San Juan Holiday Rentals

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Our top choices for San Juan holiday rentals

Apartment in Rio Segundo

Nina´s - Juan Santamaria
3.0 star property
7.2 out of 10, Good, (49)
"A spotless gem minutes from the airport offering incredible value. "
Canada
Richard
Nina´s - Juan Santamaria
3.5 star property
10.0 out of 10, Exceptional, (169)
"Host was excellent, property was very clean, and located very close to the airport, but you can hear other guests in other rooms very easily, privacy is limited. "
United States
Brock
Airport SJO Residence 2 Edward & Familia
3.0 star property
10.0 out of 10, Exceptional, (6)
"This was a wonderful first stop on our vacation as is it was midway betweeen San Jose and La Fortuna. We stayed in the family villa for 2 nights and found it to be spacious with beautifully landscaped grounds. The local waterfalls were easily accessible and we could walk to local restaurants. It was a highlight of our trip!"
United States
Susan
The price is NZ$348
includes taxes & fees
25 Dec - 26 Dec
Hotel Los Sueños de Bajos del Toro

Villa in La Garita

Villa garita inn
4.0 star property
10.0 out of 10, Exceptional, (1)
"The staff was excellent the room was nice good food in the restaurant. "
United States
Dan
The price is NZ$234
includes taxes & fees
16 Jan - 17 Jan 2026
Villa garita inn

Cabin in Venecia

Las Cabanas
3.0 star property
8.8 out of 10, Excellent, (13)
"Great place, very quiet, clean, oranges right outside the balcony 😁"
Canada
Marc
The price is NZ$78
includes taxes & fees
25 Dec - 26 Dec
Las Cabanas

Cabin in Vara Blanca

Chalets Vistas del Poas
3.0 star property
9.8 out of 10, Exceptional, (16)
"Excellent property and amazing hosts!!"
United States
pilar
The price is NZ$172
includes taxes & fees
25 Dec - 26 Dec
Chalets Vistas del Poas
3.5 star property
9.4 out of 10, Exceptional, (24)
"Nice, clean space, with everything we needed. Recommend"
United States
Yuri
The price is NZ$171
includes taxes & fees
26 Dec - 27 Dec
Aloj Entero 1km Juan Santamaría Airport

Apartment in Lagos de El Coyol

Club Heasa - Men Only
3.5 star property
10.0 out of 10, Exceptional, (1)
"Ganz neues und sehr gut durchdachtes Gay Only Hotel. Toll ausgestattet. Sehr bequeme Matratzen. Ein absoluter Traum und nur zum Empfehlen. "
Germany
Oliver
The price is NZ$198
includes taxes & fees
23 Jan - 24 Jan 2026
Club Heasa - Men Only

Aparthotel in Ciudad Cariari

Hotel Boutique CasAguacate
4.0 star property
10.0 out of 10, Exceptional, (4)
"Was great "
United States
Daniel
The price is NZ$121
includes taxes & fees
9 Jan - 10 Jan 2026
Hotel Boutique CasAguacate

Apartment in La Ribera

Apartamentos Cityzen
4.0 star property
9.6 out of 10, Exceptional, (76)
"Excellent place… will stay there again "
United States
Laura
Apartamentos Cityzen

Cabin in Sabana Redonda

Cabañas Lunas del Poas
3.0 star property
10.0 out of 10, Exceptional, (1)
"Amables, tranquilidad"
Mexico
Lalo
The price is NZ$139
includes taxes & fees
28 Dec - 29 Dec
Cabañas Lunas del Poas

Apartment in San Isidro

KEYTRI ROOMS
2.0 star property
The price is NZ$135
includes taxes & fees
28 Dec - 29 Dec
KEYTRI ROOMS

Villa in Venecia

Villas Vistas Paraiso
2.0 star property
10.0 out of 10, Exceptional, (1)
"Logement très calme en pleine nature. Maria et sa maman étaient très acceuillantes. Elles nous on fait découvrir leur région . Balade avec la maman et coco le chien près de la rivière. très très bons échanges. Super petit déjeuner copieux. Très bonne adresse"
France
BENEDITE
The price is NZ$205
includes taxes & fees
5 Jan - 6 Jan 2026
Villas Vistas Paraiso

Villa in Sabana Redonda

Villazul 2
4.0 star property
9.4 out of 10, Exceptional, (14)
"Amazing place! Really enjoyed our stay with the family. Very safe, clean and modern location"
United States
Eli
The price is NZ$173
includes taxes & fees
2 Jan - 3 Jan 2026
Villazul 2
10.0 out of 10, Exceptional, (1)
"Excelente punto de referencia para explorar la zona! Segura, limpia, pequeña, tranquila. "
Mexico
Oscar
The price is NZ$120
includes taxes & fees
27 Dec - 28 Dec
Cozy cabin for couples. Close to many attractions as Bajos del Toro Waterfalls
10.0 out of 10, Exceptional, (2)
"Great communication, easy check-in, excellent value for money, clean, and there was a bath tub - a rare find in Costa Rica."
United States
Lara Y.
The price is NZ$142
includes taxes & fees
4 Jan - 5 Jan 2026
Calas Lodge: Quiet cabin, surrounded by nature and beautiful landscapes.
10.0 out of 10, Exceptional, (7)
"It was clean and easy to check in with the app. "
United States
L G.
The price is NZ$154
includes taxes & fees
26 Dec - 27 Dec
Mountain views and beautiful sunrises 🗻

Holiday Home in Espíritu Santo

Vista Verde
10.0 out of 10, Exceptional, (2)
"Beautiful property. Host was attentive. My only concern was all the ants, but that's what happens when you live surrounded by nature :)"
United States
Raquel
The price is NZ$170
includes taxes & fees
26 Dec - 27 Dec
Vista Verde
The price is NZ$390
includes taxes & fees
25 Dec - 26 Dec
Casa del Rio, a little oasis 15 minutes from the airport

Villa in Quesada

Villa Azul
3.5 star property
The price is NZ$267
includes taxes & fees
26 Dec - 27 Dec
Villa Azul
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 San Juan Hotel Reviews

Find out more about San Juan

Everything you need to know about San Juan holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the San Juan holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect San Juan holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

San Juan holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in San Juan. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A San Juan holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of San Juan holiday rentals we have selected for you start as low as NZ$78 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on San Juan rentals

At Expedia, we put the best San Juan holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top San Juan rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream San Juan holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around San Juan. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in San Juan?

Yes, there are holiday rentals close to the most popular sights in San Juan, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that San Juan has to offer?

Las Yagrumas Condo Escazu: This holiday home rental outside San Juan offers a terrace, a private garden and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a full-sized fridge, a stovetop and a microwave, so that you can cook with friends or family.

What can I see and do in San Juan?

While exploring the area, visit family-friendly sights like Doka Estate, or get outside and enjoy nature at Parque Central. In the wider area, you’ll find San Ramon Municipal Market and Juan Castro Blanco National Park.

What are holiday rentals like in San Juan?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in San Juan. Holiday rentals provide amenities like WiFi and washers and dryers to help you enjoy your stay. If you're concerned about a sanitised environment, a holiday rental can provide a sense of privacy away from shared hotel lifts and busy concierge desks while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental a great option for family gatherings.