A coastal town with buildings on a hillside, clear turquoise waters, and a sandy beach.

Glossa Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Glossa vacation rentals

A coastal town at dusk with a marina, boats, and illuminated buildings.

1. Flisvos Beachfront Apartments

Flisvos Beachfront Apartments
Skopelos
10.0 out of 10, Exceptional, (5 reviews)
"Amazing! The ladies that work here are terrific. So much knowledge and so willing to share. We felt at home immediately! The rooms were spacious and had all the needed and wanted amenities (minus a coffee machine). The island is beautiful and we had a great time exploring the whole thing. Very much recommend this island and this hotel, you won’t regret it!!!"
United States
Daniel
The price is CA $138
CA $169 total
includes taxes & fees
Oct 9 - Oct 10
Flisvos Beachfront Apartments
A stone patio with lounge chairs and an umbrella, overlooking a body of water and a mountainous landscape.

2. LemonTree Villa Glossa Skopelos

LemonTree Villa Glossa Skopelos
Loutraki
The price is CA $415
CA $475 total
includes taxes & fees
Oct 26 - Oct 27
LemonTree Villa Glossa Skopelos
A beach with clear blue water, people sunbathing, and a rocky hillside with trees.

3. Malena Pool Villa with stunning view in a quiet location. Free WIFI and jacuz

Malena Pool Villa with stunning view in a quiet location. Free WIFI and jacuz
Γλώσσα
9.6 out of 10, Exceptional, (22 reviews)
"We loved everything about our stay! The pool and view were spectacular and the house was exactly what we needed: decent sized kitchen so it was easy to make our own meals and a short drive/taxi ride to Glossa and Loutraki when we wanted to go out. Thanks!!"
United States
Eric and Thene L.
Malena Pool Villa with stunning view in a quiet location. Free WIFI and jacuz
A pool with lounge chairs, a stone deck, and a view of the sea and hills.

4. Rodon Luxury Villas "Aura"

Rodon Luxury Villas "Aura"
Skopelos
Rodon Luxury Villas "Aura"
A white building with a red door and balcony, surrounded by greenery and red flowers.

5. Skopelos Summer Homes

Skopelos Summer Homes
Skopelos
The price is CA $111
CA $129 total
includes taxes & fees
Sep 30 - Oct 1
Skopelos Summer Homes
A balcony with wicker chairs and a table, overlooking a coastal view with buildings and the sea.

6. Sunrise Village

Sunrise Village
3.0 star property
Skopelos
9.2 out of 10, Wonderful, (23 reviews)
"Really nice rooms at a great price."
United Kingdom
Matthew
The price is CA $154
CA $183 total
includes taxes & fees
Oct 2 - Oct 3
Sunrise Village
A terrace with a round table and chairs, overlooking a coastal town with buildings and a view of the sea.

7. Design ArchitectoniKa

Design ArchitectoniKa
Skiathos
8.6 out of 10, Excellent, (95 reviews)
"Amazing stay! Highly recommend, it is very close to the port and is a 5 minute walk from the bus station. It is super clean and well maintained. The staff are very helpful and offer great suggestions for food, activities, beaches, shopping and more! I stayed here as a solo female traveller and felt very safe."
Canada
Payton
The price is CA $57
CA $68 total
includes taxes & fees
Oct 1 - Oct 2
Design ArchitectoniKa
A sunlit outdoor lounge area with a pergola, a reclining chair, and a view of a mountainous landscape.

8. Skopelos Country Villas

Skopelos Country Villas
Skopelos
10.0 out of 10, Exceptional, (1 review)
"Amazing views & so peaceful. Wonderful pool & villa. Very clean & tidy with lovely gardens. Owner gave amazing help prior to arrival with car hire (you do need 4 wheel drive or equivalent) & ferry etc & following arrival was on hand for general info' on restaurants etc. Would highly recommend."
United Kingdom
CAROL
The price is CA $312
CA $474 total
includes taxes & fees
Oct 10 - Oct 11
Skopelos Country Villas
A neatly arranged dining area with a round table set for four, a potted plant, and a bottle of wine.

9. Sofia Studios

Sofia Studios
Skiathos
9.2 out of 10, Wonderful, (7 reviews)
"One bedroom upstairs, another bedroom and everything else downstairs, with separately controlled airconditioning. The bathroom and especially the shower area is fairly small (common thing in Greece), but other areas are comfortable enough to stay there and unpack your luggage. Airport is so close you can walk there in 10 minutes, and you can see planes landing while sipping your coffee on the balcony. Don't worry, there are no flights during the night. Skiathos port and the city center is also...
Hungary
Gyorgy
Sofia Studios
A terrace with wicker furniture, a glass table, a potted plant, and a view of the sea.

10. Casa Blue Sea View

Casa Blue Sea View
Skiathos
The price is CA $79
CA $93 total
includes taxes & fees
Oct 2 - Oct 3
Casa Blue Sea View
A coastal view with a swimming pool, terraced houses, and a clear blue sky.

11. Péra Skopelos

Péra Skopelos
Skopelos
The price is CA $158
CA $192 total
includes taxes & fees
Sep 29 - Sep 30
Péra Skopelos
An outdoor seating area with tables and chairs, overlooking a body of water.

12. Physis Oikos Beachfront Apartments

Physis Oikos Beachfront Apartments
Skiathos
9.6 out of 10, Exceptional, (4 reviews)
"The outdoor breakfast area / bar area was nice near the beach. The staff were very friendly and helpful. Perhaps it was just our bungalow, but it was pretty barebones … there were hangers for clothes, but no towel bars or hooks and only one flat surface for a suitcase."
Canada
Donna
The price is CA $146
CA $169 total
includes taxes & fees
Oct 4 - Oct 5
Physis Oikos Beachfront Apartments
A balcony with a white table and chairs, blue shutters, and a wooden ceiling.

13. Casa Blue Old Port

Casa Blue Old Port
Skiathos
9.6 out of 10, Exceptional, (5 reviews)
"The location was amazing, the property was very clean, and the communication process was very easy. We loved the view from our window, and having a little balcony was such a treat! The woman who helped us get checked in was so nice and answered all of our questions. Not having a shower curtain was a little bit weird, but we had plenty of towels and managed to not make too big of a mess. It was a little bit loud at night, but that’s the price you pay when you stay in such a fun part of town. We...
United States
Alixandra
The price is CA $60
CA $72 total
includes taxes & fees
Oct 2 - Oct 3
Casa Blue Old Port
A bedroom with a bed, bedside table, lamp, and a view of a body of water through large windows.

14. Brand-New Villa 'Maison Magnolia', Infinity Pool & Sea View above Skopelos Town

Brand-New Villa 'Maison Magnolia', Infinity Pool & Sea View above Skopelos Town
Skopelos
The price is CA $384
CA $777 total
includes taxes & fees
Sep 26 - Sep 27
Brand-New Villa 'Maison Magnolia', Infinity Pool & Sea View above Skopelos Town
A modern living room with a sofa, a coffee table, and a TV mounted on the wall.

15. Vrachos house "In the heart of ​​Skopelos Town"

Vrachos house "In the heart of ​​Skopelos Town"
Skopelos
10.0 out of 10, Exceptional, (1 review)
"Fabulous stay very quick responding host and amazing location and view."
United States
craig m.
The price is CA $177
CA $205 total
includes taxes & fees
Oct 17 - Oct 18
Vrachos house "In the heart of ​​Skopelos Town"
A poolside area with two sun loungers, a stone building, and a view of the sea.

16. Golden King

Golden King
Skiathos
9.4 out of 10, Exceptional, (9 reviews)
"Fabulous Villa would definitely recommend views are spectacular "
United Kingdom
Samantha
Golden King
A wooden balcony with a view of a hillside and houses.

17. Villa Elpiniki

Villa Elpiniki
Skiathos
The price is CA $254
CA $291 total
includes taxes & fees
Oct 26 - Oct 27
Villa Elpiniki
A coastal building with a tiled roof, a balcony, and a view of the sea.

18. Apartment 'Waves Of Millos 1' with Sea View, Wi-Fi and Air Conditioning

Apartment 'Waves Of Millos 1' with Sea View, Wi-Fi and Air Conditioning
Skopelos
The price is CA $275
CA $288 total
includes taxes & fees
Sep 26 - Sep 27
Apartment 'Waves Of Millos 1' with Sea View, Wi-Fi and Air Conditioning
A modern kitchen with a long wooden table, bar stools, and a fruit bowl. There is a large window with curtains, a hanging light fixture, and a round mirror on the wall.

19. Luxury Villa with Private Pool in Skopelos,Spacious & Private, Amaryllis Kardous

Luxury Villa with Private Pool in Skopelos,Spacious & Private, Amaryllis Kardous
Skopelos, Greece
10.0 out of 10, Exceptional, (8 reviews)
"My friends and I had a great time here on our free weekend! The property was very clean and everyone was very accomodating!"
United States
Sophia E.
The price is CA $867
CA $1,132 total
includes taxes & fees
Sep 26 - Sep 27
Luxury Villa with Private Pool in Skopelos,Spacious & Private, Amaryllis Kardous
A swimming pool with a stone deck, outdoor seating, and a covered area with tables and chairs.

20. Luxury Villa with Private Pool in Skopelos, Ideal for Families, Aelia by Kardous

Luxury Villa with Private Pool in Skopelos, Ideal for Families, Aelia by Kardous
Skopelos
10.0 out of 10, Exceptional, (3 reviews)
"Best villa we have ever stayed in. Immaculately clean, beautifully furnished and the location was superb. I can’t recommend this property enough. Natassa and her family could not have been more attentive. Property was cleaned every single day. The pool was bigger than we imagined and spotless. There is not one single thing I can criticise. We would definitely stay here again. We loved our stay at Skolopes, such a beautiful Island. Thank you Natassa and family we have had a holiday we will never...
United Kingdom
Geraldine T.
The price is CA $867
CA $1,132 total
includes taxes & fees
Sep 27 - Sep 28
Luxury Villa with Private Pool in Skopelos, Ideal for Families, Aelia by Kardous
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Glossa Hotel Reviews

Natura Luxury Boutique Hotel Skopelos

Natura Luxury Boutique Hotel Skopelos

10/10 Excellent
"Warm and friendly, welcoming staff, creating a mellow vibe that was immediately relaxing. Fantastic location right on the front with great harbour and bay views, from the outdoor dining area and room balconies. The simple, unfussy rooms had all we needed and contributed to the calm, with deeply comfortable king-size beds the star of the show. We slept so well! The biggest surprise was the rooftop pool and bar, giving stunning views and making a great escape. The biggest memory is the warmth of the team, who went out of their way to make our stay relaxing and memorable."
Lucy 1-night trip
Posted 6 hours ago
Natura Luxury Boutique Hotel Skopelos

Find out more about Glossa

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Glossa. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find vacation rentals in Glossa?

Yes, we give you a choice of vacation rentals close to well known local attractions in Glossa, or you can go with a more secluded option if you're looking for a relaxing stay. Glossa is known for its waterfront and restaurants.

What's the top vacation rental in Glossa?

Magnificent Sunset: Visitors like this Glossa vacation home rental. It is located near the beach and offers a balcony, air-conditioning, and laundry facilities to help you feel perfectly comfortable in your new surroundings. Our travelers also rate Avgoustina's Home A breathtaking view house ! ! ! as a favorite home for rent in Glossa.

How many vacation rentals will I find in Glossa?

With 18 Expedia vacation rentals, you're sure to find just the right place for your Glossa stay.

What’s there to see and do in Glossa?

While you're exploring the area, Kastani Beach and Panormos Beach are a couple of picturesque spots to get outside and enjoy nature. In the larger area, you’ll find Port of Skopelos and Port of Skianthos.

What’s a vacation rental in Glossa like?

Vacation rentals are privately owned properties you can book for a long or short time in Glossa. Vacation rentals feature extras like kitchens and laundry facilities so your stay will be comfortable. If you're concerned about a clean environment, a vacation rental can offer a sense of seclusion away from shared hotel elevators and busy front desks while still allowing you to travel. You'll also find more space in a vacation rental than in a hotel, which makes a vacation rental a popular choice for family trips.