
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.

Pelion Luxury Villa Ivy
Welcome to this magnificent residence nestled in the prestigious foothills of Mount Pelion, Ano Volos. A statement of luxury and sophistication. Spanning an internal area of approximately 300 sm, with parking and guesthouse covering over 100 sm, this property is the epitome of elegant living. The Villa has been meticulously re-built offering an eclectic mix of an English country house and Greek mountain Villa all in one! SAUNA-SPA POOL - HAMMAM. PRIVATE CHEF AND MASSEUSE AVAILABLE ON REQUEST

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.

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

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!

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.

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.

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.

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

Skopelos Villa "Constantine"
The abundant bright and unlimited view from the users mood of the house, rejuvenate the soul and relax the spirit! Enjoy dinner or your child, adding the text to fill with the endless blue of the tunic and the sea! The home is only available to one customer. The pool is private and only for customers renting the house. There are no other people staying in the area of the house.

"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!

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.

Akrolithos Villa - Private Pool, Breathtaking View
Overlooking the Pagasetic gulf, Akrolithos Villa can guarantee an unforgettable experience. It is a fully equipped, stone-built property with a private infinity pool, garden and barbecue area, located at the picturesque village of Milies. The ideal choice for families, couples or friends!
Popular amenities for Thessaly rentals with a pool
House rentals with a pool

Villa IHOR- Private Pool Villa -Pieria

Seaview Villas - Villa Poseidon with private Pool

Villa with Private Pool

Elegant villa with shared pool

Villa Aster

Cozy Lux Pool House, Kriopigi

stone pool villa next to the sea 1

Villa Driades Hilltop Residence
Condo rentals with a pool

Country house with amazing sea view.

Simon King apartments

Apartment with pool in Kallithea, Halkidiki

Villa Eva

Magic holidays

Sea side apt with swimming pool & parking #1

Stone and pine

Aya Pool Apartment in Kallithea
Other vacation rentals with a pool

Summer Pearls-Villa with Private Pool

Charming pink villa in olive grove

Artemis' Garden Deluxe Apartment

Elegant Suite | Anmian Suites

Superior Villa | Kassandra Villas

Villa Nanoula

Villa Nereides

Admonis - Home in the olive grove
Destinations to explore
- Pet-friendly rentals Thessaly
- Farmstay rentals Thessaly
- Rentals with a kayak Thessaly
- Serviced apartment rentals Thessaly
- Rentals with a home theater Thessaly
- Bungalow rentals Thessaly
- Guesthouse rentals Thessaly
- Family-friendly rentals Thessaly
- Tiny house rentals Thessaly
- Villa rentals Thessaly
- Beachfront rentals Thessaly
- Rentals with beach access Thessaly
- Cycladic house rentals Thessaly
- House rentals Thessaly
- Rentals with a washer and dryer Thessaly
- Waterfront rentals Thessaly
- Bed and breakfasts Thessaly
- Rentals with an EV charger Thessaly
- Loft rentals Thessaly
- Rentals with a fireplace Thessaly
- Boutique hotels Thessaly
- Condo rentals Thessaly
- Rentals with outdoor seating Thessaly
- Aparthotel rentals Thessaly
- Ski-in/ski-out rentals Thessaly
- Fitness-friendly rentals Thessaly
- Rentals with a firepit Thessaly
- Smoking-friendly rentals Thessaly
- Apartment rentals Thessaly
- Earth house rentals Thessaly
- Rentals with a hot tub Thessaly
- Vacation home rentals Thessaly
- Rentals with a patio Thessaly
- Rentals with lake access Thessaly
- Rentals with breakfast Thessaly
- Private suite rentals Thessaly
- Hotel rooms Thessaly
- Townhouse rentals Thessaly
- Resort rentals Thessaly
- Rentals with pools Greece




