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Holiday 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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Top guest favourite
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 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, 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.

Top guest favourite
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
5 out of 5 average rating, 35 reviews

Villa Natura, Stunning Sea Views, Infinity Pool

Infinity pool villa with fabulous views across the Aegean, Peaceful. It has two floors, spacious. 800m from Stafilos beach, 4 km to Skopelos town and port. The house is set in its own fenced grounds 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 narrow rural road . The place is good for couples, families, nature lovers . Both bedrooms and living room are airconditioned.There is WIFI

Top guest favourite
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 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.
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.

Guest favourite
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 favourite
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.
Villa in Sporades
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.

Guest favourite
A shaded outdoor patio area is presented, featuring comfortable seating arrangements with natural materials. A stone path leads to a shared pool area surrounded by olive trees and sunbeds, all beneath a clear blue sky that enhances the tranquil ambiance.
Bungalow in Afytos
4.98 out of 5 average rating, 62 reviews

"Four Olives" Luxury Rooms - Mayor #FeelsLikeHome

Brand new "Four Olives" Luxury Rooms in Afitos, named after indigenous olive tree varieties - Maxima, Uberina, Regalis and Mayor. These 4 rooms give off a unique Mediterranean feeling combined with charm and luxury. A breath away from Afitos and the beach, they are the perfect get-away for a short stay away from daily routine!

Guest favourite
A contemporary villa showcases a mix of stone and modern materials, featuring large glass doors that promote natural light. Outdoor seating is arranged on a spacious patio, with a surrounding view of greenery and well-maintained landscaping, complementing the tranquil setting.
Villa in Platamon
5 out of 5 average rating, 15 reviews

Villa "OURANIA", luxury building 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 favourite
An outdoor space is featured, showcasing a well-appointed lounge area with comfortable seating, complemented by a large dining table. Natural sunlight filters through a bamboo canopy, casting playful shadows on the stone floor. Lush greenery surrounds the area, enhancing the tranquil setting.
Flat in Skopelos
5 out of 5 average rating, 5 reviews

Artemis' Garden Deluxe Apartment

♥♥♥Kick back and relax in this calm, stylish and luxurious apartment surrounded by a lush green garden. ♥♥♥ Rest assured that the all your needs will be met with a fully equipped kitchen and a large stone-built outdoors BBQ facility. A luxurious stay for your well-deserved unforgettable vacations in Skopelos!

Guest favourite
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.

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 Magnesia
4.99 out of 5 average rating, 143 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

Popular amenities for Thessaly rentals with a pool

KitchenWifiPoolFree parking on premisesAir conditioning

House rentals with a pool

Guest favourite
A serene outdoor space features a sparkling swimming pool surrounded by olive trees and comfortable lounge chairs. The architectural design includes a covered patio, providing shade and an inviting area for relaxation. Clear blue skies add to the tranquil atmosphere.
Home in Kato Lechonia
5 out of 5 average rating, 8 reviews

Iriti's Villa @ Pelion

Superhost
An aerial view presents a rectangular swimming pool surrounded by a well-manicured lawn. Two sun loungers are positioned on one side, accompanied by large umbrellas for shade. Lush greenery and stone pathways frame the pool area, highlighting a serene outdoor setting.
Home in Leptokarya
4.81 out of 5 average rating, 52 reviews

Villa with Private Pool

Guest favourite
A tranquil outdoor space features a private pool surrounded by wooden decking and lounge chairs. Soft lighting enhances the scene as dusk settles, revealing a backdrop of distant hills and a glimpse of the water. Cozy seating options invite relaxation.
Home in Χαλκιδική
4.97 out of 5 average rating, 29 reviews

Seaview Villas - Villa Poseidon with private Pool

Superhost
The living room is furnished with a comfortable sofa and a coffee table, complemented by a lounge chair and an ottoman. Soft lighting is provided by pendant lamps. A fireplace is set against a neutral wall, and a visible kitchen area includes modern appliances.
Home in Pefkochori
4.8 out of 5 average rating, 85 reviews

Dreamhouse for up to 11 in amazing location !

Top guest favourite
The exterior features a spacious villa with stone detailing, surrounded by greenery. A private swimming pool is set within a stone patio, complemented by sun loungers and an umbrella. The two-story structure showcases balconies with black railings, enhancing outdoor relaxation.
Home in Sporades
4.94 out of 5 average rating, 65 reviews

Skopelos Panormos Lux Villa Geraki

Guest favourite
Home in Sporades
5 out of 5 average rating, 11 reviews

Villa Daphne

Guest favourite
A view of a spacious garden featuring palm trees and lush greenery surrounds a large swimming pool. Sunbeds are placed near the pool, while the sea can be seen in the distance, framed by the treetops and clear blue sky.
Home in GR
4.98 out of 5 average rating, 42 reviews

Cozy Lux Pool House, Kriopigi

Guest favourite
A tranquil pool area is highlighted by a sparkling blue pool surrounded by a stone patio. Two wooden lounge chairs provide a comfortable resting spot under the shade of trees. The distant sea view is complemented by clear skies and the peaceful atmosphere.
Home in Skopelos
4.95 out of 5 average rating, 21 reviews

Pool Villa Maria O with stuning view

Apartment rentals with a pool

Guest favourite
A bright living room features a comfortable arrangement of sofa and armchairs. A coffee table sits in the center, and large glass doors open to a balcony with sea views. Soft curtains frame the windows, while a decorative fireplace adds a cozy touch.
Apartment in Possidi
4.87 out of 5 average rating, 94 reviews

Country house with amazing sea view.

A stone-built retreat is framed by lush greenery, featuring multiple levels and a spacious outdoor area. A sparkling pool lies in front, surrounded by tropical plants and shaded seating areas. The architecture blends rustic charm with modern amenities, creating a welcoming setting.
Apartment in Vourvourou
4.44 out of 5 average rating, 16 reviews

Simon King apartments

Guest favourite
A small outdoor seating area is visible, featuring a wooden table surrounded by four folding chairs. Potted plants are arranged on the table and nearby. The shaded space is enclosed by a low stone wall and greenery, complementing the inviting atmosphere.
Apartment in Kallithea
4.78 out of 5 average rating, 18 reviews

Apartment with pool in Kallithea, Halkidiki

An outdoor dining setup is featured, with a table set for four and an assortment of dishes. Glowing candles and glasses of red wine add a refined touch. A swimming pool and distant hills are visible in the background under a twilight sky.
Apartment in Sporades

Villa Eva

A dining area is set on a spacious patio, featuring a glass table surrounded by six chairs. Potted plants provide greenery, while a panoramic view of the sea and hills is visible in the background under clear blue skies.
Apartment in Siviri
5 out of 5 average rating, 4 reviews

Magic holidays

Guest favourite
The swimming pool is illuminated with soft lighting, creating a serene ambiance. The water appears inviting and clear, reflecting the surrounding structures and foliage. Poolside loungers can be seen nearby, contributing to the relaxed outdoor setting.
Apartment in Kaloutsikos
4.98 out of 5 average rating, 41 reviews

Sea side apt with swimming pool & parking #1

Guest favourite
An outdoor terrace features a round table adorned with a floral tablecloth, surrounded by four white chairs with cushions. A vibrant potted plant and a charcoal grill are visible in the background, along with greenery that adds a natural touch to the setting.
Apartment in Siviri
4.92 out of 5 average rating, 13 reviews

Stone and pine

Superhost
A dining table setting is arranged with decorative plates featuring floral designs. A woven basket holds assorted fruits, including apples and lemons. Elegant glassware is placed beside golden cutlery, while a small bouquet of flowers adds a touch of color. The pool and outdoor area are visible in the background.
Apartment in Kallithea

Aya Pool Apartment in Kallithea

Other holiday rentals with a pool

Superhost
A view from beneath a pergola adorned with lush grapevines showcases a private swimming pool surrounded by a sun terrace. The expansive sea and landscape beyond create a scenic backdrop, enhancing the tranquil atmosphere of the outdoor space.
Cottage in Skopelos
4.79 out of 5 average rating, 28 reviews

Romantic Lemonia Cottage, Private Pool & Sea View

Superhost
The exterior of the villa features a charming pink facade with blue window shutters and door. A small table with chairs is placed on a stone patio, surrounded by lush greenery and blooming flowers, providing a serene entrance to the residence.
Cottage in Skopelos
4.68 out of 5 average rating, 108 reviews

Charming pink villa in olive grove

Guest favourite
A modern stone villa is depicted beside a private swimming pool. The building features large windows and a sleek design, with an outdoor seating area partially shaded by an umbrella. The clear blue sky enhances the serene atmosphere of the property.
Villa in Nea Fokea
4.92 out of 5 average rating, 12 reviews

Exclusive new villa with private pool - 4BR

Guest favourite
Villa in Skopelos
4.92 out of 5 average rating, 12 reviews

Newly Renovated Villa with Private Pool

Top guest favourite
A dining table is set on a terrace, featuring a wooden serving board with croissants and two glasses of juice. A private pool and ocean views are visible in the background, while the surrounding landscape includes lush greenery.
Home in Sporades
5 out of 5 average rating, 9 reviews

Etherial View Villas Skiathos

Guest favourite
The open terrace features comfortable sun loungers facing the sea, with an umbrella providing shade. A table holds a drink and a fruit. Lush greenery surrounds the space, and distant views of the ocean and landscape are visible under a clear blue sky.
Flat in Vourvourou
4.92 out of 5 average rating, 12 reviews

Deluxe Suite | Anmian Suites

Guest favourite
A stone villa is depicted adjacent to a private pool, surrounded by serene hills and the sea in the distance. Stylish sun loungers are positioned near the water's edge, inviting relaxation. Clear skies and natural light enhance the tranquil outdoor space.
Home in Skopelos
5 out of 5 average rating, 6 reviews

Villa Nanoula

Guest favourite
A bright and airy studio features a spacious bed with neutral linens. Natural light floods the room through a large window, accompanied by soft curtains. A comfortable seating area is present, along with a wooden table that displays a small selection of snacks.
Flat in Paliouri
4.97 out of 5 average rating, 29 reviews

Deluxe Studio | Serenity Hill

Destinations to explore

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