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Holiday houses in Guadalupe

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Top-rated holiday rentals in Guadalupe

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

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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, 426 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
A spacious studio features a cozy sleeping area with a full bed, complemented by modern built-in shelving. A small dining table with four chairs sits near a large window, offering stunning city views, while a comfortable couch completes the inviting layout.
Loft in Barrio Escalante
4.86 out of 5 average rating, 340 reviews

Brand new 1 bed loft with spectacular city view

Keep it simple at this peaceful and centrally-located place. Experience the exclusivity of this modern studio in Barrio Escalante, with an unbeatable location just minutes from downtown San Jose, 30 minutes from Tobias Bolaños airport. Enjoy your stay surrounded by smart amenities and beautiful views of the city, complete with Wi-Fi connection, a full-size bed, private bathroom, kitchen and access to superior conveniences, such as a rooftop with jacuzzi and deck, lounge room, gym and BBQ area.

Guest favourite
Condo in Carmen
4.91 out of 5 average rating, 141 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
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, 239 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, 331 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.

Superhost
A stunning view of a sunset over the city skyline is captured, with vibrant orange and yellow hues blending into the sky. The horizon features silhouettes of distant mountains, while glass railings enclose a rooftop pool setting, reflecting the warm colors of dusk.
Loft in Curridabat
4.87 out of 5 average rating, 519 reviews

Amazing View at 20th SJO Floor Loft! Parking&Pool

There is no better way to experience the beauty of San Jose than by sleeping in the heart of the city with a spectacular vista of the north of the capital. The landscape of the Irazú volcano on the horizon will be the perfect complement to enjoying the sunrise in your bed. This apartment is perfect to start your experience in Costa Rica, relax after a business trip, or spend a romantic night with your partner. All from a privileged area within a walking distance of restaurants and shops.

Guest favourite
Apartment in San Pedro
4.87 out of 5 average rating, 386 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.

Top Guest favourite
Loft in Curridabat
4.93 out of 5 average rating, 130 reviews

Loft 18th floor. Panoramic view + pool + balcony

✨ Piso 18 con vista panorámica y brisa fresca ✨ Este loft moderno combina estilo y comodidad con un balcón integrado y cortinas blackout para mayor confort. Perfecto para parejas, viajes de trabajo o estancias largas, ofrece Wi-Fi rápido, área de iworking, piscina y parqueo privado. Ubicado en una zona segura y céntrica de Curridabat, tendrás todo a tu alcance. Como Súper Anfitrión Top 10% en Costa Rica, garantizo atención rápida y dedicada para que tu estadía sea inolvidable. 🌟

Guest favourite
A bright sitting area features wooden seating against the walls, complemented by a small step ladder leading to an upper space. Large windows allow natural light to fill the room, while a glimpse of the outdoor balcony and greenery can be seen through the open door.
Apartment in San José
4.87 out of 5 average rating, 236 reviews

Cosy & Modern MiniHouse in Private Residential

Este es un espacio nuevo que ofrece todas las comodidades, muy bien iluminado, moderno y acogedor. Totalmente equipado y privado. Además está en un residencial tranquilo, con muchas zonas verdes, privado y seguro, parqueo bajo techo, con traslado rápido a comercios, 5 minutos de la Universidad de Costa Rica, 15 minutos del centro de San Jose y restaurantes. Muchas zonas verdes alrededor. Cocina equipada, buena señal WiFi, suficiente para teletrabajo. Agua caliente, Smart TV.

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
4.93 out of 5 average rating, 197 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).

Superhost
A modern studio apartment features a spacious bed with decorative pillows, complemented by a wooden accent wall and a dining table set for two. Large windows provide natural light and city views. Two red dog sculptures add a playful element to the room.
Apartment in Barrio Escalante
4.91 out of 5 average rating, 163 reviews

Nota Escalante Great Views W/ AC

Nota Escalante is a modern tower in barrio escalante. The apartment is a very stylish and minimalistic studio with some special touches to make you feel great at a unique cozy spot just 200m from the best restaurants of Costa Rica and some fantastic night life. Barrio Escalante is a very special neighborhood in Costa Rica known for its amazing restaurants. The apartment features a electrically reclining bed and electric shades for maximum comfort.

Popular amenities for Guadalupe holiday rentals

Quick stats about holiday rentals in Guadalupe

  • Total rentals

    230 properties

  • Nightly prices starting at

    $15 AUD before taxes and fees

  • Total number of reviews

    6.1K reviews

  • Family-friendly rentals

    40 properties are a good fit for families

  • Pet-friendly rentals

    50 properties allow pets

  • Rentals with a pool

    70 properties have a pool

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