Vacation rentals with a pool in San Juan District

Apartment in Barrio Escalante

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.

4.9 out of 5 average rating, 549 reviews

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

The image captures a serene pool area surrounded by lush greenery, offering views of the city skyline and distant mountains. Bright blue skies provide a natural backdrop, while two green chairs are positioned nearby for relaxation.

4.93 out of 5 average rating, 189 reviews

30 mins SJO | Pool View | Premium Appt | Parking

Welcome to this magical space located 30 mins/9.9 mi away from SJO. It features a balcony overlooking the pool, mountains, trees, and green areas. Green is one of my favorite colors, which inspired the design of the room. It has been thoughtfully created to be accommodating, with everything needed for cooking and making you feel at home. Secrt is one of the most incredible buildings, filled with different spaces to work, collaborate, or simply relax. I welcome you and hope you enjoy your stay.

4.94 out of 5 average rating, 142 reviews

A modern kitchen area features sleek cabinetry and stainless steel appliances, complemented by a dining space with stylish chairs. Large windows allow natural light to fill the room, providing a view of the greenery outside, creating a bright and open atmosphere.

Condo in Mantica

Well located, Safe w AC Laundry & Parking San José

Luxury apartment with A/C, cozy, and perfectly located in the heart of the city. This fully equipped space, with modern and elegant decoration, offers you the freedom to live safely and comfortably while exploring everything the city has to offer. Close to tourist attractions, banks, supermarkets, and restaurants. (The condominium has 8 restaurants within the facilities) The International Airport (SJO) is 20 minutes away, La Sabana Park and the new National Stadium are 3 min away in San Jose.

Apartment 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, 140 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, 102 reviews

A sunlit living room is highlighted by a cozy brown leather sofa, complemented by a natural fiber rug. A coffee table sits in front, while large glass doors offer a view of the cityscape and allow natural light to fill the space.

Apartment in Merced

Boho-Chic Oasis A/C Luxe Amenities Great Location

Take a morning stroll in the zen garden before heading back to your perfect location, boho chic 1 br apartment that will welcome you with high-speed wifi, top-of-the-line kitchen appliances, amazing decor, comfortable beds, and sunset views from an 11th floor overlooking the city. Not only will you have access to unparalleled amenities like a cinema, gym, library, bbq areas and co-working space, you will be a walking distance from La Sabana park, best coffee shops, and grocery stores in town.

Apartment in Barrio Escalante

A cozy sitting area features a brown upholstered chair and a small wooden side table. Decorative elements include green plants and colorful throw pillows. A large window provides views of the outdoor landscape, with distant mountains visible under a cloudy sky.

4.9 out of 5 average rating, 122 reviews

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.

A corner seating area features a light-colored sofa with a matching ottoman, positioned near a large window. Lush greenery is visible outside, complemented by gentle textures in the room, including a woven rug and a stylish floor lamp.

4.92 out of 5 average rating, 140 reviews

Best View, Luxury, Full Amenities, Nearby Airport

Welcome to our stunning retreat in Sabana, the heart of San José! Enjoy a breathtaking NATURE VIEW from our cozy apartment, just 20 minutes from the airport. There are 8 international RESTAURANTS IN THE BUILDING, including a coffee shop! This tranquil sanctuary offers convenience and serenity. Relax on the balcony, take a refreshing dip in the POOL, stay active at the GYM, work in the dedicated space, or stroll through the beautiful GARDENS. Enjoy the wonders of San José. Book now!

Apartment in Mata Redonda

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.

4.97 out of 5 average rating, 140 reviews

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.

4.9 out of 5 average rating, 102 reviews

An open kitchen area features sleek cabinetry and a central island with seating. A modern dining space is visible under a stylish light fixture, complemented by contemporary decor. Natural light pours through the double-height windows, illuminating a cozy living area with a sectional sofa and greenery.

Apartment in Ulloa

New Studio 2,5 miles Airport

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, 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.

4.97 out of 5 average rating, 101 reviews

A spacious bedroom features a king bed with a light-colored quilt and decorative pillows. Two bedside lamps flank the bed, providing soft light. Floor-to-ceiling windows offer views of the surrounding landscape, while air conditioning maintains a comfortable atmosphere.

Apartment in Ulloa

Comfort & Style Near SJO Airport +Pool & Mtn Views

CR Stays Welcomes you to this fully-equipped studio just 4 miles from Juan Santamaría Airport. Enjoy breathtaking views of the Escazú mountains, a king bed, queen sofa bed, fast Wi-Fi, and air conditioning—ideal for 4 guests. The building boasts a gym, pool, BBQ terrace, private cinema, and meeting rooms. Minutes from Plaza Real Cariari’s shops and restaurants, and located in a prime business hub. 24/7 security for a safe, stylish, and comfortable stay.

4.85 out of 5 average rating, 143 reviews

The interior space features an open layout with a modern design. A comfortable gray sofa and a white accent chair are arranged around a round coffee table. A staircase leads to the upper level, while natural light floods the area through large windows, enhancing the room's brightness.

Loft in Rohrmoser

Art Loft - Luxurious Apt QBO Building, Rohrmoser

Stylish apartment in the nicest neighborhood of San Jose. The loft is in a new luxury tower with more than 10 amenities (co-work spaces, semi-olympic pool, therapeutic pool, Jacuzzi on different floors, children's garden, two gyms, and several other spaces). Supermarkets, banks, restaurants, Sabana Metropolitan Park, National Stadium, are all located nearby. Great for medical tourism, business travelers, or anyone who wants to visit San Jose.

4.93 out of 5 average rating, 139 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

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.

Popular amenities for San Juan District rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

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

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, 163 reviews

Beautiful house with private pool

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, 125 reviews

Casa Gaudi🦚Near SJO🦚Private Pool & King BD

4.92 out of 5 average rating, 37 reviews

A tranquil pool glistens in front of a modern home, surrounded by landscaped greenery. Comfortable loungers are positioned nearby, while steps lead to an elevated terrace. Lush plants and palm trees enhance the serene outdoor atmosphere, creating a welcoming environment for relaxation.

Home in Alajuela

Casa Turrú, an oasis of calm

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

4.88 out of 5 average rating, 8 reviews

The living area features a modern, open layout with a sectional sofa adorned with blue throw pillows. A circular coffee table sits atop a dark rug. Light streams through large sliding glass doors, illuminating artwork on the walls. A dining area with chairs is visible in the background.

Home in San Pedro

City Scapes Home2BR 2131ft2 Amenities Security24X7

Home in San Francisco De Dos Rios

A modern living area features light-colored walls and elegant marble flooring. A comfortable gray sofa is positioned in front of a mounted flat-screen television, which displays a serene landscape. Accents of wood are incorporated in the wall decor, and a stylish armchair complements the space.

4.88 out of 5 average rating, 41 reviews

Casa Escobar

Condo rentals with a pool

Condo in Barrio Escalante

An open studio layout is visible, featuring a dining table set for two, with blue plates and glassware. A comfortable sofa and a workspace with a chair are included. A neatly organized kitchen area is present, along with a glimpse of the bedroom area behind sliding doors.

4.86 out of 5 average rating, 248 reviews

URBN-Escalante apartment with parking

A cozy living area is presented with a plush sofa featuring an orange throw. A neon sign reading 'WELCOME TO THE CONCRETE JUNGLE' illuminates a green wall adorned with plants. A doorway leads into one of the two bedrooms, enhancing the inviting atmosphere.

4.9 out of 5 average rating, 172 reviews

Concrete Jungle Experience 25th Floor Secrt Sabana

4.86 out of 5 average rating, 137 reviews

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.

Condo in Rohrmoser

Fully equipped apartment in Nunciatura

4.94 out of 5 average rating, 156 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.

Condo in Sabana

Luxury Apartment, San José, La Sabana, Del Lago

4.88 out of 5 average rating, 109 reviews

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.

Condo in Rohrmoser

Luxury SkyView Apartment 2BR

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, 124 reviews

Joya Urbana on the 30th floor; SECRET

A living area is furnished with a pink and white patterned loveseat and a matching armchair. A glass coffee table is positioned at the center, reflecting natural light from the large glass doors that open to a lush exterior view.

4.83 out of 5 average rating, 328 reviews

Alicia's Garden Apartment at Secrt

Superhost

A modern multi-story building is illuminated at night, showcasing multiple balconies and large glass windows. Soft orange lights emit a warm glow, highlighting the architectural features. Lush trees are visible in the foreground, adding greenery to the urban setting.

Condo in Ulloa

4.82 out of 5 average rating, 274 reviews

A beautiful apartment in a condominium

Other vacation rentals with a pool

Condo in Barrio Escalante

A spacious living area features large floor-to-ceiling windows, providing sweeping views of the city. A comfortable green sofa and an ornate armchair are positioned around a round table, with a colorful area rug adding warmth to the space. Two decorative birds stand on display.

4.98 out of 5 average rating, 59 reviews

Sunsets & Style — Modern Stay in Trendy Escalante

4.94 out of 5 average rating, 17 reviews

A bright and modern living area features a light-colored sofa adorned with orange accent pillows. A round coffee table sits in front, and large windows with sheer curtains allow natural light to fill the space. A textured wall adds visual interest to the room.

Condo in Uruca Centro

URBAN LUX APT w/Prime Location•Fast WIFI•Pool•GYM

An indoor firepit is centrally located on a glass table, with flames gently rising. Nearby, a bottle of wine and two glasses are placed alongside a small plate of marshmallows, all set against a backdrop of large windows that open to a vibrant outdoor space.

4.93 out of 5 average rating, 60 reviews

Unique Industrial Apt Near Airport in La Sabana

Apartment in Barrio Escalante

A vibrant corner of the apartment features a classic arcade game cabinet decorated with colorful graphics. In the background, a cozy sleeping area with a spacious bed is visible, while a large window offers a view of the surroundings, allowing natural light to fill the space.

4.94 out of 5 average rating, 31 reviews

Retro Arcade in Escalante

4.97 out of 5 average rating, 101 reviews

A bright living area features a light-colored sofa bed, paired with a minimalist black side table. Large windows are adorned with sheer white curtains, providing a view of vibrant trees outside. A floor lamp and small potted plant add subtle accents to the space.

Apartment in Merced

NucleoSab IvoryApt-NearSJairport-FreeIndoorParking

A cozy living area features a light neutral sofa with decorative cushions, set beside a round coffee table holding potted plants and books. A guitar leans against the wall, and a dining area with a large table is visible in the background, illuminated by natural light through large windows.

4.93 out of 5 average rating, 45 reviews

Urban Lux Stay w/ Mountain View w AC+Pool+Parking

5 out of 5 average rating, 55 reviews

A bright living area features a comfortable sofa and a coffee table, with a large window offering a view of the vibrant greenery outside. Decorative artwork adorns the walls, and a potted plant adds a touch of nature indoor.

Condo in Uruca Centro

Aura-Cozy Apt Near Airport&Sabana-AC-Free Parking

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.