- 1.14 mi to center
10.0Exceptional
(108 Reviews)
3 Bedrooms
3 Baths
6 Guests
1700 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $475/Night
7 Nights - US $3,323
Luxury Holiday Rentals in North Side
Over 505+ Luxury Holiday Rentals in or Near North Side
New
Apartment
- Cayman Islands
- ·
- North Side
- 0.67 mi to center
5 Bedrooms
5 Baths
11 Guests
4467.02 ft²
- Oceanfront
- Breakfast
- Parking
- Pool
Unlock the Best Price
House
- Cayman Islands
- ·
- Rum Point
- 0.59 mi to center
7 Bedrooms
7 Baths
16 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $7,814/Night
7 Nights - US $54,698
House
- Cayman Islands
- ·
- Rum Point
- 0.45 mi to center
6 Bedrooms
10 Baths
12 Guests
- Hot Tub
- Parking
- Pool
Air Conditioner
US $7,750/Night
7 Nights - US $54,250
House
- Cayman Islands
- ·
- North Side
- 2.34 mi to center
10.0Exceptional
(11 Reviews)
8 Bedrooms
8 Baths
18 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
US $6,322/Night
7 Nights - US $44,252
House
- Cayman Islands
- ·
- North Side
- 1.37 mi to center
10.0Exceptional
(2 Reviews)
11 Bedrooms
13 Baths
28 Guests
15000 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
US $5,291/Night
7 Nights - US $37,036
House
- Cayman Islands
- ·
- North Side
- 2.25 mi to center
9 Bedrooms
11 Baths
24 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $5,097/Night
7 Nights - US $35,679
House
- Cayman Islands
- ·
- North Side
- 2.36 mi to center
8 Bedrooms
9 Baths
20 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $5,090/Night
7 Nights - US $35,630
New
House
- Cayman Islands
- ·
- Rum Point
- 0.48 mi to center
7 Bedrooms
7 Baths
18 Guests
8000 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
US $4,487/Night
7 Nights - US $31,412
Villa
- Cayman Islands
- ·
- Rum Point
- 0.43 mi to center
10.0Exceptional
(1 Review)
8 Bedrooms
8 Baths
22 Guests
7200 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
US $4,453/Night
7 Nights - US $31,172
Top-Rated Holiday Rentals with a Pool in North Side
Over 404+ The Best Private Villas and Holiday Rentals in North Side with a Pool
Condo
- Cayman Islands
- ·
- Rum Point
- 0.40 mi to center
10.0Exceptional
(108 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Hot Tub
- Parking
- Pool
- Ocean View
US $346/Night
7 Nights - US $2,425
House
- Cayman Islands
- ·
- North Side
- 2.00 mi to center
10.0Exceptional
(101 Reviews)
3 Bedrooms
2 Baths
6 Guests
2000 ft²
- Private Pool
- Parking
- Pool
- Ocean View
US $944/Night
7 Nights - US $6,606
Condo
- Cayman Islands
- ·
- North Side
- 0.96 mi to center
10.0Exceptional
(98 Reviews)
2 Bedrooms
2 Baths
5 Guests
1250 ft²
- Private Pool
- Parking
- Pool
- Ocean View
US $318/Night
7 Nights - US $2,223
Condo
- Cayman Islands
- ·
- Rum Point
- 0.66 mi to center
10.0Exceptional
(87 Reviews)
1 Bedroom
1 Bath
4 Guests
1314 ft²
- Private Pool
- Parking
- Pool
- Ocean View
US $371/Night
7 Nights - US $2,594
Villa
- Cayman Islands
- ·
- Rum Point
- 0.25 mi to center
10.0Exceptional
(85 Reviews)
5 Bedrooms
5 Baths
12 Guests
4000 ft²
- Private Pool
- Parking
- Pool
- Ocean View
US $1,072/Night
7 Nights - US $7,501
House
- Cayman Islands
- ·
- Breakers
- 0.63 mi to center
10.0Exceptional
(83 Reviews)
4 Bedrooms
3 Baths
10 Guests
3100 ft²
- Private Pool
- Oceanfront
- Breakfast
- Parking
US $645/Night
7 Nights - US $4,517
Condo
- Cayman Islands
- ·
- Old Man Bay
- 0.07 mi to center
10.0Exceptional
(83 Reviews)
3 Bedrooms
3 Baths
6 Guests
1850 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
US $632/Night
7 Nights - US $4,423
House
- Cayman Islands
- ·
- North Side
- 0.83 mi to center
10.0Exceptional
(80 Reviews)
3 Bedrooms
3 Baths
6 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $441/Night
7 Nights - US $3,087
Condo
- Cayman Islands
- ·
- Rum Point
- 0.45 mi to center
10.0Exceptional
(78 Reviews)
1 Bedroom
1 Bath
4 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $287/Night
7 Nights - US $2,011
Pet-Friendly Holiday Rentals in North Side
Over 12+ Pet-Friendly Holiday Rentals in or Near North Side
Condo
- Cayman Islands
- ·
- Rum Point
- 0.42 mi to center
10.0Exceptional
(66 Reviews)
2 Bedrooms
2 Baths
6 Guests
1200 ft²
- Hot Tub
- Parking
- Pool
- Ocean View
US $278/Night
7 Nights - US $1,949
Apartment
- Cayman Islands
- ·
- Rum Point
- 0.41 mi to center
9.2Exceptional
(5 Reviews)
2 Bedrooms
2 Baths
6 Guests
1259.38 ft²
- Oceanfront
- Hot Tub
- Breakfast
- Parking
US $417/Night
7 Nights - US $2,916
House
- Cayman Islands
- ·
- North Side
- 1.90 mi to center
10.0Exceptional
(61 Reviews)
3 Bedrooms
3 Baths
9 Guests
3000 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $547/Night
7 Nights - US $3,826
Villa
- Cayman Islands
- ·
- Rum Point
- 0.48 mi to center
6 Bedrooms
5 Baths
18 Guests
7502.45 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $3,776/Night
7 Nights - US $26,432
House
- Cayman Islands
- ·
- Rum Point
- 0.20 mi to center
10.0Exceptional
(3 Reviews)
3 Bedrooms
3 Baths
8 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $808/Night
7 Nights - US $5,653
Cottage
- Cayman Islands
- ·
- North Side
- 0.47 mi to center
9.6Exceptional
(77 Reviews)
3 Bedrooms
2 Baths
9 Guests
1900 ft²
- Oceanfront
- Hot Tub
- Breakfast
- Parking
US $715/Night
7 Nights - US $5,003
Cottage
- Cayman Islands
- ·
- Rum Point
- 0.78 mi to center
9.6Exceptional
(15 Reviews)
1 Bedroom
1 Bath
4 Guests
- Parking
- Balcony/Terrace
Kitchen- Air Conditioner
US $389/Night
7 Nights - US $2,724
Condo
- Cayman Islands
- ·
- Rum Point
- 0.41 mi to center
9.4Exceptional
(6 Reviews)
2 Bedrooms
2 Baths
6 Guests
1200 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
US $370/Night
7 Nights - US $2,588
New
Apartment
- Cayman Islands
- ·
- Rum Point
- 0.42 mi to center
2 Bedrooms
2 Baths
4 Guests
1158 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
US $384/Night
7 Nights - US $2,685
Large Holiday Rentals and Private Villas in North Side
Over 145+ Large Holiday Rentals and Private Villas in or Near North Side
Villa
- Cayman Islands
- ·
- North Side
- 1.12 mi to center
10.0Exceptional
(80 Reviews)
3 Bedrooms
2 Baths
6 Guests
1700 ft²
- Hot Tub
- Parking
- Ocean View
- Balcony/Terrace
US $400/Night
7 Nights - US $2,802
Apartment
- Cayman Islands
- ·
- Rum Point
- 0.73 mi to center
10.0Exceptional
(1 Review)
21 Bedrooms
23 Baths
54 Guests
2120.49 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $1,416/Night
7 Nights - US $9,912
Villa
- Cayman Islands
- ·
- North Side
- 1.86 mi to center
1 Bedroom
1 Bath
- Pool
- Balcony/Terrace
Internet
Child Friendly
US $761/Night
7 Nights - US $5,327
Villa
- Cayman Islands
- ·
- North Side
- 2.88 mi to center
10.0Exceptional
(71 Reviews)
4 Bedrooms
3 Baths
10 Guests
2900 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
US $1,133/Night
7 Nights - US $7,933
Villa
- Cayman Islands
- ·
- Old Man Bay
- 0.47 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
5 Baths
10 Guests
- Hot Tub
- Parking
- Pool
- Air Conditioner
US $1,398/Night
7 Nights - US $9,787
Villa
- Cayman Islands
- ·
- Rum Point
- 0.37 mi to center
10.0Exceptional
(67 Reviews)
2 Bedrooms
2 Baths
5 Guests
1900 ft²
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $498/Night
7 Nights - US $3,488
House
- Cayman Islands
- ·
- North Side
- 0.59 mi to center
10.0Exceptional
(63 Reviews)
10 Bedrooms
7 Baths
26 Guests
7000 ft²
- Private Pool
- Oceanfront
- Breakfast
- Parking
US $1,901/Night
7 Nights - US $13,305
Villa
- Cayman Islands
- ·
- Rum Point
- 0.54 mi to center
10.0Exceptional
(55 Reviews)
6 Bedrooms
6 Baths
16 Guests
7800 ft²
- Private Pool
- Parking
- Pool
- Ocean View
US $3,781/Night
7 Nights - US $26,467
Villa
- Cayman Islands
- ·
- Rum Point
- 0.55 mi to center
10.0Exceptional
(54 Reviews)
5 Bedrooms
5 Baths
12 Guests
5996 ft²
- Private Pool
- Parking
- Pool
- Ocean View
US $1,351/Night
7 Nights - US $9,457
Wheelchair Accessible Holiday Homes in North Side
Over 58+ Wheelchair Accessible Holiday Homes in or Near North Side
Condo
- Cayman Islands
- ·
- Old Man Bay
- 0.13 mi to center
10.0Exceptional
(57 Reviews)
2 Bedrooms
2 Baths
6 Guests
1624 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $460/Night
7 Nights - US $3,218
House
- Cayman Islands
- ·
- Breakers
- 0.59 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
2 Baths
6 Guests
1797.57 ft²
- Parking
- Pool
- Air Conditioner
- Internet
US $677/Night
7 Nights - US $4,739
Condo
- Cayman Islands
- ·
- Old Man Bay
- 0.10 mi to center
10.0Exceptional
(12 Reviews)
1 Bedroom
1 Bath
6 Guests
- Private Pool
- Parking
- Pool
- Ocean View
US $523/Night
7 Nights - US $3,662
House
- Cayman Islands
- ·
- Rum Point
- 0.27 mi to center
10.0Exceptional
(17 Reviews)
6 Bedrooms
6 Baths
14 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
US $3,242/Night
7 Nights - US $22,697
House
- Cayman Islands
- ·
- Old Man Bay
- 0.67 mi to center
9.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
4 Guests
1162.5 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $349/Night
7 Nights - US $2,442
House
- Cayman Islands
- ·
- Rum Point
- 0.45 mi to center
10.0Exceptional
(6 Reviews)
5 Bedrooms
5 Baths
14 Guests
4000 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
US $1,769/Night
7 Nights - US $12,386
Condo
- Cayman Islands
- ·
- Rum Point
- 0.74 mi to center
10.0Exceptional
(4 Reviews)
3 Bedrooms
3 Baths
8 Guests
2620 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $1,114/Night
7 Nights - US $7,801
Condo
- Cayman Islands
- ·
- Rum Point
- 0.74 mi to center
10.0Exceptional
(2 Reviews)
4 Bedrooms
3 Baths
10 Guests
2829 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
US $1,287/Night
7 Nights - US $9,007
Condo
- Cayman Islands
- ·
- Rum Point
- 0.74 mi to center
10.0Exceptional
(2 Reviews)
2 Bedrooms
2 Baths
6 Guests
1350 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
US $761/Night
7 Nights - US $5,324
North Side Private Villas and Holiday Homes Under $200
Over 4+ North Side Private Villas and Holiday Homes Under $200
House
- Cayman Islands
- ·
- North Side
- 1.76 mi to center
9.6Exceptional
(22 Reviews)
3 Bedrooms
3 Baths
9 Guests
3000 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $170/Night
7 Nights - US $1,192
New
Apartment
- Cayman Islands
- ·
- Old Man Bay
- 0.57 mi to center
1 Bedroom
1 Bath
2 Guests
- Air Conditioner
- Internet
- Child Friendly
Laundry
US $185/Night
7 Nights - US $1,295
Condo
- Cayman Islands
- ·
- Rum Point
- 0.72 mi to center
4.8Average
(33 Reviews)
1 Bedroom
1 Bath
4 Guests
1100 ft²
- Pool
- Ocean View
- Balcony/Terrace
- View
US $200/Night
7 Nights - US $1,400
Apartment
- Cayman Islands
- ·
- Breakers
- 0.21 mi to center
1 Bedroom
1 Bath
3 Guests
- Kitchen
- Air Conditioner
- Internet
- Laundry
US $100/Night
7 Nights - US $700
Instantly Bookable Holiday Homes in North Side
Over 262+ Instantly Bookable Holiday Homes in or Near North Side
Condo
- Cayman Islands
- ·
- Rum Point
- 0.80 mi to center
10.0Exceptional
(93 Reviews)
1 Bedroom
1 Bath
3 Guests
897 ft²
- Parking
- Ocean View
- Balcony/Terrace
- View
US $221/Night
7 Nights - US $1,547
Condo
- Cayman Islands
- ·
- Rum Point
- 0.74 mi to center
1 Bedroom
1 Bath
- Private Pool
- Oceanfront
- Parking
- Pool
US $1,309/Night
7 Nights - US $9,164
Condo
- Cayman Islands
- ·
- Rum Point
- 0.71 mi to center
10.0Exceptional
(78 Reviews)
2 Bedrooms
2 Baths
5 Guests
1450 ft²
- Parking
- Ocean View
- Balcony/Terrace
- View
US $259/Night
7 Nights - US $1,814
Condo
- Cayman Islands
- ·
- Rum Point
- 0.36 mi to center
10.0Exceptional
(76 Reviews)
2 Bedrooms
2 Baths
6 Guests
1600 ft²
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $487/Night
7 Nights - US $3,411
Condo
- Cayman Islands
- ·
- North Side
- 1.43 mi to center
10.0Exceptional
(76 Reviews)
2 Bedrooms
2 Baths
4 Guests
1250 ft²
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $358/Night
7 Nights - US $2,508
Condo
- Cayman Islands
- ·
- Rum Point
- 0.44 mi to center
10.0Exceptional
(66 Reviews)
1 Bedroom
1 Bath
2 Guests
700 ft²
- Hot Tub
- Parking
- Pool
- Ocean View
US $280/Night
7 Nights - US $1,963
House
- Cayman Islands
- ·
- Rum Point
- 0.32 mi to center
10.0Exceptional
(65 Reviews)
2 Bedrooms
2 Baths
6 Guests
2000 ft²
- Hot Tub
- Parking
- Pool
- Ocean View
US $525/Night
7 Nights - US $3,674
Condo
- Cayman Islands
- ·
- Rum Point
- 0.72 mi to center
10.0Exceptional
(63 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $287/Night
7 Nights - US $2,009
Condo
- Cayman Islands
- ·
- North Side
- 1.67 mi to center
10.0Exceptional
(62 Reviews)
2 Bedrooms
2 Baths
5 Guests
1275 ft²
- Private Pool
- Parking
- Pool
- Ocean View
US $307/Night
7 Nights - US $2,147
Book a Last Minute Place to Stay in North Side
About Casai's Private Villas and Holiday Rentals in North Side
Discover more than 514 vacation rentals available in North Side. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in North Side.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in North Side, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near North Side. On average, places to stay near North Side offer 1545.29 ft², with nightly prices averaging US $1,038.
With Casai, finding and comparing holiday rentals in North Side is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
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Top Accommodation Types in North Side
| Type | Count |
|---|---|
| Vacation Homes | 250 |
| Holiday Apartments | 68 |
| Villas | 52 |
| Cottages | 6 |
Use these Quick Filters to Find a Holiday Rental in North Side
★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in North Side.
Top Attractions Around North Side, KY
Casai offers a large selection of top attractions around North Side . Research things to do on your vacation before you visit North Side.
Other Places to Stay in North Side, KY
Frequently Asked Questions About North Side?
What are the top holiday rentals in North Side?
With numerous options available in North Side, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in North Side:
- Dream Kai -Island House #15
- Calypso Blue Luxury 6BR Oceanfront Villa Private Pool & Reef Grand Cayman
- Relax in coastal luxury - renovated oceanfront condo Kaibo phase 2 - B13
- Gorgeous Detached Sandy Beachfront Villa at Azure Breeze Villas.
- Beautiful Beachfront Condo in Cayman Kai/Rum Point
- Azure Breeze 3! Peaceful & Pristine-3Bd, 3 BATH AWAY from crowds! Beachfront!
- "Tortuga Kai" - 2 BR Oceanfront Condo At Kaibo, Grand Cayman
- Villa Esprit–Stunning beachfront villa in North Side w/pool-by Cayman Villas
- The Harvey Nicole: Modern Caribbean Ocean Front Condo Grand Cayman.
- Beautiful Ocean Front Sea Lodge in Cayman Kai
How many holiday rentals have private pools in North Side?
Discover a selection of holiday rentals with private pools near North Side with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.
- Kai Baby Waterfront Cottage Private Pool Cabana Kayaks Paddleboards & Bikes!
- Timmys Place
- Rip Kai by Grand Cayman Villas
- Nature's View: Cayman Style Tranquility at Pools of the Kai #2
Which holiday homes in North Side are best for families?
If you're searching for a family-friendly holiday home in North Side, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in North Side:
- The Retreat at Rum Point Unit #28. Stunning 3BR Oceanfront Penthouse Condo
- On the Bay #103 - Oceanfront 3BR Condo - Old Man Bay, North Side
- Northside Grand Cayman Getaway w/Private Beach!
How many Casai.nz holiday rentals are available in North Side?
As of 2026, Casai boasts over 514 properties listed in the North Side area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in North Side.
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