Holiday rentals with a pool in Guaynabo

4.99 out of 5 average rating, 142 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

Welcome to Casa Reyes! A spacious and relaxing family home fully renovated and redesigned to meet our guests’ vacation needs. Casa Reyes offers all the amenities for you and your family to relax on your stay. Located in one of San Juan’s most vibrant neighborhoods, Ocean Park, Casa Reyes is in between the tourist areas of Condado and Isla Verde. It’s walking distance to the beach, fine dining restaurants, clubs, nightlife, and many tourist attractions making it perfect for your vacation stay.

LocationFamilyWalkability

4.89 out of 5 average rating, 148 reviews

A modern two-story building is set behind a low concrete wall, with palm trees and lush greenery enhancing the entrance. The façade features clean lines and light-colored walls, while shaded areas provide a welcoming atmosphere. A separate gate leads into the property.

Flat in San Juan

ATELIER 277 San Juan, Puerto Rico.

Our place offers a true great experience. Very centric house located at the heart of the urban area of San Juan. Just 15 min from the beach with exclusive pool access to guests. We assure you a unique apartment on the 3rd floor of the Atelier which has a separate entrance, with amenities for your comfort: Queen bed, TV, wifi, and AC, fully equipped kitchen, dining table, washing machine, and bathroom. Queen sofa bed and a balcony with a lovely view. 800 sq feet safety and quietness guaranteed.

LocationValueComfort

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

Amazing views from our two bedroom lake house in Toa Alta, Puerto Rico. The house is on a hill overlooking Lake La Plata and surrounded by 12 acres of private rain forest. It is a quiet place perfect for nature lovers, bird watchers and photographers. There are about two miles of hiking trails as well as lookout points where you can enjoy sunsets and sunrises. If you use a 4x4 vehicle you can drive down to the floating dock to drop in your kayak or use ours. Please enjoy the trails and hikes.

FamilyValueOutdoor spaces

4.96 out of 5 average rating, 194 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.

LocationFamilyView

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.

Flat 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!

FamilyValueView

5.0 out of 5 average rating, 173 reviews

A spacious pool area features a heated saltwater pool accompanied by a jacuzzi. Comfortable lounge chairs are positioned around the pool, with lush palm trees providing shade. A modern covered terrace offers seating options for relaxation next to the scenic outdoor landscape.

Villa in Carolina

Luxury waterfront villa with dock and heated pool

Enjoy uninterrupted water and power at Villa Jade, with a whole-house generator and 600-gallon water cistern for peace of mind. Villa Jade is a unique luxury waterfront retreat with a heated saltwater pool, jacuzzi, and private dock on a serene lagoon. Just 10 minutes from SJU Airport and the fabulous beaches of Isla Verde. Three spacious bedrooms with private baths. Fully remodeled. As a dedicated 5-star host, I’m here to ensure a smooth, relaxing stay. Welcome!

LocationFamilyAccuracy

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.

LocationFamilyCleanliness

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.

ValueLocationGrill

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).

LocationFamilyComfort

4.86 out of 5 average rating, 306 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.

LocationValuePool

4.9 out of 5 average rating, 159 reviews

Flat 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.

ValueLocationAccuracy

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, 234 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.

ValueFamilyCheck-in

Popular amenities for Guaynabo rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.95 out of 5 average rating, 111 reviews

Home in Guaraguao Abajo

Black House

ValueLocationNearby

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

LocationValueCleanliness

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

LocationValueCondition

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

ValueLocationAccuracy

4.96 out of 5 average rating, 101 reviews

Casa Aurea - Cozy House in the Metro Center Area

LocationValueGrill

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, 119 reviews

Blessed Home…

ValueFamilyLaundry

4.88 out of 5 average rating, 166 reviews

A tranquil pool area is highlighted by a stylish stone water feature, where water cascades gently into the pool. Lush, tropical plants are visible in the background, complementing the serene atmosphere of the space.

Home in Levittown

La Pompa Beach House Beautiful Residence with Pool

LocationValueComfort

A serene outdoor space presents a heated pool surrounded by lush greenery. Comfortable seating is located under an umbrella on a wooden deck, while a large planter with tropical plants adds a natural touch. The setting is enhanced by vibrant pink flowers climbing the walls.

4.99 out of 5 average rating, 99 reviews

Old San Juan Gem | Backup Power/Water, Pool + Pkg

LocationFamilyComfort

Apartment rentals with a pool

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.

Apartment in Santurce

Ocean & City View Studio in Condado, San Juan

ValueFamilyWalkability

4.92 out of 5 average rating, 127 reviews

A spacious terrace is shown, featuring a dining table and white chairs, with views of the turquoise sea and skyline. Lush greenery is visible along the edge, and a small lounge chair is placed for relaxation under partially covered awning, inviting enjoyment of the outdoor space.

Apartment in San Juan

Romantic Oceanfront Private Patio Full Generator

ValueFamilyAmenities

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)

LocationValueNearby

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★

ValueLocationLayout

4.89 out of 5 average rating, 133 reviews

💙BLUE DREAM OCEANFRONT W/ VIEW AT ISLA VERDE 2BR

ValueLocationHospitality

A spacious room features a bright white interior with decorative tropical wall art. A large bed is positioned against a wall, complemented by a stylish nightstand. A television is mounted on a minimalist cabinet, while potted plants add a touch of greenery to the space.

4.93 out of 5 average rating, 202 reviews

Pink Bliss Studio ISLA VERDE

FamilyValueIndoor spaces

4.89 out of 5 average rating, 160 reviews

The open living-dining area features a spacious sofa and a dining table surrounded by four chairs. Large glass doors provide access to the balcony, where high-top chairs and a small table overlook the ocean. Modern pendant lights hang above the dining table.

Apartment in Santurce

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

LocationFamilyQuiet

4.98 out of 5 average rating, 123 reviews

A panoramic view showcases the vibrant skyline of Condado, with modern buildings lined along the streets. The Atlantic Ocean glistens in the background under a partly cloudy sky, while the lush greenery of local areas adds a touch of nature to the urban landscape.

Apartment in Santurce

Vista Boriken: 24 Hr. Doorman, Pool, Laundry, Gym

LocationFamilyLaundry

Other holiday rentals with a pool

4.98 out of 5 average rating, 112 reviews

Villa in Santurce

Beach Walk / Pool / Backup Power & Water

LocationFamilyHospitality

Shipping container in Gurabo

An outdoor terrace features a wooden deck with a table and chairs, providing ample seating. A cozy swing chair hangs nearby, surrounded by lush greenery and expansive views of the mountainous landscape. Decorative string lights add warmth to the inviting setting.

4.99 out of 5 average rating, 273 reviews

Vista Linda Haus

FamilyLocationKitchen

4.87 out of 5 average rating, 388 reviews

An inviting infinity pool extends toward a breathtaking view of lush green mountains and the Atlantic Ocean. The sky is filled with fluffy white clouds, creating a serene atmosphere. The pool's clear blue water reflects the vibrant landscape, offering a perfect retreat for relaxation.

Cabin in Gurabo

The Best View of PR with infinity pool with Heater

ValueFamilyBreakfast

Casa particular in Santurce

4.93 out of 5 average rating, 110 reviews

Blue lagoon

LocationValueBeach

4.99 out of 5 average rating, 147 reviews

Townhouse in Santurce

Ocean Park Beachfront & Pool | Steps to the Sand

LocationValueBack garden

4.94 out of 5 average rating, 112 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.

Flat in Pájaros

L'abitat: Luxury Retreat Escape

FamilyValueKitchen

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.

LocationValueQuiet