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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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Guest favourite
Villa in Santa Ana
4.95 out of 5 average rating, 186 reviews

Vista Oro Luxurious Villa Heated Pool 360 Views

Luxurious Mansion for a Fantastic price . Your Private Estate to enjoy,Located in the hills of Santa Ana , 25 mins from SJO airport . Perfect climate . 360 Spectacular Views Gourmet Chef Kitchen, Quality cotton linings ,beds , towels and furnishings Heated Salt Spa Pool , On Site Help ,24 hrs Security, Your Home in Paradise .10 mins Fine Dining , Supermarkets,Malls Entertainment , Private chef , Tours and driver services available .You will enjoy a Fantastic Memorable Vacation..Paradise ENJOY

Top guest favourite
A serene plunge pool captures reflections of the sky, with a gentle waterfall cascading into the water. Lush tropical plants frame the scene, while comfortable loungers invite relaxation. Expansive views of the mountains and sky create a tranquil backdrop.
Flat in Escazu
4.98 out of 5 average rating, 107 reviews

Sugar Shack @ Earth and Sky - Costa Rica

Tucked into the heart of a lush 2-acre Escazu Estate, this cozy, stylishly appointed 21 sq meter (216 sq foot) studio is ideal for the value-centric solo traveler, digital nomad or medical tourist seeking a quiet, safe refuge in an upscale neighborhood. The shared areas of the property offer a sparkling salt water pool, bright gardens and terraces with sweeping views. The Sugar Shack is close to everything, but perched above the hustle bustle below... a terrific home base for visits to San Jose.

Guest favourite
A spacious bedroom features a king-size bed adorned with soft pillows and a cozy throw. Large windows provide a view of the mountains, while a mounted television is positioned on the wall. Light-colored artwork decorates the walls, enhancing the room's ambiance.
Apartment in San José
4.9 out of 5 average rating, 213 reviews

Magical Penthouse in Prime Location+ Cima Hospital

If you are looking to stay in a great spacious Family-Business-Medical Visiting spot with amazing city and spectacular Mountains Views, in Escazu´s Prime Location,? THIS is your place! Close to dinning , 5 Minute Walking Distance to CIMA Hospital ( Best location to Medical - Dental - Pre Natal procedures. Business travelers will love easy highway access, local fusion restaurants and pubs, Entertainment and a bunch of Stores. Next to Avenida Escazu, on the 7th Floor, Elevator and Pool .

Guest favourite
An expansive infinity pool reflects the sky, merging seamlessly with the lush green landscape and distant mountains. The stone patio surrounding the pool adds a natural touch, enhancing the serene ambiance. Verdant trees frame the view, contributing to the tranquil setting.
Home in Atenas
4.83 out of 5 average rating, 140 reviews

Luxury Castle, Infinity Pool & Jaw Dropping Views!

The Luxury Castle is centrally located allowing you to take in the most tourist attractions while staying in a dream home for a great price! Close to the airport, the city center, parks, public transport, the beach, and art and culture. You’ll love the Luxury Castle because of the view from the pool, location, rooftop patio deck, the ambiance, the climate (Best in the World) and the detail in the designing and building of the house.There are many amazing restaurants in town with great prices.

Guest favourite
Two wooden chairs are positioned on a deck, facing a stunning landscape of lush green hills under a colorful sky. The view encompasses rolling mountains, with a misty ambiance adding to the tranquility of the scene.
Villa in San Mateo
4.93 out of 5 average rating, 334 reviews

Luxury Villa Ceibo - Exquisite, Private, Serene

Located just one hour from San Jose airport, Chilanga Costa Rica is the perfect place to start or finish your vacation. Spend some time to slow down, unwind and reconnect with nature. Ceibo is our private, spacious luxury villa with double occupancy. We offer a swimming pool with incredible views, jungle yoga and 10 KM of walking trails. Super fast 30 meg wifi allows you to "work from the jungle." Let our cook provide you with amazing meals made from local and farm ingredients. Come visit!

Guest favourite
Flat in Santa Ana
4.89 out of 5 average rating, 104 reviews

Peaceful Urban Escape • 1BR

✨ Welcome to Peaceful Urban Oasis — your cozy modern retreat of comfort and style! ✨ Relax in our bright one-bedroom apartment with pool, gym, and beautiful and tranquil garden. Enjoy super-fast WiFi, cable TV, a full kitchen, and in-unit laundry. Located in a safe, vibrant neighborhood within walking distance of restaurants, supermarkets, pharmacies, and shops — yet tucked away in a quiet area for restful nights. Perfect for business travelers, solo adventurers, couples, and families. 🌿

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, 106 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 private infinity pool, framed by lush greenery, reflects the sky above. The blue tiles create a vibrant contrast against the natural surroundings, while the expansive views of the mountainous landscape stretch in the background under a cloudy sky.
Flat in Ciudad Colón
4.93 out of 5 average rating, 156 reviews

Luxury New apartment! Infinity Pool! Adults only

Luxury Apartment with Private Pool and Stunning Mountain Views Escape to our brand-new, luxurious apartment, designed exclusively for adults. Nestled in a serene and safe mountain area, it offers breathtaking views and a quiet retreat. Enjoy your completely private pool on the spacious terrace, perfect for sunny days or peaceful evenings under the stars. Ideal for a romantic getaway or a chance to disconnect. Book now and experience comfort, privacy, and unforgettable views!

Top guest favourite
An infinity pool reflects the surrounding mountain vistas, flanked by a stone patio and decorative planters. A round stone feature is positioned on the lawn, complementing the tranquil outdoor atmosphere.
Villa in Atenas
5 out of 5 average rating, 102 reviews

Endless charm - Heart of the Central Valley

The beautiful Villa El Sueño is situated 8 minutes from the heart of Atenas and sits on a hill with expansive views of mountain ranges & the volcanoes of the central valley. It’s the perfect setting for a relaxing vacation and a great base for exploring the country. The house is a mix of Costa Rican hacienda and contemporary comfort. Carefully curated elements that are part of “Tico” culture and traditions have been incorporated to make this house a true Costa Rican experience.

Top guest favourite
A scenic view is captured from the property, showcasing lush greenery and rolling hills that extend towards the distant coastline. The sky is expansive, featuring soft clouds and bright blue hues, while a thatched structure stands nearby, complementing the natural surroundings.
Cabin in Jesús
4.94 out of 5 average rating, 125 reviews

Tierra Vital Athens - Villa 2

Welcome to Tierra Vital, your mountain retreat. Relax in our pool, enjoy the jacuzzi with stunning views or experience the thrill of our flying net. Located just 35 minutes from the airport and 10 minutes from downtown Athens, we offer tranquility and comfort in one place. Enjoy a walk to the beautiful nearby river, revitalize yourself with our yoga classes, or relax with a massage. Our ranch with BBQ is ideal for unforgettable moments in nature.

Guest favourite
The entrance of the mansion features a circular driveway enhanced by a central fountain, surrounded by landscaping and soft evening lighting. The façade showcases warm colors, with windows gently illuminated as the sun sets on the horizon.
Villa in San José
4.84 out of 5 average rating, 184 reviews

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!

Guest favourite
The loft features a spacious sleeping area with two queen beds, each adorned with decorative pillows. Wooden accents and ambient lighting create a calming atmosphere. Shelves and bedside tables flank the beds, and a fan enhances airflow in the room.
Loft in Santa Ana
4.98 out of 5 average rating, 134 reviews

Aranjuez Lofts - Tree Loft #6

Enjoy a wonderful tree inside the loft... Our Tree Loft #6, which we built around a tree, is one of our 12 Aranjuez Lofts located in Santa Ana. In a beautiful property with shared large garden and pool. Conveniently located upon walking distance to Santa Ana downtown, and to supermarkets, restaurants, movie theaters and much more.

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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