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

Total holiday rentals
Explore 30 holiday rentals in San Juan

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

Verified guest reviews
Over 910 verified reviews to help you choose

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

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wifi availability
30 of San Juan holiday rentals include wifi access

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

4.8 Average rating
San Juan stays are highly rated by guests – averaging 4.8 out of 5!
Top-rated rentals with a pool in San Juan
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

Cheerful private 4-Bedroom Villa. Heated pool A/C
For a group or a cozy couple, this bright and spacious home delivers comfort and style. Located in a quiet, modern, and safe neighborhood, you’re just minutes away from downtown. Great restaurants are close by and a block away from new Microsoft tower. 4 bedrooms (A/C), sleeps up to 9 , 3 full bathrooms & private heated pool. Fully equipped modern kitchen, stocked with staples and more. Starts at $195 per night for up to 4 guests, $35 per extra guest. Cleaning included. Come dive into city life.

NucleoSab IvoryApt-NearSJairport-FreeIndoorParking
Brand new luxury apartment at Nucleo Sabana. It has a minimalist style with all the appliances brand new, including A/C, 2 smart TVs. High speed internet with TVservice. Laundry room includes a washer/dryer, 2 in 1. It has a wonderful view to the top of the trees and the sky in the balcony. There is a river next to it so you can always enjoy the river sound. Complex: More than 30 amenities, including a gastronomic market(NucleoGastro). Located 10min from Juan Santamaría Int’l Airport (SJO).

Charming Apartment w A/C Near to the Int. Airport
Bienvenido a este encantador y elegante apartamento, en el piso 24; con una decoración exquisita Cuenta con dos cuartos, con camas de alta calidad: una Queen y otra matrimonial. Y un sofá cama en la sala 1 espacio de parqueo La cocina está completamente equipada. Disfruta de tus habilidades culinarias con tus seres queridos La torre cuenta con extraordinarias amenidades como piscina temperada, gimnasio y cuartos temáticos Aeropuerto: 16 km, aproximadamente 35 minutos, dependiendo del tráfico

15th Floor Apt / Amazing Views • 20 min to Airport
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.

Escazú Studio w/ pool, nature & spectacular views
A Cozy, Stylishly appointed Studio, tucked into a 2-Acre Estate w/ one of the most Breathtaking Views in Costa Rica. It is sanctuary for Value-Conscious Solo Travelers, Digital Nomads, Medical Tourists or a Romantic Get Away. "Earth & Sky - Costa Rica" has 3 Boutique Listings and features a Sparkling Heated Saltwater Pool, Bright Gardens and Beautiful Terraces. The "Sugar Shack" is our most Budget Friendly space - peaceful and private, but minutes away from popular restaurants and shopping.

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.

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.

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!

City view, A/C near the airport, 1903
It is an apartment with an excellent distribution and a modern and contemporary aspect, located near the La Sabana Metropolitan Park, an area with excellent restaurants, entertainment venues, and very close to shopping centers, Juan Santamaría airport, etc; It is on the 19th floor, with a view to the east, the mountains and the city steal the show at all hours of the day, without a doubt the sunset and night are the favorites for their colors and lights.

Apartment in Escalante Olive Loft 14th
A modern and elegant studio on the 14th floor, with an amazing sunset view. Located in the heart of Barrio Escalante, close to bars and excellent restaurants with a wide variety of cuisine, opposite one of the 100 best cafés in the world. Perfect for couples, solo travelers or digital nomads looking for comfort in a safe and walkable location. Escalante is the cultural and gastronomic epicenter of San José, with active local life at any time of the day.

Exclusive Tuscan Mansion in CR
Our Italian-Styled mansion is nestled among a lush mango-tree forest in gorgeous Santa Ana only 20min from airport. Features: - Indoor Pool (Heating Upon Request $100 extra per day and requires 24 hours of heating prior to use) - 6 Bedrooms - 6 Bathrooms - Large Living Areas - 5 min from highway 27 to beaches & rainforests - 15 min from Escazu and CIMA Hospital - 24/7 armed security - Huge Green Areas Heavenly!

Curated Luxury Stay on the 22nd Floor
Bienvenido a una experiencia sofisticada y cuidadosamente diseñada en el corazón de URBN Escalante. Cada espacio fue pensado para ofrecer una experiencia cálida, refinada y llena de estilo, combinando decoración cuidadosamente seleccionada, acabados modernos y una atmósfera acogedora que hace sentir el apartamento verdaderamente especial.
Popular amenities for San Juan rentals with a pool
House rentals with a pool

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

Casa de Colores, 2B/2B, Athens, Alajuela CR

Casa Gaudi🦚Near SJO🦚Private Pool & King BD

Villa Bugambilia: Large colonial villa with a pool.

Lux Stay Near SJO Airport | Pool, Firepit & Views

Casa Delios, Luxury Near the Airport, Private Pool

Beautiful house with pool in Heredia Centro

Smart loft in the heart of the city, A/C and Wi-Fi
Apartment rentals with a pool

Estudio c/ vista, balcón y parqueo gratis · URBN

Luxury Apartment, San José, La Sabana, Del Lago

The Madriguera Serena/ SECRT Sabana.

Comfort with A/C in the heart of La Sabana

Amazing Apart SECRT Sabana/ AC+Gym+Swimming pool

Urban Jewel on the 30th floor; SECRT

Unique Apartment in a New and Modern Condominium

The Gourmet Terrace & Coffee View w/AC
Other holiday rentals with a pool

Nebulae - Water Cube Suite & YogaDeck

Tropical-inspired urban retreat on the 22nd floor

Airport Apt/floor16 AC+Paking+Rooftop views +Tours

SECRT Escalante · 19th Floor · View + Parking

Premium | Balcony | Pool | Gym | Centric | A/C

Couples Focused Magnificent Studio Apartment

20th floor king bed apartment with A/C San José

Endless charm - Heart of the Central Valley
When is the best time to visit San Juan?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $80 SGD | $71 SGD | $68 SGD | $72 SGD | $74 SGD | $63 SGD | $68 SGD | $76 SGD | $71 SGD | $79 SGD | $84 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 |
Destinations to explore
- Smoking-friendly rentals San Juan
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- Rentals with a firepit San Juan
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- Family-friendly rentals San Juan
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- Rentals with a patio San Juan
- Rentals with a washing machine and dryer San Juan
- Flat rentals San Juan
- House rentals San Juan
- Rentals with pools San Jose Province
- Rentals with pools Costa Rica
- Jaco Beach
- Playa Blanca
- Parque Nacional Manuel Antonio
- La Sabana Park
- National Stadium of Costa Rica
- Parque Viva
- Parque Diversiones
- Marina Pez Vela
- Poás Volcano National Park
- Parque Nacional Braulio Carrillo
- Parque Nacional Los Quetzales
- University of Costa Rica
- Playa Jacó
- Turrialba Volcano National Park
- Carara National Park
- Multiplaza Escazú
- El Miro
- Children’s Museum
- Parque Central
- Hacienda Alsacia Starbucks Coffee Farm
- Britt Coffee Tour
- La Cruz del Monte de la Cruz
- Multiplaza Curridabat
- City Mall Alajuela





