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Vacation 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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Top guest favorite
An outdoor terrace features a large olive tree surrounded by a stone-paved area. Colorful planters and lounge chairs provide seating options, with a view of the pool and distant mountains visible in the background.
Home in Skopelos
5 out of 5 average rating, 17 reviews

Villa Nirvana

Escape to your own private paradise at our stunning villa, nestled just 1.5 km away from Skopelos town. Surrounded by fragrant pine and olive trees, this luxurious retreat offers the perfect blend of tranquility and convenience. With elegantly furnished spaces, and a fully equipped kitchen, our villa has everything you need for a comfortable and memorable stay. Lounge by the pool, soak up the sun on the terrace, or explore the charming town and the beautiful beaches of Skopelos with ease.

Guest favorite
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, 131 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.

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, 19 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.

Top guest favorite
Cottage in Skopelos
4.96 out of 5 average rating, 26 reviews

MULBERRY TREE COTTAGE A PERFECT ESCAPE

3 cute cottages, named Mulberry tree, Daphne and Chestnut tree, with private pool each one, and very nice surrounded terraces full of trees, plants and flowers, located at Potami (means river) area, between Agnontas beach and Panormos beach. They are full of character with elegant interior decors, entirely suited to the gloriously peaceful rural setting. They are set on the hillside overlooking the Potami valley, on land that has been in the owner's family for over 100 years.

Guest favorite
An outdoor area features a private pool surrounded by lounge chairs and a dining table with four chairs. The villa stands two stories tall, with a balcony overlooking an olive grove and the surrounding hills. Sunlight brightens the space, enhancing the serene atmosphere.
Villa in Sporades
4.96 out of 5 average rating, 50 reviews

Penelope - Private Pool Villa near stafilos beach

This fully equipped home offers everything you need for a comfortable and relaxing stay. Located just a 10-minute drive from Skopelos Town, it provides easy access to restaurants, shops, and the island’s charming harbor, while still offering complete seclusion. The road leading to the property is fully paved, and with no neighboring houses around, you’ll experience absolute tranquility — ideal for couples, families, or anyone seeking a quiet getaway close to nature

Top guest favorite
Lounge chairs are positioned on a lush green lawn beside a sparkling pool. Olive trees provide shade in the background, while a dining area is visible, surrounded by potted plants. The clear blue sky enhances the serene outdoor setting.
Villa in Sporades
5 out of 5 average rating, 43 reviews

Skopelos Blue Heaven Pool Villa in olive grove

Welcome to your perfect getaway! Blue Heaven Pool Villa is a flat villa that offers everything you need for a relaxing vacation. The villa is just 1.3 km from Skopelos Chora and 3 km from Staphylos beach. Enjoy your private pool, where you can soak up the sun or take a refreshing dip. The outdoor BBQ area is perfect for al fresco dining and making unforgettable memories with loved ones. Book your stay today and experience the ultimate comfort and relaxation!

Top guest favorite
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.
Home in Skopelos
5 out of 5 average rating, 11 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 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, 24 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.

Guest favorite
An inviting infinity pool reflects the Aegean Sea, surrounded by a spacious terrace featuring modern lounge chairs and a small table. Lush greenery enhances the serene landscape, with a scenic view of the coastline and buildings nestled among the hills in the background.
Home in Achladias
5 out of 5 average rating, 9 reviews

Petra 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
The modern villa is illuminated at night by green lighting, highlighting its architectural features. A private pool reflects the soft glow of the lights, while a shaded lounge area is positioned beside the water, surrounded by meticulously arranged plants.
Home in Kallithea
5 out of 5 average rating, 7 reviews

Villa STELiA Halkidiki Kallithea

🌴 Modern design villa with private pool in a quiet location – ideal for 1–4 guests. Enjoy stylish interiors with a sleeping gallery, cozy living area & fully equipped kitchen. Large windows, smart TV with Netflix, lounge in the water & lots of privacy. Perfect for couples, friends or families looking for something special. Only a few minutes to beaches & restaurants. Comfort meets style!

Guest favorite
A modern villa is set against a backdrop of green hills, featuring large glass windows that invite natural light. A private pool reflects the sky, while a shaded seating area with loungers is visible. Lush greenery surrounds the property, enhancing the tranquil environment.
Villa in Platamon
5 out of 5 average rating, 23 reviews

Villa "KLEIO", luxury house with 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.

Guest favorite
A serene setting is showcased with a modern stone villa beside a tranquil salt-water pool. Olive trees frame the scene, and the warm hues of sunset paint the sky. The outdoor terrace is visible, providing a comfortable area for relaxation.
Villa in Skopelos
5 out of 5 average rating, 19 reviews

Villa Serene - Petrino Villas

Stunning Villa Serene within a short drive from Skopelos Town and the main port. Excellent location with magnificent views, built for your comfort and peace of mind. Equipped with all modern amenities and a private pool for a totally relaxed holiday.

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