Family-friendly vacation 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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Guest favourite

Guesthouse in St Andrews

4.94 out of 5 average rating, 182 reviews

Self-contained cottage, 2 miles from St Andrews.

Self contained wee cottage with en-suite. Living room has feature stone wall, fully equipped kitchen and patio doors opening onto the garden. Best suited for a couple with 1 double bed in the bedroom. Chair-bed suitable for child or small adult for £20 extra. Travel cot available on request. Well-behaved pets welcome but NOT to be left on their own, garden is enclosed but not secure. Complimentary breakfast for the first morning, plus tea, coffee and condiments. Slow wifi STRICTLY NO SMOKING

Sep. 20 – 27

$177 CAD per night

Guest favourite

Cottage in Fife

4.99 out of 5 average rating, 163 reviews

Eastburn: Gorgeous 2-bed cottage near St Andrews

Eastburn Cottage was created from our lovingly converted 200 year old cartshed. 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 (the one on the right) 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.

Oct. 23 – 30

$232 CAD per night

Guest favourite

Cabin in Kincaple

5.0 out of 5 average rating, 135 reviews

Bright and Cosy Luxury Countryside Cottage

The cottage is a recently renovated (completed April 2018) luxury holiday home just 3 miles from the ancient town of St. Andrews. The house comprises one bedroom with king size bed and a double sofa bed in the living room. We would say it’s ‘small but perfectly formed’ or ‘bijou’! The cottage is set within a quiet village just a short drive from all of the amenities St. Andrews has to offer, yet rural enough to enjoy its peaceful countryside setting! Perfect for couples and small families.

Nov. 29 – Dec. 6

$212 CAD per night

Guest favourite

Home in Dairsie

4.92 out of 5 average rating, 100 reviews

St Leonards House near St Andrews

St Leonards House is a unique self-catered property in North East Fife. Located in the village of Dairsie the Victorian manse house offers spectacular countryside views, with many country walks close to the house. Perfect for groups and families St Leonards House is a 10 minute drive to St Andrews, famous for its golf courses, beaches and nightlife and 15 minutes to Dundee, home to the world renowned V&A museum. St Leonards is perfectly located to experience everything Fife has to offer.

Dec. 4 – 11

$1,127 CAD per night

Guest favourite

Bungalow in Lucklawhill

4.97 out of 5 average rating, 133 reviews

Modern Cottage, superb views, near St Andrews

The cottage is ideally situated in Lucklawhill, between St Andrews and Dundee, approximately 7 miles from each. The front of the house offering stunning panoramic views over the Firth of Tay and St Andrews Bay; the other side providing access to quiet woodland and country walks. Full spacious property available comprising two large double bedrooms, modern open lounge area, dining room, well furnished kitchen, shower room and WC. Two further beds available in loft conversion if required.

Jan. 3 – 10

$218 CAD per night

Guest favourite

Guest suite in Fife

4.96 out of 5 average rating, 275 reviews

School House Annexe Anstruther, King-sized bedroom

School House is an extended family home which offers a central location close to all amenities and is only 5 mins away from the picturesque harbour and beach and in close proximity to public transport. The property has a south facing garden with fish pond and a decked area which guests are more than welcome to use in the warmer months. Fife Coastal Path is easily accessible from the property. If you require additional accommodation please enquire for further details and prices.

Oct. 8 – 15

$150 CAD per night

Guest favourite

Apartment in Dundee City

4.95 out of 5 average rating, 186 reviews

Beach Villa, Broughty Ferry

Spacious, self contained, ground floor Victorian apartment overlooking the beach with a double bed and a superking which can be made into two singles. Ideal for families, golfers, outdoor enthusiasts and those looking for some relaxation. Broughty Ferry has a great selection of cafes, restaurants and independent boutiques, all in walking distance of the apartment. Free on-street parking at door. Easy driving distance of Dundee, St Andrews and Carnoustie. STL DD00017

Jan. 18 – 25

$222 CAD per night

Guest favourite

Castle in Ballintuim

4.91 out of 5 average rating, 505 reviews

The Bridge House, Unique 2 bedroom home on bridge!

If your looking for something a little different then The Bridge House might be just for you! My unusual 2 bedroom home was built on a bridge spanning the River Ardle in 1881. Charming original features including stone spiral stairs, traditional Scottish timber clad walls, stone/pine flooring and even a privy directly over the river below! Recently renovated. Quiet, peaceful and rural location. Pretty views from every window. Sauna. Category A listed.

Mar. 18 – 25

$392 CAD per night

Guest favourite

Home in West Wemyss

5.0 out of 5 average rating, 113 reviews

Stylish Courtyard House in Fife Coastal Village

The Wall House was converted in 2020 from an historic fishing net repair building - it's old outside but super energy efficient & modern inside. It’s a truly unique, stylish and comfortable place to be. The Wall House is also designed to be accessible to a person with restricted mobility. Set in a Fife seaside conservation village you’ll find yourself in a 'get away from it all' location but just a short drive to Edinburgh, the East Neuk & St Andrews.

Nov. 9 – 16

$177 CAD per night

Guest favourite

Loft in New Gilston

4.95 out of 5 average rating, 440 reviews

The Wynd, near Peat Inn, St Andrews

The Wynd is situated in the middle of New Gilston country hamlet, stop at the red phone box and you have found us. We are 10 minutes from StAndrews and 2 minutes from the Peat Inn Restaurant. Overall, a good quality place to stay, close enough to enjoy everything the area has to offer yet secluded and private to relax. COVID advice : Be reassured that our place is completely independent and clean. Letting Licence : FI 00301 F

Oct. 16 – 23

$185 CAD per night

Guest favourite

Guest suite in Dundee

4.97 out of 5 average rating, 144 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. Great location for a Valentines day break. Message me if you are interested in shorter break and well see what we can do. Discounts can be offered for longer stays also.

Nov. 2 – 9

$186 CAD per night

Guest favourite

Cottage in Lower Largo

4.87 out of 5 average rating, 239 reviews

Cardy Crossing Cottage - Lower Largo beach

The interior is bright and contemporary with a clever mix of modern and antique. There is a small patio area, with table and chairs at the back door for morning sunshine and an upper deck for cocktails in the afternoon. The beach is 40 yards away and every room has sea views. Perfect spot for a family holiday or romantic getaway. Super for Golfers too as a 5 minute drive to Dumbarnie Golf Links

Mar. 23 – 30

$214 CAD per night