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

Total holiday rentals
Explore 80 holiday rentals in Guadalupe

Nightly prices starting at
Guadalupe holiday rentals start at $38 SGD per night before taxes and fees

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

Family-friendly holiday rentals
10 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
60 properties have a dedicated workspace

Wifi availability
80 of Guadalupe holiday rentals include wifi 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.

Cheerful private 4-Bedroom Villa. Heated pool A/C
For a group or a cozy couple, this bright and spacious home delivers comfort and style. Located in a quiet, modern, and safe neighborhood, you’re just minutes away from downtown. Great restaurants are close by and a block away from new Microsoft tower. 4 bedrooms (A/C), sleeps up to 9 , 3 full bathrooms & private heated pool. Fully equipped modern kitchen, stocked with staples and more. Starts at $195 per night for up to 4 guests, $35 per extra guest. Cleaning included. Come dive into city life.

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.

Tastefully Furnished Penthouse + Rooftop Pool
Lets chat for a FREE early check in 24/7 security extremely safe building and neighborhood Get up in the morning in this magnificent penthouse with the most magnificent view of Irazú and Barva Volcano, enjoying a cup of the most amazing costarican gourmet coffee. Get on to the amenities to enjoy a relaxing morning/sunset dip at the pool and workout in our fully equipped gym or grab a meal in one of the more than 80 restaurants in a 5 block radius following a nice pool table session

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

Studio at 24th floor - SJO view
Exclusive apartment in the iFreses Condominium, 24th floor, near downtown San José, surrounded by shops, restaurants, bars, gastronomic neighborhoods and more. Parking available for an additional fee, pickup trucks are not allowed due to size/ Exclusive apartment at Condominio iFreses on the 24th floor, in the center of the city, surrounded by shops, restaurants, bars, gastronomic neighborhoods and much more. Parking available with an additional fee, no pickups are allowed due to size.

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.

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.

Ifreses Apartment: clean/balcony/WiFi/desk
The space is very comfortable as it is equipped with kitchen utensils, a work table, Wi-Fi, TV, air conditioning, an individual armchair, a two-person armchair, shelves, closets, etc. that make it very cozy. It also has a balcony with sliding doors that allows you to enjoy beautiful views of San José and the mountains, incredible sunsets and fresh air. Most of the ratings highlight the cleanliness of the space, something we particularly care about offering.

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.

Vivi's Hideaway
Enjoy this peaceful and centrally-located apartment, with sweeping 21st floor views of San Jose and the surrounding mountains. Fast internet, cool a/c, and a luxurious king sized, memory foam mattress await you after a day of exploring the Central Valley. Located in an exclusive high rise apartment, you will have access to one of the only rooftop pools in the central valley, a full gym, and inspiring coworking areas.
Popular amenities for Guadalupe rentals with a pool
House rentals with a pool

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

Luxury in your Home, private Pool and Jacuzzi.

Casa Delios, Luxury Near the Airport, Private Pool

Casa Gaudi🦚Near SJO🦚Private Pool & King BD

Vacation-Resort House 15 min from Arpt

Casa Escobar

Buena Vista Home

Beautiful house with pool in Heredia Centro
Apartment rentals with a pool

Studio with view, balcony and free parking · URBN

Industrial 2BR perfect location w/AC + sunset view

City view, A/C near the airport, 1903

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

Modern apartment at gastronomic epicenter

The Gourmet Terrace & Coffee View w/AC

The Madriguera Serena/ SECRT Sabana.

Urban Jewel on the 30th floor; SECRT
Other holiday rentals with a pool

Exclusive Apartment in Downtown Costa Rica

Cozy studio, best gastronomic area Escalante

URBN Barrio Escalante Fully Equipped 20th Floor

Warm studio in Barrio Escalante

Escazú Treetop Casita w/ Panoramic Luxury Views

Modern apartment in San José, Barrio Escalante

Apartment in Escalante Olive Loft 14th

Modern studio with spectacular view and amenities
When is the best time to visit Guadalupe?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $73 SGD | $73 SGD | $74 SGD | $74 SGD | $72 SGD | $69 SGD | $63 SGD | $64 SGD | $63 SGD | $68 SGD | $72 SGD | $80 SGD |
| 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
- Parque Nacional Manuel Antonio
- La Sabana Park
- National Stadium of Costa Rica
- Parque Viva
- Parque Diversiones
- Marina Pez Vela
- Poás Volcano National Park
- Chirripo National Park
- Parque Nacional Braulio Carrillo
- Parque Nacional Los Quetzales
- University of Costa Rica
- Carara National Park
- Turrialba Volcano National Park
- Multiplaza Escazú
- El Miro
- Children’s Museum
- Hacienda Alsacia Starbucks Coffee Farm
- La Cruz del Monte de la Cruz
- City Mall Alajuela
- Britt Coffee Tour
- Parque Central





