Vacation rentals with a pool in Santorini caldera

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Top-rated rentals with a pool in Santorini caldera

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite

Cycladic home in Monolithos

4.84 out of 5 average rating, 65 reviews

Villa | Private Pool | Sea View | by the beach 9p

At Theros Houses you may enjoy the relaxing vacation you need. The buildings, the private pools , the big grounds around them offer the ideal atmosphere to relax and play with your friends or the members of your family. You may also combine activities or excursions we may organize for you or enjoy special amenities like massage, baby sitting, cooking lessons or wine tasting in the house on demand. WE OFFER DAILY CLEANING AND FREE TRANSPORTATION FROM THE AIRPORT OR THE PORT WITH NO EXTRA CHARGE.

Superhost

Dome in Kamari

4.91 out of 5 average rating, 11 reviews

Felicity Villas Santorini - Victoria

Picturesque house of 102 sq. m. in Kamari village and within 5-minute walk from the pedestrian beachfront & all modern conveniences. The spacious 60 m2 pool and area (sun deck, BBQ) & splendid views of the nearby Mountain & Sea promise an enjoyable stay. Our gardens provide local fruits & vegetables depending on the season. Fully-equipped with all household amenities, it appeals to couples & families with children/babies. We are eager to give you any relevant information, advice or bookings.

Superhost

Cycladic home in Oia

4.81 out of 5 average rating, 225 reviews

Private Villa with Pool in Oia, view, parking

This is a beautiful private villa with private pool and parking very near. The views are amazing from the balcony and patio. You will have 2 bedrooms and 2 bathrooms. Both bedrooms have double beds in them. In case there is a 5th person, we add a roll away bed upstairs in the living room. You have a full kitchen too. The house is only 10-15 minutes walk to the center of Oia. A bus stop is very near to take you either to Oia or Fira. It is perfect for someone that wants to be away from crowds.

Superhost

Apartment in Vothonas

5 out of 5 average rating, 7 reviews

Villa | Duplex Suite with Private Heated Mini Pool

Situated in the residential side of the traditional village of Vothonas, right in the middle of Santorini island, my property is a Private Villa | Double Apartment with Private Heated Mini Pool, offering great views of Sunrise, Pyrgos Kallistis, and the Aegean Sea. The 76m² House features luxury, privacy, and comfort in Cycladic style combined with modern design and decoration. Catered by Greek Hospitality, handy amenities and high-end services your holidays will undoubtedly be unforgettable.

Top guest favorite

Cycladic home in Pirgos Kallistis

5 out of 5 average rating, 102 reviews

Bliss Mansion with Swimming Pool & Sunset view

Newly constructed for your every need, The Bliss Mansion in Pyrgos located in the heart of an historically preserved traditional neighborhood, perched high overlooking Santorini's dramatic landscape and world famous Santorini sunset. This property is secluded from the tourist crowds, yet a few minutes from the most popular Santorini beaches, historical sites, restaurants and bars. The Bliss Mansion can host up to 8 guests, offers a big swimming pool and a luxurious in cave hot tub.

Superhost

Home in Oia

4.87 out of 5 average rating, 167 reviews

Captain's blue, villa with private pool

Step into the past in historical captains villa with private pool near Maritime museum in quiet street near caldera path. A blend of antique style with modern facilities, spacious and comfortable with private pool, beautiful sunset sea views and large verandas & garden. New improvements:: A/C in second bedroom , 2 sofa beds in living room. new deck in garden! Our other villas: Island blue,Santorini blue,Eternity& Serenity,Secret Garden, Sailing & Sky blue ,Plateon in Athens.

Guest favorite

Cycladic home in Thera

4.91 out of 5 average rating, 11 reviews

Elegant Duplex | Hot tub | Caldera view| Pool

Elegant Duplex has the perfect location on Caldera Cliffs, right in the middle of Fira, and offers a spectacular view of the most famous sunset. This property has a private yard with a swimming pool, an indoor jacuzzi, and an outdoor jacuzzi with a Caldera view. Daily breakfast and cleaning make your stay comfortable. Each bedroom has a private outdoor entrance and a private bathroom. Within walking distance, you will find restaurants, bars, museums, and supermarkets.

Guest favorite

Home in Vourvoulos

4.93 out of 5 average rating, 14 reviews

106. Hideaway Villa with Heated Pool and Sea View

Forget your worries in this spacious and serene space. Mediterranean elements blend with tropic culture to inspire the creation of Hideaway Villa. An extremely spacious and fully equipped villa that includes three double-bed bedrooms with an individual bathroom, a kitchen, and a living room. It can accommodate up to 6 guests. It features a wonderful private terrace and a heated pool offering unique moments of quality relaxation, ambiance, and indulgence.

Top guest favorite

Cycladic home in Oia

4.99 out of 5 average rating, 105 reviews

Alonistra Oia Houses - House with private pool

Our brand new luxury traditional apartment in Alonistra Oia Houses, with non-heated splash pool is built and decorated according to the traditional style of the island with taste and elegance,relaxing colours and romantic details.Is situated in a tranquil and pleasant location in Finikia village, only 15 minutes walk from the main pedestrian of Oia. It has one king size double bed on the ground floor and one single bed in the upper floor.

Guest favorite

Place to stay in Vothonas

4.95 out of 5 average rating, 231 reviews

Mystagoge Retreat with subterranean pool/jacuzzi

Mystagoge Retreat is a unique traditional house, which can accommodate up to two people. A private heated indoor cave pool with jacuzzi will be waiting for you to offer a mystic experience. A light breakfast basket with rusks, jam, honey, tea coffee, milk and butter. Amenities included are WI-FI, air-conditioning, in all areas of house, free parking, sun filled traditional yard with sunbeds, dining area and shared BBQ.

Guest favorite

Cycladic home in Santorini

4.82 out of 5 average rating, 100 reviews

Bluewhite villa with heated private pool

Situated in the traditional village of Pyrgos Kallistis, the heart of Santorini island, my place offers a stunning panoramic view of sunrise and the Aegean Sea. The 130m² Villa features luxury, privacy, easy access and comfort in Cycladic style combined with modern design and decoration. Our new infinity pool is a must! Please note that the pool is functional only for the spring and summer season March 15- October 31st

Top guest favorite

Cycladic home in Kamari

4.99 out of 5 average rating, 161 reviews

Santoxenia luxury Villa

Stunning villa with private pool and two jacuzzis ideal for families and big companies. Quiet location near the sea for relaxation. License/registration number: 1051524 The villa is in a quiet neighborhood that offers easy access to the area's delicious restaurants, lively taverns, and bustling markets. Head to the black beach for a day of seaside activities before checking out the bars and clubs in the evening.