
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.

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

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.

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.

Modern studio with spectacular view and amenities
Good and easy access location near supermarkets, malls, night life centers, near a Main Street on Curridabat and near a train station. Spectacular amenities such as coworking space, gym, tempered pool and other common areas, as well as friendly staff in the building. The apartment is equipped with crockery and basic kitchen utensils and the bathroom is provided with soap, shampoo and conditioner. There is a private WiFi, a smart tv and A/C. There is one bed an one sofa bed.

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.

Studio with view, balcony and free parking · URBN
Stay on the 12th floor of URBN Escalante, San José’s iconic tower, with city views from your private balcony. Enjoy a queen bed, a fully equipped kitchen, fast Wi-Fi, workspace, and FREE indoor parking. Located in the heart of Barrio Escalante, with 70+ restaurants, cafés, and bars within a 5-minute walk. Building amenities include a gym, heated pool, laundry room, coworking space, library, yoga room, cinema, and rooftop views. Check-in at the lobby is available 24/7

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.

City view, A/C near the airport, 1903
It is an apartment with an excellent distribution and a modern and contemporary aspect, located near the La Sabana Metropolitan Park, an area with excellent restaurants, entertainment venues, and very close to shopping centers, Juan Santamaría airport, etc; It is on the 19th floor, with a view to the east, the mountains and the city steal the show at all hours of the day, without a doubt the sunset and night are the favorites for their colors and lights.

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.

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.

Apartment with an excellent view, A/C, parking included
Cozy apartment in one of the best neighborhoods in Curridabat. In this apartment you will find everything you need to feel at home. It has all the necessary services and amenities. Air conditioning, free parking, equipped kitchen, etc. If you need anything extra, we'll try to get it for you!! The building has a wealth of amenities designed for your well-being and comfort. Swimming pool, coworking, gym, among others.
Popular amenities for Guadalupe rentals with a pool
House rentals with a pool

New 3BR Condo | by SJO Airport & Convention Center

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
Condo rentals with a pool

Concrete Jungle Experience 25th Floor Secrt Sabana

Perfect City Sunset Retreat 18th floor

Urban Jewel on the 30th floor; SECRT

Urbn Escalante Downtown View

Alicia's Garden Apartment at Secrt

The Gourmet Terrace & Coffee View w/AC

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

5 min from Airport | Transfer ($) | Pool | Gym
Other vacation rentals with a pool

Modern and comfortable

Cozy studio, best gastronomic area Escalante

SECRT Escalante · 19th Floor · View + Parking

PoolView Loft 10 & Workspace + AC | SECRT Sabana

Aranjuez Lofts - Patio Loft # 5

★Luxurious Apt★ | Panoramic View, Pool, Gym + Pkg

Couples Focused Magnificent Studio Apartment

Rabbit's Hole in Secrt Sabana
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 a hot tub Guadalupe
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- Fitness-friendly rentals Guadalupe
- Family-friendly rentals Guadalupe
- Rentals with outdoor seating Guadalupe
- Rentals with a patio Guadalupe
- Rentals with pools San Jose Province
- Rentals with pools Costa Rica
- Jaco Beach
- Dominical Beach
- Parque Nacional Manuel Antonio
- Playa Blanca
- La Sabana Park
- 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
- Carara National Park
- Turrialba Volcano National Park
- University of Costa Rica
- El Miro
- Multiplaza Escazú
- Parque Central
- La Cruz del Monte de la Cruz
- Hacienda Alsacia Starbucks Coffee Farm
- Britt Coffee Tour
- Children’s Museum





