Holiday Homes in San Diego

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
10 Oct - 12 Oct
In two weeks
17 Oct - 19 Oct
In one month
31 Oct - 2 Nov
In two months
28 Nov - 30 Nov

Featured Holiday Homes in San Diego

Luxury Cozy house w private heated pool, A/C, 5 min from downtown San Jose, CR
Outdoor dining

Luxury Cozy house w private heated pool, A/C, 5 min from downtown San Jose, CR

10.0 out of 10, Exceptional, (36)
"Great property and easy access to downtown. "
Luxury Cozy house w private heated pool, A/C, 5 min from downtown San Jose, CR
Casa Dali - Secluded yet close to SJO Airport & INCAE - King bed, fast wifi
Terrace/patio

Casa Dali - Secluded yet close to SJO Airport & INCAE - King bed, fast wifi

9.8 out of 10, Exceptional, (14)
"We have stayed at Ursula’s place before and enjoyed the spacious comfortable layout. The back yard is enclosed and very safe for the dog. "
Casa Dali - Secluded yet close to SJO Airport & INCAE - King bed, fast wifi
Gosen Beautiful & Luxury House in the Mountains, Relax and Enjoy nature!
Exterior

Gosen Beautiful & Luxury House in the Mountains, Relax and Enjoy nature!

10.0 out of 10, Exceptional, (74)
"The property was beautiful, clean, comfortable, and well run. The host family were very kind, inviting us to breakfast and sharing recommendations for restaurants in the area.Wish we had taken more time to lounge in the lovely backyard garden area. We enjoyed our stay, and recommend this property."
The price is AU$215
includes taxes & fees
2 Oct - 3 Oct
Gosen Beautiful & Luxury House in the Mountains, Relax and Enjoy nature!
Spacious 5-bedroom house with, Pool, Gym, Sauna, and Large Yard in Escazu
5 bedrooms, iron/ironing board, Internet, bed sheets

Spacious 5-bedroom house with, Pool, Gym, Sauna, and Large Yard in Escazu

10.0 out of 10, Exceptional, (1)
"The place was amazing. It is very beautiful close to all the restaurants and malls. We had a great time. It was definitely worth it. We will definitely return to this beautiful home. Thank you for sharing your beautiful home with us."
Spacious 5-bedroom house with, Pool, Gym, Sauna, and Large Yard in Escazu
Luxury Townhouse/8p Max/Close to Airport & Medical Facilities/Pool & Fitness
Pool

Luxury Townhouse/8p Max/Close to Airport & Medical Facilities/Pool & Fitness

10.0 out of 10, Exceptional, (1)
"My friends and I had a great stay at Dom and Erik’s place. The furniture and interior decorating is as on point "
Luxury Townhouse/8p Max/Close to Airport & Medical Facilities/Pool & Fitness
Spacious house, WiFi in awesome Lindora on 18 hole golf course with private pool
4 bedrooms, iron/ironing board, WiFi, bed sheets

Spacious house, WiFi in awesome Lindora on 18 hole golf course with private pool

The price is AU$1,532
includes taxes & fees
4 Oct - 5 Oct
Spacious house, WiFi in awesome Lindora on 18 hole golf course with private pool
4-bedroom luxury farm home with spectacular views of the valley.
Exterior

4-bedroom luxury farm home with spectacular views of the valley.

4-bedroom luxury farm home with spectacular views of the valley.
Beautiful and Luxurious House for 2 on the Mountain in Gosén you will enjoy nature.
Exterior

Beautiful and Luxurious House for 2 on the Mountain in Gosén you will enjoy nature.

9.6 out of 10, Exceptional, (12)
"Lovely casita on unique, secure, private, beautiful grounds in the mountains north of San Jose. Eduardo and Betty made our first visit to Costa Rica amazingly special! They have become wonderful friends and I’m certain that we’ll stay in touch. "
The price is AU$201
includes taxes & fees
3 Oct - 4 Oct
Beautiful and Luxurious House for 2 on the Mountain in Gosén you will enjoy nature.
Elegante Casa de 4 Habitaciones a Solo 15 Minutos del Corazón de la Ciudad
Property grounds

Elegante Casa de 4 Habitaciones a Solo 15 Minutos del Corazón de la Ciudad

10.0 out of 10, Exceptional, (2)
"Clean, safe and good location if you want to be in the city."
The price is AU$197
includes taxes & fees
13 Oct - 14 Oct
Elegante Casa de 4 Habitaciones a Solo 15 Minutos del Corazón de la Ciudad
Stylish house in Escalante - Impeccable Decoration│Unique│Safe│Walk
Exterior

Stylish house in Escalante - Impeccable Decoration│Unique│Safe│Walk

10.0 out of 10, Exceptional, (4)
"This was a great house in a really good location for bars and restaurants. Needed some instructions on how to use cooker and appliances! Great stay."
Stylish house in Escalante - Impeccable Decoration│Unique│Safe│Walk
Las Yagrumas Condo Escazu
Family House, Multiple Beds, Non Smoking | Private kitchen

Las Yagrumas Condo Escazu

3.0 star property
The price is AU$593
includes taxes & fees
4 Oct - 5 Oct
Las Yagrumas Condo Escazu
Quaint Downtown Loft/WI-FI
Living area

Quaint Downtown Loft/WI-FI

The price is AU$109
includes taxes & fees
4 Oct - 5 Oct
Quaint Downtown Loft/WI-FI
4BR Casa Peces Santa Ana, Private Indoor Pool & Sauna!
Interior

4BR Casa Peces Santa Ana, Private Indoor Pool & Sauna!

9.2 out of 10, Wonderful, (44)
"The atrium pool was gorgeous. Loved my time there. Thank you! :D "
4BR Casa Peces Santa Ana, Private Indoor Pool & Sauna!
Elegant, fully equipped residence with heated pool and great views
A heated pool

Elegant, fully equipped residence with heated pool and great views

10.0 out of 10, Exceptional, (46)
"Christine and her team were amazing hosts. The property is as beautiful as it is pictured. "
Elegant, fully equipped residence with heated pool and great views
Peaceful and Quiet Vacation house, Mountain view and Birds Paradise
Pool

Peaceful and Quiet Vacation house, Mountain view and Birds Paradise

8.0 out of 10, Very good, (1)
"Excellent Hostess "
The price is AU$1,471
includes taxes & fees
4 Oct - 5 Oct
Peaceful and Quiet Vacation house, Mountain view and Birds Paradise
Exquisite 7-Bedroom Mansion in Escazú featuring Heated Pool, Jacuzzi, & Full AC.
Games room

Exquisite 7-Bedroom Mansion in Escazú featuring Heated Pool, Jacuzzi, & Full AC.

2.0 out of 10, (1)
"Very disappointing and stressful experience. We tried to contact the host many times in the weeks leading up to our trip. While we did have some communication, their average response time was over 10 days, which made planning difficult and frustrating.On the day of check-in, the host still hadn’t provided the proper check-in information. I had to contact VRBO, who was finally able to reach the host and assured us we would receive the check-in details one hour before arrival. Instead, at that...
Exquisite 7-Bedroom Mansion in Escazú featuring Heated Pool, Jacuzzi, & Full AC.
Plunge Pool Villa | Coffee Views & Adventure
TV, fireplace, offices

Plunge Pool Villa | Coffee Views & Adventure

10.0 out of 10, Exceptional, (27)
"Breathtaking views at the amazing property! Perfect for group travel. Felipe was wonderful to work with!"
The price is AU$1,151
includes taxes & fees
3 Oct - 4 Oct
Plunge Pool Villa | Coffee Views & Adventure
3-bedroom custom Tree house in welcoming Cartago with WiFi, waterfalls, trails
3 bedrooms, WiFi, bed sheets

3-bedroom custom Tree house in welcoming Cartago with WiFi, waterfalls, trails

The price is AU$262
includes taxes & fees
1 Oct - 2 Oct
3-bedroom custom Tree house in welcoming Cartago with WiFi, waterfalls, trails
Casa Aguacate
Exterior detail

Casa Aguacate

The price is AU$175
includes taxes & fees
1 Oct - 2 Oct
Casa Aguacate
Deluxe Property in Cariari
Front of property

Deluxe Property in Cariari

4.0 star property
2.0 out of 10, (1)
"This is a SCAM!! There was no address and no instructions for finding or check-in!!"
Deluxe Property in Cariari
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top San Diego Hotel Reviews

DoubleTree by Hilton Cariari - San Jose Costa Rica

DoubleTree by Hilton Cariari - San Jose Costa Rica

10/10 Excellent
"Lovely hotel, food and drinks at the restaurant were amazing only thing that was missing was a bartender at the swim up pool bar neither of the days we were there."
Blanca Maricela 2-night trip
Posted 2 days ago
DoubleTree by Hilton Cariari - San Jose Costa Rica

Find out more about San Diego

Find out more about San Diego

San Diego Holiday Homes information

Number of reviews
183
Accommodation
223 Holiday Homes
Lowest Price
AU$109
Highest Price
AU$1,532

Explore a world of travel with Expedia

Explore a world of travel with Expedia