Everything you need to know about Buying and Managing a Vacation Home in Orlando Florida
● Search Find the ideal Property ● Explore Featured Resorts ● Understand The Buying Process ● Calculate Potential Revenue
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Vacation Home Finder
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Have Questions?
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407.286.8170
Orlando Vacation Homes for Sale Buyers Guide
CLASSIC RESORTS
Houses for Sale $350k to $650k
The “Classic Resorts“, built between 1998 and 2012. These resorts have very good amenities and 24-hour security. The well established nature of these resorts makes them popular with buyers and guests. Most properties are sold as fully furnished with some level of short term rental program already in place.
As a buyer you can choose to convey the property, the contents and the business.
Aviana · Bella Vida · Emerald Island · Lake Berkley ·Paradise Palms · Providence Solana · Sonoma · Windsor Palms · Veranda Palms · Watersong · Windsor Hills
FEATURED RESORTS
The “Featured” more modern resort homes, built between 2012 and today. These resorts have large clubhouses with restaurants, bars, water-parks and outstanding amenities. All include 24-hour manned security.
Most properties are sold fully furnished with some level of short term rental program already in place. As a buyer you can choose to convey the property, the contents and the business
CONDOS
Our dedicated CONDOS FOR SALE CLOSE TO DISNEY selection is for condos in the main Orlando & Kissimmee resorts and includes hands free turn-key condo hotel options. We’ve reviewed all the best short term rental option locations so you can decide which works best for you.
SHORT TERM RENTAL COMMUNITIES
Non Resort Options. STR Communities
These communities allow short term rental but don’t have the amenity packages or offer the 24 hour gated security of the main resorts.
They are very popular for buyers looking for second homes or homes with less annual running costs.
We’ve picked out some of the best for you in the Short Term Rental Community section.
TOWNHOUSES
You will find awesome 3-5 Bedroom Townhouses in the main Featured Resorts or in a Townhouse Only Resort.
Most are stunning, fully furnished and rental ready properties with a smaller private “splash pool”.
Townhouses offer an excellent alternative to a house but at a lower price point and many families find them to be an exceptional alternative – especially those with a big deck and large pool like those at Windsor Island Townhouses.
Check out the Video Tour of the 5-bedroom Castaway Model
BRAND NEW VACATION HOMES
Brand New Vacation Villa Holiday Homes
Get creative and build a brand new vacation villa. We’ll help with all the best vendors to help you design and get it just the way your family wants it.
Windsor Cay Resort offers the best overall options for a new home but if you want to GO BIG, then you may not find any homes that are more unique or can deliver more ROI than a Reunion Custom Home.
Find all New Orlando Vacation Homes on this page.
Everything you need to know about Buying and Managing a Vacation Home in Orlando
● Search Find the ideal Property
● Explore Featured Resorts
● Understand The Buying Process
● Calculate Potential Revenue
Have Questions?
Drop us an Email!
or
Call to talk with Jerry Barker
407.286.8170
Utilize
Orlando’s Most Accurate
Vacation Home Finder
Buyer Guide 2025
Orlando Vacation Homes for Sale
CLASSIC RESORTS
The “Classic Resorts“, built between 1998 and 2012. These resorts have very good amenities and 24-hour security. The well established nature of these resorts makes them popular with buyers and guests. Most properties are sold as fully furnished with some level of short term rental program already in place.
As a buyer you can choose to convey the property, the contents and the business.
Aviana · Bella Vida · Emerald Island · Lake Berkley ·Paradise Palms · Providence Solana · Sonoma · Windsor Palms · Veranda Palms · Watersong · Windsor Hills
FEATURED RESORTS
The “Featured” more modern resort homes, built between 2012 and today. These resorts have large clubhouses with restaurants, bars, water-parks and outstanding amenities. All include 24-hour manned security.
Most properties are sold fully furnished with some level of short term rental program already in place. As a buyer you can choose to convey the property, the contents and the business
ChampionsGate · Encore Reunion · Margaritaville · Reunion Resort · Solara · Solterra · Storey Lake · Windsor Island · Windsor at Westside
STR COMMUNITIES
Non Resort Options. STR Communities
These communities allow short term rental but don’t have the amenity packages or offer the 24 hour gated security of the main resorts.
They are very popular for buyers looking for second homes or homes with less annual running costs.
We’ve picked out some of the best for you in the Short Term Rental Community section.
Calabria & Tuscany ·Formosa Gardens · Highlands Reserve · Providence · Southern Dunes · Tuscan Hills · West Haven
CONDOS
Our dedicated CONDOS FOR SALE CLOSE TO DISNEY selection is for condos in the main Orlando & Kissimmee resorts and includes hands free turn-key condo hotel options. We’ve reviewed all the best short term rental option locations so you can decide which works best for you.
Champions Gate · Reunion Resort · Storey Lake · Windsor Hills · Windsor Palms
Bahama Bay · Caribe Cove · Floridays · Lake Buena Vista · Legacy Dunes · Oakwater · The Terraces · Tuscana · The Grove · Vista Cay · World Quest
TOWNHOUSES
Townhouses For Sale
You can also find some awesome 3-5 Bedroom Townhouses in the main Featured Resorts or in a Townhouse Only Resort.
Most are stunning, fully furnished and rental ready properties with a smaller private “splash pool”.
Townhouses offer an excellent alternative to a house but at a lower price point and many families find them to be an exceptional alternative – especially those with a big deck and large pool like those at Windsor Island Townhouses.
Check out the Video Tour of the 5-bedroom Castaway Model
Champions Gate · Encantada · Paradise Palms · Regal Palms · Regal Oaks · Solara · Storey Lake · Summerville · The Enclaves · The Fountains · Tranquility · Windsor Hills · Windsor Island
BRAND NEW VACATION HOMES
Brand New Vacation Villa Holiday Homes
Get creative and build a brand new vacation villa. We’ll help with all the best vendors to help you design and get it just the way your family wants it.
Windsor Cay Resort offers the best overall options for a new home but if you want to GO BIG, then you may not find any homes that are more unique or can deliver more ROI than a Reunion Custom Home.
Find all New Orlando Vacation Homes on this page.
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