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Orlando Vacation Homes » Vacation Homes $400K to $500K

  View All Vacation Home Properties

Orlando Vacation Homes $400K to $500K

These are Orlando-area vacation properties priced $400K to $500K in resorts where short-term rentals (STR) are allowed. This range typically includes larger townhomes and smaller single-family pool homes in resorts with good amenities.

 

$400K-$500K

price range

 

STR

allowed

 

Updated

daily from the MLS

  Tips for Buying in This Price Range

  • Compare total monthly costs, including HOA fees, insurance and management, not just the price
  • Check owner usage and management rules for the resort before you make an offer
  • Ask for rental history on furnished homes and condos

  Compare by Property Type

Compare all vacation homes, townhomes, condos and condotels, or see resorts by maximum owner usage.

Prices change daily. The listings below come straight from the MLS.

  Vacation Homes $400K to $500K FAQ

What can I buy $400K to $500K near Disney?

This range typically includes larger townhomes and smaller single-family pool homes in resorts with good amenities.

Are these properties allowed to be short-term rentals?

Yes. Every listing on this page is in a resort area zoned for short-term rentals. Rules on owner usage and management vary by resort.

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

  Buying a Vacation Home $400K to $500K

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 listings in this price range. To ask about any resort or listing, Call/Text David Myers at 407.801.3286 or send us a message.

  View All Vacation Home Properties Ask About Vacation Homes

Vacation Homes $400K to $500K

7312 Oakmoss Loop, Davenport image
7312 Oakmoss Loop, Davenport $500,000 ▼

Virtually Staged. Short Sale. This home can be purchased with NO INCOME VERIFICATION needed! Seller's preferred lender is willing to contribute 1% of the loan amount towa...

  • 5 Beds
  • 4 Baths
  • Solterra Ph 2b SubDv.
  • 33837 Zip Code
2569 Reading Trail, Kissimmee image
2569 Reading Trail, Kissimmee — X $500,000 ▼

Beautifully furnished and professionally designed 4-bedroom, 3-bathroom townhome located in the highly sought-after Storey Lake Resort, just minutes from Walt Disney Worl...

  • 4 Beds
  • 3 Baths
  • Storey Lake The Cove SubDv.
  • 34746 Zip Code
4072 Oaktree Drive, Davenport image
4072 Oaktree Drive, Davenport $500,000

Located in a short-term rental–approved vacation community, this well-maintained single-story home at 4072 Oak Tree offers an excellent combination of comfort, amenities,...

  • 4 Beds
  • 3 Baths
  • Oakmont Ph 01 SubDv.
  • 33837 Zip Code
3092 Rockefeller Way, Kissimmee image
3092 Rockefeller Way, Kissimmee $500,000

Modern Resort Living Just Minutes from Disney | Turn-Key Investment Opportunity Welcome to 3092 Rockefeller Way, a contemporary, fully furnished residence located in o...

  • 4 Beds
  • 6 Baths
  • Magic Village Resort 2 SubDv.
  • 34747 Zip Code
3052 Gatsby Street, Kissimmee image
3052 Gatsby Street, Kissimmee — 3052 $500,000 ▼

This well-appointed residence is offered fully furnished within the popular Storey Lake resort community. Designed for flexibility, the property is suitable for personal ...

  • 4 Beds
  • 3 Baths
  • Storey Lake Ph 2 SubDv.
  • 34746 Zip Code
2355 Lancashire Street, Davenport image
2355 Lancashire Street, Davenport — 2355 $500,000

Welcome to the beautiful Davenport community, the perfect investment opportunity for Airbnb/VRBO rentals! No CDD here! This home, one-story, 4 bedroom home from Ashton Wo...

  • 4 Beds
  • 3 Baths
  • Glen At West Haven SubDv.
  • 33896 Zip Code
7260 Oakmoss Loop, Davenport image
7260 Oakmoss Loop, Davenport $500,000 ▼

Virtually Staged. Step into a life of luxury with this exquisite, fully-equipped five-bedroom, four-bathroom villa, ideally positioned on a corner lot within the exclusiv...

  • 5 Beds
  • 4 Baths
  • Solterra Ph 2b SubDv.
  • 33837 Zip Code
182 Hideaway Beach Lane, Kissimmee image
182 Hideaway Beach Lane, Kissimmee $499,999 ▼

Turnkey upscale seven-bedroom vacation home in the guard-gated Terra Verde Resort community. This spacious furnished property features a private south-facing screened poo...

  • 7 Beds
  • 5 Baths
  • Terra Verde Ph 02 SubDv.
  • 34746 Zip Code
5002 Tideview Circle Unit 5, Orlando image
5002 Tideview Circle Unit 5, Orlando — 5002 $499,995

This three-story townhouse offers comfort, privacy, and a flexible layout ideal for vacation getaways, business travel, or extended stays. Conveniently located near Unive...

  • 3 Beds
  • 4 Baths
  • Bayshore/Vista Cay Ph 06 SubDv.
  • 32819 Zip Code
4322 Lana Avenue, Davenport image
4322 Lana Avenue, Davenport — Na $499,990 ▼

Excellent Short-Term Rental Investment or Second Home Opportunity Near Walt Disney World Located in the highly desirable Windsor Island Resort, this 5-bedroom, 4.5-bat...

  • 5 Beds
  • 5 Baths
  • Windsor Island Residence Ph 2b SubDv.
  • 33897 Zip Code
2967 Penelope Loop, Kissimmee image
2967 Penelope Loop, Kissimmee — 2967 $499,990

Discover this spectacular 4-bedroom, 3-bathroom Townhouse with private pool in the remarkable Story Lake community, the finest vacation community in Orlando! Enjoy its tw...

  • 4 Beds
  • 3 Baths
  • Cove At Storey Lake 4 SubDv.
  • 34746 Zip Code
214 Tupelo Circle, Davenport image
214 Tupelo Circle, Davenport $499,950

An exceptionally spacious and beautiful home set on a large corner lot and offered at a great price. Currently furnished as an impressive 6 bedroom property, it can easil...

  • 6 Beds
  • 4 Baths
  • Calabay Parc SubDv.
  • 33897 Zip Code
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Realtor David MyersDavid Myers
Call/Text 407.801.3286
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David Myers - Broker Associate
My Orlando Vacation Home Team
Ziro Realty, LLC
549B Water Street
Celebration, FL 34747
Call/Text: 407.801.3286
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