Beach in Oahu
Ryan Siphers

Complete Guide to Vacation Rentals

Getting Started
Rent once and you'll never go back to a hotel vacation again. Why would you? Vacation rentals -- whether condos, homes or apartments -- offer travelers more space and, as importantly, access to a kitchen, for prices that are equivalent to those at local hotels and very often lower. Not to mention that rentals are usually in more interesting areas (unlike hotels which are often confined to commercial zones), and offer much more character in terms of décor.

Family room of vacation rental
Necessary Precautions
Purchase insurance: Cancellation policies on rentals are much more draconian than most hotel cancellation policies and usually you'll lose your entire deposit (or the cost of the rental) if you have to back out, no matter what the reason. Buying trip cancellation insurance is therefore a must, and should be factored in to the overall cost of your vacation.

Start your search earlier rather than later: That perfect hotel will likely have 100 or more rooms for you to try and snag. Really great vacation homes are one to a customer, and often get booked up well in advance. For high season rentals, you may have to book a full 6 months to a year in advance (it will vary by destination) to get the rental of your dreams.

Do your due diligence: Because by their very nature rental homes don't get the same kind of traffic that hotels do, you likely won't find individual ones reviewed in guidebooks and internet info may be limited. Instead, you need to become a detective, carefully studying photographs, asking questions and getting references from past renters. If you can, send out a scout before you rent a home, just to look it (and a few other options) over before you commit.
Female hands typing a letter on the keyboard
Websites to Visit
Owner Direct Vacation Rentals (
Rentalo (
HomeAway ( (, a rental agency, not a direct-to-owner site, specializing in Europe and the Caribbean. Key feature: it introduces you to past renters, so you can ask questions (, a site
FlipKey (, a TripAdvisor company
that handles only professionally-managed properties
Untours (, a bit different than the others, in that it provides an on-site contact. A representative gives you an orientation on the area when you arrive and is available throughout the course of your stay to help with questions and any problems that might arise.
Information Sign
Anthony Woods
Questions to Ask
1. How are problems handled? Will there be someone nearby who I can contact if I get locked out, if a fuse blows, or if some other problem occurs?
2. What does the price you're quoting me actually mean? Does it cover everything? Or will there be additional fees for utilities, WiFi, cleaning the property, use of linens, etc? Cleaning fees, in particular, can add a great deal to the cost of the rental, so get those sorted out before you close the deal.
And is this price for the property or per person (in Europe, often the price is per person).
3. Where exactly is the property? Often owners will exaggerate how close the property is to the center of town, the beach, or whatever the appealing element is in the destination. Get an exact address, and if possible a map, before you commit.
4. What's in the house? Don't assume anything! If air conditioning is important to you, make sure the property has it. Ditto for a phone, a washer/dryer, internet access, a fully-equipped kitchen (and make sure you're defining that in the same way the owner is), linens, TV.
5. Is a floor plan available to view? This will answer many questions, most important of which will be if there are enough bedrooms for everyone in your party or will some folks be expected to sleep on a fold-out couch.
6. How private is the property? You don't want to show up and find out that the owner is staying in main house, and you're in the attached guest cottage. Find out who and where you neighbors will be.
Surfboards on classic automobiles.
Stewart Pinsky/The Hawaii Tourism Authority
Hawaii Basics
Maui may be the only major tourist destination in the world where the number of vacation condo beds far outnumbers hotel beds. According to government stats, there are over 7,000 hotel units (ie rooms) on the island and over 4,000 condo units. But since many of these condos contain two and three bedrooms, it's clear that today, the majority of visitors coming to Maui are ditching hotels in favor of places where they can spread out and cook their own meals.
Image courtesy Rosewood Kauai
Rosewood Kauai
Hawaii Amenities
Perhaps Hawaiian condos have been so popular because they combine the best of hotels with the conveniences of rental properties.
Kauai condo rental.
Hawaii Companies
Big Island: Hawaii Resort Management (
Kauai: Parrish Collection Kauai ( or Rosewood Bed and Breakfast (despite the name, it also handles condos, cottages and much more;
Maui: Chase 'N Rainbows ( or Kihei Maui Vacations (
Oahu: Be Back Hawaii (
Lake Eola Park is a popular destination in the downtown Orlando area, with many people taking advantage of the beautiful surroundings.
Orlando/Orange County Convention & Visitors Bureau, Inc.
Orlando Basics
Drive south of Walt Disney World just a short bit and you'll see a puzzling sight: one gated community after another, filled with well-constructed, two-storey McMansions, each with its own private pool. That might not sound strange but look a bit closer: electronic keypads take the place of traditional locks on the doors, no mail fills the mailboxes, the doormats are free of newspapers and every single car in the driveways is a rental.
Downtown Disney Marketplace is the place to go for dining, entertainment, nightlife and shopping. It is home to the largest Disney character store in the world.
Orlando/Orange County Convention & Visitors Bureau, Inc.
Orlando Rental Categories
Cheapest of the rental properties will be condos, which will be attached to other units and will usually, though not always, share a pool. Houses will be about 30% pricier, free-standing and will almost always boast a private swimming pool.
Antiques, art galleries, clothing stores, gift boutiques, restaurants, playhouse productions, entertainment and historic buildings make up Historic Cocoa Village.
Orlando/Orange County Convention & Visitors Bureau, Inc.
Orlando Rental Agencies
Villa Direct ( Repping over 350 vacation rentals, it offers the most choices among the competition. 70% of its inventory is within 4 miles of DisneyWorld.
All Star Vacation Homes ( Prices may be slightly higher with this company, but so, too, is the quality of the offerings. And there's never a surprise with strange décor, as All Star has an on-staff decorator (who has quite good taste).
Florida Sun Vacation Homes ( often has the lowest rates of the pack, with three-bedroom units sometimes going for as little as $69/night.
Chateau de Villandry, Loire Valley
Vladimir Khirman/
France Basics
When it comes to holiday rentals in France there's just one French word you really need to know and that is "gite" (pronounced zjeet). Since 1955, the French government has overseen a network of gites -- privately owned homes of all types.
A colorful building and view of a narrow street in Arles
Anne Ackermann
French Regions and Seasons
Two factors that travelers are less likely to consider may be more significant: the date of the rental and the location. Consider this: a lovely, two-bedroom home in the Pyrenees will cost just €247 per week in the winter, up to €460 at the height of the summer season. An equivalent home (same rating, amenities and number of bedrooms) in Provence is €275 in winter, but a whopping €660 in summer.
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Richard Ellis/Flickr
The Paris Exception
The full-service agency Parisian Home (, has a wide range of options, including a number of quite affordable digs. Appartmente de Ville (, another full-service outfit, is known for the quality of its luxe apartments. For real penny pinchers, I recommend Allô Logement Temporaire (, a non-profit association which puts private owners in touch with would-be-renters. It's less hit or miss than other direct-to-owner sites for Paris, as its staff does do some oversight.
Cobblestone Bar
James Horan
Ireland and the UK Basics
There's a real divide between the new, pre-fab building boom options and the classic, thatched-roof or stone house look -- you just need to know where to look.
Photo from <a href="">Landmark Trust</a>.
Landmark Trust
Starting Your Search
Both Ireland and the UK take historic preservation seriously, and one of the ways they've been able to fund restorations and upkeep is to rent out heritage homes to the public. In the UK, the organization that does this is called the British Landmark Trust (; in Ireland, it's the Irish Landmark Trust (
Loving London Apartments
Other UK and Ireland Resources
Rent an Irish Cottage (
West Coast Holidays (, another Ireland specialist.
stayDublin (, an organization that not only leases apartments in the city but also oversees their furnishing.
Suzanne B. Cohen & Assoc (, a specialist to the UK.
Coach House Rentals (, a London expert.
Loving London Apartments (Pictured above;
One of the world's most prized wines, Brunello di Montalcino is produced in the vineyards outside this medieval hill town.
Hollenbeck Productions
Italy Basics
In Italy, you'll find as many different types of vacation homes and apartments for rent as there are different types of pasta (and if you've ever traveled in Italy, you know that the iterations for noodles and sauce are endless).
Orvieto, Italy
Elisabeth Blanchet
Italian Regions and Seasons
As with the other European destinations listed in this slideshow, prices will dip on rentals (and on airfares, too, for that matter) in the deep winter months, roughly late October through the end of March. July and August are peak season, so you'll need to book well ahead to snag a good rental then (be prepared to pay top dollar).
Villa rental from Home Base Abroad in Italy.
Home Base Abroad in Italy
Italian Companies
Roman Reference (, as the name suggests, this is for the city of Rome only.
Venetian Apartments (
Lodging in Florence (
Regione Toscana's website (, has a government run clearinghouse for farmstays in Tuscany; some are simple room rentals, others are for stand-alone homes and apartments.
Home Base Abroad (Pictured above;, good for Tuscany, Umbria, Amalfi Coast and Lake Como.