madison 12/17/2018

20 of the Best Short Term Rental Destinations for Your Holiday Vacation

We all know that the holidays are prime time to travel to amazing places.

You may be the type who likes to spend a few days someplace right before (or after) the New Year or you may be someone who wants to go all out and spend 2-3 weeks at the end of the year at some amazing destination.

Either way, we’ve got you covered.

To cut down on expenses and keep more money in your pocket, we always recommend staying at a short term rental property. Whether you decide to or not, these are the 20 best destinations to travel to for your holiday vacation (in no particular order).

If you’re reading this after the holidays, don’t fret, these are all great places to go during the summer as well.


1. Bali, Indonesia

We start off this dynamic list with Bali, Indonesia. Bali is known for its picturesque views, all-around incredible weather, and a melting pot of Eastern and Western cultures. Book a trip here and you’ll feel recharged, ready to go back to the grind for a new year!

Who should go: People who want somewhere that’s exotic but still somewhat familiar, people who want somewhere warm to go to in the Winter.

2. Florence, Italy

Heading over to Europe, we arrive in the historic city of Florence. Florence is a feast for the senses and lovers of European history and architecture. This vacation is perfect for people who need a bit of a reset, but not something too over-the-top like a luxury resort or cruise.

Who should go: Lovers of old European architecture, lovers of history, people who want reasonable accommodations.

3. Rome, Italy

Not too far away (comparatively) from Florence, we arrive in Rome. Home of the famed St. Peter’s Basilica, a stone’s throw away from the Vatican, and loaded with more history than you can shake a stick at, this is a solid European destination.

Who should go: People who want easy access to the rest of Italy, lovers of history.


4. Palm Springs, California

Throwing our attention to the other side of the Atlantic (near the Pacific), we arrive in the fabled vale of Palm Springs. The Coachella Valley is known for being a choice retirement spot in addition to hosting the famous Coachella Music and Arts Festival every year. It’s dry, low humidity heat, and easy accessibility by car or plane make it an attractive year-end destination for just about everyone.

Who should go: People who live in the United States who want a domestic vacation that may be different from what they’re experiencing in their part of the globe.

5. Oranjestad, Aruba

Aruba is known for being one of the best vacation destinations on the planet. Why’s that? Go check out its crystalline waters, white beachfront, and amazing cuisine. You’ll soon see why.

Who should go: People who want a traditional vacation where they can just relax and have fun.

6. New Orleans, Louisiana

If you want a seriously fun vacation, check out the Big Easy A.K.A. New Orleans, LA. Filled with all sorts of local shops, eateries, and boutiques, New Orleans is a perfect place for those who want an “off the beaten path” type of vacation.

Who should go: People who want something a bit different from their vacation experience.

7. Luzerne/Geneva, Switzerland

If you want a vacation with a bit of an “elevated” perspective, try out Switzerland. It’s a unique getaway filled with possibilities for hiking, dining, skiing, sightseeing, and of course - eating some fine Swiss chocolate.

Who should go: People who want a vacation filled with interesting and unique landmarks in addition to crisp mountain air.


8. Toronto, Canada

Known as the Canadian New York, Toronto boasts its status as a definitive “world city” in the Northern Hemisphere. Toronto is known for being home to thousands of attractive eateries, clubs, bars, music venues, and tons of other miscellaneous activities. If you want a vacation that’s part foreign but part domestic, here’s where you want to go.

Who should go: People who want a purely cosmopolitan vacation experience.

9. Oahu/Maui, Hawaii

Ah, Hawaii...the quintessential American getaway. If you’ve never been to this gorgeous island chain, you are missing out big time. Not only is Hawaii the only US state that grows coffee, but it’s also home to many (very active) volcanoes, wildlife, and outdoor activities. The most popular place in Hawaii is the island of Oahu, home to the capital Honolulu; but the other islands (like Maui) are worth checking out as well.

Who should go: People who want an accessible vacation, outdoorsy folks, and people who want somewhere exotic but simultaneously domestic.

10. Tokyo, Japan

Tokyo is a polar opposite from the previous entry, but it’s an exciting place all the same. Tokyo is like a clock with an endlessly supply of batteries - it never stops. If you want a vacation where you can constantly buzz with the energy of the city’s daily life and nightlife (and try some amazing sake), head to Tokyo for an unforgettable experience.

Who should go: People who want a cosmopolitan experience, amazing nightlife, and trendy attraction spots.


11. New York, New York

No list of great vacation spots is complete without New York. No matter who you are, where you’re from, or what you’re doing - New York is a place that everyone needs to visit at least once. New York is the stuff dreams are made of. With 5 distinct boroughs, thousands of entertainment options, and a diverse array of people and places, you’d need several lifetimes to see it all.

Who should go: People who want a cosmopolitan experience, people who want a very tourist-like vacation, people who want great nightlife and entertainment options.

12. Lake Tahoe, California

Heading back around to California, we come to the distinct Lake Tahoe nestled on the border of Nevada and California. During the Winter, the region is known for its diverse array of skiing, snowboarding, and snowmobiling activities. If you go during the summer, the region is entirely transformed. If you’re looking for a great vacation to enjoy the aforementioned things by day and a cozy nightlife scene, you’d be best to go here.

Who should go: People who love the outdoors, people who want a real winter vacation with various mountain-based activities.

13. Las Vegas, Nevada

Not too far from Lake Tahoe is Las Vegas. Famous for its casinos and nightlife, Las Vegas boasts other attractions such as hiking in Red Rock Canyon and Cirque du Soleil. If you want an entertainment-filled vacation that’s easy to get to, this is your trip.

Who should go: Nightlife and entertainment enthusiasts, people who want to cross “Vegas” off the bucket list.


14. Paris, France

The city of lovers is an architectural marvel in and of itself. The famous Eiffel Tower, the Louvre Museum, Arc de Triomphe, and Notre-Dame de Paris are just a few of the epic places you can visit while you’re there. Paris offers the ability to enjoy a more “sightseeing” type of vacation where you visit all of the national monuments; it also offers the chance to enjoy explore some underlooked aspectsof the Parisian experience. Whatever you decide to do, Paris is a city that offers something for someone of every stripe and background.

Who should go: Sightseers, people who want a distinct vacation that’s in a world city, nightlife enthusiasts.

15. Santorini, Greece

Santorini is a jewel (amongst many) lodged in the Mediterranean. Santorini offers an experience that’s hard to top known for its storybook sunsets, active volcanoes, and unique Grecian vibe. Scuba-diving, wine-tasting, and various other activities await the travelers that visit this gem in the Aegean.

Who should go: People who want a relaxing experience in a slow-moving environment, people who just want to unwind.

16. Auckland/Christchurch/Wellington, New Zealand

Some people think Australia and New Zealand are the same thing because they’re in close proximity, but in reality - they are like apples and oranges. New Zealand offers a completely unique experience than what many people in other parts of the world are used to. Hiking, museum hunting, and whitewater rafting are a few of the things you can do in this part of the globe. Don’t forget to say “hi” to Frodo for us, too.

Who should go: People who want to see where the Lord of the Rings was filmed, people who want a different experience and vibe from the rest of the world.


17. Castries, St. Lucia

St. Lucia is yet again another island nation that shows up on this list because it is a lovely place to take a vacation. Snorkeling, scuba diving, fishing, even ATV-ing are some of the top activities to occupy you on your stay. Let’s not forget the amazing after-dark scene, as well.

Who should go: People in search of warm weather but want something a little off the beaten path.

18. Johannesburg, South Africa

Johannesburg (also known as “J’burg”) offers great sightseeing opportunities, shopping, and nature trips. It’s one of the best places in South Africa to go if you want some of the diversity Africa offers in addition to lots of modern amenities.

Who should go: People who want to cross “Africa” off of a travel bucket list, people who want something completely different from a “standard” vacation.

19. Amalfi Coast, Italy

The Amalfi Coast is a pristine and crystalline stretch of wonder in Italy’s Sorrentine Peninsula. It’s a place that’s tucked away, yet not too distant, perfect for that “away from civilization” feel. Biking, scuba diving, beach going, and more await tourists as they explore this five-star Mediterranean paradise. Don’t be surprised if you get the feeling that you “want to live here”.

Who should go: People who want a great Mediterranean vacation filled with sun, beaches, and a sense of escape.


20. Amsterdam, Netherlands

Rounding out our list is Amsterdam. Home to long canals, various art museums, various forms of nightlife, Amsterdam is an oddity in Europe. It’s a city that offers a real cosmopolitan feel, however, it seems like everything’s a bit more “homely” and for good reason - it’s a small city that boasts a population of 820,000 people. Regardless, it’s a quirky city that everyone should visit just to say “I went to Amsterdam” at least once in their lives.

Who should go: People who want to cross “Amsterdam” off the bucket list, people who want a unique European city, art buffs.

Well, that rounds out this list. We hope this will give you some ideas for your next Winter or Summer vacation and inspire you to get out there and explore our big, blue world!

Do you have any favorite places to go on a Winter trip? Let us know in the comments.

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