Puerto Rico is a destination where the old-world Caribbean meets a new-age island paradise. This tiny tropical island has a rich history, booming culture, and world-class culinary scene, alongside exceptional jungle, beach, and mountain scenery.
The east of the island offers secluded beaches and tropical rainforests. Head to west Puerto Rico for a surf vibe and to enjoy some of the Caribbean’s best sunsets. The north of the island is home to some dramatic topographic scenes and the southern region is booming with culture, art, and historic Puerto Rican architecture. If you move inland to the Central Mountains, you’ll be overwhelmed with extraordinary jungle views and adventurous activities.
With so much to explore, it’s important to find the right vacation rental in Puerto Rico to make the most of your time there! There are loads to choose from, so we’ve put together this list of the very best ones.
Whether you’re after a luxury rental for two, planning an action-packed family vacation, or anything in between, we’ve got you covered.
Quick Answer: These are the Top 5 Vacation Rentals in Puerto Rico
Casa Lola PR
- > $$
- > 2 Guests
- > Indoor and Outdoor Showers
- > Infinity Pool
Private Modern Villa for 2
- > $$
- > 2 Guests
- > Located on a tranquil and rural hillside in Vieques Island, just off the eastern coast of Puerto Rico.
- > This spacious two-sleeper villa exudes beauty.
Above the Clouds at Casa Serena Country Villa
- > $$
- > 4 Guests
- > Swimming Pool
- > Insane Views
Types of Accommodation in Puerto Rico
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Villas
Like many beach and island locations, villas are a common type of accommodation in Puerto Rico. Located along the beautiful stretches of coastline the island has to offer and equipped with modern amenities, these are convenient and luxurious self-catering vacation rentals in Puerto Rico.
Villas are most appreciated for their convenient location and their abundance of space and privacy not offered by resorts and hotels. They’re usually more luxurious and therefore more expensive than residential rentals and are often the accommodation of choice for large families or groups travelling together, as well as long-stay visitors with high budgets looking for luxury vacation rentals in Puerto Rico.
Resort Condos
Resort condos are a reliable option for those who want the convenience of resort amenities and the privacy of their own space. Puerto Rico’s most popular beach stretches are dotted with luxury hotels and resorts, many of which rent out private condos and studios. These are a safe stay in Puerto Rico with a slightly more intimate experience than staying at a hotel chain.
The main benefit of this type of accommodation is included access to resort facilities – from swimming pools to barbeque facilities to golf courses to in-house bars and restaurants and even babysitting services. Along with the included amenities, resorts usually sit in prime locations in and amongst the hustle and bustle of popular beach districts. Resort condos are often rented out by families, couples, and weekend visitors who appreciate the convenience of room service, concierge, and a lock-up-and-go condo.
Beach Houses
Beach houses are a good and affordable alternative to villas for those on a slightly lower budget. The main difference between the two is that villas are typically designed to be rented out to holidaymakers, while Puerto Rico beach houses are often more local homes.
These homes range in size and include everything you might need from a self-catering beach vacation rental in Puerto Rico. An added benefit? Local homeowners are often more than happy to give you insider tips, so you can really get to know the area.
Top 15 Vacation Rentals in Puerto Rico
Casa Lola PR | Best Overall Vacation Rental in Puerto Rico
Casa Lola sits tucked into the mountains of Isabela, a quiet little hideout where the landscape steals the spotlight and the outside world fades into the background. The place feels made for dropping your bags, catching your breath, and settling into a slower rhythm. The cabin stands completely private at the top, wrapped in greenery and wide-open views that roll out in every direction.
Inside, the kitchen is fully equipped for easy meals and lazy mornings. The indoor and outdoor showers makes even your morning routine feel like an adventure. The loft room opens to sunrises and sunsets that sweep across the sky, and the infinity pool stretches out toward the horizon with sun chairs and a hammock ready for long, guilt-free lounging.
Rocky Road Cabin | Most Beautiful Vacation Rental in Puerto Rico
Privacy and comfort come together effortlessly at Rocky Road Cabin in Lares. Cosy yet modern, spacious yet intimate, this mountain hideaway is surrounded by nature and offers the perfect setting for couples seeking rest, relaxation, and a true break from the everyday.
Beautiful barely covers it. Even though we are from PR, stepping in feels like entering another country, a place where you could fully switch off. Stargazing from the heated pool transforms evenings into something unforgettable. The private pool and waterfall are showstoppers, and the outdoor space is peaceful, carefully arranged, and inviting.
Above the Clouds at Casa Serena Country Villa | Best Vacation Rental in Puerto Rico for Families
Casa Serena Country Villa is a quiet countryside escape where mornings start with coquis and crisp morning air. The outdoor spaces are expensive and, quite frankly, stunning. You’re in for a treat with some REAL sunsets here too. Inside, rustic calm is balanced with modern comforts, letting you relax properly without any unnecessary frills.
Families can actually enjoy it here. Getting the kids outside doesn’t feel like a mission, and the whole place makes it easy to switch off and breathe. Renting a car is essential, giving you the freedom to explore the surrounding countryside without relying on anyone else.
1 Bed Condo in Golf Resort | Best Vacation Rental in Puerto Rico for a Weekend
Nestled between some of the island’s top east coast beaches and only 20 miles from the nearest airport, this is one of the best vacation rentals if you’re staying in Puerto Rico for a weekend. It offers simple furnishings and basic self-catering amenities, as well as a great location. Don’t fancy cooking at home? There are plenty of fantastic restaurants nearby that you can easily reach on foot.
Suite with Private Pool | Best Vacation Rental in Puerto Rico with a Pool
Planning a romantic getaway with your other half? This stunning suite offers an atmosphere of tropical opulence and luxury. You’ll be treated with warm island-style furnishings, including woven carpets and basket details, fresh flower arrangements, and hanging chairs.
Kick back and enjoy the sounds of the ocean from the intimate pool on the deck, which doubles up as a Jacuzzi for colder days.
1 Bed Condo in Holiday Resort | Super Accessible Vacation Rental in Puerto Rico
This spacious self-catering condo provides comfortable accommodation near San Juan. It’s nestled amongst some of the region’s best beaches and the famous El Yunque National Forest, making it one of the best-located rentals on the island.
Enjoy warm tones, comfortable furnishings, and direct beach access from this homey condo.
Elegant yet Simple Oceanfront Studio for 2 | Most Central Vacation Rental in Puerto Rico
This basic one-bedroom condo is one of the best vacation rentals in Puerto Rico for budget vacationers. Inclusive of great internet connection, air conditioning, off-street parking as well as a washing machine and dryer, this simple condo has everything you might need for a short visit to Puerto Rico.
Located on a popular beach just outside San Juan, you’ll be well-positioned to get out and explore the bustling city.
5 Bed Modern Oceanfront Villa | Best Vacation Rental for a Large Family in Puerto Rico
This luxury beach house is built into the cliff-face and has epic views of the sea. With exposed rocks and concrete slabs, it boasts a rustic modern feel whilst still oozing luxury. The five-bedroom home is filled with modern yet simple furnishings, making for a relaxing and peaceful ocean-side escape. Lie by the pool and soak up the views under the tall palm trees while your children enjoy the private beach below the house.
3 Bed Party House on the Beach | Best Vacation Rental in Puerto Rico for a Friends Getaway
Located in the trendy Rincon beach district, this beach house is ideal for a fun getaway with friends. It sits behind a popular beach within walking distance to a variety of restaurants and nightclubs. If you’re planning a party weekend with your mates, this is the best vacation rental in Puerto Rico to do it!
The home is fitted with simple yet practical furniture following a no-fuss style, offering a casual backpacker vibe while still being private and secure.
Tiny Lake Cabin for 3 in the Woods | Most Unique Vacation Rental in Puerto Rico
When we think of Puerto Rico, we immediately think beach and ocean. However, this tropical island has some exquisite lake and river scenes for those willing to explore inland. This tiny home is steps away from a private jetty jutting out into a crystal-clear lake.
The cabin is furnished simply and complimented with a basic self-catering kitchen, outdoor barbeque facilities, and a private Jacuzzi. With its unique character and relatively low price, this unique Puerto Rico vacation rental is sure to exceed expectations!
Cozy, private oceanfront beach house in Rincón | Best Vacation Rental in Puerto Rico for Honeymooners
Honeymooners, check out this impeccably furnished beach bungalow with juxtaposed wooden and glass features and warm wooden tones. It sits on a private and secluded white-sand beach and is complete with an outdoor shower, a sand floored beach barbeque area, and a wrap around porch boasting dreamy ocean views.
What really makes this vacation rental in Puerto Rico great for honeymooners is the unrivalled privacy. Relax on the sand, kick back in the beach house, or head out for some snorkelling and scuba-diving in your backyard!
Spacious house surrounded by nature | Best Vacation Rental in Puerto Rico for Nightlife
La Placita is the island’s nightlife hub, and this house sits just around the corner from all the action. With a whopping TEN beds, it’s the ultimate base for the whole crew to gear up before hitting the bars.
When the night finally catches up with you, nothing beats a hangover surrounded by a bit of peace and greenery. The living area is huge, with space for everyone to crash on sofas or gather around the big dinner table. The patio is perfect for lazy, balmy evenings, where the only agenda is doing very little and enjoying it.
Massive Hillside Villa with Ocean Views | Best Vacation Rental in Puerto Rico with a View
This huge home boasts floor-to-ceiling windows and doors overlooking panoramic views over Fajardo. It’s got plenty of balconies from which you can take in the outstanding sea vistas. Clean contemporary design, cosy furniture and linen, and a large pool complete this luxury holiday rental in Puerto Rico.
Private Modern Villa for 2 | Most Romantic Vacation Rental in Puerto Rico for Couples
Luxurious privacy – this one-bedroom home is the perfect rental in Puerto Rico for couples ready to splash. The intimacy of Vieques island combined with acres of tropical green gardens make this the ideal romantic escape. An outdoor pool and terrace, and exquisite Caribbean ocean views seal the deal.
The luxurious villa is filled with fascinating Caribbean and African art and textiles, giving the home a culturally rich and foreign feel.
Isolated 4 Bed Jungle Villa | Most Remote Vacation Rental in Puerto Rico
By no means low-key, this over-the-top modern villa is located atop a hill in the remote Cayey jungle region. Complete with an excessive koi pond and river features and surrounded by tropical trees, this villa will make you feel like Caribbean royalty. The interior flaunts interesting wooden architecture complimented by African and Caribbean art pieces.
Don’t Forget Your Puerto Rico Travel Insurance
ALWAYS sort out your backpacker insurance before your trip. There’s plenty to choose from in that department, but a good place to start is Safety Wing.
They offer month-to-month payments, no lock-in contracts, and require absolutely no itineraries: that’s the exact kind of insurance long-term travellers and digital nomads need.
SafetyWing is cheap, easy, and admin-free: just sign up lickety-split so you can get back to it!
Click the button below to learn more about SafetyWing’s setup or read our insider review for the full tasty scoop.
Final Thoughts
Puerto Rico is overflowing with beautiful coastlines, dense tropical jungles, exciting cities and beach towns, and inland lakes.
The diverse Caribbean island has thousands of holiday rentals to choose from – from studios to apartments to villas to houses. Whether your’e dreaming of a relaxing beach vacation or a more adventurous jungle experience, there’s bound to be a holiday rental in Puerto Rico that will exceed your expectations.
