Vacation rentals with a pool in Thessaly

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Top-rated rentals with a pool in Thessaly

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite

A sunlit terrace features a private pool, set against a backdrop of lush hills and a scenic view of the sea. A shaded pergola shelters a dining area, providing an inviting space for outdoor meals.

Guesthouse in Glossa

4.97 out of 5 average rating, 35 reviews

Ysyhia - Private cottage with pool.

Ysyhia is modern, bright and airy & has a private pool which is the perfect size for flopping about in. The cottage comprises one open-plan living space including kitchen, dining and lounge, plus separate bedroom and bathroom. It is set in olive and almond groves and looks out across the sea. 1½km from the village, no other buildings are visible from here. Our house is up the hill on the same plot. Each house has its own private access and a fence separates the 'farm' from Ysyhia and its garden.

Superhost

A small pool is framed by wooden decking, reflecting the surrounding greenery and sky. Nearby, two reclining chairs are positioned under a wooden pergola. Steps lead up to a whitewashed structure adorned with simple windows, enhancing the tranquil outdoor setting.

Home in Volos

4.96 out of 5 average rating, 128 reviews

Anna's Poolside Villa

Anna's Villa is located in the dreamlike location of a traditional settlement of Makrinitsa. Walking through the traditional cobbled streets and within the dense, evergreen vegetation of the magical mountain, you will find yourself in our beautiful setting that is ideal for both families and couples, and for those of any age. Provides all-in-one amenities, giving you unique moments of relaxation and well-being.For the house you have to walk 100 meters in the traditional cobbled streets.

Top guest favorite

The villa is reflected in the still waters of the infinity pool, showcasing modern architecture with a smooth wooden deck and well-lit entrance. Comfortable outdoor lounge areas and the surrounding landscape create a serene atmosphere at twilight.

Villa in Sporades

4.89 out of 5 average rating, 18 reviews

Villa Grace

Discover unparalleled luxury on enchanting Skopelos island. Surrounded by majestic pine-clad peaks, our villa offers an oasis of serenity. Lounge by the infinity pool, enveloped in breathtaking views, or retreat to the tranquil garden oasis. Our spacious outdoor areas, including a built-in seating area, invite moments of relaxation and al fresco dining. Inside, a sumptuous kitchen awaits, ensuring every moment is one of indulgence and comfort. Your ultimate Greek island escape beckons.

Guest favorite

A modern villa with a white facade stands in a scenic setting. The private pool is surrounded by a stone terrace with comfortable sun loungers, olive trees, and steps leading to the entrance. The clear blue sky complements the tranquil atmosphere of this outdoor space.

Home in Sporades

5 out of 5 average rating, 27 reviews

Villa Olive Skopelos

Indulge in a luxurious retreat at our Villa perched atop the hills overlooking the Aegean Sea. This stunning property offers a private pool and a magnificent sun terrace with unparalleled views of Skopelos village, the harbor, Aegean Sea and the majestic mountains. Immerse yourself in the tranquil ambiance of our location, surrounded by lush greenery and hiking trails, just minutes away from the beach, making it the perfect getaway for your vacation on Skopelos.

Top guest favorite

A large private pool shimmers under the evening light, surrounded by wooden sunbeds and umbrellas. The stone-paved terrace features cozy seating areas, enhancing the outdoor space's inviting ambiance. Olive trees frame the scene, completing the tranquil hillside setting with views beyond.

Villa in Sporades

5 out of 5 average rating, 22 reviews

VillaAvaton magnificent sea view and Skopelos town

Villa Avaton is a jewel of pure and sophisticated Skopelitian architecture: a 140 square meters, two-level property, all in white, perched on a hillside with breath-taking, panoramic views over the Skopelos town and Alonissos boasting a large open plan living area indoors and outdoors and offering privacy and seclusion in a very idyllic spot. In the premises of the house a large private pool boasts, with panoramic sea views.

Superhost

Home in Skopelos

5 out of 5 average rating, 4 reviews

Villa Ascend - Petrino Villas

Spectacular Villa Ascend is within a short drive from Skopelos Town and the main port. Excellent location with panoramic views, built for your comfort and peace of mind. Equipped with all modern amenities and private pool for a totally relaxed holiday. A newly remodeled villa with a private pool, accommodating up to 8 guests and featuring an independent cottage for 2, ensuring privacy and an unforgettable stay.

Guest favorite

A contemporary villa set against a serene backdrop of the Aegean Sea features a spacious terrace and an inviting pool. Lush greenery surrounds the property, creating a peaceful atmosphere. The design emphasizes clean lines and integrates seamlessly with the natural landscape.

Home in Sporades

5 out of 5 average rating, 15 reviews

Hydrea Villa by Pelagoon Skiathos

The mesmerizing Pelagoon Villa in the quiet village of Achladies on Skiathos Island, is a beautiful example of minimalism and contemporary architecture. The chic home boasts sublime views over the glistering Aegean Sea and is easily one of the most exceptional villas on the island. Set among olive trees and verdant greenery, it is the perfect haven for those seeking tranquility and seclusion during their stay.

Guest favorite

A heated plunge pool is surrounded by white walls, creating a serene atmosphere. Soft towels drape over the edge, and a decorative pillow rests nearby. Elegant lanterns and terracotta pots add subtle accents to the tranquil outdoor space.

Home in Magnesia Prefecture

4.94 out of 5 average rating, 33 reviews

The Bower Heated Plunge Pool Private Beach

HEATED PLUNGE POOL Some photos have been uploaded, but professional ones are not available yet. In a quiet area, in Velanidia, and only a 10 minute drive to Volos city, The Bower - Volos was born. A small beach house with amazing water views and luxury amenities await your next vacation such as sunken lounge, heated plunge pool and BBQ FREE DIVING LESSON PRIVATE AND NOT IN A COMPLEX

Guest favorite

An independent home is presented with a sleek design, featuring large glass doors that open to a shaded terrace. A private swimming pool is visible, reflecting the surrounding greenery. Comfortable outdoor furniture is arranged for relaxation, promoting a serene environment.

Villa in Chalkidiki

4.96 out of 5 average rating, 27 reviews

Thespis Villa 3

No buildings and people around on 5000 m2 secured and private property. Luxurious home with big balconie and private swimming pool , build in an open field with unobstructed views. A perfect place for naturalists and lovers of marked paths / trails and just few km from the sea. It is fully furnished / equipped and can accommodate up to 4 person

Guest favorite

A contemporary villa is highlighted, showcasing a unique stone facade contrasted with smooth gray walls. The outdoor area features a pool surrounded by a spacious patio, furnished with lounge chairs and an umbrella, set against a backdrop of landscaped greenery.

Villa in Platamon

5 out of 5 average rating, 8 reviews

Villa "ERATO", luxurious house with swimming pool

A unique space of comfort and luxury, part of the SUNRISE PLATAMON VILLAS complex, the ideal choice for relaxation, surrounded by olive trees and a variety of plants and herbs. Romance at the same time with a touch of luxury, but also direct access to sea and mountain activities for the most adventurous travelers.

Top guest favorite

A modern house with a sleek design is depicted in this image, accompanied by a clear swimming pool surrounded by manicured grass. Sun loungers are arranged by the poolside, while a shaded area is visible, providing a comfortable outdoor setting.

Villa in Plaka

5 out of 5 average rating, 17 reviews

Lobster

Ένας μοναδικός χώρος που συνδυάζει την άνεση και την πολυτέλεια. Ιδανική επιλογή για χαλάρωση είτε πρόκειται για μια σύντομη απόδραση από την καθημερινότητα, είτε για πολυημερές διακοπές είτε για επαγγελματικό ταξίδι, υπόσχεται μια εμπειρία διακοπών με υπέροχες στιγμές που θα μείνουν για πάντα στην μνήμη σας.

Top guest favorite

The villa is presented with a stone façade and wooden accents, overlooking a private infinity pool that reflects the surrounding landscape. Outdoor seating areas are available, framed by lush greenery. The warm evening light enhances the inviting atmosphere, with hints of a sunset visible in the background.

Villa in Milies

4.95 out of 5 average rating, 88 reviews

Akrolithos Villa - Private Pool, Breathtaking View

Overlooking the Pagasetic gulf, Akrolithos Villa can guarantee an unforgettable experience. It is a fully equipped, stone-built property with a private infinity pool, garden and barbecue area, located at the picturesque village of Milies. The ideal choice for families, couples or friends!