Holiday 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. ✨

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.

Guaynabo, Private pool, billiard 🎱room, jacuzzi.

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.

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

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.

Family-Friendly Peaceful Jungle Oasis with POOL!

Escape the hustle and bustle at this unique and tranquil jungle 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 2 bed/2 bath guest suite, it is a house divided into 2 units. You are 20 minutes driving from the best restaurants and beaches and 30 minutes from Old San Juan. Fully stocked kitchen, gym, laundry and beach gear provided

Near SJU Airport, Old San Juan & Train to Choli!

Relax by the refreshing pool and enjoy prime access to San Juan’s highlights: explore Old San Juan, shop at Plaza Las Américas, grab essentials at 24/7 supermarkets, or ride the Urban Train with direct connection to the Choli. Your peace of mind is ensured with secure access control, three elevators, and private parking. Whether for business or leisure, you’ll love the comfort and quick connections to highways, nearby beaches, parks, and vibrant cities. Experience San Juan like a local!

⭐️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.

Peaceful Retreat with Heated Pool & Private Cabana

Escape to your own private paradise in this serene oasis featuring a heated pool and a stylish cabana. Whether you're enjoying a peaceful morning swim or hosting friends for an evening under the stars, this tranquil retreat combines comfort and luxury. The cabana offers shaded lounging, ambient lighting, and cozy furnishings, while the heated pool ensures a perfect dip no matter the season. Ideal for couples, families, or anyone seeking a peaceful escape with resort-style amenities.

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!

La Casita de Moncha/Pool/Family/BBQ

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.

Urban Forest Getaway in San Juan

Beautiful getaway home in an Urban Tropical Forest in Guaynabo, Puerto Rico. Every room equipped with A/C and Blackout curtains so you can get the best rest possible whenever needed, also TV and Internet available in every room. while outside, just Relax or have fun at this Great front terrace with Pool, this place is just perfect for hangout with family and friends, surrounded by nature but also just minutes away from the city.