
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$18,831 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
Beautiful 4 bdrm Farmhouse with ocean views, Fife.
Drinkbetween Farmhouse has recently been refurbished. Sleeping anywhere from 4 up to 8 guests it is ideally situated in a beautiful & peaceful rural setting on Banchory Farm, just 40 minutes from Edinburgh. There is a large contained garden. It has spectacular views over the fields to the ocean so you can truly relax. For those who love to explore, it’s ideally located close to some of Scotland’s most iconic towns like Edinburgh, St Andrews, Elie or Gleneagles, all just 40 minutes away.
4.98 out of 5 average rating, 136 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
Stylish Courtyard House in Fife Coastal Village
The Wall House was converted in 2020 from an historic fishing net repair building - it's old outside but super energy efficient & modern inside. It’s a truly unique, stylish and comfortable place to be. The Wall House is also designed to be accessible to a person with restricted mobility. Set in a Fife seaside conservation village you’ll find yourself in a 'get away from it all' location but just a short drive to Edinburgh, the East Neuk & St Andrews.
5.0 out of 5 average rating, 204 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
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, 293 reviews
Private Walled Garden, Hot Tub Soaks, Wood Stove
Beautiful, secluded and tranquil, choose this cosy little cottage to retreat away from your troubles or enjoy a romantic getaway. Ideal for couples or a small group of friends, Jordanstone's Gardener's Cottage is a snug, rustic retreat with plenty of home comforts. And if you have a furry friend, they’re welcome too, as the Gardener's Cottage is dog friendly.
4.93 out of 5 average rating, 252 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
Linton - Rustic and cosy cottage
Nestled into the seaside village of Kinghorn - Linton. A charming cottage with stunning views of the sea. The cosy retreat is perfect for couples or small families looking for a peaceful getaway. Whether you're looking to relax and unwind or explore the surrounding area, Linton is the perfect place to stay. FB: Linton Insta: @Welcometo2Linton
4.91 out of 5 average rating, 115 reviewsPopular amenities for Cupar house rentals
House rentals with a pool

Planners House is a detached house on the harbour
5.0 out of 5 average rating, 13 reviews
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
Luxury Lodge• Haven Seton Sands• WiFi •Blairgowrie

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

Large 3 bed home close to excellent golf courses.
4.95 out of 5 average rating, 111 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
Kinnessburn Cottage - free parking, close to golf
4.97 out of 5 average rating, 103 reviews
4 bedroom / 2 bathroom house in desirable area.
4.98 out of 5 average rating, 102 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, 63 reviews
The Old Post Office
4.9 out of 5 average rating, 31 reviewsPrivate house rentals

Comfortable private annex with a sensational view
4.94 out of 5 average rating, 17 reviews
Peaceful countryside house near Elie
4.98 out of 5 average rating, 58 reviews
Vicarsford Farmhouse
5.0 out of 5 average rating, 19 reviews
Newhall Gardens - Botanical Bliss
4.96 out of 5 average rating, 50 reviews
Strathtyrum Farmhouse, St Andrews
5.0 out of 5 average rating, 4 reviews
Exquisite beachfront Sanctuary with Bay Vista
5.0 out of 5 average rating, 55 reviews
Periwinkle Beach House
4.96 out of 5 average rating, 75 reviews
Amazing sea views on the front line in Anstruther
4.99 out of 5 average rating, 73 reviewsDestinations to explore
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- Edinburgh Waverley Station
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