
Vacation rentals with a pool in Guadalupe
Find and book unique homes with a pool on Airbnb
Quick stats about vacation rentals with a pool in Guadalupe

Total vacation rentals
Explore 80 vacation rentals in Guadalupe

Nightly prices starting at
Guadalupe vacation rentals start at G$4,185 GYD per night before taxes and fees

Verified guest reviews
Over 2,240 verified reviews to help you choose

Family-friendly vacation rentals
10 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
60 properties have a dedicated workspace

Wi-Fi availability
80 of Guadalupe vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Guadalupe rentals

4.9 Average rating
Guadalupe stays are highly rated by guests—averaging 4.9 out of 5!
Top-rated rentals with a pool in Guadalupe
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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 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.

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.

Chic Escape in Trendy Barrio Escalante
Live Like a Local in the Heart of San José Welcome to our apartment in the vibrant and walkable neighborhood of Barrio Escalante. San José’s trendiest cultural and gastronomic district. Whether you’re here to explore the city, enjoy delicious food or simply relax, this thoughtfully designed apartment offers the perfect balance of comfort, style, and local experience. You will find yourself at walking distance from San Jose’s major attractions and some of the citie’s best restaurants

Best location, cozy Apartment!
Beautiful condo in perfectly located apartment building. The whole place has a modern feel to it without losing a touch of home. The unit is composed of one bedroom with an ensuite bathroom, living room and deck to relax and enjoy the views, as well as a modern kitchen and laundry machine. This cozy and modern apartment is close to all the best restaurants and night life in San Jose, as well as museums and downtown. Major public transportation is right outside the door.

Apartment with excellent location. AC/wifi
Your 23rd-floor retreat with spectacular views! Wake up every morning in a cozy apartment located on the 23rd floor, where the sweeping views of the city from the balcony provide the perfect backdrop for your morning coffee or a sunset drink. Its location is perfect: just steps away are restaurants serving a variety of cuisines, a shopping center with a supermarket, pharmacy, and hospital, all within walking distance, making your stay convenient and worry-free.

Smart loft in the heart of the city, A/C and Wi-Fi
Enjoy the tranquility of this smart, elegant and centrally located loft with city views! Ideal for relaxing. It has all the amenities you need to make your stay the most pleasant with the highest quality. Its location is favorable as it is close to restaurants, shopping centers, and supermarkets. It's just 15 minutes from downtown San José. It has a large number of amenities such as a heated pool, cinema, study room, gym and coworking area.

Insta-worthy Apartment in a Beautiful Neighborhood
Welcome to your stylish and centrally located home away from home in San José, Costa Rica! Your custom apartment boasts a fully equipped kitchen. Relax in the comfort of the queen bed and enjoy the smart TV and FAST (200 mbps) internet. Amenities include a rooftop pool, gym, coworking area and 24/7 security for your peace of mind. Experience the best of the city with easy access to all the sights and sounds that San Jose has to offer.

10th floor Apartment w/ Sky-Level Pool in San José
Private, comfortable, and strategically located in the heart of Curridabat. This studio on the 10th floor of the iFreses building is perfect for couples, students, or travelers seeking a quiet and functional space. It offers all the essentials for a pleasant stay and is surrounded by universities, shopping centers, and restaurants. Its location makes it a strategic base to explore San José and plan your journey through Costa Rica.

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 .

Breathtaking Mountain View Apt.
Vive la experiencia de hospedarte en un apartamento único en el piso 29 de torre Secrt Sabana , con una vista panorámica impresionante de las montañas de San José , a solamente 200 metros del Parque Metropolitano de la Sabana (mejor ubicación en San José) disfrutarás de sus más de 20 amenidades, te vas a cautivar por los detalles decorativos que verás en cada rincón. ***Aeropuerto Juan Santamaria a solamente 10 millas***

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

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

Casa Gaudi🦚Near SJO🦚Private Pool & King BD

Villa Bugambilia: Large colonial villa with pool.

Casa Delios, Luxury Near the Airport, Private Pool

8p Luxury Townhouse-Concierge & Cleaning

Playa Bejuco Condominium 243

Tropical Nest | Modern Gated Home w/ Pool Near SJO

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

Loft 25th Floor | Panoramic San José View A/C

Studio with view, balcony and free parking · URBN

Luxury Apartment, San José, La Sabana, Del Lago

La Madriguera Serena/ SECRT Sabana.

9.9 mill SJO | Pool View | Cozy Loft | Parking

Charming Apartment w A/C Near to the Int. Airport

The Gourmet Terrace & Coffee View w/AC

Urbn City View Barrio Escalante 17th Floor with A/C
Other vacation rentals with a pool

Modern studio with spectacular view and amenities

Urban Modern Apartment - Roof Top Pool

Stylish Studio with Sky Bar & City Views

INSTAWORTHY CORNER VIEW * Downtown SJ * 200Mbps

NucleoSab IvoryApt-NearSJairport-FreeIndoorParking

Secrt Sabana | SJ | 22nd floor | AC |

Modern apartment in San José, Barrio Escalante

Amazing View at 20th SJO Floor Loft! Parking&Pool
When is the best time to visit Guadalupe?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$11,927 GYD | G$11,927 GYD | G$12,137 GYD | G$10,881 GYD | G$10,044 GYD | G$10,672 GYD | G$10,253 GYD | G$10,463 GYD | G$10,253 GYD | G$11,090 GYD | G$11,718 GYD | G$12,974 GYD |
| Avg. temp | 22°C | 23°C | 24°C | 24°C | 24°C | 24°C | 24°C | 23°C | 23°C | 23°C | 23°C | 23°C |
Destinations to explore
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- Rentals with pools San Jose Province
- Rentals with pools Costa Rica
- Jaco Beach
- Dominical Beach
- Playa Blanca
- La Sabana Park
- Parque Nacional Manuel Antonio
- National Stadium of Costa Rica
- Parque Viva
- Parque Diversiones
- Marina Pez Vela
- Chirripo National Park
- Poás Volcano National Park
- Parque Nacional Braulio Carrillo
- Parque Nacional Los Quetzales
- Playa Jacó
- Turrialba Volcano National Park
- University of Costa Rica
- Carara National Park
- Multiplaza Escazú
- El Miro
- Children’s Museum
- Parque Central
- Hacienda Alsacia Starbucks Coffee Farm
- Britt Coffee Tour
- La Cruz del Monte de la Cruz





