12 Best Vacation Rentals With Chef And Maid In Florida, USA - Updated 2024

Rachelle Anne
Rachelle Anne 
Updated
| 5 min read

Affectionately named the Sunshine State, Florida’s tropical climate attracts people from all over the world. With one of the longest coastlines in the country, the state has over 1000 miles (1609.3 kilometers) of beaches. While Florida is famous for its summer vibes, it’s also home to 11 national parks that have nearly half of the tree species found in the United States. Everglade National Park itself has an average of a million visitors every year with its unique ecosystem with flora and fauna such as mangroves and Florida panthers. When it comes to cuisine, the Sunshine State certainly has a flair for diverse cuisines from fresh dishes to Floribbean food. Read through this list of the best vacation rentals with chef and maid in Florida, USA.

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 February 08, 2024.

1. Villa Esperanza in Miami (from USD 907)

Welcome to Villa Esperanza, a luxurious getaway promising to deliver the ultimate Miami experience. Inside, guests will discover a chef’s dream kitchen and a spacious dining area with ample seating. The villa also boasts a large deep pool, and a generous backyard featuring a gazebo and outdoor kitchen, all set within meticulously landscaped surroundings. For the ultimate indulgence, private chef services, as well as maid/cleaning services are offered.

Located just moments away from Miami’s top attractions and the airport, the central location of this getaway makes exploring the city a breeze. Situated within easy reach of Coral Gables, Coconut Grove, Miami Beach, and South Beach, guests can experience the vibrant essence of Miami at its finest.

Stayed at this property?
Miami, Florida, United States
9.99 km (6.3 mi) from Morningside Park
58 reviews   Superhost Wifi Available
ENTIRE HOME 10 Beds 16 Guests 5 Bedrooms 4 Bathrooms

Accommodates: 16

Top guest reviews
Amenities & Room:
wifi was strong (and reached the pool area )
beds were super comfy and the neighborhood was safe and quiet
pool was a great hangout and big enough for 15 ppl
gorgeous house and yard the pool was amazing
Cleanliness:
if properly cleaned and prepped it could be great
their space was welcoming clean and comfortable
stylish comfortable and clean
the backyard was absolutely gorgeous pool was clean and outdoor kitchen…
from the moment we walked in it looked amazing was clean and smelled fantastic
Host:
hosts were very responsive
you were both amazing hosts
great hosts the home was a 10/10
she was very responsive to any questions or concerns we had
very nice hosts great airbnb
Location:
great location close to airport and easy to get around
this house is absolutely beautiful it is also so close to everything
super close to downtown and the airport i highly recommend staying here you don’t regret it
great place totally recommend it
Read more reviews

2. Pirate Palms in Naples

Indulge in the serene haven of Pirate Palms, a private cottage mere moments from the city center. This charming retreat boasts a well-appointed bathroom, while the kitchen is equipped with modern conveniences, and enjoy meals at the dining table. Outside, discover a private patio or balcony where you can relish the tranquil surroundings with the included fire pit, outdoor dining area, and grill. Additionally, Pirate Palms offers an exclusive treat with private chef services, and cleaning services ensure a pristine escape.

Nature enthusiasts can explore the “Edible Forest” on the property’s sprawling grounds, all while experiencing the beauty of Naples with its stunning beaches, wildlife preserves, and a tranquil ambiance that invites you to unwind. To mingle with the locals, visit nearby pubs and taverns, or opt for more sophisticated entertainment at venues such as the Philharmonic Center for the Arts.

Stayed at this property?
Naples, Florida, United States
155.13 km (96.4 mi) from Morningside Park
135 reviews   Wifi Available
Entire guesthouse 3 Beds 4 Guests 2 Bedrooms 1 Bathroom

Accommodates: 4

Top guest reviews
Amenities & Room:
did i mention there is a washer and dryer? the air conditioning is strong
ac works great and kitchen is fully stocked with useful gadgets etc
as a pirate fan the little details were so fun inside and all over the grounds
the rooms were super cute and the beds were comfy
Cleanliness:
the place was very clean
the place was very clean and you have use of the pool and property
everything was very clean and they had everything that you would ever need
f a b u l o u s e very clean confortable
the guesthouse was very spacious and dog friendly
Host:
they were beyond helpful
very responsive to our questions
the hosts are very responsive and friendly if you have any questions or issues
christopher and arthur are wonderful hosts
arthur and christopher were amazing hosts and definitely have the gift of hospitality
Location:
the location is perfect for naples exploration and fwy close to venture out
this place is fantastic such a great location and in a safe and secure neighborhood
very unique and fun place great safe location
we highly recommend booking at the location
the location is great and the airbnb is beautiful
Read more reviews

3. Breathtaking mansion in Kissimmee for large groups (from USD 2200)

This luxury villa is complete with themed bedrooms, a theater, a few game rooms, an outdoor kitchen, a workout room, and a spacious outdoor pool. On top of its stunning muraled walls, the mansion has free wifi, laundry facilities, a full kitchen, a dining area that can seat up to 26 people, and private chef services. While guests can enjoy the multi arcade machine and air hockey table, they also have access to Reunion Resort’s water park, golf courses, and tennis courts.

Stayed at this property?
Four Corners, Florida, United States
307.07 km (190.9 mi) from Morningside Park
villa 28 Guests 11 Bedrooms 15 Bathrooms

Top guest reviews
Amenities & Room:
the wifi is great and plenty of things to do at the house
huge home lots of space great amenities comfortable clean well managed
everyone loved the heated pool and hot tub the theatre room and the game room
this house is a wow for sure everything was wonderful bedding towels outdoor furniture bathrooms kitchen theatre room
pool and hot tub are both really nice
Cleanliness:
easy to navigate and very clean
the house itself was beautiful but it definitely wasn’t cleaned properly
Host:
management company very helpful and can hire a chef if you want
Location:
all in all this is a great place to stay and the mansion is beautiful
Read more reviews
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4. The Pelagic Blue, Dune Allen Beach (from USD 1805)

This beachfront mansion for rent in Florida is tucked away on Dune Allen Beach. It has a built-in grill, a private in-ground pool with a deck, and a pergola. Able to accommodate up to 18 guests, the house has en suite bathrooms in every room and even has an in-home elevator and a laundry in-unit. Guests can rent bicycles, head to Santa Rosa Beach Golf Club, or request an on-site massage. When it comes to meals, guests can request for a private chef, cook up a meal in the fully equipped kitchen, or dine out at one of the nearby restaurants.

Stayed at this property?
Santa Rosa Beach, Florida, United States
779.93 km (484.7 mi) from Morningside Park
PRIVATE VACATION HOME 18 Guests 7 Bedrooms 8 Bathrooms

Top guest reviews
Amenities & Room:
the availability of the beach was wonderful and the heated pool was perfect for the cooler february days
the beds were incredibly comfortable the house was gorgeous
bathrooms were huge the location was perfect and the we had best view of beach
Host:
was a great place for our staff retreat
Location:
we cooked a lot of great meals went out to the local restaurants and walked miles of beach
Read more reviews
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5. Modern oceanfront home in Marathon (from USD 650)

This upscale oceanfront Vrbo in Florida for eight boasts three spacious balconies overlooking the Atlantic Ocean, floor-to-ceiling windows, five televisions, a private pool, and a comfy sitting area. Ideal for groups or families, the home has everything guests will need for a fun and luxurious vacation getaway. Guests can enjoy direct access to the beautiful beach, and they can borrow outdoor equipment such as kayaks, paddleboards, life jackets, and a bait freezer for fishing. On top of that, the house has convenient features such as high-speed wi-fi, central heating, air conditioning, a washer and dryer, and a private chef that will visit upon request.

Stayed at this property?

151.37 km (94.1 mi) from Morningside Park
30 reviews   Wifi Available
House 8 Guests 4 Bedrooms 3 Bathrooms

Accommodates: 8
Minimum Nights: 7
Refund Policy : 100% refund if you cancel at least 60 days before check-in.

Top guest reviews
Amenities & Room:
the bed linens were very soft and comfortable
Host:
that you need to feel at home great job on the owners part
Read more reviews
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6. Brand new villa in Kissimmee near Walt Disney World Resort (from USD 439)

Tucked away in Kissimmee and only a short drive away from Walt Disney World Resort, this all-inclusive villa with a private chef in Florida can comfortably sleep up to 16 guests. The villa includes seven baths, a private pool, cribs and high chairs for kids, air conditioning and heating, and free wi-fi. Guests can spend their time working up a sweat on the on-site gym area, chilling in the hot tub, grilling out in the backyard, or enjoying a fun day at the water park at Encore Club. What’s more, guests can request pre-stocked groceries, order optional welcome packs, or request professional chef services.

Stayed at this property?
Kissimmee, Florida, United States
307.52 km (191.1 mi) from Morningside Park
58 reviews   Wifi Available
Entire villa 11 Beds 16 Guests 8 Bedrooms 7 Bathrooms

Accommodates: 16

Top guest reviews
Amenities & Room:
the resort amenities are great especially the water park and pool area
we were able to enjoy the pool grill and cook during our stay
the house was perfect for a large group as there are plenty rooms with king and queen beds
pool complex including water slides is super fun for kids
pool great for the kids- house had lots of space and worked perfectly for our vacation
Cleanliness:
my stay was awesome very clean house
the house is sparkling clean with a beautiful layout
everything was clean and the house is super spacious which is great for big groups
it was beautiful spacious clean and very well equipped
fantastic home and extremely clean
Host:
host and the management are excellent
the customer service from both the host & the resort management jeeves was outstanding
also the management company is very responsive
hulya’s place was as pictured the host was great
host is very thoughtful and great to communicate with
Location:
the location was perfect and their were many stores near by (walmart publix & a liquor store)
definitely recommend this beautiful house to anyone thinking of staying near the theme parks
nice to have somewhere close by to get a break from the amusement parks and crowds
great location for all the disney theme parks
close to the theme parks and great to come home to the pool
Read more reviews

7. Pet-friendly beach house in Fort Lauderdale (from USD 3714)

This modern beach house in Fort Lauderdale is situated in a quiet neighborhood by the beach. The pet-friendly beach house features a swimming pool, an outdoor fireplace, laundry facilities, a surround sound speaker system, and a full kitchen with modern appliances such as a blender and ice maker. Not only this, but the house has paddleboards, dive flags, sea kayaks, and bikes for days out on the beach and plenty of floaties for the pool. During their stay, guests can request for Personal Chef Carlos Fernandez from “Top Chef”, a personal trainer, and a personal massage therapist.

Stayed at this property?
Fort Lauderdale, FL, US
10 Guests 4 Bedrooms 4 Bathrooms
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8. Rustic lakeside retreat in Palatka (from USD 133)

Tucked away in the woods near Round Lake, this wooded lakeside retreat is complete with air conditioning and heating, a kitchenette, coin-operated laundry facilities, wireless internet, and ironing facilities. The home is both pet-friendly and family-friendly with its pack ‘n play, books, and board games. While guests can make use of the house’s boats for some fun in the gorgeous lake, they can also have a cozy night in with movies from Netflix, Hulu, or Amazon Prime. On top of that, the property’s owners can hook guests up with a private massage therapist or a private chef upon request.

Stayed at this property?
Palatka, Florida, United States
447.94 km (278.4 mi) from Morningside Park
Apartment 6 Guests 2 Bedrooms 1 Bathroom

Top guest reviews
Amenities & Room:
bedrooms each have a queen bed (not sure why the listing notes a king)
Cleanliness:
everything was clean and the location was perfect
Host:
the owners are responsive and helpful
the owners are on site and wonderful to meet
the owners are next door and are awesome
roberta greeted us and was very helpful
Read more reviews
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9. Waterfront property in Miami (from USD 3250)

This five-star waterfront beach villa comes complete with a gourmet kitchen, high ceilings, walk-in closets, a sub-zero wine fridge, and a built-in heated saltwater pool. With an oversized wrap-around balcony and an outdoor dining area, it allows guests to appreciate the view from almost every corner of the villa. Besides the grand pool, guests can also make use of the ground floor game room, the outdoor pool table, and the vast video library. In addition to that, guests can request for a private chef, rent bikes near the property, visit some historical places and local attractions like Miami Beach Boardwalk and Bayside Marketplace.

Stayed at this property?

2.21 km (1.4 mi) from Morningside Park
124 reviews   Wifi Available
estate 18 Guests 6 Bedrooms 6 Bathrooms

Accommodates: 18
Minimum Nights: 3
Refund Policy :

Top guest reviews
Amenities & Room:
everyone enjoyed themselves from the pool pool table outdoor patio outdoor grill
nothing to worry about and lots of room amenities and a great property manager
pool/yard/downstairs kitchen was perfect for hanging outside all day
it’s very spacious with loads of mod cons to keep you comfortable
house comfort views swimming pool offered food service communication met all expectations
Cleanliness:
claudia who took care of keeping the house clean was so sweet we would definitely stay here again
Host:
the house was amazing the entire staff was absolutely wonderful including the property manager (randy)
this home is beautiful and very accommodating
john and the care takers were fantastic to communicate and work with
randy was really helpful and looked after us beautifully - he makes an amazing steak too
besides all of these amazing things the owner john is one pretty cool guy
Location:
we couldn't find a better place to celebrate my husband's 50th birthday with college friends
Read more reviews
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10. Bright villa in Orlando with pool (from USD 153)

Only a 15-minute drive from Kissimmee Bay, this stylish vacation rental in Orlando provides guests with high-end services, including a private chef, private transport, and equipment for hire. Able to sleep eight people, the villa includes a private pool, a walk-in closet, a flat-screen cable television, a wet bar, laundry facilities, and a fully equipped kitchen. Ideal for families, it also has a room designed for children and offers babysitting services for an additional charge. If guests want to explore more of the city, the villa is near a handful of attractions, such as Gatorland, Seaworld Orlando, and Discovery Cove.

Stayed at this property?

304.99 km (189.6 mi) from Morningside Park
51 reviews   Wifi Available
villa 8 Guests 4 Bedrooms 3 Bathrooms

Accommodates: 8
Minimum Nights: 7
Refund Policy : 100% refund if you cancel at least 60 days before check-in.

Top guest reviews
Amenities & Room:
high quality beds were more comfortable than any other vrbo we've rented
the only thing to note for swimmers is that their beautiful pool was pretty cold (in february)
beautiful home tasteful decor and very comfortable
Cleanliness:
the house was clean and well equipped
home was clean comfortable and well stocked
the house is in wonderful condition clean and had everything we needed
clean comfortable home in a great location
Host:
owners left many helpful tips
owners were very helpful with anything i needed
beautiful home wonderful host
neville and gillian were extremely responsive and accommodating to us
Location:
its also very close to some great places to eat
beautiful home close to all orlando attractions and airport
we wanted peace and quiet and that’s what we got
Read more reviews
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11. Large guest home in Islamorada (from USD 3000)

This Tuscan-style gated estate sits on 2 acres (0.8 hectares) of private land and includes a private sand beach, an attached two-story guest home, laundry facilities on every floor, and an oversized hot tub. Ideal for families and groups, the villa can house up to 20 people and offers services from a five-star chef that’s included in the rental fee. With cleaning, cooking, and personal shopping all taken care of, guests can completely focus on relaxing and having fun. Enjoyable things to do include unwinding at the villa’s sunken bar, taking a stroll through the citrus orchids, floating around in the pool, or playing around on the ping pong table.

Stayed at this property?
Tavernier, FL, US
18 Guests 9 Bedrooms 8 Bathrooms
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12. Big on the Beach House, Captiva (from USD 725)

Big on the Beach House is an oceanfront retreat that provides guests access to North Captiva Island’s pools, tennis courts, tiki bar, and bike rentals. The house can fit up to 16 individuals and includes a hot tub, flat-screen televisions in every room, a golf cart, laundry facilities, a full kitchen, and wireless internet. For meals, guests can make use of the spacious kitchen, visit one of the amazing local restaurants, or request an on-site private chef. With plenty of windows and open space, the house allows families and large groups to enjoy the sea breeze and watch the sunset on the balcony

Stayed at this property?
Captiva, Florida, United States
221.3 km (137.6 mi) from Morningside Park
Wheelchair accessible Visual Aid: Braille
PRIVATE VACATION HOME 18 Guests 6 Bedrooms 3 Bathrooms

Top guest reviews
Cleanliness:
very clean and well stocked kitchen
Host:
island people were friendly and helpful
the owners were great everything went smoothly highly recommend the big on the beach house
the caretaker deborah was available whenever we had a question and gave us great advice
Location:
quite the excellent location on this lovely island
location is great both golf carts worked good
the preserve was the best for shelling but quite a long walk to get to the beach
our group all agreed it was a perfect place to relax and enjoy a beautiful location
Read more reviews
Earn OneKeyCash for every dollar spent on eligible hotels, vacation rentals, flights, car rentals, and more when you book across our family of brands.

Relax and unwind in the Sunshine State

Appreciate the luxury of the Sunshine State during your vacation trip with loved ones. Rent out any of these many vacation rentals with the chef in Florida, USA, and have fun without having to worry about what to eat.

Stayed at this property?

Frequently asked questions about best vacation rentals with chef and maid in Florida, USA

1. Which vacation rentals with a chef and maid in Florida are ideal for long-term stays?

When considering vacation rentals with a chef and maid in Florida for long-term stays, several options stand out for their combination of luxurious amenities and extended-stay convenience. A few choices to consider are Villa Esperanza in Miami and Pirate Palms in Naples.

2. Which vacation rentals with a chef and maid in Florida have parking?

Looking for vacation rentals with a chef and maid in Florida that offer convenient parking options? Look no further. Some of the options that offer parking are Villa Esperanza in Miami, Pirate Palms in Naples, and The Pelagic Blue, Dune Allen Beach.

Any must-sees we missed? Tell us about them in the comments section or write a post here to help out fellow travelers!
Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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Rachelle Anne is a person who takes pleasure in acquiring knowledge across various domains. During her leisure time, she engages in reading or listening to podcasts, accompanied by a cup of dark...Read more

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