Thessaly Holiday Rentals
House
- Thessaly
- ·
- Skiathos Town
- 0.09 mi to center
10.0Exceptional
(52 Reviews)
2 Bedrooms
2 Baths
4 Guests
646 ft²
Oceanfront
Fireplace/Heating
Ocean View
Balcony/Terrace
R4,179/Night
7 Nights - R29,255
House
- Zagora-Mouresi
- ·
- Mouresi
- 0.28 mi to center
10.0Exceptional
(198 Reviews)
5 Bedrooms
2 Baths
6 Guests
317.53 ft²
- Fireplace/Heating
- Balcony/Terrace
View
Parking
R2,158/Night
7 Nights - R15,098
House
10.0Exceptional
(142 Reviews)
1 Bedroom
1 Bath
- Fireplace/Heating
- Balcony/Terrace
Breakfast
Kitchen
R1,785/Night
7 Nights - R12,487
Villa
10.0Exceptional
(44 Reviews)
3 Bedrooms
3 Baths
6 Guests
Private Pool- Oceanfront
- Fireplace/Heating
Pool
R5,067/Night
7 Nights - R35,465
House
10.0Exceptional
(167 Reviews)
2 Bedrooms
1 Bath
6 Guests
1184.03 ft²
- Fireplace/Heating
- Balcony/Terrace
- View
Pet Friendly
R2,410/Night
7 Nights - R16,865
Villa
10.0Exceptional
(42 Reviews)
3 Bedrooms
1 Bath
6 Guests
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
R6,277/Night
7 Nights - R43,930
Villa
10.0Exceptional
(41 Reviews)
2 Bedrooms
2 Baths
4 Guests
1184 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
R7,065/Night
7 Nights - R49,444
Villa
- Thessaly
- ·
- Skiathos Town
- 0.67 mi to center
10.0Exceptional
(38 Reviews)
5 Bedrooms
5 Baths
12 Guests
4090 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
R20,895/Night
7 Nights - R146,257
Apartment
- Thessaly
- ·
- Koukounaries
- 0.97 mi to center
10.0Exceptional
(37 Reviews)
1 Bedroom
1 Bath
2 Guests
- Pool
- Ocean View
- Balcony/Terrace
- View
R1,729/Night
7 Nights - R12,098
Luxury Holiday Rentals in Thessaly
Over 7891+ Luxury Holiday Rentals in or Near Thessaly
New
Boat Rental
- Volos
- ·
- Volos City Centre
- 0.33 mi to center
4 Bedrooms
5 Baths
8 Guests
151 ft²
Child Friendly
Laundry
Barbecue/Outdoor Cooking
Security/Safety
Unlock the Best Price
Villa
- Thessaly
- ·
- Koukounaries
- 0.30 mi to center
6 Bedrooms
8 Baths
14 Guests
6458.35 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
R152,344/Night
7 Nights - R1,066,413
Villa
10 Bedrooms
8 Baths
20 Guests
2690.98 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R135,676/Night
7 Nights - R949,736
Villa
10.0Exceptional
(1 Review)
14 Bedrooms
14 Baths
28 Guests
5920.15 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
R84,164/Night
7 Nights - R589,145
Villa
10.0Exceptional
(1 Review)
8 Bedrooms
10 Baths
14 Guests
6156.96 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
R61,217/Night
7 Nights - R428,521
New
Cottage
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
Air Conditioner
Internet- Child Friendly
R55,935/Night
7 Nights - R391,547
Villa
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
- Private Pool
- Oceanfront
Spa- Fireplace/Heating
R42,309/Night
7 Nights - R296,162
Villa
- Thessaly
- ·
- Skiathos Town
- 0.21 mi to center
5 Bedrooms
6 Baths
10 Guests
2690.98 ft²
Hot Tub- Fireplace/Heating
- Pool
- Balcony/Terrace
R35,644/Night
7 Nights - R249,507
Villa
- Thessaly
- ·
- Agia Paraskevi
- 0.22 mi to center
9.6Exceptional
(5 Reviews)
6 Bedrooms
6 Baths
12 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Pet Friendly
R33,027/Night
7 Nights - R231,199
Top-Rated Holiday Rentals with a Pool in Thessaly
Over 1356+ The Best Private Villas and Holiday Rentals in Thessaly with a Pool
Hotel
10.0Exceptional
(103 Reviews)
1 Bath
- Pool
- Balcony/Terrace
- Kitchen
- Parking
R5,774/Night
7 Nights - R40,412
Hotel
- Volos
- ·
- Volos City Centre
- 0.80 mi to center
10.0Exceptional
(51 Reviews)
1 Bath
- Spa
- Fireplace/Heating
- Pool
- Balcony/Terrace
R2,762/Night
7 Nights - R19,330
Hotel
- Thessaly
- ·
- Skiathos Town
- 0.10 mi to center
10.0Exceptional
(44 Reviews)
1 Bath
- Pool
- Balcony/Terrace
- Kitchen
- Air Conditioner
R6,324/Night
7 Nights - R44,271
Villa
- Volos
- ·
- Agios Vlassios
- 0.50 mi to center
10.0Exceptional
(35 Reviews)
4 Bedrooms
2 Baths
9 Guests
1507 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
R7,995/Night
7 Nights - R55,963
Villa
10.0Exceptional
(28 Reviews)
3 Bedrooms
1 Bath
6 Guests
- Private Pool
- Hot Tub
- Pool
- Balcony/Terrace
R3,107/Night
7 Nights - R21,746
Hotel
- Thessaly
- ·
- Skopelos Town
- 1.26 mi to center
10.0Exceptional
(27 Reviews)
1 Bath
- Hot Tub
- Spa
- Pool
- Balcony/Terrace
R5,960/Night
7 Nights - R41,725
Villa
10.0Exceptional
(26 Reviews)
4 Bedrooms
4 Baths
8 Guests
753.47 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
R5,144/Night
7 Nights - R36,001
Villa
10.0Exceptional
(26 Reviews)
2 Bedrooms
3 Baths
4 Guests
1323.96 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
R4,168/Night
7 Nights - R29,173
Apartment
- South Pelion
- ·
- Milina
- 0.84 mi to center
10.0Exceptional
(25 Reviews)
3 Bedrooms
2 Baths
6 Guests
349.83 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
R860/Night
7 Nights - R6,016
Pet-Friendly Holiday Rentals in Thessaly
Over 1869+ Pet-Friendly Holiday Rentals in or Near Thessaly
Villa
10.0Exceptional
(21 Reviews)
5 Bedrooms
1 Bath
10 Guests
3229 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
R6,923/Night
7 Nights - R48,455
House
- Thessaly
- ·
- Lake Plastiras
- 2.39 mi to center
10.0Exceptional
(64 Reviews)
5 Bedrooms
5 Baths
15 Guests
290.63 ft²
- Fireplace/Heating
- Balcony/Terrace
- View
- Pet Friendly
R972/Night
7 Nights - R6,811
Apartment
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
- Balcony/Terrace
- Pet Friendly
- Parking
- Internet
R1,345/Night
7 Nights - R9,406
Villa
10.0Exceptional
(4 Reviews)
2 Bedrooms
2 Baths
5 Guests
646 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
R8,474/Night
7 Nights - R59,320
House
- Lake Plastiras
- ·
- Pezoula
- 0.09 mi to center
10.0Exceptional
(45 Reviews)
7 Bedrooms
2 Baths
6 Guests
204.51 ft²
- Fireplace/Heating
- View
- Pet Friendly
- Parking
R959/Night
7 Nights - R6,714
Villa
10.0Exceptional
(4 Reviews)
3 Bedrooms
2 Baths
7 Guests
1259 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
R5,147/Night
7 Nights - R36,033
Villa
10.0Exceptional
(3 Reviews)
3 Bedrooms
3 Baths
6 Guests
1292 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
R7,908/Night
7 Nights - R55,347
Villa
10.0Exceptional
(2 Reviews)
6 Bedrooms
4 Baths
10 Guests
2476 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
R9,051/Night
7 Nights - R63,358
Villa
- Thessaly
- ·
- Skopelos Town
- 0.61 mi to center
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
4 Guests
592 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R2,299/Night
7 Nights - R16,087
Large Holiday Rentals and Private Villas in Thessaly
Over 2241+ Large Holiday Rentals and Private Villas in or Near Thessaly
Villa
10.0Exceptional
(24 Reviews)
2 Bedrooms
2 Baths
4 Guests
1076 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
R6,137/Night
7 Nights - R42,958
Apartment
- Thessaly
- ·
- Skopelos Town
- 0.64 mi to center
10.0Exceptional
(137 Reviews)
6 Bedrooms
6 Baths
16 Guests
547.17 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R2,676/Night
7 Nights - R18,730
Villa
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Internet
R2,492/Night
7 Nights - R17,449
Villa
10.0Exceptional
(21 Reviews)
3 Bedrooms
3 Baths
6 Guests
538 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
R8,414/Night
7 Nights - R58,898
House
- South Pelion
- ·
- Kato Gatzea
- 0.19 mi to center
10.0Exceptional
(82 Reviews)
6 Bedrooms
6 Baths
16 Guests
1040.51 ft²
- Oceanfront
Skiing- Fireplace/Heating
- Ocean View
R4,794/Night
7 Nights - R33,552
Villa
10.0Exceptional
(14 Reviews)
2 Bedrooms
3 Baths
4 Guests
1507 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
R2,318/Night
7 Nights - R16,217
Villa
10.0Exceptional
(13 Reviews)
1 Bedroom
1 Bath
3 Guests
646 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
R1,477/Night
7 Nights - R10,346
Villa
10.0Exceptional
(11 Reviews)
1 Bedroom
1 Bath
4 Guests
861 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
R1,913/Night
7 Nights - R13,395
Villa
- Thessaly
- ·
- Skiathos Town
- 0.80 mi to center
10.0Exceptional
(10 Reviews)
2 Bedrooms
1 Bath
5 Guests
915 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R2,925/Night
7 Nights - R20,481
Wheelchair Accessible Holiday Homes in Thessaly
Over 459+ Wheelchair Accessible Holiday Homes in or Near Thessaly
Villa
- Thessaly
- ·
- Skopelos Town
- 0.49 mi to center
10.0Exceptional
(9 Reviews)
3 Bedrooms
3 Baths
6 Guests
1507 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
R3,618/Night
7 Nights - R25,330
Apartment
- Volos
- ·
- Volos City Centre
- 0.91 mi to center
10.0Exceptional
(35 Reviews)
2 Bedrooms
1 Bath
6 Guests
968.75 ft²
- Balcony/Terrace
- Parking
- Air Conditioner
- Internet
R1,238/Night
7 Nights - R8,660
House
10.0Exceptional
(92 Reviews)
1 Bedroom
1 Bath
- Fireplace/Heating
- Breakfast
- Kitchen
- Parking
R3,049/Night
7 Nights - R21,341
Apartment
10.0Exceptional
(2 Reviews)
2 Bedrooms
1 Bath
8 Guests
1055 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R2,567/Night
7 Nights - R17,968
House
- South Pelion
- ·
- Kato Gatzea
- 0.41 mi to center
10.0Exceptional
(18 Reviews)
1 Bedroom
1 Bath
4 Guests
430.56 ft²
Private Beach- Oceanfront
- Ocean View
- Balcony/Terrace
R1,714/Night
7 Nights - R12,000
Apartment
- Dio-Olympos
- ·
- Nei Pori
- 0.78 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
4 Guests
592 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
R2,449/Night
7 Nights - R17,141
Apartment
10.0Exceptional
(3 Reviews)
1 Bedroom
1 Bath
4 Guests
398 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Air Conditioner
R1,607/Night
7 Nights - R11,254
Villa
10.0Exceptional
(2 Reviews)
6 Bedrooms
4 Baths
10 Guests
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
R14,313/Night
7 Nights - R100,186
Apartment
10.0Exceptional
(2 Reviews)
2 Bedrooms
1 Bath
1 Guest
700 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Ocean View
R2,832/Night
7 Nights - R19,817
Thessaly Private Villas and Holiday Homes Under $200
Over 5851+ Thessaly Private Villas and Holiday Homes Under $200
Apartment
- South Pelion
- ·
- Afetai
- 0.40 mi to center
10.0Exceptional
(34 Reviews)
2 Bedrooms
1 Bath
4 Guests
431 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R1,074/Night
7 Nights - R7,524
Apartment
10.0Exceptional
(88 Reviews)
2 Bedrooms
1 Bath
5 Guests
1130.21 ft²
- Fireplace/Heating
- Balcony/Terrace
- Parking
- Air Conditioner
R2,976/Night
7 Nights - R20,838
House
- Thessaly
- ·
- Skiathos Town
- 0.40 mi to center
10.0Exceptional
(53 Reviews)
1 Bedroom
1 Bath
- Balcony/Terrace
- Kitchen
- Parking
- Air Conditioner
R1,993/Night
7 Nights - R13,962
Apartment
- Thessaly
- ·
- Alonnisos Old Town
- 0.18 mi to center
10.0Exceptional
(27 Reviews)
1 Bedroom
1 Bath
4 Guests
710 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
R2,558/Night
7 Nights - R17,903
Apartment
- Volos
- ·
- Volos City Centre
- 0.72 mi to center
10.0Exceptional
(79 Reviews)
1 Bedroom
1 Bath
4 Guests
473.61 ft²
- Fireplace/Heating
- Balcony/Terrace
- Parking
- Air Conditioner
R1,964/Night
7 Nights - R13,752
House
- South Pelion
- ·
- Milies
- 0.39 mi to center
10.0Exceptional
(3 Reviews)
3 Bedrooms
1 Bath
6 Guests
861 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R616/Night
7 Nights - R4,314
Apartment
- Volos
- ·
- Volos City Centre
- 0.52 mi to center
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
R2,381/Night
7 Nights - R16,671
Villa
- Volos
- ·
- Makrynitsa
- 0.27 mi to center
10.0Exceptional
(1 Review)
4 Bedrooms
4 Baths
8 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R2,886/Night
7 Nights - R20,206
Villa
- Thessaly
- ·
- Skopelos Town
- 1.04 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
3 Guests
474 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
R1,929/Night
7 Nights - R13,508
Instantly Bookable Holiday Homes in Thessaly
Over 1408+ Instantly Bookable Holiday Homes in or Near Thessaly
Cottage
10.0Exceptional
(15 Reviews)
2 Bedrooms
2 Baths
4 Guests
807 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R4,575/Night
7 Nights - R32,028
Apartment
- Volos
- ·
- Volos City Centre
- 0.33 mi to center
9.5Exceptional
(11 Reviews)
1 Bedroom
1 Bath
2 Guests
269.1 ft²
- Balcony/Terrace
- Parking
- Air Conditioner
- Internet
R746/Night
7 Nights - R5,222
Villa
10.0Exceptional
(6 Reviews)
4 Bedrooms
5 Baths
10 Guests
2045 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
R12,737/Night
7 Nights - R89,158
Villa
- Volos
- ·
- Platanidia
- 0.32 mi to center
10.0Exceptional
(9 Reviews)
3 Bedrooms
2 Baths
6 Guests
969 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
R5,348/Night
7 Nights - R37,428
House
1 Bedroom
1 Bath
- Private Pool
- Oceanfront
- Pool
- Ocean View
R14,412/Night
7 Nights - R100,883
Villa
10.0Exceptional
(6 Reviews)
4 Bedrooms
5 Baths
10 Guests
2045 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
R9,027/Night
7 Nights - R63,179
Villa
10.0Exceptional
(6 Reviews)
2 Bedrooms
2 Baths
4 Guests
818 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
R7,577/Night
7 Nights - R53,044
Villa
10.0Exceptional
(5 Reviews)
2 Bedrooms
2 Baths
7 Guests
915 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
R11,367/Night
7 Nights - R79,574
Villa
10.0Exceptional
(2 Reviews)
3 Bedrooms
3 Baths
6 Guests
1636 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
R6,300/Night
7 Nights - R44,093
Book a Last Minute Place to Stay in Thessaly
About Casai's Private Villas and Holiday Rentals in Thessaly
Discover more than 7900 vacation rentals available in Thessaly. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Thessaly.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Thessaly, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Thessaly. On average, places to stay near Thessaly offer 592.63 ft², with nightly prices averaging R3,321.
With Casai, finding and comparing holiday rentals in Thessaly is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
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Top Accommodation Types in Thessaly
| Type | Count |
|---|---|
| Holiday Apartments | 3812 |
| Vacation Homes | 2100 |
| Villas | 1170 |
| Cottages | 54 |
Use these Quick Filters to Find a Holiday Rental in Thessaly
★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Thessaly.
Weather in Thessaly, GR
View the weather forecast for Thessaly before booking your Thessaly Vacation Rentals to confirm your best time to go.
December - February
High 66°F Low 28°F
March - May
High 80°F Low 38°F
June - August
High 97°F Low 59°F
September - November
High 86°F Low 48°F
Top Attractions Around Thessaly, GR
Casai offers a large selection of top attractions around Thessaly . Research things to do on your vacation before you visit Thessaly.
Other Places to Stay in Thessaly, GR
Frequently Asked Questions About Thessaly?
What are the top holiday rentals in Thessaly?
With numerous options available in Thessaly, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Thessaly:
- Adis Oneirou
- Welcome Home Meteora - Kalampaka!
- Oikia Guesthouse
- Stolios Skopelos - Panoramic Seaview Gems
- La Luna Hotel
- The Storyteller Boutique House
- Mary's Modern and Elegant apartment
- Gatzeas Blue
- Palaia Luxury Suite
- Diamond Palace Trikala
How many holiday rentals have private pools in Thessaly?
Discover a selection of holiday rentals with private pools near Thessaly with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.
- Villa Arios Your little Private Resort only 5 min away from a secluded beach
- Ninemia Villa in Skopelos
- Nature Retreat Skiathos Villa
- Luxury two bedroom villa in skiathos with private pool and outstanding sea view
Which holiday homes in Thessaly are best for families?
If you're searching for a family-friendly holiday home in Thessaly, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Thessaly:
- Villa Arios Your little Private Resort only 5 min away from a secluded beach
- Diamond Palace Trikala
- Angelos Design Suites
How many Casai.co.za holiday rentals are available in Thessaly?
As of 2026, Casai boasts over 7900 properties listed in the Thessaly area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Thessaly.
People Also Ask
Finding the best prices in Thessaly
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