Vacation rentals in Pitlessie

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Top-rated vacation rentals in Pitlessie

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Guest favorite

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, 164 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 favorite

The exterior of the cottage is showcased, featuring a stone facade with a tiled roof. Windows reflect bright daylight, framing a well-maintained garden with green grass and blooming shrubs. A pathway leads to the entrance, highlighting a welcoming approach to the home.

Cottage in Ceres

4.96 out of 5 average rating, 231 reviews

Homely cottage & tranquil garden, beaches nearby

Penny Cottage is a beautiful, homely old weaver's cottage from 1783, with original features and a peaceful, secure garden, great for dogs. Space is perfect for 2–3, cosy for 4. Perfectly situated for exploring Fife's beaches, countryside, golf courses and historic settlements. Ceres is one of Scotland's 'Most Attractive Villages' - there is a shop, pub and coffee shops. St Andrews and Cupar are nearby. Airbnb policy - booking to be made by person staying at the property. Licence no: FI-00488-F

Guest favorite

The open plan living area is characterized by double-height ceilings and large windows, allowing for ample natural light. A comfortable sofa is positioned next to a sleek coffee table. A stylish wooden staircase leads to the mezzanine, while modern art adorns the walls.

Barn in Fife

4.93 out of 5 average rating, 273 reviews

Beautifully converted farm barn with mezzanine

The Barn is a newly converted farm building on a quiet farm in a rural location 1km from Lundin Links. This 1 bed mezzanine is incredibly spacious yet cozy and welcoming. Finished & furnished to a high standard the property is well equipped with everything you will need to enjoy your stay. Fully contained garden to front, and private courtyard to rear, both ideally positioned to enjoy the morning and evening sun. Only a few minutes to the local beach, pub, shops & golf courses. Pets welcome.

Top guest favorite

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, 149 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 favorite

The facade of a charming stone house is framed by vibrant greenery and a gravel pathway. Large windows on either side of the entrance provide ample light. A striking red door serves as the focal point, complemented by an assortment of potted plants scattered around the front yard.

Home in Cupar

4.99 out of 5 average rating, 342 reviews

Charming self contained annex apartment

Charming self contained annex apartment overlooking beautiful walled gardens. Located in a quiet area of the historic market town of Cupar and close to St Andrews and Edinburgh. This two floor self contained apartment has private gardens and ample off street parking. The upper floor provides an open plan kitchen, dining and snug area. The shower room and bedroom with king size bed is located on the ground floor. Cupar is a perfect location to explore Fife and surrounding areas.

Top guest favorite

The front exterior of the sandstone cottage features a welcoming blue door, complemented by white-framed windows. Flanking the entrance are potted plants and neatly trimmed shrubs, creating an inviting appearance. The slate roof adds character to this charming abode.

Cottage in Freuchie

5 out of 5 average rating, 223 reviews

Charming, vintage style cottage with free parking

Holmlea is a cosy, sandstone cottage c. 1840, nestled in a quiet, pretty little road in the friendly village of Freuchie. With light, spacious, high-ceilinged rooms, Holmlea has an arty, vintage style, and is a welcoming, comfortable and relaxing space. There is free parking in the road opposite the cottage, and a large, free car park (25m away). Most of our guests tell us they feel instantly at home on arrival, and many don't want to leave! Licence No. FI 00095 F EPC rating D

Top guest favorite

The open plan living area is characterized by light walls and soft carpeting. A spacious grey sofa with colorful cushions faces a coffee table adorned with a plant. In the background, a dining table for two is visible alongside a modern kitchen area.

Vacation home in Markinch

4.94 out of 5 average rating, 117 reviews

Bright, modern property in the heart of fife!

This is a bright and airy ground floor property. Bright, fresh and clean with everything you should need for a short stay. This main door entrance property compromises of double bedroom, open plan livingroom, diningroom and kitchen and bathroom with shower. Balbirnie hotel and Laurel bank within walking distance. Lots of local walks including the pilgrims way. 7 mins walk to train station with links to Edinburgh, Dundee and Perth all 30 mins away so great location.

Guest favorite

A traditional terraced cottage is set against a lush green hillside under a partly cloudy sky. A red-tiled roof contrasts with stone walls. Flower pots are placed near the entrance, enhancing the cottage's rustic charm. The spacious surrounding landscape invites exploration.

Cottage in Falkland

4.94 out of 5 average rating, 143 reviews

Beautiful royal-village cottage with wood-burner

Eastmost Cottage is in a wonderful position on the edge of the historic village of Falkland. It's a short walk from the fine Renaissance Falkland Palace, the heart of the medieval village with its independent shops, cafes restaurants and pub. There is great walking in the Lomond hills, accessible on foot. The wonderful Covenanter has fantastic food all day; the Hayloft and Pillars of Hercules are lovely cafes. Fine dining at the Boar's Head in nearby Auchtermuchty.

Guest favorite

Panoramic views of rolling green hills and farmland are displayed, with distant mountains visible under a partly cloudy sky. Lush fields stretch across the landscape, dotted with trees and farm buildings, creating a serene natural environment.

Home in Fife

4.98 out of 5 average rating, 144 reviews

Stunning holiday 'Retreat' with WOW factor!

In an elevated position with stunning panoramic views, the Retreat is a wonderful & unique getaway to relax and unwind - equally suitable as a romantic retreat for two as for an active family. Furnished to a high standard, with all your needs - outside play tennis, relax in the lovely garden, or enjoy the surrounding countryside, including 10 acres of private farmland. Centrally located - St Andrews (golf & beach) 20 mins. Train station to Edinburgh 10 mins drive.

Guest favorite

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.

Top guest favorite

An aerial view captures the charming coastal village, displaying a mix of colorful homes lining the shoreline. Rocky terrain transitions to grassy hills in the background, with the sea gently lapping against the shore, creating a serene seaside atmosphere.

Home in West Wemyss

4.99 out of 5 average rating, 168 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.

Top guest favorite

An open plan living area showcases a cozy seating arrangement with a light grey sofa and a wooden armchair. A wooden coffee table is positioned centrally, complemented by a shelf displaying decorative items. Natural light floods the space through the windows, enhancing the neutral-colored walls.

Condo in Lower Largo

4.95 out of 5 average rating, 202 reviews

Miramar. Cosy home nr Beach/Hotel/Pub with Parking

Private cosy ground floor apartment in Lower Largo. Situated under the iconic viaduct, a one minute walk to Railway Inn, Crusoe Hotel, beach and local grocery shop. Private parking for one car or camper. Lower Largo is one of many picturesque seaside villages situated on the Fife Coastal Path. The popular Aurrie cafe is a short stroll away and new the Castaway Sauna is nearby.