Best Vacation Homes in North Side
House
10.0(150 Reviews)
2 Bedrooms
2 Baths
6 Guests
1900 ft²
Parking
Pool
Ocean View
Balcony/Terrace
CA $559/Night
7 Nights - CA $3,915
Apartment
10.0(3 Reviews)
2 Bedrooms
3 Baths
6 Guests
1496.18 ft²
- Parking
- Pool
View
Air Conditioner
CA $494/Night
7 Nights - CA $3,461
Villa
10.0(111 Reviews)
6 Bedrooms
4 Baths
12 Guests
3600 ft²
Private Pool
Breakfast- Parking
- Pool
CA $1,843/Night
7 Nights - CA $12,902
House
10.0(3 Reviews)
1 Bedroom
1 Bath
2 Guests
796.53 ft²
Oceanfront- Parking
- Ocean View
- View
CA $382/Night
7 Nights - CA $2,675
Condo
10.0(111 Reviews)
2 Bedrooms
2 Baths
6 Guests
1150 ft²
- Oceanfront
Hot Tub- Parking
- Pool
CA $472/Night
7 Nights - CA $3,307
Villa
10.0(110 Reviews)
3 Bedrooms
2 Baths
6 Guests
1400 ft²
- Parking
- Ocean View
- Balcony/Terrace
- View
CA $579/Night
7 Nights - CA $4,057
Condo
10.0(109 Reviews)
2 Bedrooms
2 Baths
6 Guests
1200 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
CA $372/Night
7 Nights - CA $2,607
North Side Luxury Rentals
CA $10,946/Night
7 Nights - CA $76,619
House
6 Bedrooms
10 Baths
12 Guests
- Hot Tub
- Parking
- Pool
- Air Conditioner
CA $10,856/Night
7 Nights - CA $75,991
House
10.0(11 Reviews)
8 Bedrooms
8 Baths
18 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
CA $7,405/Night
7 Nights - CA $51,838
House
9 Bedrooms
11 Baths
24 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
CA $7,140/Night
7 Nights - CA $49,978
House
8 Bedrooms
9 Baths
20 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
CA $7,130/Night
7 Nights - CA $49,909
House
10.0(2 Reviews)
11 Bedrooms
13 Baths
28 Guests
15000 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
CA $6,348/Night
7 Nights - CA $44,438
New
House
7 Bedrooms
7 Baths
18 Guests
8000 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
CA $6,303/Night
7 Nights - CA $44,124
Villa
10.0(1 Review)
8 Bedrooms
8 Baths
22 Guests
7200 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
CA $6,253/Night
7 Nights - CA $43,771
North Side Pet Friendly Vacation Rentals
Condo
10.0(63 Reviews)
2 Bedrooms
2 Baths
6 Guests
1200 ft²
- Hot Tub
- Parking
- Pool
- Ocean View
CA $377/Night
7 Nights - CA $2,638
Apartment
9.2(5 Reviews)
2 Bedrooms
2 Baths
6 Guests
1259.38 ft²
- Oceanfront
- Hot Tub
- Breakfast
- Parking
CA $584/Night
7 Nights - CA $4,085
House
10.0(60 Reviews)
3 Bedrooms
3 Baths
9 Guests
3000 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
CA $800/Night
7 Nights - CA $5,597
Villa
6 Bedrooms
5 Baths
18 Guests
7502.45 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
CA $5,289/Night
7 Nights - CA $37,025
House
10.0(3 Reviews)
3 Bedrooms
3 Baths
8 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
CA $1,277/Night
7 Nights - CA $8,941
House
9.8(65 Reviews)
5 Bedrooms
4 Baths
10 Guests
2850 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
CA $1,289/Night
7 Nights - CA $9,024
Cottage
9.6(76 Reviews)
3 Bedrooms
2 Baths
9 Guests
1900 ft²
- Oceanfront
- Hot Tub
- Breakfast
- Parking
CA $967/Night
7 Nights - CA $6,767
Cottage
9.6(15 Reviews)
1 Bedroom
1 Bath
4 Guests
- Parking
Kitchen- Air Conditioner
Internet
CA $564/Night
7 Nights - CA $3,947
North Side Large Vacation Homes
Villa
10.0(106 Reviews)
3 Bedrooms
3 Baths
6 Guests
1700 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
CA $671/Night
7 Nights - CA $4,694
Apartment
10.0(1 Review)
21 Bedrooms
23 Baths
54 Guests
2120.49 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
CA $1,983/Night
7 Nights - CA $13,884
Villa
1 Bedroom
1 Bath
- Pool
- Balcony/Terrace
- Internet
Child Friendly
CA $1,066/Night
7 Nights - CA $7,462
Villa
10.0(83 Reviews)
5 Bedrooms
5 Baths
12 Guests
4000 ft²
- Private Pool
- Parking
- Pool
- Ocean View
CA $1,568/Night
7 Nights - CA $10,974
Villa
10.0(1 Review)
1 Bedroom
5 Baths
10 Guests
- Hot Tub
- Parking
- Pool
- Air Conditioner
CA $1,958/Night
7 Nights - CA $13,709
House
10.0(81 Reviews)
4 Bedrooms
3 Baths
10 Guests
3100 ft²
- Private Pool
- Oceanfront
- Breakfast
- Parking
CA $891/Night
7 Nights - CA $6,239
Villa
10.0(78 Reviews)
3 Bedrooms
2 Baths
6 Guests
1700 ft²
- Hot Tub
- Parking
- Ocean View
- Balcony/Terrace
CA $586/Night
7 Nights - CA $4,100
Villa
10.0(68 Reviews)
4 Bedrooms
3 Baths
10 Guests
2900 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
CA $1,574/Night
7 Nights - CA $11,021
Why Choose Rent By Owner for your North Side Vacation Rental Homes?
What makes our Vacation Rentals 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.
Best Times to Visit North Side
When should you plan your Vacation Rentals stay?
Choosing the ideal time to visit this destination allows you to enjoy its beautiful climate and vibrant atmosphere while making the most of your stay in North Side’s exceptional vacation rentals.
Peak Season Highlights
December to April
During the winter months, you'll enjoy warm daytime temperatures and minimal rainfall, making it ideal for outdoor activities in this region.
Average Temperature Daytime: 75°F to 85°F - Nighttime: 65°F to 75°F
June to August
Summer brings lively crowds and vibrant local events, with plenty of sunshine and calm seas perfect for water-based adventures here.
Average Temperature Daytime: 88°F to 92°F - Nighttime: 78°F to 82°F
Off-Season Highlights
May and November
Transition months feature fewer visitors and slightly lower humidity, offering a quieter experience while still enjoying pleasant weather.
Average Temperature Daytime: 80°F to 85°F - Nighttime: 70°F to 75°F
September and October
These months fall within the hurricane season, so you might encounter occasional rain, but they often offer more budget-friendly options for accommodation here.
Average Temperature Daytime: 85°F to 88°F - Nighttime: 75°F to 78°F
Weekly Weather Forecast for North Side
How to Book Your North Side Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. 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 North Side
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals 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
Outdoor Amenities
- Enjoy outdoor swimming pools that offer a refreshing escape in the warm Caribbean sun.
- Relax on spacious private patios or decks with scenic views of the area's natural beauty.
- Take advantage of lush, landscaped gardens surrounding your rental for peaceful strolls.
- Make use of outdoor barbecue areas to indulge in flavorful meals under the open sky.
- Stay active with access to well-maintained tennis courts or other sports facilities.
- Benefit from direct access to nearby beaches for sunbathing, swimming, and water activities.
- Capitalize on outdoor seating areas designed for enjoying the tranquil surroundings of this destination.
Top Attractions Around North Side
What attractions are nearby?
While staying here, you'll find a variety of nearby activities to enjoy, from exploring pristine beaches to engaging in water sports and nature excursions that highlight the region’s natural beauty.
Family Activities
- Starfish Point: Discover a family-friendly beach where gentle waters and abundant starfish create a perfect setting for children to explore safely.
- Cayman Turtle Centre: Visit this renowned attraction nearby, offering interactive experiences with sea turtles that will delight young and old alike.
- North Side Nature Trail: Embark on a scenic walk through the area's lush landscape, ideal for families seeking outdoor adventure and wildlife spotting.
- Local Snorkeling Spots: Enjoy safe, shallow snorkeling areas just off the coast, providing opportunities for your family to observe vibrant marine life together.
Adult Activities
- Snorkeling Adventures: Explore vibrant coral reefs and marine life just off the coast, perfect for discovering the region’s underwater beauty from your nearby vacation rental.
- Diving Excursions: Experience the thrill of diving in clear waters filled with colorful sea creatures, making this a must-do activity here for adventure enthusiasts.
- Fishing Trips: Enjoy deep-sea or reef fishing excursions, offering you the chance to catch local game fish while immersed in the peaceful surroundings of the area.
- Nature and Bird Watching: Visit protected areas and nature reserves close to your vacation rental to observe local flora and fauna in their natural habitat.
Other Places to Stay in North Side
Cayman Kai Public Beach
Rum Point Beach
Star Fish Point
Starfish Beach
Rum Point
Mastic Trail South Trailhead
Mastic Trail North Trailhead
Breakers
Queen Elizabeth II Botanic Park
Brinkleys
Babylon (Dive Site)
Old Man Bay
North Side Travel Tips
How Can You Make the Most of Your Stay?
- Plan Your Activities in Advance: Take advantage of the region’s natural beauty by scheduling outdoor adventures and water activities early to ensure availability and a memorable experience.
- Explore Local Dining Options: Discover the area’s authentic flavors by visiting local eateries, making your stay here both delicious and culturally enriching.
- Utilize Property Amenities Fully: Maximize your comfort by familiarizing yourself with the amenities provided at your vacation rental, ensuring a relaxing and convenient stay.
- Respect the Environment and Community: Maintain the destination’s pristine environment by following eco-friendly practices and supporting local businesses during your visit.
Transportation Options
- Car Rentals: You can easily rent a car here to explore the region at your own pace, with several local providers offering flexible options for visitors.
- Public Buses: The area is served by reliable public buses that provide an affordable and convenient way to travel around the destination and reach nearby attractions.
- Taxis and Rideshare Services: Taxis and rideshare options like Uber are available for quick, direct transportation, ensuring you can comfortably get to your vacation rental or other destinations in the region.
- Private Transfers: Private shuttle services operate in the area, offering personalized transportation solutions from the airport directly to your accommodation.
Local Customs Options
- Local Seafood Cuisine: You will find that enjoying fresh seafood dishes is a cherished tradition here, reflecting the region's rich maritime heritage.
- Island Celebrations and Festivals: Participating in local festivals allows you to experience authentic cultural expressions that are deeply rooted in the area's history and community spirit.
- Respect for Nature and Marine Life: Embracing eco-friendly practices and respecting marine environments are valued customs that help preserve the natural beauty of the region.
- Traditional Crafts and Artistry: Exploring handcrafted goods and local art provides insight into the cultural identity and artistic traditions of the area’s residents.
Frequently Asked Questions About North Side?
1. What are the top vacation rentals in North Side?
There are a lot of options in North Side. If you plan on staying in the North Side area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation 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 3 Bedroom Beachfront Villa in North Side with pool!
- Waterfront 2BR w/Pool/Jacuzzi– 7-UP Condo in Kaibo Kai
- The Harvey Nicole: Modern Caribbean Ocean Front Condo Grand Cayman.
2. How many vacation rentals have private pools in North Side?
There are 159 vacation rentals with private pools near North Side. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in North Side are best for families?
If you are looking for a family-friendly vacation home in North Side, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in North Side:
4. How many Rentbyowner vacation rentals are available in North Side?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 528 in the North Side area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in North Side.
5. What is the cancellation policy for vacation rentals in North Side, Cayman Islands?
The cancellation policy varies by property owner. You should review the specific listing details or contact the host directly to understand the terms related to cancellations and refunds for your stay.
6. Are there any additional fees I should be aware of when booking a rental here?
Additional fees such as cleaning, security deposits, or service charges are listed on each property’s page. It’s recommended to read the listing carefully or reach out to the owner for clarification before completing your booking.
7. What amenities are typically included in vacation rentals in this region?
Most properties in this destination offer amenities like Wi-Fi, air conditioning, fully equipped kitchens, and outdoor spaces. To confirm specific features, please consult the property listing or contact the host directly.
8. How far in advance should I book my stay in the area to secure the best options?
Booking well in advance is advised, especially during peak travel seasons, to ensure availability and the best choices. Check current availability and plan accordingly by browsing listings early.
9. Is it possible to find pet-friendly vacation rentals nearby?
Many hosts offer pet-friendly options, but this varies by property. Use the search filters or contact owners directly to find accommodations that welcome your pets in the area.
North Side Top Rated Vacation Rentals
Condo
10.0(106 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Hot Tub
- Parking
- Pool
- Ocean View
CA $487/Night
7 Nights - CA $3,409
House
10.0(101 Reviews)
3 Bedrooms
2 Baths
6 Guests
2000 ft²
- Private Pool
- Parking
- Pool
- Ocean View
CA $1,292/Night
7 Nights - CA $9,042
Condo
10.0(100 Reviews)
2 Bedrooms
2 Baths
4 Guests
1250 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
CA $427/Night
7 Nights - CA $2,986
Condo
10.0(97 Reviews)
2 Bedrooms
2 Baths
5 Guests
1250 ft²
- Private Pool
- Parking
- Pool
- Ocean View
CA $443/Night
7 Nights - CA $3,101
Condo
10.0(84 Reviews)
1 Bedroom
1 Bath
4 Guests
1314 ft²
- Private Pool
- Parking
- Pool
- Ocean View
CA $552/Night
7 Nights - CA $3,866
Condo
10.0(82 Reviews)
3 Bedrooms
3 Baths
6 Guests
1850 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
CA $892/Night
7 Nights - CA $6,240
House
10.0(80 Reviews)
3 Bedrooms
3 Baths
6 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
CA $616/Night
7 Nights - CA $4,312
Condo
10.0(78 Reviews)
1 Bedroom
1 Bath
4 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
CA $413/Night
7 Nights - CA $2,894
