Some info has been automatically translated. Show original language
Airbnb your place

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.

%{current} / %{total}1 / 1
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.

Guest favourite
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 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
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 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
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.
Apartment 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

Top Guest favourite
A modern villa is showcased with a large private heated pool in the foreground. The spacious structure features multiple levels, large balconies, and stone accents. Surrounding greenery complements the well-maintained lawn, creating an inviting outdoor space under clear blue skies.
Home in Nea Fokea
4.97 out of 5 average rating, 29 reviews

Sea Wind Luxury Villa with Private Heated Pool

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 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
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 !

Superhost
An aerial view showcases a private pool surrounded by a spacious patio. Two sun loungers are positioned near the edge of the pool, with two umbrellas providing shade. An outdoor dining area is visible, featuring a shaded pergola and lush greenery enhancing the setting.
Home in Sporades
5 out of 5 average rating, 4 reviews

Villa Aster

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 Skopelos
5 out of 5 average rating, 17 reviews

DAPHNE COTTAGE PRIVATE POOL PEACEFUL LOCATION

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

Condo 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.
Condo 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.
Condo in Vourvourou
4.44 out of 5 average rating, 16 reviews

Simon King apartments

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.
Condo 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.
Condo 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.
Condo 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.
Condo 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.
Condo 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.
Condo in Kallithea

Aya Pool Apartment in Kallithea

Other holiday rentals with a pool

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

Newly Renovated Villa with Private Pool

Guest favourite
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

Guest favourite
A private balcony features a small table and two chairs, complemented by potted plants. The view includes the hotel's infinity pool, surrounding greenery, and distant mountains against a clear blue sky.
Holiday home in Vourvourou
4.92 out of 5 average rating, 24 reviews

Elegant Suite | Anmian Suites

Guest favourite
An outdoor area features a refreshing salt-water pool surrounded by modern architecture. Expansive windows provide views of the sea, while greenery lines the space, adding a touch of nature. Sunlight filters through the architectural design, creating an inviting ambiance.
Villa in Chaniotis
4.89 out of 5 average rating, 9 reviews

Sunshine Villa with Private Pool | Sunrise Villas

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 out of 5 average rating, 24 reviews

VillaAvaton magnificent sea view and Skopelos town

Guest favourite
The villa is presented in an evening setting, showcasing its stone and wooden façade illuminated by soft green lighting. The structure features multiple levels and large windows, reflecting a calm atmosphere. Surrounding greenery and a pathway lead toward the entrance, enhancing the villa's tranquil environment.
Villa in Sporades
4.92 out of 5 average rating, 60 reviews

Villa Nereides

Guest favourite
A stone path leads to an inviting entrance, framed by two wooden shutters. Outdoor seating is arranged at a table with fresh fruits, complemented by additional lounge chairs. Lush greenery surrounds the area, enhancing the tranquil atmosphere.
Villa in Agios Georgios Nileias
4.9 out of 5 average rating, 10 reviews

Villa Evridiki by Pelion Esties

Guest favourite
An outdoor terrace featuring a private pool overlooks a stunning coastal landscape. Surrounding olive trees frame the view of the sea and mountains in the distance, while the clear blue sky enhances the serene atmosphere of the setting.
Villa in Sporades
4.96 out of 5 average rating, 49 reviews

Skopelos Villa "Constantine"

Destinations to explore

  1. Airbnb
  2. Greece
  3. Thessaly
  4. Rentals with pools