
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$6,278 GYD per night before taxes and fees

Verified guest reviews
Over 2,670 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 10 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.

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.

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

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.

Penthouse in San Pedro, view of the gods. Luxury, A/C.
This special place is close to everything, making it easy to plan your visit. Luxury two-story penthouse 16 and 17!A/C. View of the gods! With a unique and privileged view, in the exclusive area of Los Yoses. Close to all the Escalante cuisine. Just 3 minutes from the city of San José. With a spectacular view of the mountains to the south of the city and the beautiful sunsets to the west. Just meters from supermarkets and restaurants, parking included for our customers.

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 in Escalante Olive Loft 14th
A modern and elegant studio on the 14th floor, with an amazing sunset view. Located in the heart of Barrio Escalante, close to bars and excellent restaurants with a wide variety of cuisine, opposite one of the 100 best cafés in the world. Perfect for couples, solo travelers or digital nomads looking for comfort in a safe and walkable location. Escalante is the cultural and gastronomic epicenter of San José, with active local life at any time of the day.

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.

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 .

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

Centrally located apartment in the east of San José

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

Beautiful house with pool in Heredia Centro

City Scapes Home2BR 2131ft2 Amenities Security24X7

Casa Escobar
Condo rentals with a pool

Studio with view, balcony and free parking · URBN

La Madriguera Serena/ SECRT Sabana.

Urban Jewel on the 30th floor; SECRT

Urbn Escalante Downtown View

Industrial 2BR perfect location w/AC + sunset view

MINT Apt 17th Floor View IFreses w/ Pool Wifi AC

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

Modern apartment at gastronomic epicenter
Other vacation rentals with a pool

Cozy studio, best gastronomic area Escalante

Cheerful private 4-Bedroom Villa. Heated pool A/C

Breathtaking Mountain View Apt.

Urban Modern Apartment - Roof Top Pool

Stylish Studio with Sky Bar & City Views

SECRT Escalante · 19th Floor · View + Parking

Apartment with excellent location. AC/wifi

Amazing Contemporary Penthouse in San José Tower
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
- San José Vacation rentals
- Jaco Vacation rentals
- Tamarindo Vacation rentals
- Cahuita Vacation rentals
- Quepos Vacation rentals
- Cobano Vacation rentals
- Bahía Ballena Vacation rentals
- Nosara Vacation rentals
- Managua Vacation rentals
- Sámara Vacation rentals
- Puerto Viejo de Talamanca Vacation rentals
- Liberia Vacation rentals
- Guesthouse rentals Guadalupe
- Rentals with outdoor seating Guadalupe
- Smoking-friendly rentals Guadalupe
- Condo rentals Guadalupe
- Apartment rentals Guadalupe
- Pet-friendly rentals Guadalupe
- Rentals with a hot tub Guadalupe
- Rentals with a fire pit Guadalupe
- Family-friendly rentals Guadalupe
- Rentals with breakfast Guadalupe
- Rentals with a washer and dryer Guadalupe
- House rentals Guadalupe
- Rentals with a patio Guadalupe
- Fitness-friendly rentals Guadalupe
- Rentals with pools San Jose Province
- Rentals with pools Costa Rica
- Jaco Beach
- Dominical Beach
- Playa Blanca
- Parque Nacional Manuel Antonio
- 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
- University of Costa Rica
- Playa Jacó
- Turrialba Volcano National Park
- 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





