
Holiday rentals with a pool in Guadalupe
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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.

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!

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!

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.

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.

Whimsical 27th Floor Apt, King Bed, AC, Parking
Victorian “Steampunk” Alice in Wonderland inspired apartment! Located on the 27th floor, our comfortable apartment boasts amazing views of the city. Originally a 2-bdrm floorplan, this unit was converted into a 1-bdrm, making it larger than most 1-bdrm units in SECRT Sabana. Safe building, central location, within walking distance to the National Stadium, La Sabana Park, restaurants, and supermarkets. SECRT Sabana is a funky building, famous for its fun Alice-themed common areas.

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. 🌟

New Studio Near the Airport Hub
Welcome to our charming studio ! This space has been designed to make you feel at home from the moment you walk in. With its open layout and stunning double-height windows in each bedroom, you'll enjoy spectacular natural light throughout the day and unforgettable views of the mountains and the city. Imagine waking up each morning to the fresh breeze and a changing landscape: from the first rays of sunlight illuminating the mountains to the city lights twinkling at dusk.

Architect's Apartment, 21st Floor, Amazing View
Increíble apartamento rediseñado por el Arquitecto Andrés Brenes, único en su tipo. Perfecto para compartir una copa de vino y/o coctel. Ubicado en el piso 21 con muebles de lujo y asombrosas vistas . Amplio espacio de sala, cocina y habitación. Viva la ciudad como nunca antes. Cerca de parques, centros comerciales y restaurantes. ** Blackout en todo el apartamento. Aeropuerto: 30min Parque metropolitano La Sabana: 1km Parqueo Privado No a/c

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 .
Popular amenities for Guadalupe rentals with a pool
House rentals with a pool

Relaxing House in Condo Costa Rica

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Beautiful house with private pool

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Casa Escobar
Condo rentals with a pool

Apartment designed for your rest

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Fully equipped apartment in Nunciatura

AC and King Bed - Full Equipped Apartment

Luxury Apartment, San José, La Sabana, Del Lago

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Spectacular place

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

Ifreses Apartment: clean/balcony/WiFi/desk

Studio loft 23rd floor

WoodRechelle:Cozy, Elegance

Amazing Penthouse in San José

Beautiful apartment, overlooking the mountains.

Apartment with excellent location. AC/wifi

Luxury High-Rise | 16th Floor | La Sabana-San José

Luxury Nature Retreat with River View AC & Parking
Quick stats about holiday rentals with a pool in Guadalupe
Total rentals
70 properties
Nightly prices starting at
$31 AUD before taxes and fees
Total number of reviews
830 reviews
Family-friendly rentals
10 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
50 properties have a dedicated workspace
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- Jaco Beach
- Dominical Beach
- La Sabana Park
- Playa Blanca
- Manuel Antonio National Park
- Hotel Punta Leona
- Poás Volcano National Park
- Parque Diversiones
- Chirripó National Park
- Braulio Carrillo National Park
- Marina Pez Vela
- Los Quetzales National Park
- Playa Boca Barranca
- Cariari Country Club
- Juan Castro Blanco National Park
- Irazú Volcano National Park
- Carara National Park
- La Iguana Golf Course
- La Cruz del Monte de la Cruz
- La Cangreja National Park
- Playa Gemelas
- Turrialba Volcano National Park