10 Best Vacation Rentals With Chef In Puerto Rico

| 5 min read

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.

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.

Río Grande, Puerto Rico, Puerto Rico
Private vacation home 20 Guests 11 Bedrooms 10 Bathrooms

Top guest reviews
Amenities & Room:
beautiful ocean view nice pool and hot tub
villa tuscany is beautiful and comfortable with numerous amenities
plenty of amenities and the pool/ jacuzzi was wonderful this place is worth every penny
there was plenty of space and it was wonderful having all the bedrooms with en-suite bathrooms
the bar area with tvs by the pool was great
diana and her crew were so helpful and professional
his staff was amazing this place is 10 stars
made more perfect by all the staff
diana was great to work with- so accommodating and professional
her local reps were extremely responsive and made sure everything was perfect for our stay
Read more reviews

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.

Rincon, Rincón, Puerto Rico
18 reviews   Wifi Available
ENTIRE RENTAL UNIT 3 Beds 4 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 4

Top guest reviews
Amenities & Room:
great apartment facing the water in rincón
we enjoy our stay in rincon because this apartment have a beautiful view
the apartment was nicely decorated and clean
overall nice safe clean location
clean apartment beautiful view and close to beaches and food
gina was a very responsive host
neighborhood very safe and people were friendly
great apartment great location would recommend and come back
stunning location right on the water with easy access (either walking or driving) to so many gorgeous beaches
place was easy to get to and clear instructions for self checkin
great location and amazing views
casa riptides was clean and in a scenic location right on the beach
Read more reviews

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.

Punta Santiago, Punta Santiago, Puerto Rico
Wheelchair accessible Visual Aid: Braille
villa 18 Guests 5 Bedrooms 4 Bathrooms

Top guest reviews
Amenities & Room:
electricity was not a problem and all rooms had tv and ac
the home is nothing fancy but has everything you need including strong wifi and is very comfy
the kitchen was well equipped so that saved on having to buy cups plates utensils etc
the house had plenty of space for family of 10 and the kids loved the pool
the pool was perfect for the the kids and we all had our own space
we enjoyed the clean nice sized pool
very spacious up to date and clean property
the house was very comfortable and cleaned
the house was spacious clean and had everything needed for a stay
this vacation home we rented was immaculately clean and well stocked with everything we needed
sam the property manager was very helpful
sam our host was awesome in accommodating us in every way
cute house in a cute neighborhood so close to the beach
pretty close to walmart and gas stations
the easy close proximity to the beach and to the grocery stores was very nice
great house and very good location for our needs
so all told i would say the near-rural location is the best part of the rental
Read more reviews

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.

Rio Grande, Rio Grande, Puerto Rico
Wheelchair accessible Visual Aid: Braille
condo 8 Guests 2 Bedrooms 3 Bathrooms

Top guest reviews
Amenities & Room:
two great pools for relaxing and sunning
the beaches and pools are beautiful
very comfortable beds and furniture
you will really enjoy this comfortable apartment with all the amenities of home
great beach and pools
the property was clean and spacious and comfortable held a family of 10
the property was clean and the location was excellent
highly recommend it we had an amazing time property is nicely decorated spacious clean well equipped and great location
owner diana and property manager georgie were very responsive
georgie and his wife are very helpful and they both offered their assistance during our stay
awesome location right on the beach
we decorated excellent location walking distance of the beach and hotel
diana recommended an awesome restaurant close-by
my stay was literally hassle-free the property is in great condition and the location is perfect
the villa was very nice and the location was fantastic
Read more reviews

5. Villa Flamboyan, Borinquen (from USD 1101)

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.

Aguadilla, Aguadilla, Puerto Rico
Wheelchair accessible Visual Aid: Braille
Private vacation home 14 Guests 5 Bedrooms 7 Bathrooms

Top guest reviews
Amenities & Room:
the pool and the ocean view is amazing sunsets every night
with 10 people we had so much room and could easily accommodate our cocktail party of 30
cleanliness - very clean and having esmeralda coming daily really helped
clean and giod taste of decoration
the bedrooms were spacious and clean
he also was very responsive when we texted with questions or inquiries
our kids loved the pool and the beachfront location was beautiful
good daythe house is a spectaculsr place
although it was a beautiful location we had several issues sink the water pressure and the infestation of mosquitos
Read more reviews

6. Paraíso, Vieques (from USD 763)

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.

Vieques, Vieques, Puerto Rico
Private vacation home 8 Guests 4 Bedrooms 5 Bathrooms

7. Villa Bellamar, Humacao (from USD 1120)

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.

Humacao, Humacao, Puerto Rico
villa 16 Guests 8 Bedrooms 7 Bathrooms

Top guest reviews
Amenities & Room:
we spent the majority of our time outside by the pool admiring the ocean view
the house includes a small workout room on the 3rd level adding another fantastic view of the area
super clean house beautiful outdoor terrace serene views of the ocean and green palm trees
the grounds are clean and the house comes with a lot especially if you have a little one
home owner/property manager were also very responsive
the owner and the property manager were very responsive and made the whole rental process seamless
the property manager rico was on time and very friendly
great home wonderful views friendly and helpful property manager and property owner
rico the property manager was extremely helpful always available and attentive
we found this location to be within easy driving distance to the rainforest and other sites of interest
the best location and awesome ocean views are the key to making this house desirable
Read more reviews

8. Ocean View Paradise, Rincon (from USD 726)

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.

Bo Puntas Rincon, Rincon, Puerto Rico
Private vacation home 14 Guests 7 Bedrooms 6 Bathrooms

9. Fully serviced suite with pool access, San Juan (from USD 679)

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.

San Juan, Puerto Rico
7 reviews   Superhost Wifi Available
ENTIRE RENTAL UNIT 6 Beds 10 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 10

Top guest reviews
Amenities & Room:
the beds were all so comfortable and the furniture was not cheap 10/10
our stay was extremely comfortable safe and fun all thanks to hector
the property was beautiful and clean
the staff was kind and caring
Read more reviews

10. Eco-friendly villa, Rincon (from USD 990)

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.

Rincon, Rincon, Puerto Rico
villa 13 Guests 5 Bedrooms 4 Bathrooms

Top guest reviews
Amenities & Room:
the house interior is large spacious and comfortable with all of the essentials
our grandson really enjoyed the small pool and playing outside under the huge cabana
the house was clean and well kept
it is spacious and clean
owner was over the top helpful
the owners are very friendly and accommodating
very helpful property manager when power went out in rincon
the property manager is also readily available and helpful
rusty the owner is responsive kind and honest
perfect location on the beach and a short walk from restaurants/bars
there are a few fun bars and restaurants within walking distance and a short drive to downtown rincon
the location is absolutely amazing as the house sits right on sandy beach
restaurants and smoothie/latte stand so close rusty was a responsive and excellent host
the location is superb on a bluff overlooking the ocean with sandy beach access right out the side door
Read more reviews

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.

Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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Melanie is a freelance travel writer. She considers freelancing for Trip 101 to be a combination of two of the things she loves: writing and traveling.

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