Vacation rentals with a pool in Observatory

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Top-rated rentals with a pool in Observatory

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Top guest favorite
A spacious bedroom lounge area features a king-size bed with crisp linens and decorative pillows. A dining table with chairs is positioned nearby, along with a wall-mounted television. Natural light pours in through large sliding doors that open to a private deck, framed by soft curtains.
Apartment in Rondebosch
4.97 out of 5 average rating, 185 reviews

Doug And Sal's Rondebosch (with solar)

In Rondebosch, this secure property has beautiful views, is private and quiet with a separate entrance and off street parking, There's a lovely garden and shared swimming pool and the apartment itself is luxurious and well appointed. Living area and full en-suite - 35m² bedroom / lounge area with table and chairs and king size bed - Cupboards - Full DSTV (PVR for recording) - WIFI - Safe - Hairdryer Kitchenette - Kettle, Toaster, Nespresso coffee maker - Microwave, Fridge, Cutlery / crockery

Top guest favorite
A spacious living area features floor-to-ceiling glass doors that offer expansive views of the surrounding landscape. Natural light floods the space, highlighting the modern furnishings, including a comfortable sofa and an elegant glass dining table. A small outdoor terrace is visible, overlooking the hills.
Loft in Vredehoek
4.86 out of 5 average rating, 548 reviews

Chic Penthouse with Private Pool & Breathtaking Views

This light, airy penthouse apartment offers breathtaking views of the city, ocean, Signal Hill, Lions Head and Table Mountain. The private roof-deck offers sensational 360° views, a braai/barbecue and a plunge pool to cool off in and enjoy the wonderful views. The apartment is in a truly wonderful and centrally located City Bowl neighbourhood - Vredehoek. The area is safe, clean, and beautifully situated on the slopes of the famous Table Mountain. It's the perfect base for exploring the city.

Top guest favorite
A spacious bedroom features large glass windows offering panoramic views of the ocean and surrounding greenery. A comfortable chair sits beside the bed, which is adorned with decorative pillows. Natural light fills the room, highlighting the inviting decor and tranquil atmosphere.
Apartment in Clifton
4.98 out of 5 average rating, 389 reviews

Magnificent Clifton Retreat with Unparalleled Ocean Views

A perfect haven for couples or individuals seeking a holiday that will be truly memorable. Ezulwini is set in central Clifton, an exclusive area 5 minutes from Town and the V&A Waterfront. The apartment offers unrivalled sea and beach views. The interior is flooded with natural light, beautifully curated in a rich beachside palette of sandy hues with a touch of something nautical. Safety wise, the apartment is a lock up and go and there is battery Back with solar to deal with load shedding.

Guest favorite
Apartment in Cape Town City Centre
4.93 out of 5 average rating, 117 reviews

Stunning 3 Bed Penthouse with Ocean Views & Pool

Stunning 3-Bed Penthouse in the Heart of Cape Town at 16 on Bree. Welcome to the epitome of luxury and convenience on the 33rd floor! Located in the iconic 16 on Bree, this penthouse boasts breathtaking views and luxury living that will make you SWOON! Enjoy a leisurely barbeque on your private balcony, a true South African experience. Head to the 'sunsational' pool deck and outdoor gym on the 27th floor. The building has its own shared workspace too. *Zero power cuts in this building.

Guest favorite
A serene garden scene features a refreshing salt-water pool surrounded by lush greenery and colorful plants. A small seating area is visible, offering a cozy spot to relax. The inviting pool reflects the clear sky, creating a peaceful atmosphere for guests.
Guest suite in Woodstock
4.87 out of 5 average rating, 120 reviews

cozy garden cottage in Upper Woodstock with pool

We have added a small, cozy guest suite to our family home in upper Woodstock and welcome guests from all over the world. We, that is Kent and Susanne with our daughter Alba (10) and our lovely dog Vivienne Westwood (Vivi). Our approximately 25 square meter cottage is located in our beautiful shared garden with saltwater pool and has its own bathroom and kitchenette. Our guests appreciate the Upper Woodstock location and the garden while having us around for questions. Streetparking

Top guest favorite
A private garden is featured, containing a tranquil pool surrounded by natural stone and vibrant murals depicting serene landscapes. A dining area with four chairs is visible at one end, inviting peaceful outdoor meals. Sunlight enhances the inviting atmosphere of this outdoor space.
Guest suite in Vredehoek
4.94 out of 5 average rating, 229 reviews

Central Private Secure with pool, garden, parking

Our studio flat is at the foot of Table Mountain close to hiking trails, 8km to the nearest beach and 4km from the City Centre. It is open plan, has a queen bed (182cm*152cm), a well-equipped kitchen, private garden, a private entrance, secure off-street parking, Wi-Fi, Netflix, and an alarm system. Guests may share our solar-heated swimming pool. (It currently has some peeling in the lining. It will be repaired over winter but is still clean and refreshing).

Top guest favorite
The living area features a comfortable grey sofa paired with a yellow accent chair. Round mirrors and framed art adorn the walls, while decorative cushions add a pop of color. A glass table sits atop a soft rug, surrounded by hardwood flooring.
Home in Woodstock
4.95 out of 5 average rating, 152 reviews

Mountain and Harbour Views - Grand Vue Cottage

The property is situated in Cape Town's Walmer Estate suburb, high up the mountain below Devil's Peak. The views from the property are spectacular, you can see Lion's Head, Signal Hill, Table bay and Cape Town harbour. The property has great decor and furniture for your comfort and it's ideal for families or groups who want to be near the city but also to escape it and relax. Solar panels and battery backup system is fitted to escape electricity outages.

Top guest favorite
A spacious guest suite is presented, featuring a king-size bed dressed in white linen. A seating area with two woven chairs and a table is positioned near a large bay window. Soft drapes frame the windows, and a television is mounted to the wall.
Guest suite in Newlands
4.93 out of 5 average rating, 307 reviews

Largo House guest suite

Guest suite with a king size or two single beds, with white cotton linen and en-suite shower bathroom. No separate kitchen, no stove or sink. Counter with small fridge, microwave, kettle, toaster, crockery, cutlery and self-catering breakfast of tea, coffee, milk, rusks, cereal, yoghurt, fruit. Tv, Dstv and Wi-fi Off street parking available Our location is in the suburbs of Cape Town, 12 kms from the city centre and 20kms from the beaches.

Guest favorite
A spacious bedroom is shown, featuring a large bed with neutral-toned linens. Decorative pillows enhance the bed's look. A cozy seating area includes a blue sofa and a small coffee table. Large windows offer views of the cityscape, allowing natural light to fill the room.
Condo in Cape Town City Centre
4.84 out of 5 average rating, 136 reviews

Over The Clouds - 3003 - 16 On Bree

Load shedding free apartment. In the center of CapeTown on the ++30th++ floor over the clouds with an amazing view on TableMountain and Downtown. This self catering apartment offers you everything what you need for your stay (either business-/ family or holidaytrip). It includes a bathroom, a washing machine, dishwasher, full equipped kitchen and a balcony for a stunning dinner outside. We are happy to welcome you!

Top guest favorite
An outdoor patio area features a wooden deck with a round table surrounded by woven chairs. Scenic views of mountains and cityscape are visible in the background, showcasing a relaxed atmosphere for gathering.
Apartment in Cape Town City Centre
4.92 out of 5 average rating, 185 reviews

Bree Penthouse with Panoramic Views

Opulent penthouse in Bree Street with 270 degree city, mountain and sea views with expansive outdoor patio area. Ultra-modern and exquisitely-decorated with breathtaking views across the whole of the city bowl and waterfront/harbour out onto South Africa's most iconic landmark and Natural Wonder of the World: Table Mountain, there is no excuse to not live your very best, most exclusive life from this penthouse.

Top guest favorite
An expansive terrace features a private splash pool with a wooden deck, overlooking stunning views of the mountains and cityscape. Floor-to-ceiling sliding doors connect the terrace to the modern interior, allowing for seamless outdoor access from the en-suite bedroom area.
Apartment in Tamboerskloof
4.99 out of 5 average rating, 300 reviews

Hillside Penthouse with Spectacular Table Mountain Views

Gaze out on Cape Town from this exclusive retreat high above the city. This quiet cocoon is a place to relax, featuring contemporary furnishings, sliding floor-to-ceiling windows, terrace walkouts, panoramic views of Table Mountain, and a private splash pool. You have an expansive space over two levels to enjoy. Experience the urban buzz or the peace of the great outdoors, both just minutes from the apartment.

Top guest favorite
A charming stone cottage is surrounded by lush greenery, featuring large windows that invite natural light. An outdoor patio area with a table and chairs offers a serene space for relaxation, while various plants and rocks enhance the natural setting.
Cottage in Hout Bay
5 out of 5 average rating, 193 reviews

Stone Pine Cottage, Hout Bay

The stone & wood cottage nestles in a wild garden, the bay, beach and village just a kilometer away. The previous owner, a bachelor in his day, used to entertain girl-friends here – and romance still rules in the one-roomed stone cottage, where the mezzanine bedroom has mountain and sea views.

Popular amenities for Observatory rentals with a pool

When is the best time to visit Observatory?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$15,665 GYDG$15,456 GYDG$13,785 GYDG$11,279 GYDG$11,488 GYDG$11,070 GYDG$11,488 GYDG$10,652 GYDG$11,488 GYDG$12,950 GYDG$13,785 GYDG$16,918 GYD
Avg. temp22°C22°C21°C18°C15°C13°C13°C13°C15°C17°C19°C21°C

Quick stats about vacation rentals with a pool in Observatory

  • Total vacation rentals

    Explore 70 vacation rentals in Observatory

  • Nightly prices starting at

    Observatory vacation rentals start at G$2,089 GYD per night before taxes and fees

  • Verified guest reviews

    Over 1,710 verified reviews to help you choose

  • Family-friendly vacation rentals

    30 properties offer extra space & kid-friendly amenities

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wi-Fi availability

    70 of Observatory vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Observatory rentals

  • 4.7 Average rating

    Observatory stays receive an average rating of 4.7 out of 5 from guests