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Vacation rentals in Guadalupe

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Guadalupe

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favourite
A spacious lounge area is featured with large windows, providing panoramic views of San José. Comfortable sofas are arranged around a central coffee table, and an artistic light fixture adds a touch of elegance. Subtle decor elements enhance the inviting space.
Apartment in Barrio Escalante
4.9 out of 5 average rating, 542 reviews

Stylish Studio with Sky Bar & City Views

New and exclusive Golden Coffee Studio, inspired by the history of Costa Rican coffee this apartment brings the best views of San Jose city. Walkable of the beaten heart of trendy gastronomic area Barrio Escalante, surrounded by the local vibes this place is on the best spot downtown for you to get ready and discover Costa Rica. One master room and a unique queen wallbed make this place an inviting and fun place for couples, friends and families. Spectacular amenities 100MBps Fiber optic Wifi

Top guest favourite
A rooftop jacuzzi is positioned against a stunning sunset backdrop. It is surrounded by clear glass panels, offering a panoramic view of the city. The deck is made of dark wood, enhancing the tranquil outdoor space.
Condo in Barrio Escalante
4.96 out of 5 average rating, 447 reviews

Quiet Gorgeous Queen Bed Studio Apartment+Jacuzzi

Extremely safe doorman building located in one of the 50 coolest neighborhoods in the world according to the time out magazine. Best Location in town !!! Be received by staff who will enable an ease check-in with a smart lock into the apartment. Enjoy the view of an amazing sunset in the jacuzzi, then get ready to dine in one of the 70 restaurants in the area. Afterwards, come back to sleep in an extremely comfortable queen bed. Wake up and make an exquisite cup of gourmet costarican coffee.

Guest favourite
An aerial view showcases a charming house surrounded by lush greenery and rolling hills. The property features a curved pathway leading to the home, set against a backdrop of dramatic clouds and distant mountain views, highlighting the tranquil privacy of the location.
Home in Guadalupe
4.95 out of 5 average rating, 116 reviews

Amazing view of San Jose (20 min)- Casa los Cielos

Casa Los Cielos is elegant but rustic, with beautiful Costa Rican woodwork throughout. Rooms all have stunning views including the San Jose valley and surrounding mountains. It is nestled in a cool (78F), peaceful mountainous area, is perfect for families, retreats, or groups of friends. Enjoy the chimney, fire pit, BBQ grill and horses in neigboring lot.Pets are welcome! - 20 min from downtown San Jose - 50 min drive to Int'l airport - 1h 45m from beach - 5 min drive to restaurants, stores

Guest favourite
Condo in Carmen
4.92 out of 5 average rating, 143 reviews

Luxury 14th-Floor Apartment with Views in San José

Discover tranquility in this centrally-located haven near Barrio Escalante. Enjoy a cozy retreat just steps from the city’s top restaurants, offering local and international cuisine. You will find a grocery store just in front of the main gate. Next to the building, there is a bowling and a Mall 5 minutes waking. Immerse yourself in culture with nearby museums, cinemas, and art scenes. You’re less than an hour from stunning natural attractions-volcanoes, mountains, and beaches await!

Top guest favourite
The open living area features a glass-topped dining table surrounded by four wooden chairs. A cozy bed is visible in the background, complemented by sheer curtains that allow natural light. Colorful artwork adorns the walls, enhancing the inviting atmosphere.
Home in Amón
4.9 out of 5 average rating, 150 reviews

Tiny House-Historic Area-Short Walk to City Center

Our cozy house is located in the oldest historical district of San José, former neighborhood to four of our past presidents. A perfect location to use as base to explore the city or even the country. We are walking distance to central avenue, the National Museum, Jade Museum, Gold Museum, National Theater, Cathedral and many other sites. We are a 5 minute drive from Barrio Escalante, filled with restaurants for every taste. We have supermarkets, pharmacies, shops and parks very close by.

Top guest favourite
A spacious living area features a plush blue sofa with yellow accent pillows. Large sliding glass doors provide a panoramic view of the valley below, leading to a furnished terrace. Natural light enhances the modern design, complemented by indoor plants and wooden accents.
Home in Escazu
4.99 out of 5 average rating, 248 reviews

KING BED, deluxe stay, @HillView, green areas, A/C

Enjoy this king-bed deluxe apartment, you will find everything needed for an enjoyable stay. It is situated in a prime location yet you will feel away from the city. Close to malls, restaurants, tours, etc. You will be impressed by every beautiful detail handcrafted by Giulio, a passionate architect who loves to create harmonious and inviting spaces. The apartment is bright and cozy, with large windows that let in natural light and offer a breathtaking view of the city and the countryside.

Guest favourite
The living-dining area features a light-colored sofa with decorative pillows, set against a textured wall. A dining table with chairs is positioned nearby, while a window allows for a glimpse of the common patio outside. Neutral tones and tiled flooring provide a calm ambiance.
Apartment in Aran Juez
4.8 out of 5 average rating, 335 reviews

La Vecindá - The Studio - Unbeatable Location

A small apartment in the heart of San José, in a traditional "Vecindad" type complex: several apartments around common internal patios, due to this there’s a high Humidity in this space. No Parking available in the property. Street Parking is available. The best location: in the middle of the most culturally active neighborhoods of San José (Amón, Otoya, Escalante, San Jose, La California), with the main theaters, museums, galleries, plazas, gastronomy, nightlife, shows and much more.

Guest favourite
An outdoor balcony features a wooden table and four matching chairs, offering a sweeping view of the San Jose skyline and mountains in the distance. The space is illuminated by warm lighting, enhancing the inviting atmosphere of this private area.
Condo in Freses
4.89 out of 5 average rating, 185 reviews

NEST Suite 22nd floor

We offer you a 2-bedroom 2 full bathroom with an open balcony so you can spend a quality and relaxing time with the best view of San Jose. The apartment is in a secure building with security and concierge 24/7, several amenities that you can take advantage of like spa, gym, lounge etc. Within walking distance, you have 2 shopping centers with supermarkets, pharmacies, and several restaurant options You will also find underground secure parking. Make sure to read house rules closely.

Guest favourite
Apartment in San Pedro
4.87 out of 5 average rating, 388 reviews

Alchemy Studio- Comfort, Fast Wifi & Design

Alchemy Studio is a contemporary style comfortable space designed for single guests or couples who are looking for a private apartment that offers high end commodities at an affordable price. It is located strategically in the heart of San Pedro an academic & multicultural town located close to Bario Escalante an emerging gastronomic area & San Jose Downtown. You can find Restaurants, Public and Private Banks, ATMs, Pharmacies, Supermarkets and Public Transportation only steps way.

Guest favourite
A bright yellow wall is adorned with floral artwork, enhancing the living space. A comfortable chair with a decorative cushion sits to the left, while a kitchen area with wooden cabinetry and essential appliances is visible in the background.
Loft in Amón
4.9 out of 5 average rating, 197 reviews

Historic Barrio Amon, bright with private balcony

10 minutes waking to Downtown! Modern and very cozy apartment, with a big private balcony, ideal for exploring San José on foot or by Uber. Located next to Simón Bolívar Park (currently closed for remodeling), on a quiet dead-end street with sounds of nature, near museums and restaurants. It features 100 Mbps symmetrical fiber-optic internet, an equipped kitchen, hot water, and a double bed. Historic area with rich cultural and gastronomic offerings. Nearby paid parking options

Guest favourite
A spacious bedroom features a queen size bed with a light patterned coverlet. Two bedside tables hold modern lamps. Soft, natural light pours through a large window, illuminating the smooth tiled floor and creating a calm atmosphere.
Apartment in Guadalupe
4.96 out of 5 average rating, 48 reviews

Modern and Comfortable Apartment in Guadalupe

Spacious, comfortable and very clean apartment. Lots of natural light and ventilation. Located only 10 minutes from downtown San Jose. We invite digital nomads, local and foreign visitors, to check out the details or our accommodations. If your visit to San Jose is short stay or long term stay, for work, medical tourism or vacation, our place offers you the comfort of home away from home. We provide an attentive and respectful service and a pleasant atmosphere to our guests.

Top guest favourite
A rustic wooden coffee table is positioned in front of a cozy sofa adorned with patterned cushions. A small potted plant adds greenery, and a French press coffee maker sits beside a white mug. A remote control rests nearby, complementing the inviting living space.
Condo in Barrio Escalante
4.94 out of 5 average rating, 207 reviews

Apartment with tropical garden in Bº Escalante!

To experience the atmosphere in one of the most emblematic places in San José, Barrio Escalante, full of gastronomy, art and history. An apartment full of details, with a beautiful tropical garden and terrace in front of the rooms. With all the comforts to feel at home. An injection of life within the warmth of this old Josephine neighborhood. Close to everything you need and still on a quiet street. With parking for a small car (sedan or a compact).

Popular amenities for Guadalupe vacation rentals

When is the best time to visit Guadalupe?

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Avg. price$58 CAD$61 CAD$61 CAD$63 CAD$63 CAD$66 CAD$66 CAD$66 CAD$66 CAD$61 CAD$59 CAD$59 CAD
Avg. temp22 °C23 °C24 °C24 °C24 °C24 °C24 °C23 °C23 °C23 °C23 °C23 °C

Frequently Asked Questions

  • How much does it cost to stay in loft rentals in Guadalupe?

    Experience the best of Guadalupe with our loft rentals, starting at about $20 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do apartment rentals in Guadalupe have a kitchen?

    Absolutely! We offer over 90 apartment rentals with a kitchen in Guadalupe. Enjoy a tailored experience with all the comforts you desire.

  • Are there vacation rentals with a dedicated workspace in Guadalupe?

    Yes! Work meets play with ease at over 130 vacation rentals in Guadalupe featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there Guadalupe vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 70 vacation homes with pools in Guadalupe, available on Airbnb. Make a splash and soak up the sun in style!

  • Do apartment rentals in Guadalupe have air conditioning?

    Absolutely! We offer over 40 apartment rentals with air conditioning in Guadalupe. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for Apartment Rentals in Guadalupe?

    Enhance your stay in our Apartment Rentals with the most popular amenities: over 100 homes with wifi, over 40 homes with air conditioning, over 90 homes with a kitchen, over 40 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Do apartment rentals in Guadalupe have free parking?

    Absolutely! We offer over 40 apartment rentals with free parking in Guadalupe. Enjoy a tailored experience with all the comforts you desire.

  • Do guesthouse rentals in Guadalupe have wifi?

    Absolutely! We offer over 10 guesthouse rentals with wifi in Guadalupe. Enjoy a tailored experience with all the comforts you desire.

  • Are there pet-friendly vacation rentals in Guadalupe?

    Four-legged friends are welcome in Guadalupe. Choose from more than 50 vacation rentals for guests traveling with pets.

  • Are there family-friendly vacation rentals in Guadalupe?

    Guadalupe has more than 40 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

Quick stats about vacation rentals in Guadalupe

  • Total vacation rentals

    Explore 230 vacation rentals in Guadalupe

  • Nightly prices starting at

    Guadalupe vacation rentals start at $14 CAD per night before taxes and fees

  • Verified guest reviews

    Over 6,120 verified reviews to help you choose

  • Family-friendly vacation rentals

    40 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 50 rentals that welcome pets

  • Vacation rentals with a pool

    70 properties feature pools

  • Rentals with dedicated workspaces

    130 properties have a dedicated workspace

  • Wifi availability

    230 of Guadalupe vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Guadalupe rentals

  • 4.8 Average rating

    Guadalupe stays are highly rated by guests—averaging 4.8 out of 5!

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