Vacation rentals with a pool in Guapiles

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, 553 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

4.84 out of 5 average rating, 270 reviews

An outdoor seating area is framed by a modern structure, overlooking a pool surrounded by lounge chairs. Umbrellas provide shade, and greenery is visible in the background, enhancing the relaxing environment.

Apartment in Mantica

Núcleo Urbano: Modern Apt 15th! Amazing City Views

Experience San José from a modern apartment with panoramic city views in the exclusive Núcleo Sabana complex. Fully equipped with Wi-Fi 5G, Smart TV, full kitchen, and private parking. Enjoy premium amenities including a pool, gym, sauna, lap lanes, multi-sport court, karaoke room, and beautiful green areas. Located steps from La Sabana Park, and the National Stadium and any restaurants. Perfect for business travelers, couples, or anyone seeking comfort and style in Costa Rica’s lively capital.

4.95 out of 5 average rating, 146 reviews

The kitchen features modern appliances, including a black refrigerator and built-in oven. A small island with sleek stools offers additional seating. A plant adds a touch of greenery, while the light countertops contrast with the dark cabinetry, creating an inviting cooking space.

Condo in Mantica

Featured Apartment | 5 Stars Verified Reviews, AC

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.

4.98 out of 5 average rating, 123 reviews

A spacious deck is framed by sleek metal supports, providing panoramic views of the surrounding landscape. Lush greenery is visible in the foreground, while the sky is adorned with fluffy clouds. Potted plants and a smooth stone pathway lead into the inviting outdoor space.

Villa in Turrialba

Stunning Views • Complete Privacy • Adventures

Escape to one of Costa Rica’s most breathtaking private retreats—just less than 2 hrs from San José Airport (SJO). Set on lush mountain grounds with a waterfall, pool, and stunning panoramic 180° views, this peaceful haven offers total privacy, modern comforts, and space to unwind. Surrounded by tropical fruit trees and nature, it’s perfect for both relaxation and adventure. There are lots of fun activities nearby for the whole family. Unplug, recharge, and experience an unforgettable stay.

4.78 out of 5 average rating, 174 reviews

A textured stone wall forms the backdrop, with a sturdy wooden door prominently displayed. A simple wooden bench sits against the wall beside a small table draped in a floral tablecloth. Potted plants add greenery, contributing to the inviting outdoor space.

Apartment in Guacimo

Ambiente cálido rodeado de naturaleza

Apartamento tipo estudio con entrada independiente, baño privado, 2 camas individuales y la posibilidad de colocar un colchón de aire adicional. Ubicado en una zona llena de naturaleza , hermosos paisajes, cataratas y ríos. Por su ubicación es el lugar ideal de descanso si viene o va para las playas del Caribe, Tortuguero, si se dirige a la zona de la Fortuna, Volcán Arenal. El apartamento es pequeño ideal para un máximo de 3 personas, contamos con piscina ecológica de agua 100% natural.

4.93 out of 5 average rating, 315 reviews

Condo in Rohrmoser

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.

A contemporary kitchen area is visible, featuring a kitchen island with a stovetop. Shelves display glassware and decorative items. A cozy seating area is placed nearby, complemented by natural light filtering through sheer curtains. Greenery is suspended from the ceiling, adding a fresh touch.

4.95 out of 5 average rating, 168 reviews

Modern Cozy Apartment, Amazing Amenities

Steps from La Sabana Metropolitan Park and the National Stadium, this modern, quiet 12th-floor apartment is ideal for couples and digital nomads. You’re minutes from downtown San José with easy access to restaurants, cafés, bars, and museums. Designed around a signature coffee bar—perfect for slow mornings, focused workdays, or a cozy night in. Check in anytime via the 24/7 lobby (quick registration), then enter with a digital door lock. Enjoy a dedicated desk and fast 196 Mbps Wi-Fi.

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, 146 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.

4.92 out of 5 average rating, 143 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.

Apartment 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.

4.91 out of 5 average rating, 184 reviews

A modern two-story cabin is set amid lush greenery. Large windows invite natural light, while a wooden exterior complements the surrounding forest. A welcoming entryway features a simple design, enhancing the serene atmosphere of the property.

Cottage in Turrialba

Estancia Natural con Vista Panorámica en Turrialba

Bienvenidos a Estancia Refugio, tu oasis de tranquilidad en medio de la exuberante naturaleza de Turrialba, Costa Rica. Nuestra cabaña es el lugar perfecto para desconectar del bullicio diario y reconectar con lo esencial. English: Welcome to Estancia Refugio, your oasis of tranquility in the midst of the lush nature of Turrialba, Costa Rica. Our cabin is the perfect place to disconnect from the daily hustle and reconnect with the essence of our being.

4.97 out of 5 average rating, 104 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.

4.86 out of 5 average rating, 146 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.

Popular amenities for Guapiles 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, 27 reviews

The spacious living area features a neutral-toned sofa facing a wooden coffee table. A woven area rug anchors the seating space. Natural light filters through large windows, illuminating indoor plants and a dining table set for several guests. Modern light fixtures hang above.

Home in San Pablo

Casa Relax en Condo Costa Rica

Home in Santa Bárbara de Heredia

A serene outdoor view captures a vibrant landscape illuminated by soft garden lights at night. The distant city lights shimmer in the background, while a peaceful lawn and scattered trees frame the scene. The silhouette of the home blends into the tranquil environment.

4.71 out of 5 average rating, 7 reviews

Casa Luna Bianchini - Enchanted Retreat

5 out of 5 average rating, 3 reviews

Home in San Roque

Nebulae - Water Cube Suite

4.92 out of 5 average rating, 12 reviews

The exterior of the house features a covered porch area with two brown chairs positioned on a grassy lawn. The patio is enhanced by umbrellas, providing shaded seating options. The property is surrounded by low-maintenance shrubs and greenery, contributing to the relaxed outdoor atmosphere.

Home in La Colonia

Chill, Relax & Enjoy in a 11 bed 5 washroom house

4.96 out of 5 average rating, 47 reviews

The cabin features a bright turquoise roof, surrounded by dense green foliage. A welcoming porch is visible, with a small seating area. Two cars are parked in front of the cabin, providing easy access. The overall setting reflects a harmonious connection with nature.

Home in Guapiles

Cabaña Río Blanco: Cabin with private river access

Home in Puerto Viejo de Sarapiqui

A natural swimming pool is surrounded by lush greenery and rocks, creating a serene atmosphere. A waterfall feature adds to the ambiance, while hammocks and seating areas are visible nearby, inviting relaxation in a tranquil outdoor setting.

4.85 out of 5 average rating, 72 reviews

Casa Sonidos Del Bosque

5 out of 5 average rating, 12 reviews

An outdoor dining area features a wooden table draped with a light blue cloth, surrounded by colorful chairs. In the background, a seating arrangement is visible with four wicker chairs and striped cushions. Sunlight brightens the space, showcasing the nearby swimming pool.

Home in Bejuco District

Condominio Playa Bejuco 243

4.89 out of 5 average rating, 84 reviews

An inviting infinity pool is surrounded by lush greenery and offers views of the landscape. A shaded seating area is visible nearby, furnished with comfortable chairs and a table, providing a perfect spot for relaxation and outdoor dining.

Home in Turrialba

Volcano Views-close to hiking-waterfalls-kayaking

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.

4.87 out of 5 average rating, 253 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, 177 reviews

Concrete Jungle Experience 25th Floor Secrt Sabana

A city skyline is viewed at night, showcasing illuminated buildings and the distinctive architecture of a nearby stadium. The lights of the city create a vibrant atmosphere against the dark sky, emphasizing the scenic urban landscape.

4.88 out of 5 average rating, 190 reviews

AC and King Bed - Full Equipped Apartment

4.94 out of 5 average rating, 159 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 Jose, La Sabana, Del Lago

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, 134 reviews

Joya Urbana en el piso 30; SECRT

4.91 out of 5 average rating, 132 reviews

A modern living area features a spacious gray sofa adorned with a vibrant yellow pillow. A large flat-screen TV is mounted on the wall above a wooden media console. The sleek kitchen is visible in the background, showcasing stainless steel appliances and a marble countertop.

Condo in Uruca

Apartamento Flofy - Piscina - Parqueo - Seguridad

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, 332 reviews

Alicia's Garden Apartment at Secrt

4.94 out of 5 average rating, 108 reviews

The outdoor pool area is visible, featuring a well-maintained blue swimming pool under a partly cloudy sky. Surrounding the pool, planters with greenery add a touch of nature, while the skyline of nearby buildings can be seen in the background.

Condo in Rohrmoser

Modern & Cozy Apartment!

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, 61 reviews

Sunsets & Style — Modern Stay in Trendy Escalante

4.94 out of 5 average rating, 48 reviews

An outdoor area features two wooden chairs set beside a serene pool, reflecting the city lights below. A tall plant stands in a pot, adding greenery to the scene. The nighttime sky, filled with clouds, enhances the view overlooking the city.

Apartment in Curridabat

Loft Ifreses Curridabat con A/C y cama King Size

4.76 out of 5 average rating, 55 reviews

A circular swimming pool is surrounded by a wooden fence, complemented by vibrant yellow foliage. Lush greenery is visible in the background, framing the scene with tropical plants and palm trees, creating a secluded outdoor space for relaxation.

Cottage in Siquirres

Quinta Sandoval Piscina, Bosque, Rio, Teletrabajo

5 out of 5 average rating, 71 reviews

A swimming pool is set in a garden area, surrounded by lush greenery and vines. Two lounge chairs sit beside the pool. In the background, hills and a volcano can be seen beneath a cloudy sky, adding natural beauty to the tranquil setting.

Farm stay in Turrialba

Spacious Farmhouse with Pool & Exotic Gardens

5 out of 5 average rating, 27 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

Apartment in Uruca Centro

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, 46 reviews

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

4.9 out of 5 average rating, 96 reviews

A spacious house with a red tile roof is framed by lush greenery and surrounded by a large open area. The building features a blend of stone and wood materials, with expansive windows that allow natural light to fill the interior. A bright blue sky dotted with clouds serves as the backdrop.

Farm stay in Turrialba

Casa Lajas - farm experience, pool natural water.