
House holiday rentals in Cupar
Find and book unique houses on Airbnb
Quick stats about house rentals in Cupar

Total holiday rentals
Explore 10 holiday rentals in Cupar

Nightly prices starting at
Cupar holiday rentals start at $153 NZD per night before taxes and fees

Verified guest reviews
Over 570 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space and kid-friendly amenities

Wi-Fi availability
10 of Cupar holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Cupar rentals

4.9 Average rating
Cupar stays are highly rated by guests—averaging 4.9 out of 5!
Top-rated house rentals in Cupar
Guests agree: These houses are highly rated for location, cleanliness and more.

Hillside Well Cottage
Hillside Well Cottage is a family run 4 bedroom cottage set in a beautiful, peaceful location in the Perthshire countryside, with spectacular views of the Lomond Hills bordering Fife. It is centrally situated, and a perfect base for visiting many places of interest including Edinburgh, Glasgow, Stirling, Pitlochry, Gleneagles, St Andrews, Perth and Dundee. Also, locally, the East Neuk, Falkland and Kinross on the banks of lovely Loch Leven offer many attractions and are well worth a visit.
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Shiel House, Rumbling Bridge
Set in 3 acres of gardens and with beautiful views of the valley, Shiel House is the perfect retreat. This bespoke house was built by our family to provide an escape from the city and it has been furnished to provide a comfortable home from home. It would suit solo adventurers, couples, families (including with kids), and groups. Centrally located, and only an hour's drive from Edinburgh, Glasgow, Perth and St Andrews, it is the ideal base for golfers, walkers and visitors to Scotland.
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welcoming dogs and their servants, Hot Tub & View
Discover your perfect Scottish hideaway with our wood-fired hot tub, wildlife-filled garden, and ideal location for exploring Scotland. The Howff is the perfect base to discover sandy beaches, forests, historic towns and ancient castles nearby. We are Just minutes from St Andrews, Perth, Dundee. The Howff combines countryside charm with city convenience. Ladybank train station or Kinross Park and Ride will allow you to forget about the car and enjoy Edinburgh which is an hour away.
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Coastal 2 bedroom house - golf/ beach getaway
Lovely bright and cheerful House with access to private garden, in a lovely fife coastal village. The House has good walking access to local attractions including being only 2 minutes from Scotscraig Golf Club (13th Oldest in the World) and 10mins from the stunning Kinshaldy Beach with views over the river Tay, The village also has several charming cafes, bars and local shops. Tayport is nestled between Dundee and the Historic Town of St Andrews. Short-term let licence - F1-02837-R
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Fossil Cottage , Strathkinness close to St Andrews
Fossil Cottage, is located in the village of Strathkinness. Recently renovated and refurnished this self-contained accommodation on the grounds of Fossil House, pet friendly and the perfect spot for a week away for families or groups of 4! Features include Secure off-street parking, enclosed garden, fibre-optic broadband, wood fire and fully equipped kitchen. Ideally located 3 miles from the centre of St Andrews the home of Golf and in easy reach of the beautiful East Neuk.
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No 67 Modern 2‑Bed Nr St Andrews - Free Parking
Welcome to No 67, a bright, modern ground‑floor apartment ideally located in Leuchars, perfectly positioned between St Andrews and Dundee. The upstairs apartment, No 65, is also available on Airbnb. This comfortable two‑bedroom apartment is furnished to a high standard, with fresh, contemporary décor creating a light and airy feel throughout. Free Wi‑Fi, gas central heating, and a fully equipped kitchen make it equally suited to short breaks, longer stays, or work trips.
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Country house in pretty small glen
Dog friendly with open fire .Charming accessible country house in unspoilt setting ideal for walking/ cycling.Double height main room has minstrels gallery and open log fire, great for parties.The 14 seated dining hall has doors onto sunny terrace and grounds. A private wood comes with the house with direct access to miles of empty hill and moor..Separately a cottage that sleeps 6 is available
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Large 3 bed home close to excellent golf courses.
Large, beautiful 3 bedroom home situated in a quiet residential area. Less than a mile from Championship golf courses and local amenities are a 10 minute walk through the beautiful village of Gullane. The home is equipped with WiFi, Sky TV and a beautifully large garden ideal for relaxing and unwinding. *Please not there is a step into the property via the front door and rear door.
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The Annexe at Kirkmay Farmhouse, Crail.
The Annexe is a bright, two-bedroomed house attached to the main farmhouse. It is self-contained with it’s own parking and garden areas. The property has been completely re-wired, re-plumbed and re-decorated with new beds, kitchen and bathroom. This a convenient rental for guests attending an event in The Cow Shed at Sypsies Farm. We are roughly 300m away along the farm track.
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WOOD HOUSE *golf, beach, university, free parking*
FI 00068 EPC - C Wood House is a newly renovated 4 bedroom house with garden and plenty of parking. The town centre is a 15 minute walk away and the beach is less than 10 minutes. Luxurious soft furnishings with a welcoming fresh and cosy feel make it an ideal property for those looking for a pleasant and relaxing getaway in this historic town.
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Luxury Seaside Home with Incredible Views
Situated on the coast of Kirkcaldy, This self contained annex within a family home, is newly decorated and furnished. It directly overlooks the sea of the Firth of Forth. Only steps away from the Fife Coastal Path. A perfect base for a holiday in the Kingdom of Fife or stopping point on the way to the Highlands and beyond.
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Townhouse - central St Andrews GOLF
5 bed, 4-bath luxury townhouse located in central St Andrews. 5 mins walk to the Old Course, beaches, historical sites & charming shops, cinema, cafes, bars & restaurants of the town. Ideal base for families or groups of golfers. Large garden. Pets welcome.
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Popular amenities for Cupar house rentals
House rentals with a pool

Sir Stuarts House & Bothy House
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Planners House is a detached house on the harbour
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Luxury Lodge• Haven Seton Sands• WiFi •Blairgowrie
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Lodge 17 St Andrews
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Vacant Nests | The Belfry | Starlink | Sleeps 8
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Prestige caravan,Seton Sands holiday village, WiFi
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Static Caravan Holiday Home
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Beech Tree Cottage, Fingask Castle, Rait
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Weekly house rentals

The Vintage - A Hidden Gem close to the Old Course
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Muma Bears House
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Kinnessburn Cottage - free parking, close to golf
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Number 37, St. Andrews
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Ashtrees Cottage
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Fore Fifies
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Number•30•
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Tea Garden Cottage near St Andrews, Fife
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Private house rentals

Seaside Cottage, Wemyss Estate
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Vicarsford Farmhouse
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Comfortable private annex with a sensational view
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Peaceful countryside house near Elie
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Newhall Gardens - Botanical Bliss
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Stylish and peaceful getaway for two
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Copthorne Cottage St Andrews Coastal Golf retreat
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Skyline House St Andrews
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Destinations to explore
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- Edinburgh Waverley Station
- Edinburgh Castle
- Murrayfield Stadium
- Edinburgh Zoo
- The Royal Mile
- Scone Palace
- Edinburgh Playhouse
- Pease Bay
- The Kelpies
- The Meadows
- Holyrood Park
- University of Edinburgh
- Stirling Castle
- Knockhill Racing Circuit
- Edinburgh City Centre Churches Together
- Royal Botanic Garden Edinburgh
- Princes Street Gardens
- Glenshee Ski Centre
- Bruntsfield Links
- Jupiter Artland
- Rosslyn Chapel
- Pentland Hills
- Greyfriars Kirkyard
- The Hermitage





