Family-friendly vacation rentals in Cupar

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Cupar

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

%{current} / %{total}1 / 1
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, 134 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
A modern two-story building is presented, featuring a blend of stone and white wall exteriors. Large windows reflect the sky, allowing for abundant natural light. The driveway is paved and leads to a garage on the left, enhancing the contemporary design.
Guest suite in Longforgan
4.97 out of 5 average rating, 354 reviews

Guest Suite with Private Entrance, close to Dundee

The Studio at Broadleaf is a cosy self contained Guest Suite in Longforgan, just outside Dundee. The Studio has a private entrance and parking with entrance hall and stairs up to the suite. The suite itself has a small kitchen, living and dining area with large TV, DVD and Netflix. There is a bathroom with Shower. Longforgan is near Dundee, one of the most up and coming cities in Scotland. We are only 30 minutes from St Andrews, 1 hour from Edinburgh, Glasgow and the Highlands of Scotland.

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.
Condo in Fife
4.9 out of 5 average rating, 169 reviews

Lovely top floor flat 3 bedrooms & private parking

This is a great central flat in Cupar with the train station just a 2 minute walk away, and the taxi rank even closer, and only a 15-minute drive to St Andrew's with some amazing golf venues, ideal for a getaway, golfing trip or just to explore Scotland With speakers built into the roof it is ideal for a nice relaxing time away. And a train running to Edinburgh and Dundee every hour a vehicle will not be needed. However, Private parking is included so there is no worry about paying any meters.

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 in Peat Inn
4.99 out of 5 average rating, 252 reviews

Braeview: Cosy studio farm cottage near St Andrews

We have lovingly converted a 200 year old cartshed 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.
Condo in Fife
4.99 out of 5 average rating, 152 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 charming exterior view of the Woodside Retreat features a large window with multiple panes, surrounded by smooth stone walls. Two potted plants sit beneath the window, adding greenery to the entrance. A brick pathway leads to the property, creating an inviting approach.
Cottage in Fowlis
4.96 out of 5 average rating, 229 reviews

Woodside Retreat with Garden

Woodside Retreat is in a fantastic relaxing village location! It is a lovely, newly furbished, fresh, bright property with a private garden nestled beside woodland and located in the countryside. It is the perfect place to relax and recharge or explore and enjoy the areas nearby. Situated in Scotland near to Piperdam Golf Course, Dundee, and within easy travelling distance of Edinburgh, St Andrews, Dunkeld, Perthshire. We are dog friendly and can accommodate one house trained dog.

Top guest favourite
An outdoor sitting area features two wooden chairs painted in a soft green hue, complemented by a hanging flower basket filled with vibrant blooms. A small garden with various plants and flowers enhances the rustic charm, surrounded by gravel and a wooden fence.
Guesthouse in Angus Council
4.96 out of 5 average rating, 197 reviews

"The Wee Bothy" - Studio Annex - near Arbroath.

The “Wee Bothy” offers a great base to explore the North East Coast, our scenic Angus Glens, and nearby Towns and Cities with places of interest all around. The Seaside/Harbour town of Arbroath is a 5 min drive away, with lots of lovely Cafes, Restaurants, Cinema and Theatre. Golfing, Fishing , Kayaking round the Cliffs and Walking, are plentiful in and around the area with Carnoustie Golf Links a 15 minute drive. Bus and Train Station in town for those who want to venture further.

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.
Apartment in Fife
4.98 out of 5 average rating, 102 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
The magnificent Balmuir House showcases its classic architecture set within expansive gardens. The grounds are framed by lush greenery, including trees and flowering shrubs, providing a peaceful setting. Large windows reflect natural light, while a broad lawn invites guests to explore the serene outdoor space.
Guest suite in Dundee
4.98 out of 5 average rating, 176 reviews

Balmuir House - Apartment in Listed Mansion House

Balmuir house is a Grade B listed Mansion house built around 1750. We offer you a 2 bedroom ground floor apartment. The apartment benefits from a peaceful and secluded location with Dundee on its door step. Set in 7 acres of gardens and woodland. Discounts can be offered for longer stays. Balmuir House Apartment is licensed under The Civic Government(Scotland) Act 1982 (Licensing of Short-term Lets) Order 2022 Licence AN-01 169-F The property is Energy Efficiency Category D

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.July-Sept rate cuts

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.

Guest favourite
A bright living area features a comfortable sofa and a plush armchair positioned near a large window with red curtains. The space is complemented by a flat-screen TV and a wooden fireplace, enhancing the cozy interior. Artwork adorns the walls, adding visual interest.
Cottage in Upper Largo
4.85 out of 5 average rating, 170 reviews

Secluded Quirky Rural Bothy

One bedroom open-plan property between Upper Largo and Elie, in a secluded rural setting. Livingroom with indoor fireplace and electric heating. Kitchen with mini cooker/oven, microwave, fridge/freezer and washer/dryer. Walk-in shower with toilet and wash-hand basin, heated towel rail. Twin-bedded room located on first floor with storage cupboards.

Guest favourite
The exterior of the studio is highlighted by textured stone walls and timber detailing. Large glass doors offer views into the living space, surrounded by greenery. A low fence runs along the terrace, and the setting is enhanced by a clear blue sky.
Cottage in Moonzie
4.86 out of 5 average rating, 315 reviews

Moonzie House Stable

A recent conversion of the former stables at Moonzie house in semi open-plan style, the location is secluded with lovely views, but very near the town of Cupar. It is only 20 minutes from St Andrews or Dundee and 1 hour by train or car to Edinburgh.

Popular amenities for Cupar family-friendly rentals

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

  • Total vacation rentals

    Explore 20 vacation rentals in Cupar

  • Nightly prices starting at

    Cupar vacation rentals start at $112 CAD per night before taxes and fees

  • Verified guest reviews

    Over 890 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    20 of Cupar vacation 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!

  1. Airbnb
  2. United Kingdom
  3. Scotland
  4. Fife
  5. Cupar
  6. Family-friendly rentals