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Holiday rentals with a pool in Thessaly

Find and book unique homes with a pool on Airbnb

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 favourite
Home in Sporades
5.0 out of 5 average rating, 5 reviews

Antāma - Earth & Nature Retreat, Skopelos

Antāma is a private retreat in Agia Marina, Skopelos, where open horizons, olive trees and the calm of nature define experience. Designed with simplicity and elegance, it blends into its surroundings with uninterrupted sea and hillside views. Spend your days by the private pool, soaking in the sun and stillness or enjoy slow moments as the light shifts across the landscape. The space invites you to disconnect from the pace of everyday life and reconnect with what matters-rest, nature and quiet.

Guest favourite
The villa is depicted from an elevated perspective, showcasing its modern architecture nestled among lush greenery. A spacious terrace leads to a serene overflowing swimming pool, highlighting the tranquil outdoor living space and the sloping landscape surrounding the residence.
Home in Kalandra
4.94 out of 5 average rating, 35 reviews

Villa Roje

The villa, located in Halkidiki, offers a unique view on the gulf of Posidi and Olympos Mountain. The residence of 250 m2 has a capacity to accommodate 7 people: the living room, the kitchen, 3 rooms (2 rooms with a double bed, one room with 2 single beds), 2 bathrooms with toilets and an independent toilet are situated at the first floor. A master room with its bathroom and the office are situated at the second floor. The house is ideal for 2 couples with 2 kids each or 6 adults with 2 kids.

Guest favourite
A wooden deck is featured with two lounge chairs positioned near a small pool, offering views of the mountains and water. A table with refreshments is also present, inviting relaxation in a serene outdoor setting.
Home in Volos
4.95 out of 5 average rating, 141 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 favourite
A serene outdoor space is showcased with a modern pool overlooking the sea and town of Skopelos. Sun loungers are positioned beside the pool, while gentle clouds drift across a colorful sky. Natural stone and a smooth deck enhance the tranquil atmosphere of the surroundings.
Villa in Skópalos
5.0 out of 5 average rating, 19 reviews

Jonina Resort

Jonina Resort is for those who are looking to stay at a small paradise on earth with a breathtaking view of the sea and the town of Skopelos. If you have relaxation and tranquility as a priority on your holidays then you are looking for the right accommodation! Here you will find privacy and enjoy the filling of calmness and peacefulness beside the pool waterfall. Visit Jonina Resort so you can make unforgettable memories in your own small heaven on earth.

Top guest favourite
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
5.0 out of 5 average rating, 31 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.

Top guest favourite
An infinity pool extends toward the Aegean Sea, framed by olive trees and sun loungers. The serene water reflects the sky, and distant islands can be seen on the horizon. The minimalist design complements the tranquil setting, ideal for relaxation.
Home in Sporades
5.0 out of 5 average rating, 20 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 favourite
The modern villa is surrounded by lush greenery, featuring a private pool with sun loungers and umbrellas arranged nearby. Natural stone walls complement the structure, which has a welcoming glow from the interior lights. Panoramic views of the landscape are visible in the background.
Home in Skopelos
5.0 out of 5 average rating, 8 reviews

Villa Ascend - Petrino Villas

Spectacular Villa Ascend Nestled in a privileged location just a short drive from Skopelos Town and the main port, Villa Ascend offers breathtaking panoramic views and a peaceful setting designed for ultimate relaxation. Enjoy long sunny days by your private swimming pool, unwind on the spacious terraces overlooking the stunning Skopelos landscape, and experience complete privacy surrounded by nature.

Guest favourite
Villa in Sporades
5.0 out of 5 average rating, 25 reviews

Villa Mariel Skopelos

Inspired by Greek island architecture, Villa Mariel is a newly built private villa located on the hillside above Skopelos Town. Featuring whitewashed interiors and minimal décor, the home offers a serene and contemporary island experience with complete privacy. Guests can enjoy a private pool, a lounge patio, and a gas barbecue, making it ideal for relaxed outdoor living and entertaining.

Guest favourite
A private swimming pool is framed by wooden decking, creating a relaxing outdoor space. Comfortable seating areas are positioned near the water. The home features large glass doors that open to the pool, allowing for natural light and seamless indoor-outdoor flow.
Villa in Chalkidiki
5.0 out of 5 average rating, 17 reviews

Thespis Villa 2

No buildings and people around on 5000 m2 secured and private property. Luxurious home with big balconies, 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 6 person

Guest favourite
A serene pool area is framed by lush green grass, offering expansive views of the Aegean Sea and distant mountains. This space features a private swimming pool, sun loungers, and an umbrella-shaded seating area, ideal for relaxation and outdoor dining.
Home in Skópalos
5.0 out of 5 average rating, 52 reviews

Villa Savvina with stunning view

1 bedroom villa exclusively for 2 pax, mostly for couples With private swimming pool (8.00x3,80) Shower cabin made of transparent glass Washing machine in the shower / toilet restroom Big terrace with comfortable built in sofas under the shade of a sturdy sun tent. Total sq: 106m2 Essential car.

Top guest favourite
The private infinity pool reflects the soft evening light, framed by a stone pavilion with outdoor dining. Spectacular views of the Pagasetic Gulf and distant hills are visible, creating a serene outdoor space perfect for relaxation.
Villa in Milies
4.96 out of 5 average rating, 94 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!

Top guest favourite
An aerial view showcases a country house surrounded by lush olive trees. A private pool is visible next to a spacious wooden deck with lounge chairs. The home features a stone exterior and a shaded outdoor area, blending seamlessly with the natural landscape.
Cottage in Magnisías
4.99 out of 5 average rating, 152 reviews

country cottage at pilio mountain

old coutry house situeted in tsagarada ,stone made dated 1911 , BBQ place (URL HIDDEN) TV ,hot water ,heating,fireplace,hairdryer, iron ,alarm system 7 min from milopotamos beach and 6 from village tsagarada,perfect for summer and winter

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