Family-friendly holiday rentals in Cupar

Find and book unique family-friendly homes on Airbnb

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 $256 NZD per night before taxes and fees

  • Verified guest reviews

    Over 1,040 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

  • 4.9 Average rating

    Cupar stays are highly rated by guests—averaging 4.9 out of 5!

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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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, 145 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.

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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
4.94 out of 5 average rating, 127 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...

Indoor spacesKitchenGetting around

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, 173 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.

Indoor spacesFamilySleep quality

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, 233 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.

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Top Guest favourite
An open plan living area features high exposed wood beams and a cozy seating arrangement with a blue sofa and armchair. A wooden coffee table sits centrally, and light filters through double doors leading to the outside. A dining space and kitchen area are visible in the background.
Barn in Fife
5.0 out of 5 average rating, 102 reviews

The Roundel in Fife

Reconnect with nature at this unforgettable escape. ‘The Roundel’ near Cupar is a beautiful restored barn with its own private entrance. It offers a unique and private sanctuary for guests exploring the beautiful surrounding areas. This lovely open plan space forms part of what was once a traditional farm steading and sits in a quiet and peaceful setting. Guests also have use of a tennis court within the grounds. St Andrews, with its famous golf courses and beaches is just 20 mins by car.

KitchenFamilyComfort

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, 176 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.

FamilyIndoor spacesAccuracy

Superhost
A modern wooden cabin is set against a clear blue sky, surrounded by a gently sloping landscape. Natural stone features and flowering plants adorn the grounds, enhancing the rustic yet contemporary aesthetic.
Holiday home in Fife
4.94 out of 5 average rating, 110 reviews

Rustic Cabin 10, sea views & highland cows

Kinkell Byre Cabins, 2 miles from St Andrews. 1 of 10 new cabins Cabin 10 accepts pets - £20 extra for pet cleaning fee - charged when booked Stunning views of sea & rewilding in action. We also offer nature tours. Double or two single beds sleep 1/2 guests. En-suite bathroom/shower. Microwave, kettle, toaster. Perfect for wedding guests, golfers & explorers of St Andrews & the coastline. Free Wifi available 2 EV Chargers (7kw and 22kw), advanced booking recommended. No TV in the cabins

Indoor spacesKitchenCheckout

Top Guest favourite
An open plan living area features a round wooden dining table surrounded by four black chairs. Two red and gray striped armchairs are positioned nearby, next to a wooden cabinet. Natural light enters through two large windows with beige curtains, while a stone wall adds character.
Cottage in Blebocraigs
4.98 out of 5 average rating, 123 reviews

Clatto Bothy, self catering cottage.

Clatto Bothy is a recently refurbished, fully furnished semi-detached cottage less than five miles from St Andrews. The self catering accommodation consists of a spacious open plan kitchen and dining area and a large living space. There is one double bedroom and a large shower room. The cottage sleeps two and offers peaceful surroundings within easy reach of St Andrews. The kitchen is fully equipped including washing machine and dishwasher. The Bothy has its own private parking area.

KitchenIndoor spacesAccuracy

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, 133 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.

KitchenIndoor spacesBathroom

Guest favourite
A charming entrance is visible with a set of stairs leading to a Shepards hut, surrounded by greenery. Potted plants and a small wooden table with two folding chairs create a welcoming outdoor space for relaxation.
Shepherd’s hut in Perth and Kinross
4.95 out of 5 average rating, 152 reviews

Cosy heated Shepard’s hut with beautiful views

A very comfortable, heated, beautifully appointed Shepards hut with stunning views over the Tay valley. An ideal location to relax, reconnect and explore the magic of Perthshire. We have ancient Caledonian woodlands for you to explore, full of incredible wildlife and a wild swimming pond for those looking for a cold water fix - look us up under cotwild The Shepards hut sleeps 2 adults & 2 children under 12yrs on a sofa bed sleeping bag. 2 well behaved dogs welcome.

FamilyIndoor spacesHiking

Top Guest favourite
Castle in Dollar
4.98 out of 5 average rating, 225 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.

KitchenIndoor spacesLaundry

Top 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, 123 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

KitchenFamilyAccuracy

Popular amenities for Cupar family-friendly rentals

When is the best time to visit Cupar?

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Avg. price$274 NZD$268 NZD$274 NZD$312 NZD$312 NZD$320 NZD$298 NZD$302 NZD$293 NZD$285 NZD$262 NZD$281 NZD
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