
Vacation rentals with a pool in Guadalupe
Find and book unique homes with a pool on Airbnb
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.

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.

Cityscape iFreses, 20th floor! AC, TV and Pool
Discover this elegant, fully furnished apartment in one of the safest residential-commercial areas of San José, featuring 24/7 security. Situated in the exclusive iFreses Condominium, this apartment offers stunning city views and amazing amenities! Its strategic location places you within walking distance of shopping centers, supermarkets, coffee shops, restaurants, banks, and universities. Bus and taxi stops are just 50 meters away, and the train station is 200 meters away.

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.

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.

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 .

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.

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

Relaxing House in Condo Costa Rica

Nebulae - Water Cube Suite

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

Casa Maria

Casa Delios, Luxury Near the Airport, Private Pool

Luxury Townhouse (8p max)-Pool & Fitness-Escazu

City Scapes Home2BR 2131ft2 Amenities Security24X7

Casa Escobar
Condo rentals with a pool

URBN-Escalante apartment with parking

Fully equipped apartment in Nunciatura

Modern/comfort great views 2Bath 2Bdr Escalante

Luxury SkyView Apartment 2BR

Modern & Cozy Apartment!

Industrial 2BR perfect location w/AC + sunset view

Super view and WiFi, 2 bedrooms, 2 bathrooms and 2 parking spaces

Modern apartment at gastronomic epicenter
Other vacation rentals with a pool

Sunsets & Style — Modern Stay in Trendy Escalante

Apartment in EscalanteOlive Loft 14th

Panoramic Penthouse 21 Escalante

Loft Ifreses Curridabat with A/C and King Size bed

Escalante Relax 12th

WoodRechelle: Warmth, Elegance

Amazing Penthouse in San José

Modern apartment with pool in Bö Escalante
Quick stats about vacation rentals with a pool in Guadalupe

Total vacation rentals
Explore 70 vacation rentals in Guadalupe

Nightly prices starting at
Guadalupe vacation rentals start at G$4,182 GYD per night before taxes and fees

Verified guest reviews
Over 1,590 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
70 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!
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- National Stadium of Costa Rica
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- Marina Pez Vela
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