10 Vacation Rentals with Pools in Santorini Starting at $200

Ever wondered what it’s like to swim in a pool perched on the edge of a caldera? How about waking up for a swim with views of the Aegean Sea at your doorstep? Dive into our guide to the best vacation rentals with pools in Santorini, and discover places where luxury meets stunning vistas. In […]

Ever wondered what it’s like to swim in a pool perched on the edge of a caldera? How about waking up for a swim with views of the Aegean Sea at your doorstep? Dive into our guide to the best vacation rentals with pools in Santorini, and discover places where luxury meets stunning vistas.

Sun loungers beside the pool of a vacation rental in Santorini.
Sun loungers beside the pool of a vacation rental in Santorini. | Photo credit: Estate Suite in Thera

In a world where travelers increasingly value comfort, privacy, and flexibility, vacation rentals have carved out a significant niche against traditional hotels. In Santorini, these attributes are amplified—combining the privacy and space of home with the stunning backdrops of one of Europe’s most iconic islands. 

Amidst the azure domes and sunlit terraces, these vacation rentals with pools in Santorini truly come into their own. Each offers a unique experience that resonates deeply with modern travelers. From cozy cave houses to luxurious estates, let’s explore how these properties provide an exceptional stay on the island, starting with some of the most inviting yet affordable options.

Affordable Luxury: Vacation Rentals with Pools Under $300

Santorini isn’t just about high-end luxury; it’s also about accessible indulgence. For those looking to enjoy the quintessential Santorini experience without breaking the bank, here are several stunning vacation rentals with pools that promise comfort and style.


Nestled in Megalochori village, Villa Patitiri offers a unique blend of traditional architecture and modern amenities. This cave house features two bedrooms, a private pool, and a quaint patio that boasts inner courtyard views. 

Despite its seclusion, this villa is just a short drive from major attractions like the Archaeological Site of Akrotiri and the bustling Santorini Port. Thus, it’s a perfect retreat if you wish to soak in the island’s peaceful ambiance while enjoying modern comforts like free WiFi and air conditioning.


Perched near the edge of the Akrotiri caldera, this estate suite offers breathtaking views across the Aegean Sea. The property is a true testament to luxury with its spacious design, outdoor heated jacuzzi, and handcrafted decor. 

Guests can relax on the large patio, enjoying endless sea views, or unwind in the suite’s heated jacuzzi. Needless to say, it’s an ideal spot for couples seeking romance and privacy.


Dreaming of waking up to the sound of the waves? The Incognito Beach Villa in Kamari is a great choice. Just a few steps from Agia Paraskevi Beach, this villa offers an infinity pool and direct beach access, making it ideal for sun-seekers and water lovers who wish to remain, well, incognito. 

The villa boasts modern amenities, including a satellite flat-screen TV and a fully equipped kitchen. It is also coupled with the luxury of an outdoor picnic area and proximity to Monolithos and Kamari beaches.

A pool of a vacation rental in Santorini with the views of the mountains and white-washed buildings.
A pool of a vacation rental in Santorini with views of the mountains and white-washed buildings

Mid-Range Marvels: Vacation Rentals with Pools in Santorini Below $500

Meanwhile, if you’re looking to indulge in a bit more luxury without splurging excessively, these fantastic vacation rentals with pools in Santorini promise an elevated stay. All you need that’s still within your budget. 


Spread across three levels, R882 Luxury Villa epitomizes Cycladic charm blended with modern luxuries. The ground floor introduces a well-equipped kitchen and cozy parlor, perfect for family gatherings. Ascend to the first floor to discover two serene bedrooms with king-size beds and a sleek bathroom. 

However, the real allure lies in its basement, where luxury takes center stage with a private sauna and a lavish bathroom. Then again a private pool jacuzzi invites guests outside to unwind under the Grecian sky, while the expansive veranda with a dip pool offers a refreshing retreat amidst panoramic views. 


In the quaint village of Exo Gonia, the Cavern House Anthea presents a unique blend of traditional Santorinian architecture and modern amenities. This restored 1840s home now serves as a luxurious retreat for up to six guests, offering three double bedrooms and a spacious living area that opens to a charming outdoor courtyard. 

The villa is also just steps away from the heart of the village, yet it offers a peaceful hideaway with stunning views of vine-covered hills. The interior features a blend of local art and modern facilities, including a fully equipped kitchen and entertainment options like Netflix. Outside, the sun terrace with a plunge pool and a plush sofa provides a perfect vantage point to enjoy the lush landscapes and the serene environment. 

Opulent Escapes: Vacation Rentals with Pools in Santorini Over $500

For those willing to indulge in ultimate extravagance, Santorini is never short of some truly opulent escapes. These properties feature luxurious amenities and stunning views that ensure an unparalleled experience. 

Here’s a look at two exceptional properties where lavish comfort meets breathtaking beauty:


Perched on the scenic cliffs of Imerovigli, Villa Harun offers a chic retreat with breathtaking views of the Caldera. This villa blends stylish retro with modern luxury, featuring a master bedroom that provides optimum comfort complemented with sleek furniture. 

Not only that, but it also stuns with an en-suite bathroom, boasting an oval-shaped shower positioned against a large window that frames the Aegean Sea. Furthermore, the villa’s compact, yet fully-equipped kitchen features brightly colored appliances, enhancing the cheerful atmosphere of the place. Outdoors, a jacuzzi awaits you with a double daybed that sits in a courtyard. Talk about creating the perfect spot to enjoy the dramatic Santorinian landscape right before your eyes!


Just a stone’s throw from Monolithos Beach, La Maison Private Villa is likewise a masterpiece of Cycladic architecture combined with modern comforts. This villa boasts four elegant bedrooms, a cozy living room with a fireplace, and a fully equipped kitchen. The outdoor area features a private pool and a stone-paved sun terrace, offering majestic views of the Aegean Sea. 

Add to this, an all-around space that’s well-appointed with air conditioning, an LCD satellite TV, and a DVD player, ensuring comfort and entertainment at your fingertips. What’s more, two luxurious bathrooms, one with a spa bath, prove to be an extra layer of opulence to your stay. 

You might also like: Luxury Vacation Rentals in Santorini Offering Unmatched Views

A pool of a vacation rental in Santorini with mountain views.
A pool of a vacation rental in Santorini with mountain views | Photo credit: La Maison Private Villa

Discover the Finest Stays in Santorini with Casai

Santorini is more than just a dream destination for its iconic landscapes and sunsets. Santorini is a certified holiday favorite for its exquisite range of accommodations. From cozy villas perfect for couples to luxurious estates suitable for larger groups, this island offers something special for every traveler. 

With our guide to the best vacation rentals with pools in Santorini, we hope that we’re able to help you narrow down your choices on where to stay, no matter what your budget is. As your travel partner, Casai is committed to offering you the best places to stay, tailored to your preferences and needs. Our selection of properties combines local charm with unmatched luxury, ensuring your travelers are as comfortable as they’re memorable. 

So, why wait? 

Start planning your Santorini getaway with Casai, and prepare to soak in the beauty and exclusivity of one of Europe’s most stunning destinations. 

Your island escape is just a few clicks away!

Author: Katie

Katie strikes the balance between luxury and adventure, with a taste for the finer things and a spirit for solo travel. For her, indulging in the plush and posh isn't just a whim—it's the main event. Her stories are all about sharing those "treat yourself" moments, wrapped in witty banter and a keen eye for that next lavish escape that’s as unique as a secret handshake.

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