Family-friendly holiday rentals in Cupar

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Top-rated family-friendly rentals in Cupar

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A round stone structure features a grand portico with an ornate archway and decorative details. Lush green grass surrounds the building, complemented by a backdrop of trees displaying autumn foliage. The clear blue sky adds brightness to the tranquil setting.
Tower in Edinburgh
4.94 out of 5 average rating, 231 reviews

Craigiehall Temple (historic property built 1759)

Make you trip to Edinburgh truly memorable with a stay at Craigiehall Temple. Built in 1759 and situated in its own grounds on a former part of the Craigiehall Estate, it's Grade A listed for its stunning portico displaying the arms of the 1st Marquess of Annandale. A plaque on the wall carries a quote from Horace: "Dum Iicet in rebus jucundis vive beatus", "Live happy while you can among joyful things". We hope that a stay at the Temple will deliver this experience and stay true to this vision.

Guest favourite
A charming two-story stone building features a dark front door with side windows. Flower boxes adorn the windowsills, while neatly trimmed bushes line the stone boundary. The facade displays a warm, inviting character, set along a quiet street.
Apartment in Cupar
4.99 out of 5 average rating, 137 reviews

Luxury central ground floor flat (nr St Andrews)

Lovely 2 bedroom ground floor flat in the centre of Cupar, Fife. Private entrance. Outdoor enclosed seating area/courtyard (sun trap when weather is good). Quirky, cosy & comfortable. High quality kitchen & shower room. 20 min. drive to St Andrews, Dundee & East Neuk. Train station/buses less than 10 min. walk. Very central - one way quiet street. Supermarkets, Butcher, Baker, Post office, Chemist, Cafes, Take-away, Deli, Bars, Bistros and car parking all within a few minutes walk.

Guest favourite
An open-plan kitchen and living area features a circular kitchen island with seating. A ladder leads to a loft space, and natural light enters through a skylight and window. Warm wood flooring complements the decor, while a red accent curtain adds a touch of color.
Cottage in Fife
4.95 out of 5 average rating, 167 reviews

Romantic Cottage, nr St. Andrews with hot tub

Balass Hayshed Cottage finished to the highest standard and enjoyed by couples on mini moons, golf trips, weddings, visiting children at St Andrews University or just getting away from busy lives. The property has its own hot tub for the exclusive use of Hayshed guests only. There is a loft space with a further double bed. Enjoy the surrounding countryside. Edinburgh an hour by train. Dundee’s V and A 25 minutes. Rent along with the Stables Cottage for larger parties. Ultra fibre broadband.

Top guest favourite
The open plan living area is characterized by double-height ceilings and large windows, allowing for ample natural light. A comfortable sofa is positioned next to a sleek coffee table. A stylish wooden staircase leads to the mezzanine, while modern art adorns the walls.
Barn in Fife
4.93 out of 5 average rating, 307 reviews

Beautifully converted farm barn with mezzanine

The Barn is a newly converted farm building on a quiet farm in a rural location 1km from Lundin Links. This 1 bed mezzanine is incredibly spacious yet cozy and welcoming. Finished & furnished to a high standard the property is well equipped with everything you will need to enjoy your stay. Fully contained garden to front, and private courtyard to rear, both ideally positioned to enjoy the morning and evening sun. Only a few minutes to the local beach, pub, shops & golf courses. Pets welcome.

Top guest favourite
A charming stone cottage is set against a clear blue sky, surrounded by lush green lawns and trees. The building features large windows and a red roof, providing a welcoming appearance. The well-maintained grounds offer ample outdoor space for relaxation.
Cottage in Fife
4.99 out of 5 average rating, 218 reviews

Eastburn: Gorgeous 2-bed cottage near St Andrews

Eastburn Cottage was created from our lovingly converted 200 year old cart shed. On 13 acres of grounds accessed via a 400 metre track, Braeside Farm is tranquil yet a 10-15 minute drive to St Andrews and less than an hour from Edinburgh Airport. Eastburn is a 2 bedroom cottage with a kitchen and living room upstairs and a master bedroom (en suite) and smaller bedroom (with a triple bunk bed), bathroom and WC downstairs. Front door is at the top of the steps in the gable. A car is required.

Top guest favourite
A gravel pathway leads through a landscaped area featuring colorful flowering plants and lush greenery along a stone wall. The buildings are visible in the background, showcasing a modern design with a gabled roof and large windows reflecting the outdoor scenery.
Apartment in Dairsie
4.99 out of 5 average rating, 170 reviews

The Bothy; Cosy Country Hideaway near St Andrews

Welcome to The Bothy ! A recently renovated barn space forming a stunning 1 bed apartment enjoying spectacular views across local countryside. The property consists of a beautiful bedroom with superking bed (can also be set up as twin single beds) with views over a walled garden. The living area has a new kitchen and sitting room with woodburning stove. Located just 7 miles from St Andrews you can enjoy the tranquil location within easy reach of the historic town 10 minutes drive 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 Fife
4.98 out of 5 average rating, 193 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, 118 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
A cozy living space features a soft gray sofa and armchair, complemented by natural decor elements. A wood accent shelf holds a basket and plaid throw, while a lamp stands beside a textured side table. Light enters through an open door, illuminating the room.
Cottage in Fife
4.98 out of 5 average rating, 251 reviews

Escape to a luxury country cottage and ocean views

Built in 1829 Drinkbetween East has had a complete renovation and make over. Every detail has been thoughtfully selected to ensure the most comfortable and luxurious stay possible. The cottage is ideally located on Banchory Farm a 40 minute drive from Edinburgh, St Andrews and Gleneagles with easy access to public transport links. With your own private garden and fire pit enjoy the peacefulness and calm that beautiful rural Scotland has to offer so you can truly relax and unwind.

Top guest favourite
An airy open-plan kitchen and dining area features a wooden countertop, stove, and modern appliances. A cozy seating space with a sofa is illuminated by skylights. A decorative chandelier hangs above the area, and a small dog is seated by the dining table.
Flat in Fife
4.98 out of 5 average rating, 114 reviews

Old Town Loft - stylish apartment

Set within the Conservation area of Cupar this chic apartment has a private entrance, 2 bedrooms, shower room, open lounge / dining / kitchen area and utility room. The property is tucked away along a lane with a pleasant old town aspect. Restaurants, cafes and shops are all nearby. There is a well appointed kitchen and dining table with 4 stools. Utility room with washing machine, drying and ironing. Towels, body wash, shampoo and conditioner provided. Up to 2 dogs welcome.

Top guest favourite
Castle in Dollar
4.98 out of 5 average rating, 204 reviews

The Great Hall, Dollarbeg Castle

This 2 bedroom apartment is the beautifully converted former Great Hall of Dollarbeg Castle. Built in 1890, Dollarbeg Castle was the last gothic baronial style building of its type ever built. Beautifully restored in 2007 to the very highest standards, it was converted into 10 luxury properties, one of which is a conversion of the original "Great Hall" with its vaulted ceiling and majestic views across the formal grounds towards the Ochil Hills in the distance.

Guest favourite
The traditional stone cottage stands amidst lush greenery, featuring a charming black front door and symmetrical windows. The sloping roof and elegant dormer windows enhance its character. A well-maintained lawn extends in front, providing a welcoming outdoor space.
Cottage in Cupar
4.91 out of 5 average rating, 109 reviews

Garden Cottage, nr St Andrews. Spring 10% off

Garden Cottage is a traditional 2 bedroom cottage with central heating, free wi-fi and its own garden, & access to our tennis court. Located on our private country estate about 9 miles from St Andrews. Price includes bed linen, towels, wi-fi & electricity, starter pack of coal, & logs for the fire. Sleeps 4 adults + child/baby, in 1 double bed, 2 single beds & futon. Cot provided. EV charger. STL licence no. FI-00612-F, by Fife Council. Sorry, no pets.

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Quick stats about holiday rentals that are family-friendly in Cupar

  • Total holiday rentals

    Explore 20 holiday rentals in Cupar

  • Nightly prices starting at

    Cupar holiday rentals start at $141 SGD per night before taxes and fees

  • Verified guest reviews

    Over 940 verified reviews to help you choose

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    20 of Cupar holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Cupar rentals

  • 4.8 Average rating

    Cupar stays are highly rated by guests – averaging 4.8 out of 5!

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