San Juan, Puerto Rico’s capital, ranks among America’s most well-preserved colonial cities. Walk the cobblestoned paths among colorful colonial houses, historic churches, and laid-back plazas with the aquamarine waters of the Atlantic Ocean as your backdrop. The city’s abundance of bars, casual eateries called fondas, and farm-to-table bistros serving mofongo make it a foodie’s paradise. Tree-lined playas with powdery sands and turquoise waters are snowbirds’ havens. Adrenaline junkies will love El Monstruo, formerly the longest zipline on the planet, and nature lovers must explore Laguna Grande and El Yunque National Forest. This tiniest isle of Greater Antilles offers not just tourist attractions but also cool and cozy accommodations! Choose the top Airbnbs with private pool in San Juan, Puerto Rico, for luxurious lodgings while you’re exploring the island.
1. Villa Bohemia II (from USD 698)
This chic, bohemian villa in Condado is within walking distance of nighttime entertainment, beaches, and restaurants. It’s comprised of three sections, with the main house containing the bedrooms and bathrooms. The other two sections feature a fully stocked kitchenette and rooftop balcony offering alfresco dining with views of the splash pool below.
The private pool area features a grassy portion with outdoor furniture on each end. It’s accessible from the patios of the master bedroom, guest bedrooms, and rooftop balcony. Do note that house rules forbid guests from entering the pool with sand when they come back from the beach.
Top guest reviews
Amenities & Room:
really nice setup close to calle loiza and la placita good for groups of 8 nice pool and amenitiesHost:
the host was very responsive and flexibleloved this place accommodating hostsgreat communication by the staff and excellent venue/locationRead more reviewsLocation:
great location and great house with cute decorthe location is excellent on a residential streetsecure off street parking is a bonuswalking distance to the beach restaurants supermarket everything we needed for a perfect stay was at our fingertipsi recommend this place to all
Superhost
2. Villa Blanca (from USD 518)
Villa Blanca is the ideal home base if you want to be near the beach and city. This contemporary, all-white villa offers three elegant bedrooms and an extra bedroom in an attached studio, housing ten guests in all. The wide-open living area and some of the capacious rooms have access to the patio and pool.
Guests will enjoy refreshing dips in the outdoor pool with waterfall features and tropical-themed surroundings. There’s a dining area on the patio by the pool where guests can enjoy barbecues and a family-sized meal.
The services of a private chef and bartender, massage therapist, and caterer are also available upon request.
Top guest reviews
Amenities & Room:
the grill/pool area is an amazing touchif you like room there is enough room for easy 10 guestthe pool & outside was amazingthis house was perfect for our vacation we had 6 adults staying and had more than enough roomCleanliness:
it was clean trendy and comfortablehouse was clean and welcomingit was clean spacious and the pool was fantasticsean and cristina’s place was very clean and comfortable: it had everything we neededsuper cozy and cleanHost:
overall we had a great experience and the hosts were very quick with their responses highly recommendsean and cristina are the sweetest and most considerate hoststhe host are amazing and responded to my messages quickly and accommodated us with what we neededcristina was very responsive and tended to all our need during the staysean & cristina are amazing host and very attentiveRead more reviewsLocation:
love it great location and close to everythingclose to airport which is really nicegreat place to stay we rented a car so it was close to everythingawesome home and pool located very close to the beachsuch a beautiful home and close to everything would highly recommend (:
3. Shades of Blue House (from USD 130)
This rental is in a two-floor residential building in a quaint neighborhood. It’s a contemporary home with interiors in shades of white and blue with gray and yellow accents. This self-catering home offers two bedrooms and one-and-a-half bathrooms that are a good size for five guests.
Outside the house is a spacious rooftop featuring a patio and private pool area. You can dine and grill barbecue on the shaded patio or take a dip in the outdoor pool. At night, you can turn on the pool light to enjoy swimming under the stars with a view of the neighborhood.
Top guest reviews
Amenities & Room:
air conditioning is great and the place is so beautifulprivate pool patio and grill area were the bestthe a/c units quickly cool down the space after being out all daythere is a great set of chargers for every phone in the living roomloved the patio area and the poolCleanliness:
very clean as wellit was very clean and the owners communication was greatgreat place clean & comfortablenice place very clean perfect locationthey need to clean more an efficientHost:
host very helpful and kindhost is very nice and fast with respondingthe neighborhood scared us but host reassured us that our car & us will be safethe vending machines were also helpfulamazing stay the pictures does its justice and the owner is 100% on point with communicationRead more reviewsLocation:
i loved the location of the house tooand it is super close to so many thingsbakery and super market 5 to 10 minute walklove this place it was its own paradise in paradise thank you so much for hosting uswonderful place in the center of all
4. Cute home with splash pool (from USD 138)
The rental is on the second floor of a private home in the San José neighborhood, which is within 20 minutes of various beaches, malls, bars, and live entertainment.
This home, with a minimalist motif and a black and white interior, hosts five guests comfortably. It features two air-conditioned bedrooms and a spacious open living area. Guests have access to a furnished terrace with a barbecue area and an outdoor living area.
Tucked in the corner of the ground floor patio is a private splash pool with a water fountain. It’s shallow and safe for kids to play in with supervision. Guests have complete privacy in the pool, so they can take a dip at any time of the day. On the pool deck, there’s patio furniture where you can drink or dine while others enjoy their swim.
Top guest reviews
Amenities & Room:
the patio was amazing and the kids loved the poolRead more reviewsLocation:
very nice location was very convenient and the pool was really cutethe location is close to tourist spots but far enough you to have a truly authentic visitit's was a great stay and wonderful experience and locationhenry’s place is very nice friendly neighbourhoodhenry's place is just perfect little gem
5. Modern villa with spa bath (from USD 1307)
This renovated three-story villa in the Ocean Park neighborhood offers privacy and modern comforts for large groups. It offers plenty of outdoor areas where you can lounge, dine, or drink around the pool. Each floor is surrounded by tall bay windows offering vistas of the beach. The bedrooms and bathrooms are spread over three floors, with the second and third floors each featuring a roof deck.
From the main living area, you can access the patio surrounding the heated private outdoor pool with a spa bath. Lean back on the loungers to catch some sun or dive into the therapeutic saltwater. There’s an outdoor shower discreetly hidden by the pool where you can rinse off after your dip or when you come from the beach.
Top guest reviews
Amenities & Room:
ac systems was easy to use and customize for each roommultiple tvs with streaming devices in every room were great to have for the kidsthe beds were super comfortable and the bathrooms were stylish and sleekand the beds the girls are still talking about how it was like sleeping on cloudswe had a private chef come and the dining table easily and comfortably sat all 12 of usCleanliness:
very clean and modernthe house is very clean modern and spaciousevery room was sparkling clean (the master bathroom was esp gorgeous)safe and clean home especially during this covid-19 pandemicthis home is incredible the place is clean and well stocked with everythingHost:
peter is a great hostthe host provided us with great info and a lot of advice on places to go and seepeter was the most gracious host with very quick responses when needed and helpful local recommendationspeter is a great host and is quick to answer any questions you may havebeautiful place and great hostRead more reviewsLocation:
great location steps from beachand the location was perfectgreat location and really easy to get aroundthe house and the location are outstandingpeter’s place was in an excellent location
6. Casa Ocean PR (from USD 425)
This lovely, two-level, gated home is in the safe neighborhood of Ocean Park. It allows pets and is equipped for long stays. It boasts a stylish first floor with a living area, two bedrooms, and easy access to the patio and pool. Guests can huddle in the family room to watch Netflix or do remote work in the mini office on the second floor. There’s an outdoor deck and terrace for lounging or grilling.
The L-shaped outdoor lap pool with a triple fountain is in a corner at the back of the house. Jump into the pool and feel instant relaxation after a day of exploring the town.
Top guest reviews
Amenities & Room:
you will not be disappointed even that air conditioner was on pointthe pool was the perfect touch and the rooftop lounge was our go to breakfast spotpool in the city to cool off and awesome office space with great viewbeautiful home with a nice poolhaving the garage and the pool was greatCleanliness:
super clean great appliances comfy beds and 1000 count sheetsthis place was clean the pool was a great touchpool was clean house was hugewhen you enter the house is clean and spotlesshouse is very nice and cleanHost:
elvin was an amazing hostelvin was a great hostelvin the host was greatgreat host with an even better homeelvin was one of the best host i’ve hadRead more reviewsLocation:
great property close to the airport & beachgreat location next to beach all types of foodeverything’s is close by easy to commute and beaches are right by as wellthe location was also great just a short walk to the beach and great restaurantseverything was great a beautiful location
7. Elegant villa with pool and tennis court
Enjoy your stay in this elegant villa that allows pets in a private, fenced-in neighborhood. It has a classic Puerto Rican theme with high-beamed ceilings, white brick walls, wood-slatted windows, and accordion doors that open to a furnished patio for lounging and outdoor dining. Featuring a large U-style kitchen, open living and dining area, and six stylish bedrooms, this villa hosts six guests with a resort-like feel.
The patio terrace overlooks the lap pool and a tennis court. It’s surrounded by thick foliage for guests to enjoy swimming or playing tennis with full privacy. You can light up the pool so that you can have a relaxing nighttime dip.
San Juan, Puerto Rico
8.72 km (5.5 mi) from La Plaza del Mercado de SanturceAccommodates: 6
Top guest reviews
Amenities & Room:
the a/c worked beautifullythe house was extremely comfortable for a family of 13 with 4 kidsthe outdoor spaces with the decks and pools were dramatic and beautifulthe pool isn’t heated and was pretty cold in januarythe house and pool was amazing there was plenty of space for usCleanliness:
the place is clean and comfortableit was beautiful and cleanwe had enough bathrooms and beds the house was clean and well maintainedthe home was very clean and it had amazing amenitiesthe place itself was very neat and clean and just plain beautifulHost:
the host was great and made us feel welcomed and gave great suggestionsshe was very friendly and informationalgreat place and great hostmaria was a great host that attended our every needoverall the service was really good and they were responsive and helpful when it came to parking carsRead more reviewsLocation:
the location was perfectplus pr is just a great placebeautiful home in a beautiful locationalthough not right in san juan it was still in a good locationthe neighborhood was extremely safe and quiet
8. Blessed Home (from USD 310)
Blessed Home is a corner lot property in an exclusive, gated neighborhood. This plush villa offers swish lodgings that include a private outdoor pool and gym and garage parking for one car. It has two bedrooms with enough beds to host eight guests and their pets for extended stays.
You can float in the pool from morning until night without worrying about neighbors looking over the high perimeter wall. A grill area and lounge area are on opposite sides of the pool so that you can swim and socialize on the deck. It also features a Bluetooth floating speaker and dominoes table for you to enjoy music while swimming and playing with your inflatable toys.
Top guest reviews
Amenities & Room:
the pool/patio area was perfect as wellotherwise beautiful home with large great poolCleanliness:
beautiful home and very cleanthe house was beautiful clean and perfect for our familyeverything was beautiful and cleandefinitely recommend the location is great super clean host was very nice and communication was easyHost:
this was one of the best houses i have stayed at the host was wonderful and so helpfuleverything was great the host even had some nice easter gifts for our kidsthe owners were very helpful with everything would definitely recommend this place to anyoneeverything went smooth and as described ingrid was an wonderful host and very attentiveingrid was a awesome hostRead more reviewsLocation:
the location it’s perfect because everything it’s near youclose by the airport and easy to get togreat location this house is a must for your next tripthe location of the airbnb is about ~15mins from old san juan in a good locationit’s a beautiful place to stay
9. Pet-friendly villa with pool and cabana (from USD 336)
Nine guests will enjoy this cozy villa with well-appointed interiors featuring two capacious bedrooms, a chef’s kitchen with a breakfast island, and indoor and outdoor living and dining areas. It also admits pets for an additional 75 USD per animal, although service dogs are allowed for free.
The pool area is where you’ll spend most of your time swimming and entertaining. It has a barbecue area, swings, and a tiny cabana where you can take afternoon naps when you’re not submerged in the water. It’s surrounded by a tropical garden with a grassy area where your pets can play.
Top guest reviews
Amenities & Room:
the house is beautiful but the wifi did not work despite whatever he saysgreat house nicely put together and comfortable with awesome pool and yardCleanliness:
everything was clean and beautifulclean and updated good poolthe pool was very clean as wellit was very nice and cleanhis place was very cleanHost:
great host with fast response beautiful place thank youarmando was an excellent host and made sure our stay at his home was perfecthe was prompt with answering any questions and was very helpfulhost was super easy to get in touch with if anything was needed immediatelygreat location great host i was enlightened by the small touchesRead more reviewsLocation:
first of all gorgeous spot for such a close spot to the san juan airportthis was the perfect place for our trip to san juan the villa has a secure luxury feeli absolutely loved this place wasn’t too far from anythingsuch a quiet welcoming neighborhoodif you stay i recommend gd cakes for breakfast would definitely book this place again
10. Mediterranean-style villa with stunning backyard (from USD 1255)
This Mediterranean-style villa in the wealthy section of San Juan is ideal for 16 guests. It’s surrounded by a thriving garden with a huge patio where you can grill barbecue, have cocktails on the patio lounge, or dine alfresco. Don’t forget to take a breather and plunge into the private lap pool for a refreshing swim. It’s surrounded by lots of greenery, statues, and fountains.
Sleep in opulent guest suites equipped with deeply cushioned beds and marble-tiled bathrooms, two of which have hot tubs. You can request to hire a personal chef to whip up a gourmet meal in the Italian-style kitchen and have it served in the elegant dining area. Housekeeping services are also available.
Top guest reviews
Amenities & Room:
the patio/pool area is absolutely perfect pictures don’t do it justicegreat setup for large groups - dining table inside & patio table outside able to seat entire groupCleanliness:
the house was clean and spacioussome of the sheets and bathrooms were definitely not cleanedHost:
host quick to help with any questions or concernspablo was such a great host & very informativepablo was extremely helpful and quick to respond to any requests we had as wellwe found it in this house the owners were great from check in to check outgreat space terrific location and enjoyed working with the hostsRead more reviewsLocation:
great place walking distance to many things including beachthe villa is beautiful and the location was greatthe good: great location walkable to everythingif you want something spacious nice and in a great location look no furthergreat location i would recommend and would even stay again limited parking if you are having an event
Lovely homes with pools
There’s plenty to discover in San Juan. The smallest apartments to the biggest villas offer the comforts of a private pool, an exciting feature in any home that helps keep you stress free and entertained. Book one of these accommodations for your stay on this great little island for a memorable vacation in Puerto Rico.
History
Get Trip101 in your inbox
Unsubscribe in one click. See our Privacy Policy for more information on how we use your data
Create an account to bookmark our articles, like local expert tips, receive great stories in your inbox, and follow writers and topics that you love.
Log in with Google ×