Vacation rentals with a pool in Fife

“Sea Whispers”: Relaxation in a beautiful setting

Relax and admire the beauty of nature through the expansive patio doors whilst enjoying cooking in the open plan kitchen or a conversation at the breakfast bar. The modern sleek kitchen with a mirrored kitchen backsplash is a perfect backdrop to the lounge which includes an L shaped sofa bed and matching storage footstool and armchair. The wall mounted fire, dining chairs and bar stools work perfectly with the comfortable seating. The lovely lighting throughout can be adjusted to suit your taste

Planners House is a detached house on the harbour

Planners House is a historic detached house built in 1750, situated right on the harbour front at St Monans with wonderful sea views. Colourful and quirky, the house sleeps six in 3 double bedrooms with 3 bathrooms, one with a copper bath. Luxuriously appointed, the house has every comfort and direct access to the Fife Coastal path and minutes from St Monans tidal pool. Excellent restaurants and cafes on the doorstep. Dog friendly with no charge for dogs. Luxury hamper and personal management.

Iconic Beach-Front Fisherman’s Cottage

Enviably located in an iconic row of fisherman’s cottages a few feet from the beach at West Shore, Pittenweem, our 3 bedroom cottage is accessed from the historic harbour by a pedestrian pathway. Stunning sea views over the Firth of Forth to the Bass Rock & North Berwick, make it the perfect beachfront retreat. All facilities of this lively picturesque fishing village are within easy walking distance including coffee shops, pubs, restaurants and Independant galleries. 20 minutes to St Andrews.

Sir Stuarts House & Bothy House

Our place is approximately half way between Perth and Dundee, 1 hour from Edinburgh and 1hr 15 mins from Glasgow. A large house that sits on the side of the lake, the house is ideal for families, larger groups, or smaller groups who need separate bedrooms, and well behaved pets. There are 6 bedrooms - 1 double room, 4 twin rooms and 1 room to be used as a small sitting room or a bedroom with one day bed and an occasional camp bed. Pets are welcome - please do not leave them alone for long.

Luxury Retreat with Hot tub & Leisure Facilities

Luxury Villa + Private Hot Tub | Kilconquhar Castle Estate | Sleeps 8 19th–26th September 2026 Escape to one of Fife's most sought-after holiday destinations. Enjoy a luxurious 3-bedroom villa with private hot tub, full access to the estate's swimming pool, sauna, tennis courts, golf range and stables set in 120 acres of grounds. Perfect for families, golfers, couples and friends looking for a luxury Scottish escape with onsite dining. Nearby coast. Enquire now to secure this exclusive week

Luxury 3 bed Home close to Gleneagles. Complimenta

Enjoy a relaxing stay in this modern 3‑bed, 3‑bath lodge, perfect for families and golfers alike. With spacious living areas, ensuite bedrooms, high-speed Starlink WiFi and a peaceful setting, it’s the ideal base for exploring nearby attractions and world‑class golf courses. Comfortable, convenient, and designed for easy getaway living. On-site Restaurant/Bar, Games Area, Pool, Steam Room, Sauna & Hot Tub. PLEASE NOTE: A security deposit of £150 will be required 14 days before check in.

Lodge 17 St Andrews

Lodge 17 St Andrews is the perfect luxury retreat to enjoy St Andrews and all that the stunning East coast has to offer. The Lodge is set on a peaceful and immaculate holiday park with shared spa facilities. The Lodge is within easy driving to so many attractions and places of interest. With hill walking and cycling amenities nearby. The town of St Andrews offers many amazing gastric delights from seafood, Italian, street food the list is endless! Not to mention of course….. Golf!

Spacious 4 bedroom house with sea views, Pitmilly

Beechwood is a boutique apartment in The Steading at Pitmilly. It sleeps up to 8 people in four bedrooms: one king sized double on the ground floor and three upstairs rooms which can be made up as super kingsize doubles or twins to suit your requirements, all of which have en-suite shower rooms. If you prefer a bath, there is a bathroom on the ground floor, with complimentary toiletries. Extremely spacious living area. The house is fitted with underfloor heating throughout.

The Stables, Pitmilly near St Andrews

The Stables is a Courtyard property at Pitmilly. It looks out onto the children’s play park and open fields from its large open-plan living area. It has a country-style kitchen and dining space, a double room, a family bunk bedroom and another room which can be either twin or double. The Stables has a bathroom and a shower room, and is on ground floor level. The Stables sleeps 6, and can accommodate 8 if the sofa bed is used.

The Byre Cottage, Pitmilly near St. Andrews

The Byre is a Courtyard cottage on ground floor level, and can be accessed via its own front door . The cosy apartment has an open plan living room, country-style kitchen and bathroom. The beautifully oak fitted bedroom can be made up as a twin or super king room, which looks over a courtyard garden. The Byre sleeps 2, and by using the double sofa bed in the living room can comfortably accommodate 4 people.

Farriers Cottage, Pitmilly near St. Andrews

Farriers Cottage in the Courtyard, has two bedrooms which can be set with superking double or twin beds. There is an open plan living area, country-style kitchen, dining space and patio door access to the courtyard garden. All accommodation is on ground floor level. Farriers Cottage sleeps 4, and by using the sofa bed in the living room can comfortably accommodate 6

Studio Apartment with Seaview, Pitmilly

This contemporary studio apartment is upstairs and ideal for a couple. Enjoy the sea and countryside view from your private balcony. It has a bedroom with super kingsize bed (which can also be converted to two single beds), beautiful oak furniture and en-suite shower room with fluffy towels and robes.