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

Total holiday rentals
Explore 40 holiday rentals in Guapiles

Nightly prices starting at
Guapiles holiday rentals start at $13 SGD per night before taxes and fees

Verified guest reviews
Over 620 verified reviews to help you choose

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

Pet-friendly holiday rentals
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
30 of Guapiles holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Guapiles rentals

4.7 Average rating
Guapiles stays receive an average rating of 4.7 out of 5 from guests
Top-rated rentals with a pool in Guapiles
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

SECRT Escalante · 19th Floor · View + Parking
Modern apartment in the heart of Barrio Escalante, a top dining area in San José. Apartment 1907 on the 19th floor offers city views, 1 bedroom with queen bed and AC plus sofa bed in living room, 1 bathroom and . Building with 20+ amenities: pool, gym, coworking and social areas. Private parking inside the building included. Ideal for couples, business travelers and tourists. Due to the central location, occasional city noise may be heard. Fast 300 Mbps WiFi, self check-in and 24/7 security.

The Gourmet Terrace & Coffee View w/AC
Newly renovated space, located in the heart of the city. Barrio Escalante will not only show you one of most iconic & trendy neighborhoods of San José, it is also one of the greatest gastronomical places in the San José. If you like the experience of walking around, discovering amazing places to have Breakfast & Brunch, or a good lunch, or having cocktails in one of the highest rooftops in town or grabbing a late dinner with great music & wine, in a distinctive environment. This is for you.

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.

Bö Escalante 507
Stylish, Calm, Relax at this peaceful and centrally located studio apartment within Barrio Escalante. Zona Rosa de San José, just steps from this building, there are shops, restaurants, bars, cafes, theme stores, varied cuisine, and nearby you will have museums, parks, malls, cinemas, in short, it has an unbeatable location, in the center of everything. You can get around by car, bus, train, or taxi to other places, everything in the area is walkable, in one of the safest areas of the city.

A warm atmosphere surrounded by nature
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.

Chill, Relax & Enjoy in a 11 bed 5 washroom house
Escape to nature, our home has 4 bedrooms, 11 beds and capacity for 14 people. Ideal for couples, families, events up to 50 people. Enjoy spacious green areas, bbq areas and a cozy living space. the back of the property consists of a beautiful relaxing river, the front of the property features a fire pit area for roasting marshmallows there also is a play area for preteens, for teens & adults we offer a basket ball area for some 1v1 & lots of space in the back to kick around a soccer ball

House in Sonidos del Bosque
Consiéntete en una estancia única donde solo escucharás la naturaleza. Se encuentra en una propiedad de 10000m2, tiene como objetivo conseguir que tu visita sea lo más relajante posible. Es el refugio perfecto para desconectarte. Cuenta con una piscina 100% natural y riachuelos con peces. Fácil acceso a las principales atracciones de la zona. Cuenta con: Casa equipada para 7 personas y apartamento independiente para 4 personas. Ideal para quienes buscan privacidad, confort y tranquilidad.

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

cabaña privada con piscina cerca del Río Corinto#2
Disfruta de una suite privada con dormitorio, baño y cocina equipada con todas las comodidades. El espacio cuenta con aire acondicionado, ducha y todo lo necesario para una estancia cómoda. También podrás disfrutar de amplias zonas verdes y piscina compartida con otros huéspedes, rodeado de vegetación y aves que crean un ambiente tranquilo para conectar con la naturaleza. El ingreso a la propiedad cuenta con portón eléctrico y cámaras de seguridad para mayor tranquilidad.

Warm studio in Barrio Escalante
Experience Barrio Escalante, the city's most vibrant and gastronomic area. This apartment combines elegance and comfort, offering you an ideal space to rest after exploring unique restaurants, cafes and bars, all just steps from your door. All on the 13th floor with a beautiful view of the best sunsets and without neglecting the possibility of having access to highways that connect with other nearby tourist destinations, such as volcanoes, mountains and beaches.

Fully-Eqpd 2BR 2BA in Luxury GC w/Pool+Gym+24/7Sec
Welcome to Apartment 406, your stylish 786ft² (73m²) sanctuary in Costa Rica—the largest unit in the Bambú Rivera Residential Complex! Perfect for digital nomads and vacationers, this modern 2-bedroom apartment is fully equipped for a comfortable stay. With 24/7 security and a wealth of amenities, you're just a short distance from the city center and its attractions. Whether you're here to work, explore, or unwind, this is the ideal home base for your trip.

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.
Popular amenities for Guapiles rentals with a pool
House rentals with a pool

Rancho Roca Fuerte. House sourrounded by nature

Hacienda Cacaotera in front of the forest

Caribbean Pearl Villa • Pool, Games & Relax

Casa Linda Vista – Turrialba

La Parada House

A house of relaxation and nature.

Tico House Villa Complete

Casa Rincon de Paz - Pool & BBQ & A/C & Wi-Fi
Apartment rentals with a pool

Coffee in the balcony

Bö-hemian 1201

Bo-Escalante. Parking, A/C, WiFi, Pool, Gym

¡Vive con estilo en San jose TIBAS! Apartamento.

Brand new top floor fully equipped apartment

Luxurious Mountain-View Condo

Apartment in Bö Escalante

WoodRechelle:Cozy, Elegance
Other holiday rentals with a pool

Cabin #4 with one bed – La Pochita Cabins

beautiful view 901

Vino Spot - AC-Free parking

Escalante Relax 12th

Modern Stay Near Airport • Pool, Gym & Rooftop

Modern Stay in the Trendiest District of San Jose

Zen Studio

Luxurious Apartment
When is the best time to visit Guapiles?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $96 SGD | $96 SGD | $96 SGD | $92 SGD | $96 SGD | $96 SGD | $96 SGD | $96 SGD | $80 SGD | $80 SGD | $96 SGD | $96 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 |
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- Rentals with pools Costa Rica
- La Sabana Park
- National Stadium of Costa Rica
- Poás Volcano National Park
- Parque Diversiones
- Parque Nacional Braulio Carrillo
- Parque Viva
- Irazú Volcano National Park
- Parque Nacional Los Quetzales
- Turrialba Volcano National Park
- University of Costa Rica
- Children’s Museum
- Catarata del Toro
- Pre-Columbian Gold Museum
- City Mall Alajuela
- San Jose Central Market
- Jade Museum
- Britt Coffee Tour
- Parque Central
- Multiplaza Escazú
- Hacienda Alsacia Starbucks Coffee Farm
- Río Agrio Waterfall
- Multiplaza Curridabat
- Plaza de la Cultura
- Basilica De Nuestra Señora De Los Ángeles




