by Wyndham Vacation Rentals
Shortlist

Fife

As you might expect from the ancestral home of Scotland’s monarchs, Fife has a rich heritage and some wonderful historic attractions, as well as a stunning coastline, quiet beautiful countryside and one of the highest concentrations of top class golf courses in Britain.

This small county is packed with a great diversity of landscapes, extending from the Firth of Forth in the south which includes Dunfermline (Scotland’s former capital) and the famous Forth Road and Rail bridges, to St. Andrews and the rural north. All along extends its eastern coastline with pretty bays, dramatic cliffs, Blue Flag sandy beaches and old fishing villages.

St. Andrews is well known for its golf courses and is home to Royal and Ancient Golf Course. But in addition the town, which is Scotland’s oldest university town, has a charming old-world feel and is close to an expansive beach. St Andrews cathedral may be a shadow of its former self, but well worth visiting. You can spend hours exploring the history and admiring the views here.

Exploring to the south of St. Andrews the coastline is dotted with small fishing villages, such as Crail, Anstruther, Pittenween, East Nuek and St. Monans. The Fife Coastal Path extends along this coastline and is perfect for bracing walks and magnificent sea views, where if you’re lucky you might see Grey seals, dolphins and basking sharks. Boat trips are available from Anstruther to the Isle of May where many sea birds nest at certain times of the year.

Of note is Falkland Palace, which was a rather regal holiday home for many Stuart monarchs, including Mary, Queen of Scots. Beautifully maintained, you can explore the palace and gardens at your leisure – including Britain’s oldest tennis court. Also of interest are Kellie Castle and Garden which dates back to the 14th century and contains fascinating interiors and lovely wooded gardens.

For those looking for an active holiday Fife has plenty of activities for all ages from great walking and biking trails to horse riding and clay pigeon shooting to first class water sports.

If you’re ready to begin your exploration of the region take a look at our selection of holiday cottages in Fife.
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98 cottages are available
  • Upper Largo, Leven, Fife
    Upper Largo, Leven, Fife×

    Kirkside Cottage

    Upper Largo, Leven, Fife

    4
    2
    1
    2
    Ref: SOON
    Key Features:
    - Coastal Property - Wifi - Pub within 1 mile - Coast within 1 mile - Ground Floor Facilities - Open Fire - Baby and Toddler Friendly

    Just 10 miles from St Andrews, this charming, single-storey holiday cottage is attached to another property on a tiny...

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  • Anstruther by St Andrews, Fife
    Anstruther by St Andrews, Fife×

    Guillemot Rise

    Anstruther by St Andrews, Fife

    4
    2
    2
    0
    Ref: CC526018
    Key Features:
    - Coastal Property - Wifi - Pub within 1 mile - Coast within 1 mile - Sea View
    Guillemot Rise is a delightful self-catering apartment in the heart of the seaside village of Anstruther. Just a few...
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  • St. Fort Wormit near Newport-on-Tay, Fife
    St. Fort Wormit near Newport-on-Tay, Fife×

    Valentines

    St. Fort Wormit near Newport-on-Tay, Fife

    4
    2
    2
    0
    Ref: CC526038
    Key Features:
    - Wifi - Garden / Patio - Rural Location - Woodburning Stove
    Discover this B Listed Arts and Crafts house designed by Mackay Hugh Baillie Scott, one of only two in Scotland. Set in...
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  • Anstruther, Fife
    Anstruther, Fife×

    The Marches

    Anstruther, Fife

    5
    3
    2
    0
    Ref: 23412
    Key Features:
    - Coastal Property - Wifi - Car parking on site - Enclosed Garden / Patio - Pub within 1 mile - Coast within 1 mile - Detached Property - Garden / Patio - Baby and Toddler Friendly

    Ideally located in the bustling fishing village of Anstruther, this deceptively spacious detached holiday home is set...

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  • Crail near Anstruther, Fife
    Crail near Anstruther, Fife×

    Hendersons Way

    Crail near Anstruther, Fife

    5
    2
    2
    0
    Ref: CC526041
    Key Features:
    - Coastal Property - Luxury Property - Wifi - Enclosed Garden / Patio - Pub within 1 mile - Coast within 1 mile - Detached Property - Garden / Patio
    In the heart of the picturesque conservation village of Crail and just a minutes walk from the picture-postcard harbour...
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  • Cellardyke near Anstruther, Fife
    Cellardyke near Anstruther, Fife×

    Making Waves

    Cellardyke near Anstruther, Fife

    5
    3
    1
    0
    Ref: CC526026
    Key Features:
    - Coastal Property - Wifi - Enclosed Garden / Patio - Pub within 1 mile - Coast within 1 mile - Garden / Patio - Sea View
    Aptly named ‘Making Waves’, this stunning property sits right on the sea shore in the pretty fishing port...
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  • Cairneyhill near Dunfermline, Fife
    Cairneyhill near Dunfermline, Fife×

    Ross Cottage

    Cairneyhill near Dunfermline, Fife

    5
    3
    1
    0
    Ref: CC526030
    Key Features:
    - Coastal Property - Pub within 1 mile - Garden / Patio - Rural Location
    This cosy holiday cottage in the garden of the owner’s home, but completely private, offers comfortable...
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  • by Kinghorn, Fife
    by Kinghorn, Fife×

    Piteadie Castle Cottage

    by Kinghorn, Fife

    5
    3
    2
    0
    Ref: CC526032
    Key Features:
    - Coastal Property - Wifi - Garden / Patio - Sea View - Ground Floor Facilities - Rural Location - Woodburning Stove
    Set in the peaceful grounds of Piteadie House, surrounded by farmland and with super views, this well-presented, yet...
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  • Crail, near St. Andrews, Fife, Fife
    Crail, near St. Andrews, Fife, Fife×

    Puffin Cottage

    Crail, near St. Andrews, Fife, Fife

    5
    2
    1
    1
    Ref: S62
    Key Features:
    - Coastal Property - Wifi - Coast within 1 mile - Garden / Patio - Baby and Toddler Friendly

    This charming stone holiday cottage in the heart of the picturesque village of Crail, in the historic East Neuk of...

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  • Lundin Links, Fife
    Lundin Links, Fife×

    Fingals

    Lundin Links, Fife

    5
    2
    2
    2
    Ref: 27824
    Key Features:
    - Coastal Property - Enclosed Garden / Patio - Pub within 1 mile - Pets go free - Coast within 1 mile - Detached Property - Garden / Patio - Ground Floor Facilities

    Delightfully tucked away, this detached holiday cottage is just 15 minutes’ drive from St Andrews and 2 minutes...

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  • St. Monans, Fife, Fife
    St. Monans, Fife, Fife×

    Seaspray

    St. Monans, Fife, Fife

    5
    3
    2
    3
    Ref: 23252
    Key Features:
    - Coastal Property - Car parking on site - Pub within 1 mile - Coast within 1 mile

    This delightful, spacious holiday home is set just 2 minutes stroll from the harbour of the picturesque fishing village...

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  • St Monans, Fife
    St Monans, Fife×

    Moorings

    St Monans, Fife

    5
    2
    1
    1
    Ref: CC526015
    Key Features:
    - Coastal Property - Wifi - Enclosed Garden / Patio - Pub within 1 mile - Pets go free - Coast within 1 mile - Garden / Patio - Woodburning Stove
    Moorings is a fisherman’s cottage situated in the quaint harbour village of St Monans on the Fife coast. This...
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Looking for something with a little more?

Cotages with Hot tubs Cottages part of our Luxury collection Something with a swimming pool A place near the Coast
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