
Holiday 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.

Romantic Cape Town Cottage with Mountain Views
This stand alone cottage on our private property is located in the Bishopscourt area of the Western Cape. The cottage is an open plan lounge,bedroom with two big verandas, a kitchenette and a large bathroom with a shower and bath that opens out to a very private balcony with sun loungers and an outside shower. With magnificent views of the mountain and terrains, one can fully unwind and relax in this more than spacious cottage. This private cottage will be all yours during your stay. There are multiple lounging areas inside and outside the cottage. Our long serving housekeeper, Maks, will be there to look after you and make sure you always have what you need.She cleans and does the washing daily except on a Sunday. Located within walking distance to many stunning hikes, walking routes, mountain biking, and cycling routes. There are many places nearby that you can rent bikes and there is ample storage at the house for bikes to be stored. There is ample and secure parking on our property for the vehicle you bring along for your stay. I am usually here and am very happy to help with advice at all times. This home is in a quiet residential area with beautiful houses and leafy streets. Close to the botanical gardens and near the city. Uber Available.Safe parking on the grounds of the property. No need for Air Conditioning units as the mountain air in the mornings and evenings will be cool and crisp all year long. There is a ceiling fan, if you need additional cooling. Towels,beach towels,picnic basket all available at the cottage. The space is about 60sqm +

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.

Stylish Studio N with Extraordinary View
Your Home Away from Home – Perfect for Work and Relaxation. Enjoy a stylish and functional stay with a dedicated, laptop-friendly workspace featuring a comfortable desk chair, Nespresso machine and a breathtaking view to keep you inspired. Stay connected and productive with uncapped high-speed Wi-Fi, access to a printer, and a UPS to keep you powered during load shedding. We have two identical studio apartments available – be sure to also check out our Stylish Studio S high above Cape Town!

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.

16 on Bree | Penthouse Living One Bedroom
Experience the absolute best in ultra-modern living in Cape Town’s tallest residential tower. Situated on Bree Street, the trendiest street in Cape Town, this residential block is the culmination of sleek urban design and highly functional lock up & go living. The unit is perfectly aligned to the needs of both the businessperson (in the CBD, high-speed fibre optic connectivity) and the tourist (close to trendy restaurants, contemporary bars, art galleries, antique shops and design stores).

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

217 On The Beach, Cape Town
Welcome to this beachfront property. The light and open apartment is an easy 8km from Cape Town's city center. The spacious apartment has direct access to the beach as well as breathtaking table mountain and sea views. Fall asleep to the sound and smell of the ocean and wake up ready to enjoy the pool, Beach and Cape Town's many attractions. Has battery backup for WiFi and TV during load shedding. The following TV streaming services are included: AmazonPrime Video, Disney plus.

Primaview, Camps Bay, Cape Town
Primaview is situated in beautiful Camps Bay, Cape Town. Offering comfortable accommodation, alongside an inviting pool and surrounded by panoramic views of mountains and sea. Camps Bay is a scenic residential area, close to the city, as well as the famous Clifton Beaches. There are shops and popular restaurants along the Camps Bay Promenade. The Table Mountain Cable Way is a few minutes drive away. Access to nearby hiking trails are within a few minutes walk.

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.

African Chic with Incredible Views & Pool Deck
Welcome to the greatest views imaginable from a stylish, brand new & tastefully decorated apartment high up in the Cape Town sky. Enjoy the 'sunsational' pool deck and outdoor gym on the 27th floor or simply step out onto your very own large wrap around balcony for breakfast while enjoying the finest views of Table Mountain, The sparkling azure of the Atlantic Ocean or the Robben Island & The Cape Town Stadium. *Zero power cuts in this builidng.

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.

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
Popular amenities for Observatory rentals with a pool
House rentals with a pool

Bungalow 21 - Clifton 3rd by Steadfast Collection

Blackwood Log Cabin

Newly Renovated Family Home with Plunge Pool

Grace Cottage-Spacious flat in family neighborhood

Tranquil Waterfront Hideaway with Stunning Views

Hidden Woodstock Retreat

Mountain House

Casa dos Gêmeos
Apartment rentals with a pool

Insta-Worthy, Front-Row Ocean & Mountain View’s

Contemporary, Sea Point pad, w/ views & inverter

Modern Cape Town City Apartment & amazing views

913 - Table Mountain Views: Woodstock's WEX1

Sailor’s Away - 3004 - 16 On Bree

Modern Ocean View Retreat in Camps Bay

Zebra Paradise - 2908- 16 On Bree

Breathtaking city and harbour views
Home rentals with a private pool

Elegant guest wing with own private garden & pool.

Watch the Sunrise in a Home with a Mountain View

Modern Contemporary Zen Tree House With Pool

Villa Claybrook - Sun. Sea. Serenity.

Glen Beach Penthouse A on Glen Beach in Camps Bay

Upper Constantia Guest House
Rooftop Pool | Views | 24h power

Chic Boutique-Hotel Feel at a Seafront Pad, Clifton
When is the best time to visit Observatory?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $98 SGD | $97 SGD | $86 SGD | $71 SGD | $72 SGD | $69 SGD | $72 SGD | $67 SGD | $72 SGD | $81 SGD | $86 SGD | $106 SGD |
| Avg. temp | 22°C | 22°C | 21°C | 18°C | 15°C | 13°C | 13°C | 13°C | 15°C | 17°C | 19°C | 21°C |
Quick stats about holiday rentals with a pool in Observatory

Total holiday rentals
Explore 70 holiday rentals in Observatory

Nightly prices starting at
Observatory holiday rentals start at $13 SGD per night before taxes and fees

Verified guest reviews
Over 1,710 verified reviews to help you choose

Family-friendly holiday rentals
30 properties offer extra space & child-friendly amenities

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wifi availability
70 of Observatory holiday rentals include wifi 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
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- Glencairn Beach
- Fish Hoek Beach
- Muizenberg Beach
- Long Beach
- Big Bay Beach
- Boulders Beach
- Clifton 4th
- GrandWest Casino and Entertainment World
- Woodbridge Island Beach
- Green Point Park
- Hout Bay Beach
- Sandy Bay, Cape Town
- St James Beach
- Babylonstoren
- District Six Museum
- Two Oceans Aquarium
- Durbanville Golf Club
- Noordhoek Beach
- Mojo Market
- Jonkershoek Nature Reserve
- Erinvale Estate Hotel and Spa
- Waterkloof Wine Tasting Lounge
- Steenberg Tasting Room
- Newlands Forest




