Holiday rentals with a pool in Thessaly

A cozy living space features a wooden beam ceiling and warm lighting. A modern fireplace is set into a natural wood mantel. Comfortable seating includes a plush chair and a sectional on a soft area rug, complemented by a glass coffee table and decorative accents.

5 out of 5 average rating, 13 reviews

Valdita Sunrise Tsagkarada

Sunrise Tsagkarada is a 2-5min drive from the beaches of Mylopotamos and Fakistra, while they offer several options for traditional or elegant lunch/dinner options It has started to sell online, and it is really selling fast. The location is here: https://goo.gl/maps/5LSxA6uFfBp All villas are fully equipped with the latest technology and comfort combined with traditional style and color. The Villas carry extra premium Cocomat beds, 1 or 2 bathrooms, large living room and dining place, fully equipped kitchen, A/C, Flat TVs in each room, access to Pool and Kiosk with free sunbeds and towels, WiFi, parking next to Villa

4.95 out of 5 average rating, 131 reviews

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.

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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.

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.

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

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.

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!

5 out of 5 average rating, 11 reviews

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.

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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.

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.

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.

An aerial view of a private pool surrounded by a stone terrace features two sunbeds with towels neatly placed on them. A small side table is positioned next to a sunbed, offering a convenient space for refreshments. Lush greenery is also visible, creating a serene atmosphere.

5 out of 5 average rating, 21 reviews

Villa Mariel Skopelos

Villa Mariel is a newly build private villa of 80 sq.m, located on the hillside above Skopelos Chora. Its design was inspired by the Greek island architecture, including white-washed interiors and minimal interior decoration. ♥ Breathtaking eastern view ♥ Total privacy ♥ Just 2km from Skopelos port ♥ Luxurious facilities (SONOS speaker, Netflix, SMEG appliances) ♥ Private pool + outdoor lounge area ♥ Gas BBQ

An open-air terrace features comfortable seating arrangements and a dining table, overlooking a private swimming pool. Soft outdoor lighting enhances the serene atmosphere, while lush greenery surrounds the space, creating a secluded retreat. The structure's large glass doors provide a seamless transition to the indoor living area.

4.96 out of 5 average rating, 28 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

An airy living and dining area features large windows with ocean views, complemented by natural light. A comfortable sofa and a cozy pouf are situated near a minimalist entertainment unit. A wooden dining table with six chairs invites leisurely meals, while a textured rug enhances the space.

5 out of 5 average rating, 6 reviews

Villa Phos Two Skiathos

Experience the perfect blend of comfort, elegance, and breathtaking surroundings at Villa Phos Two Skiathos, a beautifully designed upper-floor retreat that invites you to relax and unwind. Spanning 120 square meters, this villa is an ideal haven for couples, families, or groups of friends seeking a serene escape in the heart of the Aegean.

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.