House holiday rentals in Cupar

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Top-rated house rentals in Cupar

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Top Guest favourite
A low stone wall borders the sea view, adorned with a mix of textured plants. Two light blue seating benches are positioned on a pebble-strewn area, offering a serene outdoor space to enjoy the coastal landscape.
Home in Saint Monans
4.95 out of 5 average rating, 222 reviews

Waterfront Cottage, St Monans, Amazing Sea Views

Waterfront is steps away from the coastal path. Downstairs has a galley kitchen leading off to conservatory/dinning area at one side,utility room and WC/shower room at the other. The living/dinning room is spacious and bright with magnificent sea views and a cosy wood burning stove, a bathroom and hall. Upstairs, is a double en-suite with stunning sea views over the Firth of Forth and a twin room. A small garden at seaside with seating and a patio to the rear. 20mins drive away from St.Andrews

Guest favourite
The exterior of the property features a well-maintained white facade with large glass doors leading into a bright interior. Paved walkways surround vibrant green planters, and a small garden area offers additional greenery against a clear blue sky.
Home in St Andrews
4.91 out of 5 average rating, 115 reviews

Number 37, St. Andrews

Step into tranquillity at this charming single-storey house in of St. Andrews. Just a leisurely stroll from the East Sands beach and the picturesque St. Andrews Harbour, this recently refurbished abode promises a delightful retreat. Ideal for families, golf enthusiasts, and four-legged companions alike, this enchanting abode promises a memorable summer holiday or a cosy winter getaway, where the crackling warmth of the log burning stove sets the scene for cherished moments with loved ones.

Guest favourite
A cozy sleeping area features a wooden bed framed against a wall adorned with a vintage map. Soft bedding with subtle patterns is complemented by two decorative pillows. A bedside table and a window seat add functional charm to the space.
Home in Auchtermuchty
4.92 out of 5 average rating, 250 reviews

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.

Top Guest favourite
The lounge features a light-toned sofa and an armchair adorned with colorful cushions. A coffee table is positioned in the center, complemented by a plant. A modern television is mounted on the wall, with a corner fireplace adding a cozy touch. Natural light flows through a large window.
Home in Polwarth
4.98 out of 5 average rating, 188 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 00160F

Top Guest favourite
A spacious living area is highlighted by a comfortable brown leather sofa and a large ottoman. A television is positioned against the wall, while a soft glow is provided by a lamp beside a fireplace. Light enters through the window, complementing neutral wall tones.
Home in Fife
4.95 out of 5 average rating, 115 reviews

Balass Lodge near The Old Course St. Andrews

Luxury country home 10min drive from the historic golfing town of St. Andrews and 1hr 20min from the stunning Cairgorms. Three bedrooms contain super king sized beds which can also be split into singles - one with an ensuite bathroom, the other two share a large main bathroom. The fourth bedroom has a king sized double bed and an ensuite shower room. The house has a games room with a pool table, smart TVs with full Sky HD, as well as a wood burning stove and a hot-tub on the terrace.

Top Guest favourite
The exterior of a cottage is presented, featuring a blend of stone and wooden materials. A raised deck with a railing is visible, accompanied by outdoor seating for several people. The surrounding greenery includes tall trees under a partly cloudy sky.
Home in Wellbank
4.98 out of 5 average rating, 145 reviews

Tranquility in the woods.

At this unique and tranquil getaway, we suggest you try leaving your phone turned off during your visit so you can fully appreciate tranquility in the woods. Enjoy the slow life, destress and go for country walks and look out for Deer, Buzzards, Horses and Sheep. Wake to the wonderful sound of birds chirping away. The cottage is small and cozy with a wood burner. 1 toilet and shower. 2 double-bed bedrooms upstairs accessed by a spiral staircase. We also have good WiFi.

Top Guest favourite
A stone cottage is set among a landscaped garden, featuring a gravel pathway. The structure displays a traditional design with multiple windows and a slate roof. Colorful flowers bloom in front, contributing to the rural charm of the setting.
Home in Wester Balgedie
4.99 out of 5 average rating, 183 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 & Levens Larder both less than 10 minutes walk from the Cottage. Its a great place to explore towns and villages around the East Neuk of Fife, Edinburgh, St Andrews, Gleneagles, Stirling and Glasgow all within 60 minute drive. Its a great place to base yourself if you are planning to explore the Lowlands and Southern Highlands of Scotland.

Top Guest favourite
An aerial view captures the charming coastal village, displaying a mix of colorful homes lining the shoreline. Rocky terrain transitions to grassy hills in the background, with the sea gently lapping against the shore, creating a serene seaside atmosphere.
Home in West Wemyss
4.99 out of 5 average rating, 177 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.

Guest favourite
The kitchen features modern grey cabinetry and a bright yellow wall, with a stainless-steel oven and microwave. A washing machine is present, along with essential appliances like a kettle and toaster. Natural light streams through the window, illuminating the space.
Home in Leuchars
4.87 out of 5 average rating, 252 reviews

No 67 Leuchars (St Andrews) Free Off Road Parking

No 67 is one of 2 properties in Leuchars (nr St Andrews and Dundee). Excellent bus service - every 7 mins daytime 20 mins evening. Free Wi-Fi. Modern décor/furnishings make the place bright and airy. Gas central heating. Fully fitted kitchen, Hob, Oven, Microwave, Air Fryer , washing machine and fridge freezer. 42" TV and dining table. Ground Floor - Lounge and Kitchen First Floor - 2 Bedrooms - 1 Super King Bed and Bunk Beds.

Top Guest favourite
A historical farmhouse is covered in vibrant red climbing vines, creating an appealing exterior. A dark vehicle is parked nearby on the gravel driveway, with well-maintained garden areas visible in front. The surrounding green lawn offers a spacious setting.
Home in Crail
4.99 out of 5 average rating, 259 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.

Guest favourite
The cottage is set against a clear blue sky, surrounded by lush greenery and vibrant flowers. The stone exterior is accented by a traditional roof, and the windows allow natural light to fill the interior spaces.
Home in Alyth
4.93 out of 5 average rating, 217 reviews

Charming, well-equipped garden cottage and hot tub

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.

Top Guest favourite
The entrance to the modernised Steading features a white door framed by a stone wall. The pathway is lined with square pavers and small flowering plants. A step leads up to the entrance, with additional steps leading to the left.
Home in Anstruther
4.86 out of 5 average rating, 402 reviews

The Steading - quaint, compact and comfortable

Located centrally in the quaint seaside village of Anstruther in the East Neuk o' Fife, this modernised Steading has everything you will need for a comfortable stay. One good sized double bedroom. Part of historic Cunzie House, dating back to the early 19th century.

Popular amenities for Cupar house rentals

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 $104 NZD per night before taxes and fees

  • Verified guest reviews

    Over 890 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!

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