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Holiday rentals with a pool in Santa Rosa

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Santa Rosa

Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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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.
Serviced apartment in San Rafael de Escazú
4.82 out of 5 average rating, 161 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 ✨

Top guest favourite
Apartment in Rohrmoser
4.93 out of 5 average rating, 318 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.

Top guest favourite
A large, inviting pool is surrounded by lush greenery and colorful plants. Comfortable lounge chairs are positioned under umbrella shade near the pool. A covered patio area with a dining setup is visible in the background amidst the vibrant garden setting.
Flat in Ciudad Colón
4.89 out of 5 average rating, 102 reviews

Villa Kandelaria - A/C, Large Pool & Lush Gardens

Enjoy the experience of being surrounded by a lush garden full of colorful plants and palms. You will forget that you are close to the city when you stay in this one of a kind property. Enjoy the pool and ranch during your free time and you can even have fresh fruits off the trees. Villa KANDELARIA is a brand new unit perfect for the guest that needs to get away but still has nearby everything from the local health clinic, restaurants and grocery store. Perfect to work and enjoy paradise.

Guest favourite
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.
Apartment in Mata Redonda
4.95 out of 5 average rating, 169 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.

Top guest favourite
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
4.97 out of 5 average rating, 151 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.

Guest favourite
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
4.85 out of 5 average rating, 148 reviews

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.

Top guest favourite
A treehouse nestled among vibrant pink bougainvillea, overlooking lush greenery and distant mountains. The structure features a balcony where a person can be seen enjoying the view. Bright clouds add depth to the scenic backdrop of rolling hills.
Treehouse in Atenas
4.99 out of 5 average rating, 144 reviews

Treehouse on a Coffee Farm with Ocean View

Enjoy the authentic Costa Rican experience away from the tourist traps in a treehouse with beautiful natural views! The property is located in Atenas, just 45 minutes from San José International Airport, surrounded by rolling green hills and coffee farms and populated with plenty of wildlife. From our property, you can take in the views right from the pool, enjoy the best climate in the world, and spot a variety of animals.

Guest favourite
The exterior of the Poolside Villa is showcased, featuring a wooden deck that leads to a spacious entrance. Lush greenery surrounds the home, maintaining privacy and enhancing the natural setting. Large windows provide a view of the inviting outdoor space.
Villa in Escazu
4.9 out of 5 average rating, 360 reviews

Private villa with jacuzzi in Escazu

The Poolside Villa is a separate, private home located on our property.. The Poolside Villa has a deck, overlooking a beautiful garden and is only steps away from the shared pool and jacuzzi. Our property is located in the quiet neighborhood of Bello Horizonte, in the hills above Escazu. We are 15 minutes from San Jose, 15 minutes from the Escazu mall and Cima hospital, and 25 minutes from the international airport.

Top guest favourite
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.
Apartment in Rohrmoser
4.96 out of 5 average rating, 581 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

Guest favourite
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
4.89 out of 5 average rating, 128 reviews

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

Casa Peces is located in nice neighbourhood, near to. the best private hospital, shopping centers, Gastronomic areas , theatres, hipódromos la Cañada as well just 60min from volcanos, water rafting Pacuare River and the best beaches of Costa Rica. Beautiful contemporary Style family town home in Rio Oro, Santa Ana, with 4BR, 3 baths and private indoor pool.

Guest favourite
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.
Apartment in Rohrmoser
4.87 out of 5 average rating, 145 reviews

Fully equipped apartment in Nunciatura

One-bedroom Apartment completely equipped with a Queen bed and a queen sleeper sofa. With A/C. Beautiful neighborhood in the heart of the capital. The apartment is on the 4th floor, the same as most of the amenities. You can use the steam room and go back to get a glass of water or grab a drink from the refrigerator while you cook something in the BBQ area.

Guest favourite
A modern living area showcases a green sofa adorned with colorful cushions. Bright wall art featuring playful designs adds a lively touch. Large glass doors provide access to a balcony with expansive views, while a bedroom is visible through an open doorway, decorated with floral wallpaper.
Serviced apartment in Mata Redonda
4.94 out of 5 average rating, 406 reviews

Hideout in downtown San Jose

Inspired in the magical world of Alice in Wonderland, this brand new uniquely stylized apartment is a jewel. It is very conveniently located in downtown San Jose: 10 min from the National Theater and multiple eating venues, 90 min from the beach and very accessible by public transportation. Amazing views from the 21st floor and just waiting for you.

Popular amenities for Santa Rosa rentals with a pool

Quick stats about holiday rentals with a pool in Santa Rosa

  • Total holiday rentals

    Explore 1,510 holiday rentals in Santa Rosa

  • Nightly prices starting at

    Santa Rosa holiday rentals start at $13 SGD per night before taxes and fees

  • Verified guest reviews

    Over 68,410 verified reviews to help you choose

  • Family-friendly holiday rentals

    660 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 490 rentals that welcome pets

  • Rentals with dedicated workspaces

    1,130 properties have a dedicated workspace

  • Wifi availability

    1,470 of Santa Rosa holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Santa Rosa rentals

  • 4.8 Average rating

    Santa Rosa stays are highly rated by guests – averaging 4.8 out of 5!

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