Best Vacation Homes in Hillsborough
2 Guests
1 Bedroom
1 Bathroom
Ocean View
Apartment
- Oceanfront
- Ocean View
- Balcony/Terrace
CA $135/Night
For 7 Nights CA $943
5 Guests
2 Bedrooms
1 Bathroom
Free Cancellation
Villa
- View
- Parking
- Air Conditioner
CA $259/Night
For 7 Nights CA $1,814
1 Bedroom
1 Bathroom
Family Friendly
House
- Balcony/Terrace
- Pet Friendly
- Kitchen
CA $203/Night
For 7 Nights CA $1,419
2200 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Ocean View
House
- Ocean View
- Balcony/Terrace
- View
CA $543/Night
For 7 Nights CA $3,800
2 Guests
1 Bedroom
1 Bathroom
Free Cancellation
House
- View
- Parking
- Air Conditioner
CA $184/Night
For 7 Nights CA $1,286
3 Guests
2 Bedrooms
1 Bathroom
Ocean View
Apartment
- Oceanfront
- Ocean View
- View
CA $191/Night
For 7 Nights CA $1,334
5 Guests
2 Bedrooms
1 Bathroom
Ocean View
Apartment
- Oceanfront
- Ocean View
- Balcony/Terrace
CA $233/Night
For 7 Nights CA $1,632
1400 ft²
18 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Cottage
- Oceanfront
- Ocean View
- Balcony/Terrace
CA $234/Night
For 7 Nights CA $1,637
Hillsborough Luxury Rentals
1615 ft²
8 Guests
4 Bedrooms
2 Bathrooms
Ocean View
Villa
- Oceanfront
- Pool
- Ocean View
CA $1,357/Night
For 7 Nights CA $9,501
12 Guests
5 Bedrooms
5 Bathrooms
Ocean View
Villa
- Private Pool
- Pool
- Ocean View
CA $1,141/Night
For 7 Nights CA $7,985
CA $1,061/Night
For 7 Nights CA $7,428
8 Guests
4 Bedrooms
4 Bathrooms
Family Friendly
Villa
- Fireplace/Heating
- Pool
- Kitchen
CA $999/Night
For 7 Nights CA $6,992
8 Guests
3 Bedrooms
3 Bathrooms
Ocean View
Villa
- Private Pool
- Oceanfront
- Pool
CA $653/Night
For 7 Nights CA $4,568
4000 ft²
6 Guests
2 Bedrooms
4 Bathrooms
Ocean View
House
- Oceanfront
- Ocean View
- View
CA $374/Night
For 7 Nights CA $2,620
6 Guests
3 Bedrooms
3 Bathrooms
Villa
- Air Conditioner
- Internet
- Child Friendly
CA $306/Night
For 7 Nights CA $2,143
CA $292/Night
For 7 Nights CA $2,041
Hillsborough Pet Friendly Vacation Rentals
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Cottage
- Balcony/Terrace
- Pet Friendly
- Kitchen
CA $92/Night
For 7 Nights CA $647
796.53 ft²
4 Guests
2 Bedrooms
1 Bathroom
Free Cancellation
Apartment
- View
- Pet Friendly
- Parking
CA $44/Night
For 7 Nights CA $307
CA $1,040/Night
For 7 Nights CA $7,277
646 ft²
4 Guests
2 Bedrooms
1 Bathroom
Ocean View
House
- Oceanfront
- Ocean View
- Balcony/Terrace
CA $132/Night
For 7 Nights CA $927
645.83 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- View
- Pet Friendly
- Parking
CA $124/Night
For 7 Nights CA $865
2 Guests
1 Bedroom
1 Bathroom
Couples Retreat
Apartment
- Pet Friendly
- Air Conditioner
- Internet
CA $96/Night
For 7 Nights CA $672
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Pet Friendly
- Kitchen
- Parking
CA $62/Night
For 7 Nights CA $432
6 Guests
3 Bedrooms
1 Bathroom
Family Friendly
House
- Pet Friendly
- Child Friendly
- Security/Safety
CA $144/Night
For 7 Nights CA $1,008
Hillsborough Large Vacation Homes
7 Guests
3 Bedrooms
1 Bathroom
Ocean View
Villa
- Oceanfront
- Ocean View
- Balcony/Terrace
CA $183/Night
For 7 Nights CA $1,279
516.67 ft²
19 Guests
6 Bedrooms
6 Bathrooms
Free Cancellation
Apartment
- Oceanfront
- Ocean View
- Balcony/Terrace
CA $177/Night
For 7 Nights CA $1,238
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Villa
- Oceanfront
- Pool
- Ocean View
CA $330/Night
For 7 Nights CA $2,310
1650 ft²
12 Guests
6 Bedrooms
2 Bathrooms
Family Friendly
Villa
- Private Pool
- Pool
- Balcony/Terrace
CA $1,286/Night
For 7 Nights CA $9,005
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Villa
- Pool
- Balcony/Terrace
- Kitchen
CA $324/Night
For 7 Nights CA $2,269
2 Guests
1 Bedroom
2 Bathrooms
Family Friendly
Villa
- Kitchen
- Laundry
- TV
CA $151/Night
For 7 Nights CA $1,056
1650 ft²
8 Guests
5 Bedrooms
2 Bathrooms
Family Friendly
Villa
- Private Pool
- Pool
- Balcony/Terrace
CA $1,337/Night
For 7 Nights CA $9,357
10 Guests
5 Bedrooms
6 Bathrooms
Group Friendly
Villa
CA $1,097/Night
For 7 Nights CA $7,678
Why Choose Rent By Owner for your Hillsborough 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 Hillsborough
When should you plan your Vacation Rentals stay?
Choosing the optimal time to visit this destination ensures you enjoy favorable weather and a vibrant local atmosphere, making your stay in Hillsborough even more memorable and seamless when booking through trustworthy vacation rentals in the area.
Peak Season Highlights
December to April
During this peak season, you can enjoy warm, sunny days perfect for exploring the region's natural beauty and relaxing at your vacation rental in Hillsborough. The weather remains dry and inviting, making it ideal for outdoor activities.
Average Temperature Daytime: 28°C - Nighttime: 22°C
July to August
This period marks another busy time, with visitors taking advantage of the warm summer climate. It’s an excellent opportunity to experience the lively atmosphere while staying in a comfortable vacation rental here.
Average Temperature Daytime: 30°C - Nighttime: 24°C
Off-Season Highlights
May to June
In the shoulder months, fewer travelers visit, offering a more relaxed experience with pleasant weather that’s still suitable for enjoying the region’s scenic surroundings from your vacation rental.
Average Temperature Daytime: 27°C - Nighttime: 23°C
September to November
As this destination transitions into the rainy season, you might find better deals on vacation rentals and fewer crowds. The lush landscape enhances your stay during this quieter time of year.
Average Temperature Daytime: 29°C - Nighttime: 24°C
Weekly Weather Forecast for Hillsborough
How to Book Your Hillsborough 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 Hillsborough
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 a private outdoor swimming pool to relax and unwind in the warm Caribbean climate.
- Take advantage of lush, tropical gardens that surround your outdoor space for added privacy and tranquility.
- Cook up a barbecue at the designated outdoor grilling area to savor local flavors with family and friends.
- Relax on spacious verandas or patios that offer stunning views of the region’s scenic landscape.
- Make the most of outdoor dining areas perfect for enjoying meals al fresco amidst the area's natural beauty.
- Utilize outdoor lounging furniture designed for soaking up the sun and enjoying the peaceful surroundings.
- Explore well-maintained walking paths and garden spaces ideal for leisurely strolls in this scenic destination.
Top Attractions Around Hillsborough
What attractions are nearby?
In this charming destination, you can explore a variety of outdoor activities and cultural experiences just moments from your accommodation, making it easy to enjoy the best that the region has to offer during your stay.
Family Activities
- Zion Hill Waterfall: Immerse yourself in the natural beauty of the region by exploring Zion Hill Waterfall, a perfect spot for family picnics and refreshing swims amidst lush surroundings.
- Hillsborough Market: Experience local culture firsthand at this vibrant market where you can sample fresh produce and handmade crafts, making it an engaging activity for all ages.
- Grand Anse Beach: Enjoy a relaxing day along one of the region's most beautiful beaches, ideal for swimming, sunbathing, and building sandcastles with your family.
- Belmont Estate Tour: Discover the area’s rich history and taste traditional Grenadian cuisine during a guided tour of Belmont Estate, offering an educational experience for the entire family.
Adult Activities
- Sailing and Boating: Experience the region’s scenic coastlines by renting a boat or joining a sailing tour to explore hidden coves and pristine beaches nearby.
- Local Market Visits: Wander through the vibrant markets to discover fresh produce, local crafts, and authentic Grenadian flavors that showcase the area's rich culture.
- Hiking Adventures: Embark on nature trails and hillside walks that offer breathtaking views of the region’s lush landscapes and coastline.
- Historical and Cultural Tours: Discover the area's island history and heritage through guided visits to local sites and landmarks that tell the story of this Caribbean destination.
Other Places to Stay in Hillsborough, FL
Saint George
Saint David
Hillsborough Travel Tips
How Can You Make the Most of Your Stay?
- Explore local markets and eateries: Take time to experience the authentic flavors and crafts that reflect the vibrant culture of this destination, enhancing your overall stay.
- Plan outdoor excursions wisely: Maximize your enjoyment by scheduling visits to nearby attractions during the cooler parts of the day, making your trip more comfortable and memorable.
- Book your accommodation early: Securing your vacation rentals well in advance ensures you have a wide selection of properties close to the area's best spots, offering convenience and peace of mind.
- Learn about the region’s customs: Familiarizing yourself with local traditions and etiquette can enrich your experience and help you connect more meaningfully with the community here.
Transportation Options
- Taxis: Taxis offer convenient and reliable transportation around this destination, allowing you to explore the region comfortably at your own pace.
- Car Rentals: Renting a car provides the flexibility to discover hidden gems and navigate this area at your leisure, perfect for an independent exploration experience.
- Public Buses: Public buses are an affordable option for getting around here, connecting you to key locations within the region efficiently.
- Private Transfers: Private transfer services ensure a seamless arrival and departure experience, giving you peace of mind upon reaching your vacation rentals in the area.
Local Customs Options
- Respect for Local Traditions: When visiting the area, you’ll find that respecting local customs and traditions is highly valued by the community.
- Celebrating Festivals: Participating in and observing regional festivals offers an authentic way to experience the vibrant culture of this destination.
- Language Etiquette: Learning a few basic phrases in Grenadian Creole can enhance your interactions with locals during your stay.
- Community Hospitality: You may notice the warmth and friendliness that define the region’s welcoming atmosphere towards visitors.
Frequently Asked Questions About Hillsborough?
1. What are the top vacation rentals in Hillsborough?
There are a lot of options in Hillsborough. If you plan on staying in the Hillsborough area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Hillsborough:
- Beautifully Furnished And Modern Self Contained One Bedroom Apartment
- Secluded villa overlooking black sand beach
- One of the best locations on the island!
- luxurious two bedroom apartment
- TURTLE COTTAGE - 2 bed 2 bath self catering Cottage
- ComfyCabin is rustic with modern amenities, has deck with great view. Peaceful.
- HIBISCUS COTTAGE Almost Paradise - 1 bed Caribbean Hideaway
- BLUE COTTAGE Almost Paradise
- Sunset Plaza Apartments 2
- Sea Breeze Apartment in Sauteurs with everything close by
2. Which vacation homes in Hillsborough are best for families?
If you are looking for a family-friendly vacation home in Hillsborough, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Hillsborough:
3. How many Rentbyowner vacation rentals are available in Hillsborough?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 80 in the Hillsborough 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 Hillsborough.
4. What is the cancellation policy for booking a vacation rental in Hillsborough, Grenada?
The cancellation policy varies by property and owner. You should review the specific listing details or contact the host directly to understand the terms and any applicable fees.
5. How do I confirm my reservation at a vacation rental in this region?
Reservation confirmation typically requires completing the booking process online and receiving a confirmation email. For further assistance, reach out to the property owner through the platform.
6. Are there any specific check-in and check-out procedures I should be aware of in Hillsborough, Grenada?
Check-in and check-out times are set by individual hosts. Details are usually provided in the listing or during your booking process. Contact the host if you need special arrangements.
7. What amenities are usually included in vacation rentals here?
Amenities vary by property but often include essentials like Wi-Fi, kitchen facilities, and air conditioning. For precise details, review the listing information carefully or contact the owner directly.
8. Is a security deposit required when booking a vacation rental in this area?
Many hosts require a security deposit to cover potential damages or extra charges. The amount and conditions are specified in the listing or during the booking process. Confirm these details with the owner before finalizing your reservation.
Hillsborough Top Rated Vacation Rentals
CA $235/Night
For 7 Nights CA $1,642
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Bed & Breakfast
- Pool
- Balcony/Terrace
- Breakfast
CA $96/Night
For 7 Nights CA $673
699.65 ft²
2 Guests
1 Bedroom
1 Bathroom
Free Cancellation
Apartment
- Oceanfront
- Pool
- Ocean View
CA $218/Night
For 7 Nights CA $1,529
699.65 ft²
2 Guests
1 Bedroom
1 Bathroom
Free Cancellation
Apartment
- Oceanfront
- Pool
- Ocean View
CA $196/Night
For 7 Nights CA $1,372
900 ft²
2 Guests
1 Bedroom
1 Bathroom
Ocean View
Apartment
- Oceanfront
- Pool
- Ocean View
CA $169/Night
For 7 Nights CA $1,186
3 Guests
1 Bedroom
1 Bathroom
Ocean View
Apartment
- Oceanfront
- Spa
- Pool
CA $293/Night
For 7 Nights CA $2,048
667 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Pool
- Balcony/Terrace
- Child Friendly
CA $339/Night
For 7 Nights CA $2,370
3 Guests
1 Bedroom
1 Bathroom
Family Friendly
Villa
- Pool
- Child Friendly
- Bedding/Linens
CA $302/Night
For 7 Nights CA $2,111
