Holiday rentals with a pool in Guaynabo

The modern two-story home features a clean, contemporary design with large windows and a welcoming entrance. Lush palm trees are planted in the front yard, complementing the well-maintained landscaping. A driveway and garage are visible, providing convenient parking options.

4.82 out of 5 average rating, 269 reviews

Case Del Sole Duplex w/ Solar-Powered Backup

Welcome to San Juan! This 4-Bed 2-Bath second floor home is centrally located to provide you accessibility to everything you want to do in San Juan PR and close municipalities. When you're not exploring the island, the house has a gorgeous pool & outdoor chairs for an entertaining day. Great place for small family gatherings and couples vacations, but fully equipped as well as needed for long-term rentals. Now, with Solar-Powered backup system and Tesla batteries, prepared for the unexpected.

4.96 out of 5 average rating, 195 reviews

A two-story home sits gracefully on a gently sloping landscape, surrounded by lush greenery. The exterior features large windows that invite natural light, with vibrant flowering plants cascading along the walls. A spacious driveway leads up to the front of the house.

Home in Bayamón

Casalta: A Unique Villa Experience in Puerto Rico

Welcome to our dream home, a labor of love meticulously designed and built by us. Nestled on 2.3 acres of Bayamon mountain terrain, our property offers breathtaking panoramic views that will leave you in awe. We're delighted to be a pet-friendly destination. Conveniently situated just 25 minutes from San Juan Airport, San Juan's beautiful beaches and the historic of Old San Juan. Our home is the perfect setting for creating cherished memories, for any special occasions you have in mind.

A modern kitchen features sleek black cabinetry and a central island with two black bar stools. Stainless steel appliances, including a refrigerator and microwave, complement the open layout. Natural light enters through large windows covered with shades, enhancing the functional design.

4.89 out of 5 average rating, 120 reviews

Blessed Home…

Have fun with the whole family at this stylish place. 15 minutes to the airport 15 minutes from Old San Juan tourist site 10 minutes to Mall of San Juan 7 minutes to Plaza las Americas 12 minutes to Isla Verde and Ocean Park 3 minutes to Walgreens We have Solar Panels for the benefit of our guests in case there is no electricity! 🚨 Come and spend your vacation with your family and make it an unforgettable magic of comfort. Completely remodeled, spacious and stylish house.

4.97 out of 5 average rating, 175 reviews

The dining area is highlighted by a dark wooden table surrounded by four light-colored chairs. A spacious kitchen with modern appliances is visible in the background. Large sliding glass doors provide access to a balcony, with natural light enhancing the room's ambiance.

Apartment in Caguas

Sunset Delight

🌅 Welcome to Sunset Delight! A spacious two-story penthouse in the heart of Caguas. Relax on your private rooftop terrace with hot tub, or cook in the modern kitchen. Stay cool with A/C, enjoy Wi-Fi & Smart TV, and unwind in comfort. Perfectly located—20 min to Cayey, 30 min to San Juan & La Placita, and 1 hr to Luquillo Beach. Ideal for couples, families, or business travelers looking to relax or explore Puerto Rico. Self check-in, with host support just a message away!

A serene outdoor space features a private pool with tranquil blue water, surrounded by lounge chairs and lush greenery. An inviting seating area is visible, alongside a bar with high stools. A well-lit space creates an atmosphere for relaxation and enjoyment.

4.98 out of 5 average rating, 137 reviews

Villa Celestial Luxury Home

Discover comfort and style at Celestial, our newly renovated 3-bedroom, 3-bathroom retreat in Urb. Los Angeles, Carolina, Puerto Rico. Just 5 minutes from the airport and a short drive to Isla Verde's beaches, this stylish home is ideal for up to 10 guests. Enjoy the remodeled interior, private pool, BBQ area with a full outdoor kitchen, ample parking, and security cameras. Experience luxury and convenience at Celestial – your gateway to the best of Puerto Rico.

4.87 out of 5 average rating, 241 reviews

A private pool area is visible through an elegant gate, showcasing a well-maintained pool surrounded by lounge furniture and tropical plants. The setting features a shade sail overhead, providing a comfortable space for relaxation. A distant view of greenery complements the tranquil atmosphere.

Villa in Guaynabo

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.

An aerial view captures a private pool surrounded by a tiled patio. The pool, featuring steps for easy access, is bordered by fencing for safety. Two reclining chairs are positioned nearby, with lush greenery visible beyond the pool area.

4.96 out of 5 average rating, 117 reviews

Traveler’s cozy house | Private Pool Near Airport

Welcome to La Casa del Viajero! Cozy house with unique design, 2 bedrooms with direct access to the pool and outdoor area to relax. Located in a quiet neighborhood, less than 10 minutes from San Juan Airport (by car). Close to beaches, restaurants and tourist areas such as Old San Juan, Isla Verde, Condado and Piñones. Easy access to the PR-66 to Luquillo, Río Grande and the East Coast.

The living area features a brown leather couch complemented by a round coffee table and decorative elements. A ceiling fan and modern light fixtures are present, along with plants that enhance the space. Glass doors open to a private outdoor area, blending indoor and outdoor environments.

4.9 out of 5 average rating, 125 reviews

Mid-Century Modern house

Experience the magic of a recently renovated 1962 house, meticulously designed in the Mid Century style, where nature and abundant natural light take center stage. Embrace the seamless integration of open spaces, lush greenery, and a patio that flawlessly blends with the interior. The house has 3 bedrooms. It can comfortably accommodate 6 people, (2 per room).

4.85 out of 5 average rating, 307 reviews

Tent in Guaynabo

"Stellita Glamping"

Disconnect from the routine and enjoy the tranquility of the countryside in the city of Guaynabo, Puerto Rico, with a private pool and different decks where you can relax. The tent has a cozy queen bed, one air conditioners, books and board games. You'll also have your private bathroom and outdoor area with bbq, refrigerator, pool and a cozy seating area.

4.95 out of 5 average rating, 111 reviews

Home in Guaraguao Abajo

Black House

Casita Negra is a magical place (retreat) in the mountains of the metro area of Puerto Rico. The property has a swimming pool, 1 bedroom and 1 bathroom. This Casita is a couples retreat and the perfect getaway for you and your loved one to disconnect from the daily routine. Air conditioning is available, although the house captures the country breezes.

4.9 out of 5 average rating, 159 reviews

Apartment in Levittown

Unit #1 | Modern Pool Apartment Near San Juan

Modern open-concept apartment with a queen bed, sofa bed, in the same place,Smart TV, air conditioning, and WiFi. Includes a full kitchen, private bathroom, and free parking. Ideal for couples, small families, or remote work stays. Conveniently located just minutes from the beach, restaurants, and supermarkets—offering a comfortable and hassle-free stay.

A refreshing pool area is surrounded by natural greenery, with stone accents and a sunlit patio. The pool features clear water and a small seating area, creating an inviting outdoor space. Lush foliage frames the scene, enhancing the serene atmosphere.

4.98 out of 5 average rating, 235 reviews

Villa Estrella PR (near Airport & Beach)

Have fun with the whole family at this stylish place. It's close to all the essentials such as the Airport and Beaches (5 minutes), Old San Juan, Plaza Las Américas (15 minutes). Located near several prestigious restaurants such as Bebo's BBQ, Metropol, and the Piñones tourist area where you can find typical food from our island.

Popular amenities for Guaynabo rentals with a pool

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.99 out of 5 average rating, 143 reviews

A bright outdoor area features a rectangular pool surrounded by light-colored tiles. White walls enhance the spacious feel, while an adjoining open-air space reveals a modern kitchen area with a shaded seating area. Lush greenery provides a natural accent, complemented by a clear blue sky.

Home in Santurce

Casa Reyes

4.96 out of 5 average rating, 102 reviews

Casa Aurea - Cozy House in the Metro Center Area

A sparkling swimming pool is illuminated by soft purple lights, creating a relaxing atmosphere in the evening. The pool is surrounded by smooth stone tiles and white walls, providing a sense of privacy and comfort.

4.86 out of 5 average rating, 173 reviews

The Leaves Apartments #2

4.96 out of 5 average rating, 284 reviews

Home in Gurabo

Escape to your own private Tropical Oasis.

A modern interior space features an open layout with a sleek kitchen against one wall. A spacious living area is highlighted by a large television displaying an image of an airplane on a runway. Contemporary lighting offers bright illumination throughout.

4.94 out of 5 average rating, 112 reviews

Casa Hélice 3 min from airport -Placas Solares-

4.97 out of 5 average rating, 106 reviews

A spacious living area features large glass doors that provide views of the surrounding greenery. A comfortable gray sofa is positioned near a circular mirror, with a decorative pouf and a small plant nearby. Natural light brightens the open space.

Home in Toa Alta

Hacienda Lucero: Your Tropical Lakefront Escape

A heated swimming pool is showcased in the foreground, reflecting clear blue skies. Surrounding greenery enhances the scene, with a white structure visible nearby featuring multiple windows. A gazebo is situated to the right, complementing the outdoor space.

4.85 out of 5 average rating, 144 reviews

Urban Paradise

4.92 out of 5 average rating, 227 reviews

The image displays a private pool area featuring a circular jacuzzi and a larger swimming pool, surrounded by lush tropical vegetation. The exterior of the two-story house is visible, with multiple glass doors providing access to the outdoor space, enhancing natural light.

Home in Trujillo Alto

Luxury Villa: PrivatePool, Generator&Water Cistern

Condo rentals with a pool

A modern living room features turquoise accent walls, a comfortable sofa adorned with decorative pillows, and a neutral area rug. A coffee table sits in the center, surrounded by a few decorative elements. A Smart TV is mounted on the wall, and ambient lighting enhances the space.

4.92 out of 5 average rating, 420 reviews

★Luxurious Beachfront Apt in Isla Verde+free pkg★

4.89 out of 5 average rating, 133 reviews

BLUE DREAM Oceanfront W/ VIEW AT Isla VERDE 2BR

4.82 out of 5 average rating, 130 reviews

A panoramic view of the ocean is captured from a height, showcasing the rolling waves and sandy beach below. The coastline is lined with palm trees, and the clear blue sky complements the shimmering water.

Condo in Santurce

Ocean & City View Studio in Condado, San Juan

A spacious bedroom is furnished with a large bed covered in a soft grey blanket. Natural light flows through the floor-to-ceiling window, highlighting the modern decor and warm wood accents. A cozy seating area features a pouf and a small side table, with additional wooden lounge chairs arranged nearby.

4.85 out of 5 average rating, 133 reviews

The best, Amazing Designer Beach Front Loft Apt

A bright living area showcases expansive glass doors that open to a private balcony with views of the ocean. Comfortable seating arrangements include a sectional sofa and two outdoor chairs. A modern coffee table sits centrally on a textured rug, enhancing the open and inviting atmosphere.

4.96 out of 5 average rating, 157 reviews

Deja Blue BeachFront Apartment @ Isla Verde (Green Island)

A private balcony is depicted, featuring a small table and two chairs. A partial view of the sea and city skyline is visible in the background. The modern building and pool area can also be spotted from this vantage point.

4.95 out of 5 average rating, 193 reviews

Isla Verde Beachfront Studio near restaurants,bars

4.83 out of 5 average rating, 145 reviews

Condo in Santurce

Breathtaking Ocean View 3BR/2BA in Condado Beach

4.82 out of 5 average rating, 727 reviews

A spacious studio apartment is showcased, featuring a king-sized bed with white linens and a plush gray upholstered headboard. Light wood flooring complements the modern decor. A seating area with a couch can be seen in the background, along with a small kitchenette and a smart TV.

Condo in Santurce

Chic Apartment in Ocean Front Condado Condo

Other holiday rentals with a pool

4.94 out of 5 average rating, 113 reviews

A refreshing private pool is framed by lush greenery, with tall plants positioned along the edges. The pool features clear blue water under a cloudy sky, creating a serene atmosphere. Large glass doors lead into the nearby living space, enhancing the connection with nature.

Apartment in Pájaros

L'abitat: Luxury Retreat Escape

Casa particular in Santurce

4.93 out of 5 average rating, 112 reviews

Blue lagoon

4.97 out of 5 average rating, 90 reviews

A game room showcases a green felt pool table, complete with cues and colorful balls arranged on the edge. A large wall-mounted television displays a serene beach scene, and ambient blue lighting enhances the modern atmosphere. A couple of chairs are positioned nearby.

Home in Guaynabo

Guaynabo, Private pool, billiard room.

5.0 out of 5 average rating, 96 reviews

A wooden bench with a slatted design is positioned against a white wall, featuring a decorative pillow with a bold text print. Above the bench hangs a large wall art piece depicting palm trees in front of a light-colored building, adding a tropical touch.

Home in Guaynabo

⭐️Casa De Las Palmas 🌴🌴

4.87 out of 5 average rating, 54 reviews

A private pool is visible, featuring clear blue water and a gentle waterfall feature. Surrounding the pool, a patio area includes light-colored seating, an umbrella, and a BBQ grill. Lush greenery frames the space, adding a natural touch.

Home in Guaynabo

Guaynabo Pool House • 3BR/2BA • Family Stay

The image displays a luxurious home surrounded by lush tropical greenery. A swimming pool is situated in front of the house, with a deck and patio space visible. The structure features a distinctive red-tiled roof and multiple outdoor areas for relaxation.

4.78 out of 5 average rating, 76 reviews

Green Nest at the Hills

A spacious outdoor area features a pool surrounded by well-maintained landscaping. Multiple lounge chairs are positioned around the pool, with the house visible in the background. Clear blue skies overhead enhance the sunlit scene, promoting a relaxing environment.

5.0 out of 5 average rating, 28 reviews

Beautiful home in San Juan