Holiday rentals with a pool in Santa Rosa

Find and book unique homes with a pool on Airbnb

Quick stats about holiday rentals with a pool in Santa Rosa

Total holiday rentals
Explore 1,600 holiday rentals in Santa Rosa
Nightly prices starting at
Santa Rosa holiday rentals start at £7 per night before taxes and fees
Verified guest reviews
Over 75,270 verified reviews to help you choose
Family-friendly holiday rentals
600 properties offer extra space & child-friendly amenities
Pet-friendly holiday rentals
Find 480 rentals that welcome pets
Rentals with dedicated workspaces
1,120 properties have a dedicated workspace
Wifi availability
1,570 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!

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

An inviting outdoor area features a private heated pool surrounded by tropical plants and potted flowers. Comfortable seating options, including a hammock and lounge chairs, are positioned around the pool, with a cozy dining area visible in the background under soft lighting.

Villa in Mata Redonda

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.

4.96 out of 5 average rating, 142 reviews

Top guest favourite

Villa in Orotina

Your Costa Rican Vacation, Elevated by Nature

Welcome to Quinta La Regia, a private family retreat where nature, comfort, and genuine hospitality come together. Just 45 minutes from SJO International Airport, Quinta La Regia is surrounded by lush tropical flora, wildlife, mountains, and the breathtaking beauty of Costa Rica. Here, mornings begin with birdsong, afternoons invite you to slow down by the pool, and evenings end under unforgettable sunsets. But what makes Quinta La Regia truly special isn’t only the property- its our services.

4.97 out of 5 average rating, 132 reviews

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

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.

4.83 out of 5 average rating, 142 reviews

Top 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

Luxury Jungle Villa - 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 Starlink 250 Meg wifi allows you to "work from the jungle." Our cooks provide you with amazing meals made from local and farm ingredients. Visit!

4.93 out of 5 average rating, 353 reviews

Top guest favourite

A modern outdoor space is illuminated at night, featuring a glowing plunge pool with a waterfall. Colorful lights create an inviting ambiance. Comfortable seating is arranged under eaves, with plants adding a natural touch. The expansive view of the twinkling lights in the valley is visible.

Bungalow in San Rafael

Escazú Treetop Casita w/ Panoramic Luxury Views

Modern Loft-Style Casita w/ Private Terrace. 2-Acre Gated Estate in a Safe and Peaceful, Upscale Neighborhood -- One of the most Spectacular Views in Costa Rica. Expertly designed w/ every Creature Comfort -- All brand new and high-end. Ideal for Dental / Medical Tourists. Super Fast WIFI and Standing Desk for Digital Nomads. Full Kitchen, precisely stocked w/ everything you need to eat well. Sparkling Heated Salt Water Pool w/ Waterfall. Bright Gardens. Cool Breezes. Affordably Priced.

4.99 out of 5 average rating, 145 reviews

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

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.

4.99 out of 5 average rating, 109 reviews

Guest favourite

A contemporary cabin sits on a lush, green hillside, surrounded by trees and natural landscape. The structure features large glass windows, allowing for abundant natural light. The sun casts a warm glow over the scene, enhancing the serene and peaceful mountain setting.

Cabin in Santa Eulalia

Casa Balcón: secluded, pool & amazing views

Off-grid cabin in Costa Rica mountaintop. Disconnect from it all in this unique, secluded, off-grid home with spectacular views of the Central Valley and 4 of its surrounding volcanoes. Just a 40 minute drive from SJO airport and on the way to some of the most famous beaches, you can experience beautiful hiking trails, bird watching and taking a dip in the private pool, all in the comfort of this cabin which is completely powered by solar energy and supplied by well water.

4.95 out of 5 average rating, 117 reviews

Guest favourite

A modern home with large glass windows is positioned atop a hillside, surrounded by lush greenery. A sparkling pool occupies the foreground, while a landscaped area with palm trees and shrubs frames the space, leading up to the entrance of the house.

Villa in Grecia

Beautiful Mountain Views with Pool & A/C near SJO

Escape to our luxurious Costa Rican sanctuary! Immerse yourself in mountain-view bliss at our modern home with a sparkling pool and exclusive clubhouse. Just 35-40 min from the SJO airport, discover the ultimate in comfort with six air- conditioned bedrooms, seven beds, two living rooms, and more. Marvel at breathtaking 270-degree mountain views. Unwind in privacy and serenity. Book now for an unforgettable tropical experience for you and your family in Costa Rica.

4.95 out of 5 average rating, 111 reviews

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

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.

4.94 out of 5 average rating, 148 reviews

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

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.

4.99 out of 5 average rating, 160 reviews

Guest favourite

A private home is set in a lush garden, featuring a swimming pool framed by potted plants. The patio area is visible, offering seating arrangements with a covered terrace, showcasing the inviting outdoor space for relaxation and dining.

Villa

Casa Maria

Welcome to your own private oasis in Costa Rica! This beautiful home is in a guarded community that backs to an 18-hole golf course and includes a pool and a lovely private guest cottage, "La Casita". This home is also located in the Mesa Central area of Costa Rica, which is known for its fantastic weather; low humidity, the perfect temperature during the day, and a little chilly at night - no AC needed

4.94 out of 5 average rating, 174 reviews

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

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.

4.9 out of 5 average rating, 137 reviews