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.
Condo in Cupar
4.99 out of 5 average rating, 143 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.

Top Guest favourite
The exterior of the lodge is illuminated by a warm light, showcasing the natural wooden logs. A vivid sunset fills the sky with hues of pink and purple, creating a serene backdrop. Silhouetted trees are visible in the distance, enhancing the tranquil atmosphere.
Cabin in Killiecrankie
4.94 out of 5 average rating, 473 reviews

The Hayloft River Garry Lodges with hot tubs.

The Hayloft is one of our newly built luxury lodges situated amongst some of the most stunning countryside in Highland Perthshire. Each log cabin has its own private hot tub & balcony with barbecue area over looking the hills. Each lodge has 2 bedrooms,shower room & toilet, fully equipped fitted kitchen & lounge,tv,dvd etc. Park up in your private parking space there is plenty room for 2 -3 cars. We do welcome well behaved dogs max 2 per lodge Our other lodges are The Stable & The Farmers Den

Top Guest favourite
A wooden gate with a sign labeled 'Treehouse' opens to a path leading through lush greenery. Tall trees surround the entrance, with the Treehouse visible in the background, nestled among the branches and foliage.
Treehouse in Letham
4.95 out of 5 average rating, 102 reviews

Real Fairytale Treehouse

Set within the grounds of Fernie Castle a beautiful authentic Treehouse with 6 living Trees growing and thriving. Equally beautiful in all seasons especially winter being so very cozy, it is fully heated with lots of hot water for the freestanding bath for two. With all the amenities of a 5 star bedroom, a large freestanding bath on the second floor with a small balcony with views to the stunning countryside it does indeed feel like a fairytale just remember to bring your favourite bubbles...

Top Guest favourite
A wooden railing frames a scenic view of the Tay estuary, showcasing calm waters reflected under a cloudy sky. In the distance, a bridge spans the river, integrating nature and structure in a tranquil setting.
Condo in Fife
4.99 out of 5 average rating, 247 reviews

The Waterfront

Overlooking the Tay estuary this stunning flat has views to take your breath away. A patio, a deck, and a quirky waterfront garden create an idyllic paradise. A luxe new shower room and stylish bedrooms create a unique holiday spot. Enjoy dinner on the deck or walk to excellent neighbouring restaurants. This newly launched flat from the 1860s is recently refurbished. It is close to Dundee and St Andrews and on the fife coastal path. A golfers paradise. An hour to the Cairngorms or Edinburgh.

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, 168 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
A spacious living area is shown, featuring large windows that provide expansive views of the surrounding landscape. Comfortable seating includes two leather armchairs and a sofa adorned with cushions. A light coffee table sits on a patterned rug, contributing to the inviting atmosphere.
Home in Glenfarg
4.97 out of 5 average rating, 194 reviews

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.

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.
Condo in Fife
4.99 out of 5 average rating, 174 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
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, 258 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.

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.
Apartment in Fife
4.96 out of 5 average rating, 127 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 rustic brick structure is set against a backdrop of green trees and grass. Outdoor seating areas are visible under the shade of a large tree, with a pathway leading towards the entrance of the building.
Guesthouse in Currie
5 out of 5 average rating, 136 reviews

The Sidings: cosy retreat near Edinburgh

Cosy countryside retreat with easy access to Edinburgh centre. Newly built. Log burning stove, super insulated, south facing with views to the fields Great local walks straight from the doorstep. We're at the foot of the Pentland Hills. 5 minutes walk to bus stop for Edinburgh (30 - 40 min ride). Or a 25 minute drive. 15 - 20 min drive to Edinburgh airport. Traffic free cycle path to Edinburgh. Shared garden and boot and utility room. Electric car charging at cost.

Top Guest favourite
Castle in Dollar
4.98 out of 5 average rating, 217 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
A distinctive cabin features a bold architectural design, highlighted by a large circular window. Lush greenery and vibrant purple flowers surround the structure, contributing to the inviting outdoor setting. A woven fence can be seen in the background, creating a sense of privacy.
Cabin in Craigrothie
4.93 out of 5 average rating, 103 reviews

Dream Tower Cabin

This uniquely designed cabin is a rural dream pad. Perfect for a quiet getaway, a romantic hideout or a base to explore the beauty of Fife. The leafy deck looks out over fields with horses and sheep. With a separate dedicated workspace it’s also a perfect place to write or create something special. The dynamic shapes of the building are designed to keep your eye satisfied and to encourage the curiosity required to be creative. 🏳️‍🌈 🏳️‍⚧️ LGBTQIA friendly

Popular amenities for Cupar family-friendly rentals

When is the best time to visit Cupar?

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Avg. price$229 AUD$224 AUD$229 AUD$195 AUD$237 AUD$241 AUD$249 AUD$252 AUD$245 AUD$238 AUD$219 AUD$235 AUD
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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 $171 AUD per night before taxes and fees

  • Verified guest reviews

    Over 980 verified reviews to help you choose

  • Pet-friendly accommodation

    Find 10 rentals that welcome pets

  • Wi-Fi availability

    20 of Cupar holiday rentals include Wi-Fi 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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