Orlando Vacation Homes » Orlando Vacation Home Buyers Guide

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How to Buy an Orlando Vacation Home

  1. Decide How You Will Use the Home

Most buyers use their holiday home for a trip or two each year and rent it the rest of the time. If you want long stays or may retire there, look for resorts with unlimited owner usage; some resorts cap owner stays at 6 months a year.

  2. Choose a Property Type

Condotels are the most hands-off, condos and townhomes balance price and space, and single-family pool homes sleep the biggest groups and earn the highest nightly rates. Our guide to choosing a condo, townhome, pool home or condotel compares them side by side, and new construction vs resale covers buying from a builder.

  3. Pick the Right Resort Area

Each area has a different feel: West Hwy 192 and Lake Buena Vista are closest to Disney, International Drive is closest to Universal, Champions Gate has golf resorts and large homes, and East Hwy 192 and Hwy 27 offer a wide range of prices. See how to choose an Orlando resort.

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  4. Only Buy Where Short-Term Rentals Are Allowed

Many Orlando-area neighborhoods do not allow nightly rentals. Every resort on this site is zoned for short-term rentals (STR), but rules on minimum stays, owner usage and management still differ, so confirm them for the resort you choose. Our laws, taxes and regulations guides cover each county.

  5. Plan Your Management

Decide whether you will use an on-site rental program, a 3rd-party manager or self-manage. On-site programs are the most hands-off but may limit owner use; outside managers may face extra fees or amenity rules at some resorts. See condotel 3rd-party management restrictions.

  6. Budget for the Full Cost of Ownership

• HOA or condo fees, which often cover resort amenities
• Property insurance and, where needed, flood insurance
• Property taxes and utilities
• Management fees, cleaning, pool service and maintenance
• Florida sales tax and county tourist development tax on rental income, usually collected by your manager or booking platform
• Furnishing, theming and photos if the home is not sold furnished

Check for a community development district (CDD) too – its charges sit on the property tax bill. See HOA fees vs CDD fees and the true cost of owning an Orlando vacation rental.

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  7. Arrange Financing Early

Lenders treat a home you plan to rent as an investment property, and condo-hotel units can be harder to finance. Talk to a lender who works with vacation rentals before you start making offers. Our guide to financing an Orlando vacation home compares investment, DSCR, second-home, condotel and foreign national loans.

  8. Make an Offer and Close

Ask for rental history on furnished homes, review HOA documents and any rental program agreement, and order an inspection. Many buyers close remotely, and showings can be done by live video if you cannot be in Orlando.

Buying a home that's already renting? See what to check and what doesn't transfer. If the seller lives outside the US, the buyer must withhold tax for the IRS – see buying from a foreign seller (FIRPTA).

  Download the Full Guidebook

Want the full version? Download our free How to Buy an Orlando Vacation Home guidebook, or browse all our buying and investing guides.

This guide is general information, not legal, tax or financial advice. Rules, fees and taxes change; confirm current details before you buy.

Rental rules, management policies and HOA fees can change. Contact us to confirm current HOA and Management Company fees before you buy.

  Ready to Start Your Search?

We help you compare resorts by owner usage, management, HOA fees and rental appeal before you buy. The latest listings appear below and update daily from the MLS – view all available vacation homes. To ask about any resort or listing, Call/Text David Myers at 407.801.3286 or send us a message.

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