The 20 Most Expensive Airbnb Listings in 2019

Airbnb had been a brilliant idea from the start in 2008. They let you rent space in someone’s home or property just as though it was a hotel. Alternately you could rent out a room, guest house or other available living space on your property for extra cash. The alternative to traditional hotels offers more privacy and variety than most hotel rooms, often at a better cost. Sometimes the most straightforward ideas are the best, and Airbnb took off like wildfire. Now they offer over 80,000 accommodations in 191 countries.

Already innovators in the field, offering peerless artistic experiences through their partnership with the Louvre and Bob Ross certified painting instructors among their programs, they have gone a step further. Without expansion, business stagnates, so Airbnb decided to create the Plus program. These exclusive homes and other rentals are verified to be the height of good taste. With the upgraded appearance and services, there’s often a higher fee. Just how high? Check out our collection of the most expensive Airbnb locations in the world for a luxury vacation destination nonpareil (all prices are cost per night).

20. All Together Now, Key West, Florida – $3,732

Quiet and coastal, this tropical getaway has thirteen bedrooms and a pool. Key West is one of the most desirable escapes to visit in North America. From glorious golden weather to swaying palm trees, island living has it all. This is as far south as you can get without leaving the USA, and despite the island location, there is a highway that connects to the mainland over the water so you can drive right down. You can bring everyne when you rent this block of houses for your vacation or event.

19. New Orleans, Louisiana – $4,000

The height of southern refinement can be rented for the night. If you ever wondered what it’s like inside a New Orleans mansion, then this option in Audubon Park is perfect. The turn-of-the-century style harkens back to a simpler and more elegant time when men wore hats, and you could attend a ball every evening if you knew the right people. Fireplaces, chandeliers, and sweeping grounds are standard. Special features include the amazing salt water pool, cabana and a butlers pantry for guests.

18. Tsheshepe Safari Lodge, Welgevonden Game Reserve, Limpopo, South Africa – $4,500

If you plan to visit Africa for a safari, it’s important to consider your destination very carefully. The Tsheshepe Safari Lodge on the Welgevonden Game Reserve is in a malaria free zone. You can take tours with an experienced guide twice a day to spot the local wildlife including rhinos, elephants, and lions to say the least. When you’re done enjoying nature and read to relax at days end, you can order from the chef, visit the fitness center. The infinity pool is a great way to watch an African sunset, and there are outdoor rain showers and soaking tubs to help you cool off after the heat of the day has passed. If you want to fly in, there’s even a private airstrip.

17. Kailua-Kona, Hawaii – $4,900

Hawaii is always a popular destination. With volcanoes, sand, surf, sun and hula dancers it’s hard to imagine vacation planning without at least considering the islands. If you want a truly singular experience, then rent this five bedroom, 6,300 square foot home beside the Four Seasons Resort. If you don’t surf, you can still relax in the outdoor infinity pool. With a fire pit, hot tub and outdoor showers, you can enjoy the best of this tropical adventure and never even have to track sand inside.

16. Tuscany, Italy – $6,525

Not every elite listing is in an important city or tropical destination. This charming restored fortification was home to the local nobility and still plays host to a staff that will give you the royal treatment. Feel free to bring your friends and loved ones along for the ride since this rental has 34 bedrooms. You’ll be located just a few km from Siena, and you will find plenty of amenities inside and out. If you need a break from the constant pampering, then check out the local woodland areas or go for a bike ride. This dream wedding destination is a steal compared to some on this list, especially since you can bring 49 friends and split the bill.

15. Stein Eriksen Condo, Park City, Utah – $8,839

For a stylish experience, you can stay in this Deer Park condominium. It’s known for its fireplaces and proximity to Silver Dollar ski run. As a Stein Eriksen residence, you know you’ll get the same quality as the rest of their famed experiences in this sweet and petite offering.

14. Nafsika Estate, Megalochori, Santorini, Greece – $9,255

Looking for something timeless and classic? You can end your search in this regal 17th-century abode. With breathtaking ocean views of the Aegean and a lovely pool, you can take your repose and watch the waves. One of the most unique features of this property is access to a private helipad, in case you want to fly in style and skip the airports.
*economic changes in Greece have deeply affected the cost of visiting at this time, however, we’ve left this stunning listing here for you to enjoy. Book it now before the price goes back up!

13. Yacht in Juneau, Alaska – $10,000

There’s living, and then there’s life aboard a yacht in Juneau Alaska. Eat delectable gourmet meals on your trip that are provided by the onboard staff. You can view the Aroura Borealis if you’re fortunate enough to catch it, or go whale watching in the cool northern waters. You’ll have the chance to see waterfalls and sunsets over the waves. If things get too chilly, you can always sit in the hot tub with up to seven friends.

12. Mansion, Hamilton, Illinois – $10,000

A view of the Mississippi with its stately riverboats and historically significant waters may be just the thing to help you enjoy your next vacation. This massive four bedroom, seven bathroom listing offers water activities within easy reach, and it’s located near a small airport that takes private planes. Situated on an entire city block and fenced in, you’ll have all the privacy you need at this posh pad.

11. Austin, Texas – $10,075

Why rent one place when you can rent three instead? This distinguished villa features two main houses and a guest house. You can bring fifteen friends, or some family and your staff if you prefer. Though we know this particular listing is available for the South by Southwest festival, we aren’t sure it’s available year round. You’ll want to inquire well in advance to book the most ideal Airbnb option in Texas.

10. Park City Castle Mansion, Utah – $11,528

Sometimes you just want to feel like royalty. When you need a truly opulent experience, try renting a castle for the evening. You’ll enter through the private gatehouse and have 16,000 square feet of breathtaking decor indoors. Outside you can “ski in and ski out” if you wish to do so in the winter. With the massive fireplace and in-house gym, you won’t lack for amenities. Nothing quite says sophistication the way sleeping in a castle can. *price may have gone down to $2271 or may be less in the offseason

9. Brisas Del Mar Beach Oasis – $11,600

A one of a kind hillside hacienda in Mexico with several infinity pools looks out over the beach. You can book this location through more than one travel site, so you want to check well in advance to get the dates you want. Lots of luxury locations have pools, but this one has a swim up bar. You’ll want for nothing with the private chef and butler service here, and the Sea of Cortez is so gorgeous you’ll never want to leave.

8. Villa Machiavelli, San Casciano, Tuscany – $11,658

Are you a fan of Chianti? This marvelous manse is located in the center of Italian wine country. Unfortunately, you usually can’t book a single night as Villa Machiavelli has a four-night minimum and will set you back almost $50,000 once the $3,318 service fee gets added to your tab. In the offseason you might be able to book a night for around $10,000 On the plus side, you can bring up to 15 friends to share the ten bedroom experience. The marble and views alone make this one of the most alluring options on the list.

7. Amazing Grace West Indies Plantation in Turks and Caicos – $12,000

This truly fabulous location is called Amazing Grace, and you might feel blessed by the divine when you stay in this stunning Airbnb rental in the West Indies. If you go in the offseason, you can book this elegant and aesthetically enchanting offering for around $6776. If you want to spend a winter night, with up to nine friends, in the tropical stunner with its white sandy beach, 9000 square feet of space and private pool, then you’ll have to pay the premium.

6. Red Rock Ranch, Missouri – $12,000

Not many listings include ATVs, guns and fishing equipment as part of the standard package, but this 80-acre ranch has more features than most. It is situated right on a lake and can accommodate a party of 16 easily. With a fully stocked bar and a chef on call, you can relax in this expansive estate without a care in the world. If outdoor adventures are your style, you can enjoy nature at this location, and with all that space you don’t have to worry about disturbing the neighbors.

5. Bel Aire, Beverly Hills, California – $13,950

Like many properties, you might catch a discount on a Tuesday in the offseason, but a Saturday night in this palatial gated estate in Bel Aire will set you back over $13,000. Hillcrest is a classic manse, worth seeing, but it has some uniquely updated features as well. There’s a skateboard ramp on the tennis court. Lovers of the classic will adore this 1938-built beauty, replete with statues and a library. Additionally, you can browse the “vinyl lover’s delight’ room and listen to your favorite albums from their collection.

4. Denver, Colorado – $15,000

For the perfect family-friendly vacation you may want to check out this posh listing in Colorado. With the main house, barn and cottage on 30 acres there’s plenty of space to bring the whole family, or up to 22 of them anyhow. Explore the pond, pool, and playground with the kids. You can use the gym and the BBQ as you like while you’re staying at this popular wedding destination.

3. Pointe Milou, St. Barts – $19,000

With an infinity pool by the sea, this St. Barts abode is one of the more visually arresting homes on the planet. You and your guests can enjoy 7000 square feet of stunning space. The ocean views alone are worth a little extra, and the exclusive location is a playground for the wealthy. You might snag this sweet space for as little as $3330 during the offseason if you get lucky, but during the winter holiday peak, you’ll have to put down a lot more for a night in this paradise.

2. Chateau in Burgundy, Burgundy France – $19,491

Picturesque fairytale living, or at least visiting, can be yours at this incredible Airbnb gem. A 28 bedroom/33 bed castle can be yours for a minimum two-night stay. Though this hidden Airbnb gem is typically used by wedding parties, you can bring whoever you want. You’ll feel like royalty when you stay in this French castle.

1. Stein Eriksen Residences – 5 Bedroom, Park City Utah – $49,999

The top of our list are the Stein Eriksen residences. There are several available with different numbers of bedrooms, but all of them will set you back nearly $50,000 per night and you have to put in a special inquiry to get an exact quote. You can relax with up to 9 friends and family members, right on the Silver Dollar ski run in the Uinta mountains. These refined rentals are truly a skier’s paradise.

Final Thoughts

For those seeking the exclusive and erudite escape for a night or even a few days, these incredible Airbnb offerings have all the sumptuous grandeur of the finest hotels, without the need to encounter other guests. You can seclude yourself from the world, or merely step away from it at the end of a day in town at any one of these delightfully unexpected locales. The only real question is where to go first.


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