
Holiday rentals with a pool in Guadalupe
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Guadalupe
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

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

Urban Modern Apartment - Roof Top Pool
Centrally located near La Sabana Metropolitan Park, my apartment offers a perfect blend of relaxation and functionality. The space is designed for comfort and it’s ideal for virtual work, with a fully equipped kitchen for energizing breakfasts or intimate dinners. Enjoy restful sleep, complete privacy, and the convenience of a full and half bathroom. The unique contemporary ambiance enhances your stay. Additionally, the apartment offers free parking within the building for added convenience.

Smart loft en el corazón de la Ciudad A/C y wifi
Disfruta de la tranquilidad de este smart loft, elegante y céntrico con vista a la ciudad! Ideal para relajarse. Cuenta con todos los servicios necesarios para hacer de tu estadía la más agradable con la más alta calidad. Su ubicación es favorable ya que se encuentra cerca de restaurantes, centros comerciales y supermercados. Está a solo 15 min del casco central de San José. Cuenta con una gran cantidad de amenidades como piscina temperada, cine, sala de estudio, gimnasio y área de coworking.

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!

Apartamento Ifreses: limpio/balcón/WiFi/escritorio
El espacio es muy cómodo ya que está equipado con utensilios de cocina, mesa de trabajo, wifi, tv, aire acondicionado, sillón individual, sillón para dos personas, estantes, closets, etc que lo hacen muy acogedor. Además cuenta con un balcón con puertas corredizas que permite disfrutar de hermosas vistas hacia San José y montañas, atardeceres increíbles y aire fresco. La mayor parte de las calificaciones destacan la limpieza del espacio, algo que particularmente nos preocupamos en ofrecer.

Exclusive Apartment in Downtown Costa Rica
This penthouse is in one of the most exclusive areas of Costa Rica, excellent restaurants, the nightlife is intense, full of life. The apartment has places to work inside the building, a gym, an pool, 24-hour security and the apartment is spacious, the view it has is impressive! day or night "it takes your breath away" its minimalist decoration gives you peace in a world "full of complications" …you are a winner, and you deserve a night that brings you closer to that top level you deserve!

Studio con hermosa vista/ Amazing View Studio
Ubicado en el piso 23 de torre iFreses en Curridabat, cuenta con vista a la zona Sur de 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.

21st Floor Cozy Apartment w A/C
Your home away from home awaits you. An industrial design unit with both antique and contemporary accents are throughout this cozy space to help make your experience unforgettable. Welcome to this tastefully decorated sanctuary located in San José’s Barrio Escalante district, known for its eclectic cuisine and selection as one of the world’s “Coolest Neighborhoods” by Time Out magazine. This unit is perfect for singles and couples. Enjoy the breathtaking sunsets from the private balcony.

Penthouse en San Pedro vista de dioses. Lujo, A/C.
Este lugar tiene una ubicación estratégica: ¡será muy fácil planear tu visita!. Penthouse de lujo de dos pisos 16 y 17.!.A/C. Vista de dioses!. Con vista única y privilegiada, en la zona exclusiva de los Yoses. Cerca de toda la gastronomía Escalante. A sólo 3 minutos de la ciudad de San José. Con una vista espectacular a las montañas del sur de la ciudad y a los hermosos atardeceres al oeste. A sólo metros de supermercados y restaurantes, Estacionamiento incluido para nuestros clientes.

Gorgeous sunsets at charming apartment in downtown
We welcome you to your new and luxurious apartment in the center of the city, located in one of the most iconic residential buildings in the country, with a variety of amenities and just a 5-minute walk away from the most famous gastronomic area of San José. The neighborhood is safe, and has different areas according to your preference (whether it's a night out, or a quiet afternoon in the park). A/C, WiFi 500 mbps, and parking included.

Couples Focused Magnificent Studio Apartment
FREE early check-in upon request!! Escape stress in our stunning 23rd-floor adult-only apartment, offering an erotic touch . Enjoy 24/7 self-check-in, secure parking, and a rooftop with a heated pool for sunset relaxation. Fully equipped kitchen and numerous restaurants, coffee shops and markets nearby. Perfect for couples local looking for a quick get away or the best option for foreigners to start or end their Costa Rica trip .

Upscale apartment at URBN Escalante
Luxurious 26th-floor condo in the heart of Barrio Escalante, San José, Costa Rica! Fully furnished with 2 bedrooms, 2 bathrooms, a modern kitchen, washer/dryer, and HD Smart TVs. Enjoy URBN Escalante’s 24/7 lobby, heated pool, gym, and proximity to top restaurants, cafes, and nightlife. Perfect for travelers or remote workers seeking comfort and convenience in this vibrant urban hub. Stays of 6+ days allow guest visitors.
Popular amenities for Guadalupe rentals with a pool
House rentals with a pool

Casa Relax en Condo Costa Rica

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

Beautiful house with private pool

Casa Gaudi🦚Near SJO🦚Private Pool & King BD

5 beds | SJO | Fast Internet | Heredia |

Luxury Townhouse (8p max)-Pool & Fitness-Escazu

Casa de verano acogedora

City Scapes Home2BR 2131ft2 Amenities Security24X7
Condo rentals with a pool

Apartamento pensado para tu descanso

URBN-Escalante apartment with parking

Fully equipped apartment in Nunciatura

AC and King Bed - Full Equipped Apartment

Modern/comfort great views 2Bdr 2Bath Escalante

Apartamento Flofy - Piscina - Parqueo - Seguridad

Espectacular alojamiento

Industrial 2BR perfect location w/AC + sunset view
Other holiday rentals with a pool

Sunsets & Style — Modern Stay in Trendy Escalante

Apartamento en EscalanteOlive Loft 14th

Loft Ifreses Curridabat con A/C y cama King Size

Modern Oasis iFreses, 18th floor! AC, TV and Pool

Unique Industrial Apt Near Airport in La Sabana

WoodRechelle:Calidez, Elegancia

INSTAWORTHY CORNER VIEW * Downtown SJ * 200Mbps

Amazing Penthouse in San José
Quick stats about holiday rentals with a pool in Guadalupe

Total holiday rentals
Explore 70 holiday rentals in Guadalupe

Nightly prices starting at
Guadalupe holiday rentals start at $36 NZD per night before taxes and fees

Verified guest reviews
Over 830 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wi-Fi availability
60 of Guadalupe holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Guadalupe rentals

4.8 Average rating
Guadalupe stays are highly rated by guests—averaging 4.8 out of 5!
Destinations to explore
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- Rentals with a patio Guadalupe
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- Fitness-friendly rentals Guadalupe
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- Family-friendly rentals Guadalupe
- House rentals Guadalupe
- Rentals with breakfast Guadalupe
- Rentals with a washing machine and dryer Guadalupe
- Rentals with pools San Jose
- Rentals with pools Costa Rica
- Jaco Beach
- Dominical Beach
- La Sabana Park
- Playa Blanca
- Manuel Antonio National Park
- Poás Volcano National Park
- Parque Diversiones
- Chirripó National Park
- Marina Pez Vela
- Braulio Carrillo National Park
- Cariari Country Club
- Los Quetzales National Park
- Playa Boca Barranca
- Juan Castro Blanco National Park
- Irazú Volcano National Park
- Carara National Park
- La Iguana Golf Course
- La Cangreja National Park
- La Cruz del Monte de la Cruz
- Turrialba Volcano National Park
- Playa Gemelas
- Playa Savegre




