Family-friendly holiday rentals in Cupar

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Top-rated family-friendly rentals in Cupar

Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

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Top 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
4.99 out of 5 average rating, 136 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.

Superhost
The exterior of the Hay Shed showcases a wooden deck area with a sunken bath and festoon lights adorning the space. Large glass doors provide a view of the interior, enhancing the connection to the outside. The tranquil landscape beyond offers glimpses of sea views.
Cabin
4.84 out of 5 average rating, 224 reviews

The Hay Shed - St Andrews

Located only 2 miles out of St Andrews, the Hay shed is the perfect place to unwind and enjoy sea views. It is positioned in the grounds of a large house with views over a field and then towards the sea. The Hay Shed offers a luxury glamping experience, think outside bath whilst watching the stars, cosy firepit and twinkling festoon lights. Perfect for a getaway for two people but also room for two kids in the mezzanine area (mattress provided but no bed linen for this bed). One dog allowed.

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
4.93 out of 5 average rating, 306 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
The cottage features a stone exterior with a red-tiled roof, complemented by large glass doors opening to the garden. A well-maintained lawn surrounds the structure, with a solitary tree positioned nearby against a bright blue sky, creating a peaceful outdoor setting.
Cottage
4.99 out of 5 average rating, 268 reviews

Braeview: Cosy studio farm cottage near St Andrews

We have lovingly converted a 200 year old cart shed into 2 cottages. Braeview Cottage at Braeside Farm is a spacious studio space with a king size bed on the mezzanine floor. Downstairs next to a modern kitchen you have an open area with large french doors to a patio with a great view across the brae. On a farm set in 13 acres and 500 m from the nearest road, you will savour the tranquillity yet it's a 10 to 15 min drive to St Andrews and an hour from Edinburgh Airport. 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
4.99 out of 5 average rating, 168 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
4.98 out of 5 average rating, 192 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
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
4.98 out of 5 average rating, 110 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
A light-filled living area features a comfortable grey sectional sofa adorned with colorful cushions in teal and purple. A soft area rug lies beneath a sleek white coffee table, while a large flat-screen television is mounted on the wall opposite. Shuttered windows allow for adjustable light control.
Apartment
5 out of 5 average rating, 132 reviews

The Loft @ 136

The Loft @ 136 is a spacious apartment, recently refurbished, it is suitable for 2 adults. Situated in the heart of St Andrews, close to the West Port and the medieval core of the town and within a 10 minute walk of the famous Old Course Golf Course, Cathedral and beaches. It is the perfect place to explore St Andrews and the East Neuk of Fife. Experience an unrivalled selection of golf, walks, restaurants, scenery, history and everything else life in St Andrews has to offer.

Top guest favourite
Castle
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
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.

Top guest favourite
A charming stone cottage with a modern metal extension is set amidst a lush green lawn. Large windows provide natural light, while outdoor seating is arranged on a gravel patio, ideal for enjoying the surrounding countryside views.
Cottage
4.98 out of 5 average rating, 108 reviews

Stylishly converted Bothy by River Earn

The Bothy is stylishly converted from two jold stone farm cottages into a luxurious 2 bedroom cottage. The decor is a mix between birch ply panelling and polished cement, giving it a modern Scandi/Scottish feel, yet not losing its original charm and farm history. Some of the furniture has been made from beech and cedar from our farm. With view across the River Earn and surrounding hills, this is a perfect place to come, explore, unwind and relax.

Guest favourite
The kitchen features modern cabinetry with a light finish, complemented by a wooden countertop. A built-in oven and stovetop are prominently displayed. Natural light floods the space through large windows, highlighting the neutral tile floor and providing a bright cooking environment.
Apartment
4.9 out of 5 average rating, 175 reviews

Lovely top floor flat 3 bedrooms & private parking

This centrally located flat in Cupar is just a 2-minute walk from the train station, with the taxi rank even closer. St Andrews is only a 15-minute drive away, making it ideal for a golfing trip, relaxing getaway, or exploring Scotland. The flat features built-in ceiling speakers for a comfortable, relaxing stay. Trains run hourly to Edinburgh and Dundee, so a car isn’t essential, though private parking is included for added convenience.

Popular amenities for Cupar family-friendly rentals

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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 £82 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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