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Vacation rentals in Guadalupe

Find and book unique accommodations on Airbnb

Quick stats about vacation rentals in Guadalupe

  • Total vacation rentals

    Explore 250 vacation rentals in Guadalupe

  • Nightly prices starting at

    Guadalupe vacation rentals start at G$2,093 GYD per night before taxes and fees

  • Verified guest reviews

    Over 7,990 verified reviews to help you choose

  • Family-friendly vacation rentals

    50 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 50 rentals that welcome pets

  • Vacation rentals with a pool

    80 properties feature pools

  • Rentals with dedicated workspaces

    140 properties have a dedicated workspace

  • Wi-Fi availability

    250 of Guadalupe vacation rentals include wi-fi 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!

Top-rated vacation rentals in Guadalupe

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

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Top guest favorite
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 Escalante
4.95 out of 5 average rating, 520 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 favorite
A cozy bedroom features a spacious bed with soft blue linens and decorative textured throw. Flanking the bed are two nightstands, each topped with a simple, modern lamp. A deep blue wall creates a calming backdrop, enhancing the overall tranquility of the space.
Apartment in Guadalupe
4.94 out of 5 average rating, 68 reviews

Guadalupe Apartment near Hospital La Catolica

Experience a spacious, comfortable, and impeccably clean apartment with abundant natural light and excellent ventilation. Whether you’re here for a short stay or a long-term visit, for work, medical tourism, or vacation, our accommodations offer the comfort of home away from home. We warmly welcome nomad workers, retired couples, and individuals to explore the details of our offerings. Enjoy attentive and respectful service in a pleasant atmosphere, ensuring a delightful stay for all our guests.

Guest favorite
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 Escalante
4.87 out of 5 average rating, 402 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 favorite
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
4.98 out of 5 average rating, 330 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 favorite
A spacious bedroom features a wooden bed against a backdrop of large windows, providing a panoramic view of the urban landscape below. The room is equipped with light-colored bed linens and a nearby white cabinet, enhancing the minimalist design.
Loft in Curridabat
4.9 out of 5 average rating, 410 reviews

Studio with a beautiful view/ Amazing View Studio

Located on the 23rd floor of Torre iFreses in Curridabat, it overlooks the South area of San José. Dentro del estudio encontrá todo lo necesario para su estadía, podrá hacer uso de las amenidades del condominio como la piscina y iwork. Located on the 23rd floor of iFreses tower in Curridabat, with great view of the south of San José city. Inside, you will have all that you need. You could use some of the amenities of the condo like pool and iwork. Check-in 3:00pm and Check-out 11:00am.

Superhost
The unique architecture of the loft is showcased with an angled facade and large glass windows that reflect the surrounding greenery. A small deck area features modern outdoor seating, inviting relaxation amidst the natural landscape.
Villa in San Roque
4.86 out of 5 average rating, 608 reviews

Nebulae Loft · Design Stay with Jacuzzi & Firepit

Nebulae Loft is a contemporary architecture and design experience, created for guests who want to stay in a space that feels different, comfortable, and full of character @ 20m from SJO airport. Surrounded by trees, the loft offers two BDs, two BRs, a living room, and a fully equipped kitchen. Outside, it features two balconies, a terrace with a firepit, a jacuzzi, and a BBQ area, ideal for enjoying and sharing. Events allowed with prior authorization. Special events at Nebulae/Laureal.

Guest favorite
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 Escalante
4.93 out of 5 average rating, 252 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).

Guest favorite
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
4.88 out of 5 average rating, 268 reviews

Cozy & Modern MiniHouse • Cerca UCR • Seguro

This is a modern space that offers all the comforts, very well lit and cozy. Fully equipped and private. It is also in a quiet residential, with many green areas, private and safe, indoor parking. Quick transfer to shops, 5 minutes from the University of Costa Rica, 15 minutes from downtown San Jose and restaurants. Lots of green area around. Equipped kitchen, good WiFi signal, enough for teleworking. Hot water, Smart TV with Netflix, YouTube and more.

Superhost
A simple living area features a sleek gray sofa adorned with decorative cushions in various colors. A small white table with a mirror is positioned in front, accompanied by a potted plant. Natural light filters through sheer curtains on a nearby window.
Apartment in San Pedro
4.81 out of 5 average rating, 209 reviews

Tropical Escape

El apartamento se encuentra completamente equipado con todas las amenidades de entretenimiento, cocina y lavado para ser su segundo hogar en la ciudad. Es un lugar seguro, espacioso, elegante y muy céntrico perfecto para escapar del bullicioso y acelerado ritmo citadino y transportarse a la pacífica esencia tropical de Costa Rica. IMPORTANTE: Este es un condominio de ambiente FAMILIAR y TRANQUILO. MULTA DE $50 por ruido.

Guest favorite
Loft in San Pedro
4.84 out of 5 average rating, 112 reviews

Centrally located studio in San Pedro | 200+ reviews

Centrally located studio in San Pedro, with an excellent rating and over 200 guest reviews. Ideal for getting around on foot and enjoying San José with ease. Comfortable, safe, and fully equipped space, perfect for short or long stays. Convenient location close to the UCR, restaurants, supermarkets, and public transportation. Ideal for solo travelers or couples. Host with extensive experience and excellent guest reviews.

Guest favorite
Loft in Curridabat
4.89 out of 5 average rating, 296 reviews

BeST RANkED SuPERHOST * 18th Floor * KInG sIZE BeD

Studio Apartment on the 18th floor. Peaceful and centrally-located place. KING SIZE BED GREAT VIEW of the mountains. The apartment is close to supermarkets, shopping malls, restaurants, and cafeterias. Located in a beautiful and fancy neighborhood. Close to bus stops and San Jose Metro-Area Fast Uber rides. *** This building is smoke free, therefore is not allowed to smoke in any location nor in the apartment ***

Guest favorite
Tiny home in Escalante
5 out of 5 average rating, 7 reviews

Secret Garden Private

Secret Garden Prive is a tiny house with a private terrace and garden, creating a peaceful jungle-like retreat in the city. Located within walking distance of Barrio Escalante, known for its top restaurants and nightlife. Unlike most stays in the area, this is not a high-rise tower, offering more privacy, greenery, and a relaxed atmosphere. Nature, comfort, and location in one place.

Popular amenities for Guadalupe vacation rentals

When is the best time to visit Guadalupe?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$10,672 GYDG$10,672 GYDG$10,881 GYDG$9,416 GYDG$9,416 GYDG$9,835 GYDG$9,835 GYDG$9,835 GYDG$9,835 GYDG$10,044 GYDG$10,253 GYDG$11,300 GYD
Avg. temp22°C23°C24°C24°C24°C24°C24°C23°C23°C23°C23°C23°C

Frequently Asked Questions

  • Are there family-friendly vacation rentals in Guadalupe?

    Guadalupe has more than 50 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

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

    Experience the best of Guadalupe with our house rentals, starting at about $10 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • 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 vacation rentals with a dedicated workspace in Guadalupe?

    Yes! Work meets play with ease at over 140 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 80 vacation homes with pools in Guadalupe, available on Airbnb. Make a splash and soak up the sun in style!

  • Do condo rentals in Guadalupe have air conditioning?

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

  • Do house rentals in Guadalupe have a kitchen?

    Absolutely! We offer over 30 house rentals with a kitchen in Guadalupe. Enjoy a tailored experience with all the comforts you desire.

  • Do loft rentals in Guadalupe have wifi?

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

  • Do house rentals in Guadalupe have free parking?

    Absolutely! We offer over 20 house rentals with free parking in Guadalupe. Enjoy a tailored experience with all the comforts you desire.

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

    Enhance your stay in our House Rentals with the most popular amenities: over 20 homes with free parking, over 30 homes with a kitchen, over 40 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.