Holiday rentals with a pool in Thessaly

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.

Home in Volos

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.

5 out of 5 average rating, 35 reviews

A dining area features a table set with fruit and drinks, surrounded by white chairs. An umbrella provides shade, and panoramic sea views are visible in the background, enhancing the serene ambience. The scenery includes hills and clear blue waters under a bright sky.

Villa in Stafylos

Stunning Sea Views, Infinity Pool, Peaceful, wI-FI

Peaceful pool villa, two floors, spacious, 800m from Stafilos beach, 4 km to Skopelos town and port.There is private infinity pool. The house is set in its own fenced grounds with fabulous views across the Aegean and is surrounded by almond and olive trees. You are free to walk over the private grounds. It is reached from the main road through a 500m long dirt road .The place is good for couples, families,nature lovers . Fast Wifi. Both bedrooms and living room are airconditioned.

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.

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.

Home in Skopelos

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.

5 out of 5 average rating, 9 reviews

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

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.

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

5 out of 5 average rating, 15 reviews

A spacious sleeping area features a large bed with a light-colored coverlet and decorative pillows. An eye-catching octopus mural adorns the wall behind the bed. Natural light enters through large glass doors, which offer views of the surrounding landscape.

Home in Sporades

"Candlelight" with stunning views Alonissos

"Candlelight" cottage offers stunning views of the sea towards Skopelos. The cottage lies in the middle of old olive trees and is at walking distance to small beaches with crystal clear water. The whole property is surrounded by forests, mediterranean herbs and shrubs creating a totally secluded environment. Ideal place for demanding nature lovers!

4.96 out of 5 average rating, 28 reviews

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.

Villa in Chalkidiki

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

5 out of 5 average rating, 23 reviews

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

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.