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Vacation rentals in Guadalupe

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Top-rated vacation rentals in Guadalupe

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

Guest favorite

Guesthouse in San Antonio

4.98 out of 5 average rating, 152 reviews

Amazing City Views/Guest house Escazú (2 Guests+2)

Welcome to Arcadia! Explore upscale Escazú at our unique property offering a stay at the adjacent guest house 'Casa Iduna,' featuring serene views of a freshwater pond, volcanoes, and the San José skyline. Lush gardens, exotic fruit trees, a swimming pool, and a cozy rancho surround the guest house, ensuring a relaxing stay. IMPORTANT: Booking includes two guests; extra guest charges apply. No special events are permitted, and only one pet per booking is allowed. Uber Eats delivery available.

Guest favorite

Apartment in Escalante

4.96 out of 5 average rating, 228 reviews

Queen Bed Yogui Studio + Hot Tub

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

Apartment in Santa Ana

4.93 out of 5 average rating, 40 reviews

Tranquil Oasis: 1BR Retreat

Experience tranquility in our one-bedroom retreat, where modern elegance meets comfort. Dive into the refreshing pool, savor outdoor delights with our barbecue, and stay fit in the on-site gym. Your cozy haven features super-fast WiFi, cable TV, full kitchen, and laundry stack. Ideal for business travelers, couples, solo adventurers, and families alike, this meticulously designed apartment offers contemporary charm and thoughtful amenities. Book at Tranquil Oasis now for your ultimate escape.

Guest favorite

Condo in Mata Redonda

4.95 out of 5 average rating, 84 reviews

Concrete Jungle Experience 25th Floor Secrt Sabana

Welcome to the Concrete Jungle Experience! Nestled in Secrt Sabana, one of the most beautiful condos in San Jose, Costa Rica, our full apartment offers a unique stay. Located just 200 meters from La Sabana Park and a short drive from Downtown and Juan Santamaria Airport, our place combines urban convenience with tropical charm. Enjoy top-notch amenities like a pool, cinema, gym, and photo-worthy spots. Experience the essence of Costa Rica's tropical forests right in the heart of the city!

Guest favorite

Apartment in San Rafael de Escazú

4.89 out of 5 average rating, 18 reviews

Upscale comfy in top-rated area

Treat yourself to the perfect fusion of style, comfort & nature bliss. Stay in: Take a relaxing sunbath on the rooftop and unwind at the jacuzzi while enjoying the view of lush scenery. Work from home at the mezzanine: Spacious, high-speed Wi-Fi + A/C. Re-energize by going for a stroll in the free-of-traffic neighborhood. Explore: Wander around many restaurants, shops, cafes, health centers, and embassies within a 5–15-minute drive/walk while your home feels safe, peaceful, and secluded.

Guest favorite

Villa in Pilas, Alajuela Province,

4.93 out of 5 average rating, 180 reviews

Private Spacious Villa w/ Pool & Views near SJO

Villa Cielo Grande is our main house and the crown jewel among our four villas. Here’s what makes it truly exceptional: - A private villa spacious enough for families or groups. (3 BR, 3 BA. 11 guests). -Enjoy exclusive access to your own private pool and BBQ area. - Access to patios, beautiful gardens, and a charming gazebo. - Proximity to SJO airport, grocery stores, restaurants, and the City Mall. - Perfect temperatures, creating an ideal retreat for relaxation and exploration.

Superhost

Cabin in San Isidro

4.85 out of 5 average rating, 394 reviews

Cabaña Mountain View

Cabaña Rodeada de Montaña, muy privada, cerca de un río y catarata de agua cristalina, el lugar es muy tranquilo y seguro, Si quieres despejarse y salir de la rutina, realizar yoga, leer un libro o simplemente disfrutar de la tranquilidad. Este es el lugar perfecto, para disfrutar de un tour a caballo por las faltas del Parque, y así podrás disfrutar de los paisajes que la rodean. La calle esta recién asfaltada, para facilidad de ingreso.

Superhost

Condo in Sabana

4.76 out of 5 average rating, 17 reviews

Wanderlust Wonderland: Work & Relax in Costa Rica

Welcome to Wanderlust Wonderland! A unique and stay in San Jose, Costa Rica. Step into the magical world of Alice in Wonderland in our one-bedroom apartment in an avant-garde San Jose tower. This is not just a place to stay; it’s an experience. With 15 unique amenities and theme rooms inspired by the classic tale, your stay will be nothing short of magical. Experience the magic of Wonderland in the heart of San Jose. Book your stay today!

Guest favorite

Condo in Rohrmoser

4.92 out of 5 average rating, 132 reviews

Luxury, comfort and strategic location San José

Experimenta el lujo en este apartamento en el piso 10, con 2 habitaciones, 2 baños, cocina, sala y lavandería. Disfruta de las impresionantes vistas al Parque del Café y la ciudad desde tu ventana. Este refugio urbano de lujo también te brinda acceso a más de 10 comodidades en el edificio, incluyendo una piscina y un gimnasio. Además, cuenta con 1 espacio de estacionamiento para tu comodidad. ¡Una experiencia única te espera!

Guest favorite

Loft in Curridabat

4.86 out of 5 average rating, 199 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

Apartment in Escalante

4.9 out of 5 average rating, 190 reviews

Amazing Private Terrace Flat A/C+Pool+Gym+100MB

Our Terrace apartment is located in an exotic, Unique, Hip, Cool, and Relaxing High Rise 5 stars Resort Style Condo centrally located in the Gastronomic district of San Jose Costa Rica. the Resort Style Condo has it all! Pool, Gym, Co-working areas, 29th Story Terrace, Private Meeting Rooms, Theater Room, Laundry.

Guest favorite

Condo in San Rafael

4.84 out of 5 average rating, 19 reviews

3BR Home w/ AC & high speed internet near airport

Relax with the whole family in this peaceful place to stay. 3 bedroom apartment in a housing complex with trails, lake, swimming pools, full of green areas, beautiful views. With an excellent location very close to the main highway of Costa Rica ("27"), just 10 minutes from Juan Santamaría Airport.

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Guadalupe vacation rentals

Kitchen
Wifi
Pool
Free parking on premises
Air conditioning

Stay near Guadalupe's top sights

Barrio Escalante190 locals recommend
Jade Museum272 locals recommend
National Museum Of Costa Rica186 locals recommend
Pre-Columbian Gold Museum133 locals recommend
National Theater of Costa Rica127 locals recommend
Hospital La Católica12 locals recommend

Other great vacation rentals in Guadalupe

Guest favorite

Condo in Río Oro

4.87 out of 5 average rating, 62 reviews

Modern Lakeview Penthouse: Pool/Gym

Superhost

Place to stay in Montecito

5 out of 5 average rating, 4 reviews

Casa de Montaña 12 Hab. (+27 guests) Wifi+GYM

Superhost

Condo in San José

4.72 out of 5 average rating, 131 reviews

Penthouse with incredible views of the city

Guest favorite

Apartment in Mata Redonda

4.92 out of 5 average rating, 24 reviews

Blue Nun at 29's

Guest favorite

Apartment in La Uruca

4.86 out of 5 average rating, 22 reviews

The Relax Hub Downtown w/ AC 20 Min From Airport

Superhost

Townhouse in Alajuela

4.83 out of 5 average rating, 53 reviews

House in condominium. With pool, 2 bedrooms.

Superhost

Apartment in Rohrmoser

4.77 out of 5 average rating, 26 reviews

Penthouse apartment

Superhost

Apartment in San José

4.68 out of 5 average rating, 31 reviews

New mountain view 2 bedroom - amazing amenities.

Show all

Quick stats about vacation rentals in Guadalupe

  • Total rentals

    210 properties

  • Nightly prices starting at

    $10 before taxes and fees

  • Total number of reviews

    5.1K reviews

  • Family-friendly rentals

    40 properties are a good fit for families

  • Pet-friendly rentals

    50 properties allow pets

  • Rentals with dedicated workspaces

    110 properties have a dedicated workspace

Frequently Asked Questions

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

    Experience the best of Guadalupe with our guesthouse 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.

  • Do house rentals in Guadalupe have a kitchen?

    Absolutely! We offer over 40 house 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 110 vacation rentals in Guadalupe featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do apartment rentals in Guadalupe have air conditioning?

    Absolutely! We offer over 10 apartment rentals with air conditioning 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 40 homes with a kitchen, over 30 homes with free parking, over 60 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Do apartment rentals in Guadalupe have free parking?

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

  • Do apartment rentals in Guadalupe have wifi?

    Absolutely! We offer over 60 apartment 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.

Destinations to explore