Vacation rentals with a pool in Guaynabo

Green Nest at the Hills

Green Nest is a luxurious home with dreamy views, located in one of the most exclusive gated communities in Puerto Rico’s metro area. Surrounded by lush rainforest, it offers a peaceful escape from the city—without ever leaving it. With elegant European architecture, five bedrooms, a private pool, generator and spacious indoor-outdoor living areas, it’s perfect for families or groups seeking privacy, comfort, and an unforgettable island stay. Experience Green Nest where magic meets the island. ✨

Value · Family · Indoor spaces

Beautiful home in San Juan

Located just 15 minutes from the airport closed to all the amenities and major roads you need be at ease and enjoy the island. House is in a gated community with surveillance 24/7 The home features unobstructed views of the city from your huge back yard with a professional maintained landscaping for your enjoyment. The house is equipped with an automatic solar panels with a Tesla battery back up system as well as 500 gallons water tank reserve so the property will function at 100% all the time.

Location · Family · Quiet

Guaynabo, Private pool, billiard room.

Beautiful and modern house located in Guaynabo, one of the most popular cities of the metro area. Walking distance from the Torrimar train station, pharmacy, supermarket and gas station. Three minutes drive from Costco Los Filtros and the Bayamon Golf Course. Easy access to the Martinez Nadal highway; 15-20 minutes drive to Old San Juan, popular beaches, airport and 10 minutes drive to Plaza Las Americas Shopping mall. It includes full facility, Wi-Fi, 24-hour security in a gated neighborhood.

Value · Family · Pool

Amapola House with pool (near the city)

My grandparent's 50 years house is located in Guaynabo in a family gated area (country area). 15 minute drive to San Juan, beaches, mall and mayor roads to initiate a trip anywhere on the island. The house was remodeled with love and care. A few original items were left to reconcile with the new. Surrounded by nature, flowers, birds. A one-story house perfect for those in search of some fresh environment away from the city stress but close enough to get everything you need thru a short drive.

Location · Family · Quiet

⭐️Casa De Las Palmas 🌴🌴

Breathe, relax and enjoy Casa de las Palmas, surrounded by beautiful palm trees that characterize our island of Puerto Rico. Live life, and stay where locals do. Open, bright, and spacious 3-bedroom/2.5 bathroom property located in the city of Guaynabo, about 12-18 minutes from Old San Juan and Condado. Very safe and upscale neighborhood with restaurants, shops, gas stations, and supermarkets walking distance or 5 min by car. Easy access to main road leading directly to Old San Juan.

Value · Family · Accuracy

Metropolitan Stylish Retreat

Early check-in (3pm) available subject to bookings. Enjoy a stylish experience at this centrally-located place. Just 7 minutes from Old San Juan and 12 minutes from the airport makes this place your perfect place to relax and enjoy. Outdoor/Indoor space with Pool Table and Heated Pool that will amaze you. Next to shopping malls, restaurants and many other places to enjoy. Two parking spots available on weekdays. Uber/Taxi readily available and recommended. Power generator included.

Family · Value · Cleanliness

We have water! Pool House • 3BR/2BA • Family Stay

Relaxing and Cozy Oasis with a Private Pool and BBQ and perfect location. Enjoy a cool,relaxing oasis with a private pool, patio area and BBQ on your trip to PR. This tropical and cozy home will fit up to 7 guests. The patio area with trees views is perfect to enjoy a pool day. This beautiful designed house offers cozy details and the warmth that only a tropical house would. This is pet friendly house with 24 hours check in. You’ll love staying at La Casita de Moncha.

Family · Location · Hospitality

Spacious Family Jungle Oasis with POOL! Sleeps 10

Forget your worries in this spacious and serene getaway in the mountains of Guaynabo - one of Puerto Rico’s most desirable neighborhoods. Enjoy warm evenings grilling by the pool and cool mornings with a coffee listening to the sound of birds. This is a 4 bed/3.5 bath home. You are 20 minutes driving from the best restaurants and beaches and 30 minutes from Old San Juan. Access to 2 fully stocked kitchens (indoor and outdoor), gym, pool, laundry and beach gear provided.

Location · Value · Cleanliness

Nidus | Romantic Nature Apt + Private Round Pool

Welcome to Nidus, part of the Nova Spatia Collection — a curated series of design stays across Puerto Rico created for travelers who value serenity, beauty, and connection. Nidus is a romantic one-bedroom apartment surrounded by nature, offering the perfect balance between comfort, privacy, and style. Every detail — from the quartz kitchen to the private pool — was designed to help you slow down, breathe, and reconnect.

Value · Location · Accuracy

Seaside Villa with private yard and pool

Escape to the San Juan Bay in this stunning waterfront property. Recently renovated with all new amenities including A/C, kitchen, and bathroom. Relax by the pool with stunning views of the bay. Located in a peaceful residential neighborhood, just 10 min from Casa Bacardi & 5 min from the $1 Cataño ferry to Old San Juan. Immerse in local culture & enjoy breathtaking views in this serene oasis. Book your stay today!

Value · Location · Laundry

Villa w Pool/Mountain View Near Airport San Juan

Escape to a serene 3-bedroom mountaintop villa in Puerto Rico with stunning views, just 20 mins from San Juan. Perfect for 6 guests, this sanctuary features a private courtyard pool with a waterfall. Enjoy the blend of peaceful seclusion and city convenience. Bedrooms have AC, dedicated workspaces, and reliable Wi-Fi. A unique retreat for families or facilitators seeking rest and reconnection.

Location · Family · Beach

Intimate Paradise- Private Pool, Terrace & Comfort

Enjoy our spacious home with a large patio and private pool. With 2 king beds, 2 queen beds, and a bunk bed, each room includes a private bathroom for total comfort. The house features solar panels and a backup battery for a reliable stay. Located in a secure gated community, you’re just 15 minutes from the beach and airport, offering both privacy and convenience for your getaway.

Value · Family · Walkability