Tranquil Villa Overlooking Mediterranean Sea
Ibiza, Spain
Private poolSea viewWaterfront
Nov 13 – 20 · $240,989 for 7 nights
The Collections
Summer Villa Escapes
Our summer pick: villas with private pools and sea views on Mykonos and the Greek islands, Ibiza and Saint Barts. Chosen by the Smiling House team for the months when a house near the water is worth everything.
View all 593 homesSummer Escapes
Three places, three kinds of summer
This collection is deliberately narrow. Most of it is Greece, and most of the Greek part is Mykonos, from houses on the hills above the port to villas over the south-coast beaches. Ibiza is the second pillar and Saint Barts the third, with a few houses on Santorini, Crete and Kythnos for those who want a quieter island.
They are not interchangeable. Mykonos is sun, wind, whitewash and a long night if you want one. Ibiza is greener, larger and more varied than its reputation, with quiet valleys in the north as well as the beach clubs of the south. Saint Barts in summer is the island at its most relaxed, warm and uncrowded, with the trade-offs that come with the season.
Nearly every house here has a private pool and air conditioning, and many come with a chef or daily service. What separates them is the view, the wind and the walk to the water, which is where the team earns its keep.
Homes593
Countries3
Typical size5 bedrooms
Sleeps up to72 guests
Mykonos Villa Complex With Stunning Sea Views
Mykonos, Greece
Private poolSpa
May 2 – 9 · $162,360 for 7 nights
Curated Luxury Facing Mykonos Sunset
Tourlos, Greece
Private poolSea view
Apr 2 – 9 · $129,841 for 7 nights
Ultra Luxury Sunset View Villa Overlooking Mykonos
Mykonos Town, Greece
Tourlos
Sea view
May 1 – 5 · $59,351 for 4 nights
Sunset Views Villa with Delightful Furniture
Mykonos Town, Greece
Tourlos
Private poolSea viewWaterfront
Apr 1 – 8 · $129,841 for 7 nights
Exclusive Ibiza Mansion Near Coast
Ibiza, Spain
Private poolSea view
Apr 1 – 8 · $101,178 for 7 nights
Stunning 8BR Top-luxury Villa With Beach Views
Mykonos, Greece
Sea view
May 1 – 6 · $55,635 for 5 nights
Paradise villa in sought-after Es Cubells on Ibiza’s beautiful south coast
Ibiza, Spain
Private poolSea viewWaterfront
Nov 13 – 20 · $96,582 for 7 nights
Relaxing 17Br Villa With Deluxe Pool Loungers
Mykonos Town, Greece
Mykonos
Private poolSea view
From $13,085 per night
Charming Mykonos Villa With Infinity Pool
Kalafati, Greece
Mykonos
Private poolSea viewSpa
May 2 – 9 · $82,017 for 7 nights
Elegant and Authentic Caribbean Style Villa
Saint Barts, Saint Barts
Saint-Barthelemy
Private poolSea viewWaterfront
Nov 13 – 20 · $82,792 for 7 nights
Ideal Mykonian Villa with Mesmerizing Sunset Views
Mykonos Town, Greece
Mykonos
Sea view
May 1 – 6 · $55,635 for 5 nights
01
Mykonos: choose your side of the island
On Mykonos, which side of the island you are on matters more than the size of the house. The meltemi, the strong north wind of high summer, can make exposed north-facing terraces hard work for days at a time. The south coast, around Ornos, Psarou and Elia, is more sheltered and closer to the best-known beaches, and Kalafati in the east is quieter again.
Agia Sofia and Tourlos, on the hills above the old and new ports, are about the sunset. Villas there look west over the town and the sea, and dinner in town is a short drive away.
Most Mykonos villas are built in the Cycladic way: white cubes stepped down the hillside, infinity pools, and long outdoor tables under pergolas. Many are built for large groups, with suites spread across several levels. Stairs come with the hillside, so if anyone in your party struggles with steps, tell us and we will look for a house on fewer levels.
02
Ibiza beyond the clubs
Ibiza is the most misunderstood island in the collection. The south has the beach clubs and the late nights, but the north and the interior are farmland, pine forest and quiet fincas, and the west coast, around Sant Antoni and the cliffs beyond it, has the island's best sunsets.
Choose by what you want your evenings to be. Houses near Ibiza Town and the southern beaches put restaurants and clubs a short drive away. Inland villas around Santa Gertrudis are central and calm, a good base for exploring the whole island. Clifftop houses on the west coast and around Es Cubells are about the view.
Ibiza enforces its holiday-rental licensing firmly, and party rules are part of most contracts. Many houses forbid events outright, and those that allow them set curfews. If you want to host a celebration, look at our events collection, or tell us early so we can check with the owner.
03
Saint Barts out of season
Saint Barts in summer is a different island from the one in the winter magazines. The sea is warm, the beaches are close to empty, and villas that are booked solid over the festive season become available. It is a good choice for families and couples who want the island without the crowds.
There are trade-offs, and we would rather you heard them from us. Summer and early autumn are hurricane season in the Caribbean, with the risk rising towards the end of summer, and some restaurants and shops close for a few weeks late in the season. Ask us about cancellation terms and travel insurance before you book, and we will tell you which weeks are lively and which are very quiet.
Villas on the island are mostly modern and open to the breeze, with a pool and a view rather than direct beach access, so plan on hiring a car.
04
How a summer villa week runs
Most summer villas are let by the week from a fixed changeover day, and the best weeks of high summer go early, often to returning guests. Daily housekeeping is common. A chef for some or all meals, a boat for a day, a driver for the evenings and beach-club reservations are what the team arranges most often.
On Mykonos and Ibiza in high season, book restaurants and beach beds before you arrive. Hire a boat at least once: the coastline looks different from the water, and the best coves are reached that way.
Plan for the heat. Shaded terraces, air-conditioned bedrooms and a pool long enough to actually swim in matter more than an extra bedroom. If you are travelling early or late in the season, ask whether the pool is heated.
Summer Escapes in pictures
Where to go
Where this collection is strongest
Greece · Spain · Saint Barts
Before you book
Planning a summer villa
Book the high-summer weeks early; the best houses go to returning guests first.
On Mykonos, ask which way the terraces face, because the meltemi decides how much you use them.
On Ibiza, choose the area for your evenings: the south for clubs, the north and interior for quiet, the west for sunsets.
For Saint Barts in summer, check cancellation terms and hurricane cover before you pay.
Reserve restaurants and beach clubs ahead in high season; the team can do it for you.
On hillside villas, ask how many steps lie between the car, the house and the pool.
Look at June and September: the sea is warm, the islands calmer and the houses easier to get.
Where is the best place for a summer villa in Greece?
For beaches, restaurants and energy, Mykonos, which is where most of this collection sits. For something calmer, Santorini for the views, or Crete and Kythnos for space and quiet. On Mykonos, the south coast is more sheltered from the summer meltemi, and the hills above the port are the place for sunsets.
Which part of Mykonos is best for a villa?
The south coast, around Ornos, Psarou and Elia, is sheltered from the north wind and close to the best-known beaches. Agia Sofia and Tourlos, above the ports, have the sunset views and the shortest drive into town. Kalafati and the east are quieter. Tell us whether you want nightlife, beaches or calm, and we will suggest the area first, then the house.
Is Ibiza only for party villas?
No. The north and the interior of Ibiza are quiet, rural and good for families, and many villas there forbid parties. The south and the area around Ibiza Town put you close to beach clubs and restaurants, and the west coast is known for its sunsets. Choose the area for the evenings you want, then choose the house.
Is Saint Barts worth visiting in summer?
Yes, if you accept the trade-offs. The island is quieter, the sea is warm and the best villas are easier to book. Summer and early autumn are also hurricane season, and some restaurants close for part of the late season. We will tell you which weeks are lively, and help you with cancellation terms and travel insurance before you commit.
Do the summer villas have private pools?
Nearly all of the houses in this collection do, and air conditioning is close to universal. Many pools are infinity-edged and set on terraces, which matters if you are travelling with small children, so ask us about fencing. If you are travelling early or late in the season, ask whether the pool is heated as well.
How far ahead should I book a summer villa?
For the peak weeks of high summer, as early as you can; the best houses are often reserved by returning guests the season before. June and September leave more room to choose. If the house you want is taken, the team can suggest close alternatives on the same stretch of coast, with the same view or the same walk to the beach.
Can the villa arrange a chef, a boat or a driver?
Usually, yes. Daily housekeeping is common, and the team can arrange a private chef, a boat with a skipper for the day, drivers and beach-club reservations. Tell us what you want when you book. In high season, the good chefs and boats are reserved well ahead, and it is much easier to secure them early than on arrival.
Smiling House also offers a concierge for private chefs, transfers, ski instructors, yachts and cars, a VIP Club with first access to new residences and member rates, chalets for sale in the Gstaad region through its real estate division and instantly bookable homes with live availability.