Puerto Rico is one of the most popular vacation destinations in the Caribbean, thanks to its beautiful scenery and fun offerings. History lovers will want to visit Viejo San Juan and explore its colonial architecture. One of the famous landmarks there is Castillo San Felipe del Morro, a citadel built sometime between the 16th and 18th centuries and is recognized as a UNESCO World Heritage Site. Of course, a trip to Puerto Rico won’t be complete without talking about its beaches. Flamenco Beach, with its white sand and numerous water sports offerings, is a prime example of the tropical paradise that awaits you. You also can’t go wrong with trying local food, such as alcapurrias, bacalaítos, and piñones. Scroll down for a list of the best vacation rentals with chef in Puerto Rico, so you can easily enjoy local cuisine in the comfort of your room.
We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on April 11, 2024.
1. Luxe mansion inside Wyndham Resort Spa and Casino, Río Grande (from USD 5000)
Booking this luxury mansion will allow you to enjoy the services of a chef, a masseuse, and a chauffeur. In addition, you can also inform the host if you need a housekeeper to help tidy up the area. Contact the concierge service to enjoy outdoor activities, such as surfing, sailing, fishing, and kayaking.
The spacious home is well-appointed and comes with a fully equipped kitchen. It takes its reputation for being a luxury mansion seriously, for it boasts amenities, such as a saltwater pool, a hot tub, a sauna, and a game room.
Top guest reviews
Amenities & Room:
beautiful ocean view nice pool and hot tubvilla tuscany is beautiful and comfortable with numerous amenitiesplenty of amenities and the pool/ jacuzzi was wonderful this place is worth every pennythere was plenty of space and it was wonderful having all the bedrooms with en-suite bathroomsthe bar area with tvs by the pool was greatRead more reviewsHost:
diana and her crew were so helpful and professionalhis staff was amazing this place is 10 starsmade more perfect by all the staffdiana was great to work with- so accommodating and professionalher local reps were extremely responsive and made sure everything was perfect for our stay
2. Casa Riptides, Rincón (from USD 305)
Choosing this rental will mean having a worry-free holiday. You can request to have groceries purchased for you even before arrival, and the private chef can whip up the ingredients to make delicious food. The ocean is just a few steps away, and you can enjoy the views of the water right from the villa.
Challenge yourself to try water activities, such as snorkeling, kayaking, stand-up paddleboarding, and tarpon fishing. Alternatively, you can request a yoga class if you want to de-stress both mind and body.
Top guest reviews
Amenities & Room:
great apartment facing the water in rincónwe enjoy our stay in rincon because this apartment have a beautiful viewCleanliness:
the apartment was nicely decorated and cleanoverall nice safe clean locationclean apartment beautiful view and close to beaches and foodRead more reviewsLocation:
great apartment great location would recommend and come backstunning location right on the water with easy access (either walking or driving) to so many gorgeous beachesplace was easy to get to and clear instructions for self checkingreat location and amazing viewscasa riptides was clean and in a scenic location right on the beach
Superhost
3. Beautiful villa with a pool and hot tub, Río Abajo (from USD 487)
This villa is in a guarded neighborhood, making it a perfect choice for travelers who are concerned about safety. The rental comes with a gourmet kitchen, but you don’t need to touch the kitchenware since you can pay extra to hire the services of a private chef. Let the cook whip up delicious meals while you relax and bask in the sun on the outdoor deck. Moreover, daily housekeeping can be requested as well.
This rental features a pool and a hot tub to unwind peacefully. Pool toys, beach chairs, umbrellas, and life vests are also provided here.
Top guest reviews
Amenities & Room:
electricity was not a problem and all rooms had tv and acthe home is nothing fancy but has everything you need including strong wifi and is very comfythe kitchen was well equipped so that saved on having to buy cups plates utensils etcthe house had plenty of space for family of 10 and the kids loved the poolthe pool was perfect for the the kids and we all had our own spaceCleanliness:
we enjoyed the clean nice sized poolvery spacious up to date and clean propertythe house was very comfortable and cleanedthe house was spacious clean and had everything needed for a staythis vacation home we rented was immaculately clean and well stocked with everything we neededHost:
sam the property manager was very helpfulsam our host was awesome in accommodating us in every wayRead more reviewsLocation:
cute house in a cute neighborhood so close to the beachpretty close to walmart and gas stationsthe easy close proximity to the beach and to the grocery stores was very nicegreat house and very good location for our needsso all told i would say the near-rural location is the best part of the rental
4. Beachfront apartment with access to resort amenities, Río Grande (from USD 950)
Staying at this apartment will make you feel like you’re enjoying a tropical holiday. The rental is just a few steps away from the water and offers access to the resort’s amenities, which include a golf course, clay courts, and pools. Restaurants, cafés, and stores are also easily accessible from here.
You also have the option to avail of the services of a private chef, a chauffeur, a housekeeper, and even a masseuse. Rent a car from the host should you wish to explore the neighborhood.
Top guest reviews
Amenities & Room:
two great pools for relaxing and sunningthe beaches and pools are beautifulvery comfortable beds and furnitureyou will really enjoy this comfortable apartment with all the amenities of homegreat beach and poolsCleanliness:
the property was clean and spacious and comfortable held a family of 10the property was clean and the location was excellenthighly recommend it we had an amazing time property is nicely decorated spacious clean well equipped and great locationHost:
owner diana and property manager georgie were very responsivegeorgie and his wife are very helpful and they both offered their assistance during our stayRead more reviewsLocation:
awesome location right on the beachwe decorated excellent location walking distance of the beach and hoteldiana recommended an awesome restaurant close-bymy stay was literally hassle-free the property is in great condition and the location is perfectthe villa was very nice and the location was fantastic
5. Villa Flamboyan, Borinquen (from USD 1000)
Villa Flamboyan is just a short drive from Rafael Hernández International Airport, making it an ideal choice for travelers who don’t want to miss their flight. This rental features outdoor decks where you can enjoy ocean views. There’s an infinity pool where you can lazily float in. Surfing enthusiasts will love the fact that this rental gives you easy access to Aguadilla, Rincon, and Isabela.
Enjoy the tasty meals prepared by a private chef and avail yourself of the services of a housekeeper and a concierge during your stay. You can request a massage right on the property to unwind after a long day.
Top guest reviews
Amenities & Room:
the pool and the ocean view is amazing sunsets every nightwith 10 people we had so much room and could easily accommodate our cocktail party of 30Cleanliness:
cleanliness - very clean and having esmeralda coming daily really helpedclean and giod taste of decorationthe bedrooms were spacious and cleanHost:
he also was very responsive when we texted with questions or inquiriesRead more reviewsLocation:
our kids loved the pool and the beachfront location was beautifulgood daythe house is a spectaculsr placealthough it was a beautiful location we had several issues sink the water pressure and the infestation of mosquitos
6. Paraíso, Vieques (from USD 700)
Paraíso is appropriately named because staying here will make you feel like you’re in paradise. Enjoy strolling in the lush gardens on the property. Rest and relax by taking a dip in the heated pool. Meanwhile, beach essentials, such as towels, umbrellas, and chairs, can be provided should you wish to enjoy the sand and surf.
Restaurants, galleries, and shops are nearby, but you don’t need to dine out since the host can provide the services of a chef upon request. You can also request a housekeeper to clean up everything.
7. Villa Bellamar, Humacao (from USD 1140)
Villa Bellamar is located in a gated resort community allowing guests to enjoy ocean views. The rental is dotted with fruit trees and boasts a pool and a jetted tub. Golf carts are available for rent to make it easy for you to get around the community, which includes restaurants, tennis and golf facilities, and shops. You also get to enjoy beach access here.
Feel free to treat yourself to a relaxing holiday by making arrangements with the host to enjoy the services of a housekeeper and a masseuse. You can also look forward to enjoying the delicious meals prepared by the private chef.
Top guest reviews
Amenities & Room:
we spent the majority of our time outside by the pool admiring the ocean viewthe house includes a small workout room on the 3rd level adding another fantastic view of the areaCleanliness:
super clean house beautiful outdoor terrace serene views of the ocean and green palm treesthe grounds are clean and the house comes with a lot especially if you have a little oneHost:
home owner/property manager were also very responsivethe owner and the property manager were very responsive and made the whole rental process seamlessthe property manager rico was on time and very friendlygreat home wonderful views friendly and helpful property manager and property ownerrico the property manager was extremely helpful always available and attentiveRead more reviewsLocation:
we found this location to be within easy driving distance to the rainforest and other sites of interestthe best location and awesome ocean views are the key to making this house desirable
8. Ocean View Paradise, Rincon (from USD 766)
This holiday home is perched on a hill, giving guests fantastic views of the ocean. The rental is family-friendly and comes with a high chair and some games and toys for kids. Make sure to coordinate with the host if you want to avail the offered catering service.
Begin your days by taking a relaxing dip in the infinity pool. You can also take in the views from one of the house’s balconies or explore the garden if you want to de-stress. Enjoy scrumptious meals prepared by the private chef during your stay. In addition, this property also puts you just a short walk from the beach and nightlife.
9. Fully serviced suite with pool access, San Juan (from USD 693)
This accommodation lets you enjoy sumptuous meals prepared by a private chef whenever you’re hungry, and there’s a driver ready to take you wherever you want to go. The host can also help you arrange various tours around the island if you want to try out the top activities in the area, including hiking Pico Rodadero, zip lining, and cliff jumping. Feel free to ask for assistance from the concierge if you want to celebrate a special occasion.
This rental also has a pool, but you’ll have to follow a schedule if you want to swim here.
Top guest reviews
Amenities & Room:
the beds were all so comfortable and the furniture was not cheap 10/10our stay was extremely comfortable safe and fun all thanks to hectorCleanliness:
the property was beautiful and cleanRead more reviewsHost:
the staff was kind and caring
10. Eco-friendly villa, Rincon (from USD 1124)
This property puts you just a few steps away from Sandy Beach. The hosts take pride in the fact that this is a sustainable property powered by solar panels. Also, efforts are made to reduce unnecessary water consumption. Hammocks are available if you want to nap outdoors or enjoy the breeze. In addition, coin-operated laundry facilities are available if you need to wash your clothes.
The rental also provides a chef, a housekeeper, and a massage therapist upon request and for additional charges.
Top guest reviews
Amenities & Room:
the house interior is large spacious and comfortable with all of the essentialsour grandson really enjoyed the small pool and playing outside under the huge cabanaHost:
owner was over the top helpfulthe owners are very friendly and accommodatingvery helpful property manager when power went out in rinconthe property manager is also readily available and helpfulrusty the owner is responsive kind and honestRead more reviewsLocation:
perfect location on the beach and a short walk from restaurants/barsthere are a few fun bars and restaurants within walking distance and a short drive to downtown rinconthe location is absolutely amazing as the house sits right on sandy beachrestaurants and smoothie/latte stand so close rusty was a responsive and excellent hostthe location is superb on a bluff overlooking the ocean with sandy beach access right out the side door
Eat, sleep, and enjoy in Puerto Rico
Puerto Rico is considered one of the best holiday destinations in the Caribbean. Book one of these rentals, so you’ll have a place to sleep, enjoy delicious local food, and serve as a jump-off point to enjoy fun activities around the area.
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