Holiday rentals in Gillitts

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Top-rated holiday rentals in Gillitts

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite
A cozy bedroom showcases a plush bed adorned with decorative pillows and a soft throw blanket. A wooden bench is positioned at the foot of the bed. A sliding barn door leads to a modern bathroom, and a large mirror reflects the serene atmosphere.
Guest house in Hillcrest
4.97 out of 5 average rating, 174 reviews

Stacey's Cornerstone Apartment

Step into our new, timelessly decorated luxurious apartment with Grand doors & exquisitely high ceilings. Indulge in a calming shower, snuggle on decadently large plush daybeds, watch your fav Netflix series, enjoy uncapped WIFI or fall into a peaceful sleep. Slip into our lush Queen bed for a rejuvenating night while gazing at the stars. Create perfect lighting for a romantic rendezvous or a working holiday, & don't forget to savour a cup of the finest filter coffee in our quaint private garden

Top guest favourite
A comfortable lounge area features a cozy sofa and two armchairs adorned with green cushions. A dining table is visible in the background, complemented by warm wood cabinetry. Natural light fills the space, enhancing the neutral tones of the furnishings.
Guest house in Winston Park
4.98 out of 5 average rating, 47 reviews

Fever Tree Cottage

Nestled in the charming suburb of Winston Park, this cottage offers a tranquil retreat with breathtaking views of the valley and surrounding bird life. Unwind in the comfortable lounge, equipped with a 55-inch Samsung TV and access to Netflix, Disney and Prime. The well-appointed kitchenette and dedicated workspace with WiFi ensure a relaxing and productive stay. Enjoy easy access to the M13, just a short drive from shopping centers and restaurants. Plus, take advantage of pool use upon request.

Top guest favourite
The image depicts a spacious garden featuring a swimming pool bordered by stone paving. Lush greenery surrounds the pool, including various plants and trees. A black dog is seen walking across the neatly maintained lawn, adding a serene and natural element to the outdoor space.
Guest suite in Kloof
4.93 out of 5 average rating, 177 reviews

Upstairs on Impangele

Next to Makaranga (currently closed), the unit has 2 bedrooms with a shared bathroom. The kitchen area has a table & chairs, fridge/freezer, kettle, toaster, induction cooker, air fryer & microwave. Stocked with tea, coffee & sugar. Each of the rooms have a king size bed which can be split into 2 singles, so can sleep 4 people. One of the bedrooms has an aircon & the other a fan and heater. Deck has a bistro table & chairs as well as a daybed for relaxing. Off street parking for 1 car.

Top guest favourite
An open plan interior space is illuminated by natural light, featuring high ceilings with exposed beams. A dining table is surrounded by wooden chairs, while a kitchen is visible in the background, equipped with modern appliances. Decorative elements, such as a lamp and art pieces, add character.
Home in Crestholme
4.96 out of 5 average rating, 103 reviews

Alegria Barn Self-catering house -Solar Power

Alegria Barn is set on a quiet smallholding situated right on the edge of the Crestholme Conservancy. The Barn was once a farm building which was recently converted into an open plan, double volume space that's perfect for both long & short term stays. The personal touches make the space perfect for professionals needing to travel for business. It is also ideal for couples & small families wanting to travel. It is equipped with everything needed to make your stay relaxing and enjoyable.

Top guest favourite
An iconic caravan is depicted with a unique glass roof that offers a view of the night sky. Surrounding vegetation is illuminated softly, highlighting the natural setting. The caravan features large windows, providing glimpses of the cozy interior.
Place to stay in Gillitts
4.95 out of 5 average rating, 350 reviews

Masinga - a uniquely beautiful experience

Beyond a uniquely beautiful space, Masinga is a restorative experience. It’s about how it makes you feel. Many of our guest reviews speak of this quality and experience. Sleep in a pimped caravan with it’s clear & elevated roof to watch the night sky. Air conditioning for summer, electric blankets for winter & a Turkish chandelier - well - that’s for all occasions. Set in beautiful yellowwood trees with your private lapa & deck extending into and around the trees. Inspired.

Guest favourite
A cozy seating area features a blue sofa adorned with yellow geometric cushions. Natural light enters through nearby windows, illuminating the space. Decorative plants and wall-mounted shelves with greenery add to the tranquil ambiance of the cottage.
Cottage in Hillcrest
4.87 out of 5 average rating, 174 reviews

Tennis Cottage - Surrounded by a verdant garden.

Based in central Hillcrest, the Tennis Court Cottage is a recently renovated, self catering garden cottage located on a well secured property within a lush, green garden. The space is a private and peaceful, equipped with all the amenities required by the business or leisure traveler. Self check in and out is quick and easy via a keypad at the main gate, a key box is located at the entrance to the unit. Due to its size the unit is ideally suited for short term stays.

Guest favourite
A modern living area features a gray sofa adorned with decorative cushions. A round coffee table positioned at center is surrounded by a geometric area rug. A sleek entertainment unit is located against the wall, with a flat-screen television mounted above.
Flat in Winston Park
4.86 out of 5 average rating, 35 reviews

Gorgeous Garden Villa 2

Gorgeous Garden Villa 2 is a calm, private escape designed for rest and productivity. The unit overlooks a peaceful back garden with lovely surrounding scenery and enjoys soft sunrise views. Located in a very quiet area, it's ideal for couples or business travellers. The space includes a work-from-home setup, free parking, a modern bathroom with shower, and external security cameras for added safety. A comfortable, well-positioned base for a relaxed stay.

Guest favourite
A spacious bedroom is highlighted by a plush headboard and soft bed linens. Two bedside tables with matching lamps frame the bed. Decorative pillows add subtle elegance, while a wall-mounted bull skull provides a unique focal point. Warm tones are introduced through a textured throw blanket.
Apartment in Kloof
4.84 out of 5 average rating, 108 reviews

Contemporary & Spacious Courtyard Unit

This beautifully decorated unit is modern, clean and spacious. It offers a separate bedroom en suite and dressing room. The lounge area opens out onto a private courtyard area with a peaceful outlook. There is a sleeper couch which could accommodate young children on request. The kitchenette has all the essentials and a table area for eating/workspace. There is secure parking for one car. Situated close to the M13 and shops.

Guest favourite
A bright room features a comfortable queen-size bed with a soft blanket, facing a garden view through glass sliding doors. A wooden dining table with chairs and a cozy armchair enhance the inviting layout, complemented by light curtains and indoor plants.
Guest suite in Kloof
4.92 out of 5 average rating, 121 reviews

Guest suite in Kloof

Comfortable, garden-facing room with separate entrance adjacent to the main house. Sleeps 2 guests comfortably in a queen-size bed. Accommodation includes an ensuite bathroom, coffee/tea station, fridge, microwave, airfryer, free WiFi and secure parking. Peaceful and quiet neighbourhood with easy access to shopping, main routes, nearby parks and short drive to Hillcrest Hospital and other medical facilities.

Top guest favourite
The exterior of the renovated container is showcased, featuring a vibrant mural of a Purple-crested Turaco. The structure is complemented by a wooden deck with railings and a shade sail overhead. Lush greenery surrounds the entrance, creating a serene atmosphere.
Shipping container in Hillcrest
4.96 out of 5 average rating, 74 reviews

Loerie Loft

Nestled amongst trees you will find the Loerie Loft. Peaceful, private and unique, this renovated container has a beautiful Purple-crested Turaco mural on one wall, expertly painted by local artist, Giffy. As you sit out on the deck, you may be fortunate enough to catch a glimpse of one of these spectacular birds soaring from tree to tree. Relax by the braai or fire pit, making memories to last a lifetime.

Guest favourite
A modern room is highlighted by large windows, providing a view of the horizon at sunset. A spacious bed is positioned near the window, with neutral tones and striped pillows. A cozy seating area is visible, along with a small workspace complemented by plants and wooden shelves.
Guest suite in Westville
4.84 out of 5 average rating, 478 reviews

The Hidden Lookout (Green Room)

This modern, creative space is one of two hidden gems in the leafy suburb of Westville (also see Yellow Room at The Hidden Lookout) Up high in the trees, our space is a tranquil, beautiful, simple space, perfect for a break from the city, but close enough to everything to still have fun! If you are coming for business we have a fast and dependable WiFi & work station & GENERATOR if necessary.

Top guest favourite
Cottage in Hillcrest
5 out of 5 average rating, 27 reviews

Springside Cottage

Enjoy easy access to all the local attractions Hillcrest has to offer from this centrally located gorgeous cottage. This property is ideally located for quick access to shops and restaurants (2 min drive) and is the perfect stayover for parents visiting children at nearby boarding schools. During the Comrades Marathon access to the route along Old Main Road is only a 5-minute walk away.

Popular amenities for Gillitts holiday rentals

Frequently Asked Questions

  • Are there Gillitts vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 40 vacation homes with pools in Gillitts, available on Airbnb. Make a splash and soak up the sun in style!

  • Where should I stay in Gillitts?

    Make yourself at home in Gillitts by choosing from our most frequently booked neighborhoods. We have over 190 vacation rentals in Winston Park, over 520 vacation rentals in Gillitts, and over 500 vacation rentals in Chelmsfordville.

  • How much does it cost to stay in apartment rentals in Gillitts?

    Experience the best of Gillitts with our apartment rentals, starting at about $20 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there pet-friendly vacation rentals in Gillitts?

    Four-legged friends are welcome in Gillitts. Choose from more than 10 vacation rentals for guests traveling with pets.

  • Do house rentals in Gillitts have free parking?

    Absolutely! We offer over 20 house rentals with free parking in Gillitts. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly vacation rentals in Gillitts?

    Gillitts has more than 30 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do house rentals in Gillitts have air conditioning?

    Absolutely! We offer over 10 house rentals with air conditioning in Gillitts. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Gillitts have wifi?

    Absolutely! We offer over 10 apartment rentals with wifi in Gillitts. Enjoy a tailored experience with all the comforts you desire.

  • Are there vacation rentals with a dedicated workspace in Gillitts?

    Yes! Work meets play with ease at over 40 vacation rentals in Gillitts featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do guesthouse rentals in Gillitts have a kitchen?

    Absolutely! We offer over 10 guesthouse rentals with a kitchen in Gillitts. Enjoy a tailored experience with all the comforts you desire.

Quick stats about holiday rentals in Gillitts

  • Total holiday rentals

    Explore 90 holiday rentals in Gillitts

  • Nightly prices starting at

    Gillitts holiday rentals start at $25 SGD per night before taxes and fees

  • Verified guest reviews

    Over 1,960 verified reviews to help you choose

  • Family-friendly holiday rentals

    30 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Holiday rentals with a pool

    40 properties feature pools

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

  • Wifi availability

    80 of Gillitts holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Gillitts rentals

  • 4.8 Average rating

    Gillitts stays are highly rated by guests – averaging 4.8 out of 5!