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

Total vacation rentals
Explore 10 vacation rentals in Cupar

Nightly prices starting at
Cupar vacation rentals start at G$18,830 GYD per night before taxes and fees

Verified guest reviews
Over 570 verified reviews to help you choose

Family-friendly vacation rentals
10 properties offer extra space & kid-friendly amenities

Wi-Fi availability
10 of Cupar vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, 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.
4.97 out of 5 average rating, 201 reviews
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.
4.89 out of 5 average rating, 233 reviews
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
4.97 out of 5 average rating, 220 reviews
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.
4.96 out of 5 average rating, 142 reviews
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.
4.87 out of 5 average rating, 284 reviews
The Vintage - A Hidden Gem close to the Old Course
The Vintage... A well-struck 2-iron away from the 1st tee of the Old Course, 100 yards from the seafront and close to the town center. Tucked away but in the middle of it all, The Vintage is a delightful, free-standing, fully renovated, three bedroom house with a large conservatory and a unique private patio garden. Located in the conservation area, with no direct access for cars, the only noise one hears is the wind and the occasional seagull flying overhead.
4.96 out of 5 average rating, 172 reviews
Ashtrees Cottage
Ashtrees Cottage is in a beautiful rural location and has Loch Leven Nature Reserve on its door step. The Balgedie Toll Tavern & Loch Levens Larder both less than 10 minutes walk from the Cottage. It’s a great place to explore towns and villages around the East Neuk of Fife, Edinburgh, St Andrews, Gleneagles, Stirling and Glasgow. Its a great place to base yourself if you are planning to explore the Lowlands and Southern Highlands of Scotland.
4.99 out of 5 average rating, 200 reviews
Kinnessburn Cottage - free parking, close to golf
Kinnessburn cottage is a modern two storey open plan house set in the town centre but in a quiet cul de sac, well back from the main thoroughfare through the town. It is a short walk from the shops, university, cathedral, beaches and the Old Course. 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. Licence Number FI 00076 P
4.97 out of 5 average rating, 103 reviews
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.
4.95 out of 5 average rating, 111 reviews
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.
4.99 out of 5 average rating, 292 reviews
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.
4.92 out of 5 average rating, 225 reviews
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.
4.99 out of 5 average rating, 199 reviewsPopular amenities for Cupar house rentals
House rentals with a pool

Sir Stuarts House
4.77 out of 5 average rating, 75 reviews
Royal Mansion with Therapy Pool & Hot Tub
5.0 out of 5 average rating, 6 reviews
Planners House is a detached house on the harbour
5.0 out of 5 average rating, 13 reviews
Luxury Lodge• Haven Seton Sands• WiFi •Blairgowrie

Lodge 17 St Andrews
4.88 out of 5 average rating, 8 reviews
Static Caravan Holiday Home
4.7 out of 5 average rating, 61 reviews
Vacant Nests | The Belfry | Starlink | Sleeps 8
5.0 out of 5 average rating, 15 reviews
Prestige caravan,Seton Sands holiday village, WiFi
5.0 out of 5 average rating, 22 reviewsWeekly house rentals

Country house in pretty small glen
4.84 out of 5 average rating, 256 reviews
Converted stables in Elie 2 mins walk to the beach
4.99 out of 5 average rating, 170 reviews
Muma Bears House
4.98 out of 5 average rating, 177 reviews
4 bedroom / 2 bathroom house in desirable area.
4.98 out of 5 average rating, 102 reviews
Stylish Courtyard House in Fife Coastal Village
5.0 out of 5 average rating, 204 reviews
Number•30•
4.96 out of 5 average rating, 24 reviews
Tea Garden Cottage near St Andrews, Fife
4.98 out of 5 average rating, 62 reviews
The Old Post Office
4.9 out of 5 average rating, 30 reviewsPrivate house rentals

Peaceful countryside house near Elie
4.98 out of 5 average rating, 58 reviews
Comfortable private annex with a sensational view
4.94 out of 5 average rating, 16 reviews
Copthorne Cottage St Andrews Coastal Golf retreat
4.92 out of 5 average rating, 39 reviews
Strathtyrum Farmhouse, St Andrews
5.0 out of 5 average rating, 4 reviews
Newhall Gardens - Botanical Bliss
4.96 out of 5 average rating, 50 reviews
Exquisite beachfront Sanctuary with Bay Vista
5.0 out of 5 average rating, 55 reviews
Stylish and peaceful getaway for two
5.0 out of 5 average rating, 33 reviews
Skyline House St Andrews
4.92 out of 5 average rating, 39 reviewsDestinations to explore
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