
Holiday rentals with a pool in Guaynabo
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Top-rated rentals with a pool in Guaynabo
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

Villa Maxine Retreat: Mountainview Escape
Sits on a quiet mountaintop with stunning views, the perfect sanctuary for conscious families and facilitators seeking rest, grounding, and reconnection. Wake to birdsong, fall asleep to coquí under the moonlight—and all just 20 minutes from the airport. A private pool at the heart of a serene courtyard, thoughtfully designed for indoor-outdoor flow and nourishing energy. This is more than a stay—it’s a space that holds you. Maximum 6 guests No parties No self check-in A/C in bedrooms only

La Pompa Beach House Beautiful Residence with Pool
Whether it's work or a family experience, it's the perfect place. This beautiful property has an excellent location minutes from Punta Salinas Beach and steps from restaurants, supermarkets, pharmacies and nightclubs. La Pompa Beach House is an Eco friendly residence that operates and produces solar energy. Fun, Elegance and Hospitality is a priority that is why we have a beautiful kitchen, private pool, luxury rooms, GYM equipment, parking plus work area. Close to highway and Old San Juan.

Vista Linda Haus
At Vista Linda Haus, from the moment you start the journey to the beautiful town of Gurabo, the adventure begins. A unique experience towards the favorite destination. You will find panoramic landscapes, lakes, mountains, farms, cities, and a community with the Puerto Rican warmth of our mountains. Just 35 minutes from the Luis Muñoz Marín International Airport, over 1,000 feet above sea level, you will breathe freedom and peace, in a harmonious environment full of energy and pure nature.

Super comfortable Family Home w/ private pool
Welcome to our exclusive property located in a private community with 24/7 security, just 15 min from Old San Juan, Condado, touristic places. Only 20 min from SJU Airport. Furnitures, decoration and equipment were chosen to be of the outmost comfort and everything in the house is new. There are TVs with cable TV in all rooms and WiFi available. Patio is nice with large pool & BBQ area to enjoy. Ideal for families and group of friends. This is NOT a young people's party home!

The Best View of PR with infinity pool with Heater
Campo Cielo, es el lugar perfecto para desconectarte y estar en completa conexión con la naturaleza. Disfrutarás del más bello amanecer, desde las montañas del Bosque Nacional El Yunque. Te relajarás y recargarás con aire puro y fresco, mientras te deleitas con la mejor vista en la piscina infiniti y en la terraza. La mejor experiencia para disfrutar de la naturaleza y sentirte a un solo paso del cielo, lo encontrarás en nuestro tesoro escondido, Campo Cielo Mountain Retreat.

Beautiful View Chalet
Enjoy the lovely setting of this romantic & magical cozy home . Hidden in the mountains of Naranjito . 45 minutes from the airport, you can immerse yourself in a unique, romantic experience in PR surrounded by nature. The view from the moment you enter our property is magical. Here you can find a hugely inspiring environment for your writing, reading, music, to spend quality time with your partner, to spend time alone. A magical place of art, peace, and inspiring.

Best location with pool, steps from beach!
Wake up in a luxurious king bed with premium bedding, gazing out at your private pool framed by lush palm trees. Start the day with breakfast from the fully equipped kitchen, then catch up online with blazing-fast Wi-Fi under the shaded pergola. Cool off in the pool or rinse in the outdoor hot shower before walking just 50 yards to San Juan’s best beach. Ideal for couples, solo travelers, remote workers, or small families seeking comfort and style.

Hidden Moon
We are the first independent concept experience hostel in Puerto Rico located in Barranquitas. We've designed a space that makes you feel like you're on the moon. We have a furnished black dome over 20 feet, an Infinity pool with heater, a fire pit, a relaxation waterfall, Wi-Fi, TV, movie apps, board games, and more. The experiences are fully controlled with Alexa. Every person who arrives becomes a tourist astronaut on the island.

Musa Morada | Creative cabin in the mountains!
The first and only creative cabin in Puerto Rico. Here you won't find unnecessary luxuries, but a space where the most beautiful things were not built by humans: the peace, harmony, and inspiration that those seeking a Reset in their life need. Sometimes all it takes is a hidden corner where you can reconnect with yourself, let nature speak to you and let your creativity flow. Connect and create. Welcome to Musa Morada!

Luxury waterfront villa with dock and heated pool
Villa Jade is a unique luxury waterfront retreat with a heated saltwater pool, jacuzzi, and private dock to a serene lagoon. It is just 10 minutes from SJU Airport and the fabulous beaches of Isla Verde. Three spacious bedrooms with private baths. Fully remodeled. Equipped with a generator and cistern for peace of mind. As a dedicated 5-star host, I’m here to ensure a smooth, relaxing stay. Welcome!

Villa Estrella PR (near Airport & Beach)
Diviértete con toda la familia en este alojamiento con estilo. Esta cerca de todo lo esencial como el Aeropuerto y Playas (5 minutos), Viejo San Juan, Plaza Las Américas (15 minutos). Localizado cerca de varios restaurantes con prestigio como Bebo’s BBQ, Metropol, y el área turística de Piñones donde podrán encontrar comida típica de nuestra isla.

Secret Dome 2 with a view of the lake
Reconnect with nature at this unforgettable escape. Secret Glamping was born from two 100% Puerto Rican people, entrepreneurs and lovers of the innovative. Our desire is to ensure that guests can connect with nature, peace and tranquility, as well as delight in the beautiful views and landscapes of our surroundings.
Popular amenities for Guaynabo rentals with a pool
House rentals with a pool

Case Del Sole Duplex w/ Solar-Powered Backup

MY BEAUTIFUL SUMMER

The Heart of Caguas

Unique luxury house-Private pool-Power generator

Turquoise Villa Private pool nearby airport

The Leaves Apartments #2

Nena’s place, Carolina PR w electric generator

Casa Kenia
Apartment rentals with a pool

Isla Verde Beach-Pool/New/ Downtown

Amazing Designer Beach Front Loft Apt Open Space

Isla Verde-Alambique Beach Modern Condominium

Pink Bliss Studio ISLA VERDE

Palms & Ocean View 1br 1bth + Pool + Beach Access

💕Ocean Front Isla Verde Beach Remodeled Pool Pkg

Amazing Beachfront Suite: King Bed/Full Kitchen

ESJ Tower beachfront airport free park amazingView
Other holiday rentals with a pool

Guaynabo, Private pool, billiard 🎱room, jacuzzi.

Family-Friendly Peaceful Jungle Oasis with POOL!

⭐️Casa De Las Palmas 🌴🌴

Charming Tree House with a Pool

La Casita de Moncha

La Gloria

Chalet De Los Vientos (Chalet of the Winds)

Paseo Arce Guest House #1 · Modern & Open-Concept
Quick stats about holiday rentals with a pool in Guaynabo
Total rentals
50 properties
Nightly prices starting at
$26 SGD before taxes and fees
Total number of reviews
2K reviews
Family-friendly rentals
40 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Destinations to explore
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- Rentals with pools Puerto Rico
- Mosquito Bay Beach
- Liquillo Beach
- Praia de Luquillo
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- Playa del Dorado
- Playa Mar Chiquita
- Distrito T-Mobile
- Playa de Vega
- Playa Puerto Nuevo
- The Saint Regis Bahia Golf Course
- Playa Sun Bay
- Rio Mar Village
- Peñón Brusi
- Toro Verde Adventure Park
- Coco Beach Golf Club
- Los Tubos Beach
- Carabali Rainforest Park
- Playa Maunabo
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- Punta Bandera Luquillo PR
- Playa el Convento
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- Beach Planes
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