Holiday rentals with a pool in Guachipelín

4.9 out of 5 average rating, 547 reviews

A spacious lounge area is featured with large windows, providing panoramic views of San José. Comfortable sofas are arranged around a central coffee table, and an artistic light fixture adds a touch of elegance. Subtle decor elements enhance the inviting space.

Flat in Barrio Escalante

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

Flat in San Rafael de Escazú

A spacious bedroom features a large bed with a blue throw and decorative pillow, complemented by wooden nightstands with lamps. Bright light shines through large windows leading to a sunlit terrace. A colorful wall art piece adds a touch of interest to the neutral decor.

4.83 out of 5 average rating, 157 reviews

Cozy and Spacious in Prime Escazu+Views+Pool+AC

🌟 Stunning & Spacious 1BR/1BA Condo! Perfect for medical tourism, remote work, business, or family stays, in the most exclusive area of Escazú! Enjoy breathtaking Central Valley & mountain views 🌄, just minutes from Multiplaza Mall, top dining, pubs, shops & artisanal cafés. 🚗 Private parking, 24/7 security, elevator & stairs. Plus, relax with a pool, gym & lightning-fast 100Mbps WiFi! 💻🏊‍♂️💪 Cozy comfort & convenience—experience it all and leave your journey with us !- AC in master BR ✨

Flat in Urbanización Castro

An infinity pool is seen on the rooftop, overlooking a city skyline at sunset. The water reflects the colors of the sky, while glass railings provide unobstructed views of the surrounding area and mountains in the distance.

4.96 out of 5 average rating, 139 reviews

Urban Modern Apartment - Roof Top Pool

Centrally located near La Sabana Metropolitan Park, my apartment offers a perfect blend of relaxation and functionality. The space is designed for comfort and it’s ideal for virtual work, with a fully equipped kitchen for energizing breakfasts or intimate dinners. Enjoy restful sleep, complete privacy, and the convenience of a full and half bathroom. The unique contemporary ambiance enhances your stay. Additionally, the apartment offers free parking within the building for added convenience.

4.93 out of 5 average rating, 310 reviews

Industrial 2BR perfect location w/AC + sunset view

Take a morning stroll in the park before heading back to your centrally-located, industrial 2 br apartment that will welcome you with high-speed wifi, top-of-the-line kitchen appliances, amazing decor, comfortable beds, and sunset views from a 12th floor overlooking the city. Not only will you have access to unparalleled amenities like a semi-Olympic pool, saunas, gym, and co-working space, you will be a walking distance from the best restaurants, coffee shops, and grocery stores in town.

4.94 out of 5 average rating, 246 reviews

A modern studio space is showcased with a double bed and a cozy seating area featuring a gray sofa. A wooden coffee table is placed centrally, complemented by stylish chairs. The kitchenette and dining area are visible, emphasizing an open layout with natural light.

Apartment in Río Oro

Modern & bright Studio at ARBOREA Flats Santa Ana

Modern, clean and light studio with views to the trees and mountains. A rare gem in such a central city location. The studio is fully equipped with a double bed, luxury sheets and towels, full kitchen amenities, high speed Wifi and TV. A perfect place to rest, because it is quiet and peaceful, yet close to shopping, restaurants, airport and freeway. Arborea Flats is a new, modern condominium with great services like co-working spaces, gym and pool, and has a very hip, modern feeling.

4.94 out of 5 average rating, 181 reviews

A spacious mansion is positioned on a lush green landscape, featuring large arched windows and a red-tiled roof. The exterior is painted in soft tones, while vibrant greenery surrounds the structure, enhancing the serene atmosphere. The rolling hills and distant views create an inviting backdrop.

Villa in Santa Ana

Vista Oro Luxurious Villa Heated Pool 360 Views

Luxurious Mansion for a Fantastic price . Your Private Estate to enjoy,Located in the hills of Santa Ana , 25 mins from SJO airport . Perfect climate . 360 Spectacular Views Gourmet Chef Kitchen, Quality cotton linings ,beds , towels and furnishings Heated Salt Spa Pool , On Site Help ,24 hrs Security, Your Home in Paradise .10 mins Fine Dining , Supermarkets,Malls Entertainment , Private chef , Tours and driver services available .You will enjoy a Fantastic Memorable Vacation..

4.97 out of 5 average rating, 139 reviews

A cozy bedroom is highlighted by a tufted headboard and plush bedding. Soft lighting is provided by two bedside lamps. Artwork featuring Alice in Wonderland decorates the wall above. A large window offers expansive views of the city and landscape beyond.

Flat in Mata Redonda

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.

4.91 out of 5 average rating, 134 reviews

A spacious sleeping area features a large bed with crisp white linens and a deep blue blanket. A television is mounted on the wall opposite, while double-height windows offer views of the outdoors. A small balcony with two chairs is visible, enhancing the room's natural light.

Flat in Ulloa

New Studio Near the Airport Hub

Welcome to our charming studio ! This space has been designed to make you feel at home from the moment you walk in. With its open layout and stunning double-height windows in each bedroom, you'll enjoy spectacular natural light throughout the day and unforgettable views of the mountains and the city. Imagine waking up each morning to the fresh breeze and a changing landscape: from the first rays of sunlight illuminating the mountains to the city lights twinkling at dusk.

4.89 out of 5 average rating, 114 reviews

A spacious living area features a modern white sofa and a textured area rug beneath a glass coffee table. A dining table with dark chairs is visible in the background. A floral arrangement provides a focal point, while large windows frame views of the surrounding mountains.

Flat

Exclusive Penthouse with an excellent location

Penthouse located in an exclusive area in San Rafael de Escazu (Guachipelin). Close to important commercial areas such as Multiplaza, Banks, restaurants, CIMA Hospital and pharmacy. We are close to the main roads to the beaches, downtown and Juan SantaMaria airport. This penthouse has beautiful views of the mountains and hills of its surroundings from all its spaces. Modern style design. Each space has everything you need for a very comfortable stay.

Home in Provincia de Heredia

A private home is set in a lush garden, featuring a swimming pool framed by potted plants. The patio area is visible, offering seating arrangements with a covered terrace, showcasing the inviting outdoor space for relaxation and dining.

4.93 out of 5 average rating, 162 reviews

Beautiful house with private pool

Welcome to your own private oasis in Costa Rica! This beautiful home is in a guarded community that backs to an 18-hole golf course and includes a pool and a lovely private guest cottage, "La Casita". This home is also located in the Mesa Central area of Costa Rica, which is known for its fantastic weather; no humidity, very sunny (during the summer), the perfect temperature during the day, and a little chilly at night - no AC needed at all!

The living room features large windows offering expansive city views. A stylish, beige tufted couch and two plush orange chairs are arranged on a richly patterned area rug. Modern lighting fixtures enhance the contemporary design, while dark cabinetry provides functional storage.

4.96 out of 5 average rating, 564 reviews

Architect's Apartment, 21st Floor, Amazing View

Increíble apartamento rediseñado por el Arquitecto Andrés Brenes, único en su tipo. Ubicado en el piso 21 con muebles de lujo y asombrosas vistas . Amplio espacio de sala, cocina y habitación. Zona muy transitable, cerca de parques, centros comerciales y restaurantes. Aeropuerto: A 16 km, serían 35 min aproximadamente, dependiendo del tráfico. Parque metropolitano La Sabana: 1km Parqueo Privado No A/C

4.97 out of 5 average rating, 274 reviews

The loft features a spacious bed adorned with neutral bedding and decorative pillows. A wooden mezzanine area with a hammock is above, while wooden stairs offer access. Soft lighting is cast from bedside lamps, complementing nautical-themed artwork on the walls.

Loft in Santa Ana

ARANJUEZ LOFTS - Nautical Loft #7

Enjoy a nautical experience, the favorite of kids and young adults... Our Nautica Loft #7, is one of our 12 Aranjuez Lofts located in Santa Ana. In a beautiful property with shared large garden and pool. Conveniently located upon walking distance to Santa Ana downtown, and to supermarkets, restaurants, movie theaters and much more.

Popular amenities for Guachipelín rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

5 out of 5 average rating, 33 reviews

A modern outdoor area is presented with an inviting swimming pool surrounded by a spacious deck. Comfortable seating arrangements are visible, along with tropical plants framing the scene. The clear blue sky complements the sleek architecture of the home in the background.

Home in Ulloa

New 3BR Condo | by SJO Airport & Convention Center

4.89 out of 5 average rating, 123 reviews

An indoor pool is framed by vibrant green walls and a wooden ceiling. Comfortable lounge chairs in light green surround the pool. A hammock is elegantly positioned nearby, while an open sliding door reveals a spacious living area with cozy seating and organized shelving.

Home in Río Oro

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

Home in Finca La Ponderosa

A modern structure featuring an infinity pool that blends seamlessly with the surrounding landscape. The pool's clear water reflects the cloudy sky, while the terrace provides access to the building. Lush greenery and trees are visible in the background, enhancing the serene atmosphere.

5 out of 5 average rating, 8 reviews

Green Escape with Style

Superhost

The outdoor area features a private pool with steps and a ramp for accessibility. A covered terrace with seating overlooks the pool. Lush greenery surrounds the space, enhancing the natural atmosphere. A pool lift is visible, ensuring inclusivity for all guests.

Home in Alajuela

4.9 out of 5 average rating, 121 reviews

Casa Gaudi🦚Near SJO🦚Private Pool & King BD

Home in San Joaquín de Flores

5 out of 5 average rating, 10 reviews

Hidden Paradise Resort, 10 min from SJO Airport

5 out of 5 average rating, 24 reviews

An inviting dining area features a glass table surrounded by green upholstered chairs. The space is illuminated by a unique pendant light fixture. Large sliding glass doors open to a landscaped outdoor area, allowing natural light to fill the room.

Home in San Antonio

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

4.83 out of 5 average rating, 65 reviews

The exterior of the house features a welcoming white front door, flanked by two windows. Well-maintained hedges line the path leading to the entrance, with a concrete walkway on one side. The bright blue sky complements the home's neutral exterior and red roof accents.

Home in San Rafael

Cozy summer house

4.93 out of 5 average rating, 134 reviews

A spacious bed with neutral-toned bedding is positioned near large glass windows, offering a nighttime city view filled with twinkling lights. Soft curtains frame the windows, complementing the warm color palette of decorative pillows arranged on the bed.

Home in Curridabat

Smart loft in the heart of the city, A/C and Wi-Fi

Apartment rentals with a pool

4.84 out of 5 average rating, 178 reviews

A cozy sleeping area features a spacious bed with a light-colored linen, complemented by a vibrant orange towel as an accent. A study desk is positioned nearby, and a ceiling fan is installed for air circulation. Natural light is filtered through floor-to-ceiling windows, draped in soft curtains.

Apartment in Ulloa

Studio: Pool, Security, Peace

A sleek lap pool is surrounded by lush greenery and tropical plants, providing a serene atmosphere. The pool features a stone border and is set against a wooden deck. Steps lead down to the pool area, with a panoramic view of the surroundings.

4.86 out of 5 average rating, 135 reviews

Fully equipped apartment in Nunciatura

4.94 out of 5 average rating, 155 reviews

An open-concept living space is showcased, featuring a dining table surrounded by chairs and a comfortable sofa nearby. A modern kitchen is visible with sleek cabinetry and stainless steel appliances. Large windows provide a view of the city skyline, while polished tiles complete the space.

Apartment in Sabana

Luxury Apartment, San José, La Sabana, Del Lago

Apartment in Mata Redonda

A modern kitchen space features a central island with a variety of food options displayed. Greenery adorned with soft lights hangs from the ceiling, adding a touch of decor. In the background, a cozy seating area is visible next to large glass doors that open to a scenic view.

4.96 out of 5 average rating, 121 reviews

Urban Jewel on the 30th Floor; SECRT

A spacious living area features a large gray sofa and a flat-screen TV mounted on the wall. Natural light floods the room through floor-to-ceiling windows, offering views of the surrounding cityscape. Houseplants are arranged on a sleek white entertainment unit, enhancing the inviting space.

4.88 out of 5 average rating, 109 reviews

Luxury SkyView Apartment 2BR

A modern living space is presented, featuring a green sectional sofa with decorative pillows and a wooden accent chair. A small round table accompanies two chairs in the dining area. The kitchen is visible in the background, equipped with a refrigerator and various appliances.

4.95 out of 5 average rating, 152 reviews

Comfortable apartment in upscale neighborhood

Apartment in Mata Redonda

4.9 out of 5 average rating, 227 reviews

Skyline Loft 22nd Fl | Panoramic Views · San José

Apartment in Uruca Centro

A modern living room features a comfortable sectional sofa adorned with decorative pillows. A sleek side table sits beside the sofa, and a round coffee table with wooden legs is centered on a patterned rug. Natural light is diffused through vertical blinds.

4.9 out of 5 average rating, 103 reviews

An oasis in the middle of the city

Other holiday rentals with a pool

4.97 out of 5 average rating, 32 reviews

A tranquil pool reflects the night sky, illuminated softly by surrounding lights. Palm trees stand majestically nearby, casting shadows across the serene water. The scene captures a peaceful atmosphere, inviting guests to unwind by the poolside under the stars.

Apartment in Río Oro

Artistic Place in Santa Ana 30min from SJO.

Superhost

An open-concept living space features a contemporary kitchen island with seating. Modern wood cabinetry contrasts with white countertops. Light floods the area through large windows, illuminating a dining set and lounge area. A bedroom in the background is partially visible, inviting comfort.

Flat in Ulloa

4.76 out of 5 average rating, 29 reviews

New and cozy Apartamento

4.96 out of 5 average rating, 74 reviews

A bright living area is illuminated by large windows, offering views of the outdoors. A comfortable white sofa and a modern armchair are positioned around a stylish coffee table. A television is mounted on the wall, while a door leads to a bedroom.

Apartment in Santa Ana

River view apartment, spacious & central /condo

4.85 out of 5 average rating, 34 reviews

The spacious living and dining area leads to a terrace through large sliding glass doors. Natural light fills the room, showcasing a comfortable seating area, a dining table, and a bedroom visible through a doorway. Lush greenery can be seen outside the terrace.

Apartment in Santa Ana

1 BEDROOM CONDO WITH TERRACE AVALON SANTA ANA

Flat in San Rafael de Escazú

4.92 out of 5 average rating, 51 reviews

Casa Vintage Escazú: Design and Spacious Panorama

4.96 out of 5 average rating, 55 reviews

A sleek outdoor lounge area showcases modern seating arranged around a central table, framed by vertical black slats. A large pool is visible in the background, lined with sun loungers and shaded by umbrellas, surrounded by lush greenery.

Flat in Uruca Centro

Luxury High-Rise | 16th Floor | La Sabana-San José

4.92 out of 5 average rating, 25 reviews

The modern three-story building features a mix of white and brown façades, with large glass windows that allow natural light to enter. A well-maintained garden surrounds the entrance, enhancing the welcoming appearance of the property.

Flat in Pozos

Apto 3 Hab Santa Ana cerca de todo. Full Equipado.