MyOrlandoVacationHome.com
  • Home
  • Advanced Search
  • Sell Your Vacation Home
  • Condotels
  • Condos
  • Homes
  • Townhomes
Login
407-801-3286

Sign in to your account

Need to reset your phone number?

Don't have an account with us?

Click here to sign up.

 

The Hwy 27 Resort Area

Orlando Vacation Homes › Hwy 27 Resort Area

Owning a Vacation Home in the Hwy 27 Resort Area

Regal Palms Resort in the Hwy 27 Resort Area of OrlandoThe Hwy 27 Resort Area is just a little further West but offers some fantastic resort home options at lower prices than you would find at properties closer in to the parks.  

Southwest of the West Hwy 192 resort area, Hwy 27 offers a handful of resorts which offer townhome, condo or single family home options. 

While there are dedicated resorts in this area, it is also home to a mix of 55+ communities and residential neighborhoods some of which allow short term rentals.

Where is the Hwy 27 Resort Area in Orlando?

The Hwy 27 Resort Area is located completely along Hwy 27 South of Hwy 192 but North of I-4 in Polk County. 

This area is the Westernmost of the Orlando Vacation Resort areas and provides the quickest access to Florida's West coast beaches and cities via I-4.

How Far from the Hwy 27 Resort Area to...

  • Walt Disney World: 10 miles
  • Universal Studios: 25 miles
  • Sea World: 21 miles
  • Busch Gardens Tampa: 60 miles
  • Kennedy Space Center: 74 miles
  • Cocoa Beach: 81 miles
  • Daytona Beach: 92 miles
  • Clearwater Beach: 84 miles
  • Orlando International Airport: 32 miles
  • Port Canaveral Cruise Ships: 76 miles

Hwy 27 Resort Area Vacation Home Properties

Bahama Bay Resort ClubhouseOrlando Vacation Properties in the Hwy 27 Resort area include:

  • Bahama Bay Resort - 2 to 3 Bedroom Condos
  • Bella Piazza Resort - 2 to 4 Bedroom Condos
  • Regal Palms Resort - 3 to 4 Bedroom Townhomes
  • Solana Resort - 4 to 7 Bedroom Homes
  • Windsor Cay - 5 to 10 Bedroom Homes

 

Attractions within the Hwy 27 Resort Area

There are no real attractions short of a county park within this resort area because it is just a bit further out from the parks and because it is a mixed residential and vacation resort area.  However, your are located in-between the West Hwy 192 and the Champions Gate Resort areas with their attractions, dining and shopping options.

 

Hwy 27 Resort Area Vacation Homes for Sale

2090 Lelani Circle, Davenport image
2090 Lelani Circle, Davenport $989,000 ▼

Welcome to your Florida dream home! Located just 5 miles from Walt Disney World and 15 miles from Universal Orlando, this sprawling 8-bedroom, 6-bathroom estate offers ov...

  • 8 Beds
  • 6 Baths
  • Windsor Island Resort SubDv.
  • 33897 Zip Code
3048 Mahalo Drive, Davenport image
3048 Mahalo Drive, Davenport $988,900 ▼

Welcome to Windsor Island Resort, situated in a desirable area of Davenport, close enough for day trips to nearby attractions yet tucked away for tranquility. This stunni...

  • 10 Beds
  • 8 Baths
  • Windsor Island Residence Ph 2b SubDv.
  • 33897 Zip Code
2126 Lelani Circle, Davenport image
2126 Lelani Circle, Davenport $980,000

Exceptional investment opportunity in the highly sought-after Windsor Island Resort. This impressive single-family home features 10 bedrooms, 8 full bathrooms, and a priv...

  • 10 Beds
  • 8 Baths
  • Windsor Island Residence SubDv.
  • 33897 Zip Code
3625 Lily Lane, Davenport image
3625 Lily Lane, Davenport $980,000 ▼

Welcome to your dream home in Davenport! This stunning, spacious residence offers 8 bedrooms and 6 bathrooms, providing ample room for a large family or someone who needs...

  • 8 Beds
  • 7 Baths
  • Windsor Island SubDv.
  • 33897 Zip Code
4117 Lana Avenue, Davenport image
4117 Lana Avenue, Davenport $969,000 ▼

Stunning 10-Bedroom Investment Opportunity | Windsor Island Resort 4117 Lana Ave, Davenport, FL Discover this exceptional Clearwater Grand model, a high-capacity 10-b...

  • 10 Beds
  • 8 Baths
  • Windsor Island Residence Ph 3 SubDv.
  • 33897 Zip Code
3723 Lana Avenue, Davenport image
3723 Lana Avenue, Davenport $950,000

Experience the pinnacle of luxury vacation home ownership at Windsor Island Resort with this spectacular 10-bedroom, 8-bathroom retreat offering nearly 4,400 square feet ...

  • 10 Beds
  • 8 Baths
  • Windsor Island Residence Ph 2b SubDv.
  • 33897 Zip Code
2210 Lelani Circle, Davenport image
2210 Lelani Circle, Davenport $950,000 ▼

Step into a world of enchantment and luxury at 2210 Lelani Circle! A fully furnished and turnkey 10-bedroom, 8-bathroom home that is meticulously decorated to deliver a t...

  • 10 Beds
  • 8 Baths
  • Windsor Island Residence SubDv.
  • 33897 Zip Code
4425 Kaipo Road, Davenport image
4425 Kaipo Road, Davenport $949,000

Beautiful 10-bedroom, 8-bath single-family home located in the highly desirable Windsor Island Resort. Built in 2023, this fully furnished vacation home offers 4,399 sq f...

  • 10 Beds
  • 8 Baths
  • Windsor Island Resort Phase 3 SubDv.
  • 33897 Zip Code
4494 Kaipo Road, Davenport image
4494 Kaipo Road, Davenport $949,000 ▼

PRICE IMPROVEMENT! Seller has reduced the price by $46,000! Luxurious Ten-Bedroom Home at Windsor Island Resort, Minutes from Disney World! This stunning, fully furnished...

  • 10 Beds
  • 8 Baths
  • Windsor Island Residence Ph 3 SubDv.
  • 33897 Zip Code
3520 Lavender Drive, Davenport image
3520 Lavender Drive, Davenport $899,999 ▼

Imagine stepping into the ultimate vacation home, a place where every detail is designed for unforgettable family getaways and incredible returns. Welcome to 3520 Lavende...

  • 8 Beds
  • 6 Baths
  • Windsor Island Resort SubDv.
  • 33897 Zip Code
4473 Kaipo Road, Davenport image
4473 Kaipo Road, Davenport $899,990

*** FULLY FURNISHED *** Heated - Saltwater Pool and Spa with full automation.!!! *** Professionally Decorated by world renowned interior decorator *** Character Themed ro...

  • 8 Beds
  • 6 Baths
  • Windsor Island Residence Ph 3 SubDv.
  • 33897 Zip Code
3715 Lana Avenue, Davenport image
3715 Lana Avenue, Davenport $880,000 ▼

Exceptional Value in Windsor Island Resort! Luxuriously Upgraded & Themed Vacation Home. Discover the perfect blend of luxury, fun, and investment potential with this stu...

  • 10 Beds
  • 8 Baths
  • Windsor Island Residence Ph 2b SubDv.
  • 33897 Zip Code
3217 Lilac Way, Davenport image
3217 Lilac Way, Davenport $879,900 ▼

LUXURY 8BR/6BA TURNKEY VACATION HOME IN WINDSOR ISLAND RESORT Welcome to this exceptional, fully furnished 8-bedroom, 6-bathroom pool home located in the highly desirabl...

  • 8 Beds
  • 6 Baths
  • Windsor Island Res Ph 2a SubDv.
  • 33897 Zip Code
4157 Lana Avenue, Davenport image
4157 Lana Avenue, Davenport $875,000 ▼

Fully Upgraded & Themed Vacation Home in Windsor Island! Step into a world of luxury and imagination with this spectacular 10-bedroom, 8-bathroom vacation home. Designed ...

  • 10 Beds
  • 8 Baths
  • Windsor Island Residence Ph 3 SubDv.
  • 33897 Zip Code
3711 Lana Avenue, Davenport image
3711 Lana Avenue, Davenport $860,000 ▼

Experience the ultimate Florida getaway at 3711 Lana Avenue, a stunning 4,399-square-foot luxury villa located in the famous Windsor Island Resort. This 2022-built maste...

  • 10 Beds
  • 8 Baths
  • Windsor Island Residence Ph 2a SubDv.
  • 33897 Zip Code
2320 Lelani Circle, Davenport image
2320 Lelani Circle, Davenport $854,900

**3D Tour Available** - Welcome to your new home at 2320 Lelani Cir, Davenport, FL 33897, a 10 bedroom, 8 bath pool and spa home located in the highly sought-after Windso...

  • 10 Beds
  • 8 Baths
  • Windsor Island Residence SubDv.
  • 33897 Zip Code
3740 Lana Avenue, Davenport image
3740 Lana Avenue, Davenport $849,000 ▼

Fully furnished 10-bedroom, 8-bathroom luxury resort home located in the highly sought-after Windsor Island Resort. Designed for both exceptional rental performance and u...

  • 10 Beds
  • 8 Baths
  • Windsor Island Residence Ph 2b SubDv.
  • 33897 Zip Code
3005 Mahalo Drive, Davenport image
3005 Mahalo Drive, Davenport $828,900 ▼

Like a brand new house, 10 beds could sell with or without furniture, you can use the turnkey vacation home to generate great income, or design it as you wish. One of the...

  • 10 Beds
  • 8 Baths
  • Windsor Island Phase 2a Pb 187 Pgs 31-34 Lot 450 SubDv.
  • 33897 Zip Code
4125 Lana Avenue, Davenport image
4125 Lana Avenue, Davenport $825,000 ▼

Escape to luxury in this immaculate Windsor Island Resort home in Davenport, Florida. This 8-bedroom, 6-bathroom residence offers a full sun, south-facing pool, and an op...

  • 8 Beds
  • 6 Baths
  • Windsor Island Residence Ph 3 SubDv.
  • 33897 Zip Code
4470 Kaipo Road, Davenport image
4470 Kaipo Road, Davenport $800,000

Discover this impressive seven-bedroom, 5.5-bath home in the desirable Windsor Island Resort, just minutes from Disney. Enjoy the parks during the day and return to elega...

  • 7 Beds
  • 6 Baths
  • Windsor Island Residence Ph 3 SubDv.
  • 33897 Zip Code
4428 Kaipo Road, Davenport image
4428 Kaipo Road, Davenport $799,000

Turnkey 7-bedroom short-term rental home located in the highly sought-after Windsor Island Resort! This beautifully furnished vacation home offers no rear neighbors and a...

  • 6 Beds
  • 5 Baths
  • Windsor Island Residence Ph 3 SubDv.
  • 33897 Zip Code
2031 Lelani Circle, Davenport image
2031 Lelani Circle, Davenport $799,000 ▼

PRICE REDUCED – SELLER MOTIVATED!!! Best-priced 10-bedroom home in Windsor Island Resort — fully furnished and turnkey! Discover the charm of this exquisite home perfect ...

  • 10 Beds
  • 8 Baths
  • Windsor Island Residence SubDv.
  • 33897 Zip Code
3712 Lana Avenue, Davenport image
3712 Lana Avenue, Davenport $795,000

Discover an exceptional opportunity in one of Central Florida's most sought-after communities. This immaculate, fully furnished 8-bedroom, 6-bathroom residence in Windsor...

  • 8 Beds
  • 7 Baths
  • Windsor Island Residence Ph 2b SubDv.
  • 33897 Zip Code
4458 Kaipo Road, Davenport image
4458 Kaipo Road, Davenport $780,000 ▼

Beatiful 7 bedrooms 5.5 baths fully equipped and ready for you and your family to have fun and make income , at the biggest clubhouse in the community windsor island reso...

  • 7 Beds
  • 6 Baths
  • Windsor Island Residence Ph 3 SubDv.
  • 33897 Zip Code
3281 Lilac Way, Davenport image
3281 Lilac Way, Davenport $750,000

Experience the perfect combination of luxury, comfort, and investment potential in this beautifully appointed 7-bedroom, 5.5-bathroom home located in the highly sought-af...

  • 7 Beds
  • 6 Baths
  • Windsor Island Res Ph 2a SubDv.
  • 33897 Zip Code
1891 Summer Drive, Davenport image
1891 Summer Drive, Davenport $750,000

Don't miss GEM.This spacious luxury home in the exclusive Windsor Island Resort, offering the perfect combination of comfort, style, and an unbeatable location. Just minu...

  • 7 Beds
  • 6 Baths
  • Windsor Island Resort SubDv.
  • 33897 Zip Code
1897 Summer Drive, Davenport image
1897 Summer Drive, Davenport $750,000

Welcome to this spacious luxury home in the exclusive Windsor Island Resort, offering the perfect combination of comfort, style, and an unbeatable location. Just minutes ...

  • 7 Beds
  • 6 Baths
  • Windsor Island Resort SubDv.
  • 33897 Zip Code
2316 Lelani Circle, Davenport image
2316 Lelani Circle, Davenport $749,000 ▼

Discover this stunning, fully furnished 9-bedroom, 6-bathroom vacation home located in one of Central Florida’s most sought-after short-term rental communities — Windsor ...

  • 9 Beds
  • 6 Baths
  • Windsor Island Residence SubDv.
  • 33897 Zip Code
3044 Mahalo Drive, Davenport image
3044 Mahalo Drive, Davenport $745,000 ▼

LIVE VIRTUAL TOUR! Fully furnished pool home located in a desirable short-term rental resort community in the Kissimmee/Davenport area, offering an established history of...

  • 8 Beds
  • 6 Baths
  • Windsor Island Residence Ph 2b SubDv.
  • 33897 Zip Code
2036 Lelani Cir, Davenport image
2036 Lelani Cir, Davenport $729,000 ▼

Discover the epitome of luxury in Windsor Island Resort, one of the premier vacation home communities near Disney! This fully furnished residence offers 8 spacious bedroo...

  • 8 Beds
  • 6 Baths
  • Windsor Island Res SubDv.
  • 33897 Zip Code
4063 Lana Avenue, Davenport image
4063 Lana Avenue, Davenport $729,000 ▼

Exceptional property alert. Come see this amazing Windsor Island 6-bedroom vacation home. This property is brand new and features custom decor and furnishings. If you wan...

  • 6 Beds
  • 5 Baths
  • Windsor Island Residence Ph 3 SubDv.
  • 33897 Zip Code
3404 Lilac Way, Davenport image
3404 Lilac Way, Davenport $720,000

Welcome to an exceptional income-producing home located in the highly sought-after, guard-gated Windsor Island Resort in Davenport, Florida. This fully furnished 7-bedroo...

  • 7 Beds
  • 6 Baths
  • Windsor Island Resort SubDv.
  • 33897 Zip Code
1806 Summer Drive, Davenport image
1806 Summer Drive, Davenport $719,000 ▼

LOCATION! LOCATION! LOCATION! EXCELLENT BOOKING HISTORY AND FUTURE BOOKINGS CAN CONVEY! Just a few steps from the fabulous clubhouse! Welcome to 1806 Summer Drive in Dave...

  • 7 Beds
  • 6 Baths
  • Windsor Island Resort SubDv.
  • 33897 Zip Code
3787 Lana Avenue, Davenport image
3787 Lana Avenue, Davenport $715,000

Premium Lot - Fully Furnished Stunning 6-Bedroom Pool Home in Davenport – Perfect for Families and Investors Welcome to this exceptional two-story home located in one ...

  • 6 Beds
  • 5 Baths
  • Windsor Island Residence Ph 2b SubDv.
  • 33897 Zip Code
1711 Kona Lane, Davenport image
1711 Kona Lane, Davenport $714,900

Turn-key short-term rental property located inside the sought-after Windsor Island Resort — a gated community approved for short-term rentals. This beautiful and well-mai...

  • 5 Beds
  • 6 Baths
  • Windsor Island Residence SubDv.
  • 33897 Zip Code
3436 Lilac Way, Davenport image
3436 Lilac Way, Davenport $709,300 ▼

***TURN KEY RENTAL HOME*** Schedule your showing today and come see this stunning 7 bedroom home in the sought-after Windsor Island Resort!! This home offers the perfect ...

  • 7 Beds
  • 6 Baths
  • Windsor Island Residence Ph 2a SubDv.
  • 33897 Zip Code
3348 Lilac Way, Davenport image
3348 Lilac Way, Davenport $699,900 ▼

Escape to your own private oasis just moments away from the magic of Disney at Windsor Island Resort. This exquisite vacation home offers the ultimate in luxury and conve...

  • 7 Beds
  • 5 Baths
  • Windsor Island Residence Ph 2a SubDv.
  • 33897 Zip Code
3783 Lana Avenue, Davenport image
3783 Lana Avenue, Davenport $695,000 ▼

An Exciting 7 Bedroom Vacation Home in Windsor Island is looking for a new owner. Close to the Disney Parks! Beautifully furnished with high end furniture. 5 King Bedroom...

  • 7 Beds
  • 6 Baths
  • Windsor Island Residence Ph 2b SubDv.
  • 33897 Zip Code
1671 Kona Lane, Davenport image
1671 Kona Lane, Davenport $690,000

Stunning two-story home, fully furnished and thoughtfully designed to offer comfort, sophistication, and excellent investment potential. A charming front porch and landsc...

  • 7 Beds
  • 6 Baths
  • Windsor Island Residence SubDv.
  • 33897 Zip Code
3835 Lana Avenue, Davenport image
3835 Lana Avenue, Davenport $690,000

Welcome to your dream vacation home just minutes from Disney, this exceptionally furnished 7-bedroom, 5.5-bathroom pool home offers the perfect blend of luxury, comfort, ...

  • 7 Beds
  • 5 Baths
  • Windsor Island Residence Ph 2b SubDv.
  • 33897 Zip Code
4051 Lana Avenue, Davenport image
4051 Lana Avenue, Davenport $690,000

Welcome to this stunning, fully furnished 7-bedroom, 5.5-bathroom home in the highly desirable Windsor Island Resort, where short-term rentals are allowed. This turnkey p...

  • 7 Beds
  • 6 Baths
  • Windsor Island Residence Ph 3 SubDv.
  • 33897 Zip Code
1837 Summer Drive, Davenport image
1837 Summer Drive, Davenport $689,000 ▼

Exceptional corner-lot vacation home located just steps from the clubhouse in the highly sought-after Windsor Island Resort. This beautifully maintained and fully furnish...

  • 7 Beds
  • 6 Baths
  • Windsor Island Residence SubDv.
  • 33897 Zip Code
2060 Lelani Cir, Davenport image
2060 Lelani Cir, Davenport $688,000 ▼

Discover an outstanding opportunity in Windsor Island Resort, one of the most desirable vacation home communities near Disney! This beautifully furnished 8-bedroom, 6-bat...

  • 8 Beds
  • 6 Baths
  • Windsor Island Residence SubDv.
  • 33897 Zip Code
3373 Lilac Way, Davenport image
3373 Lilac Way, Davenport $679,000

MOTIVATED SELLER! TURNKEY 5-BEDROOM VACATION HOME IN WINDSOR ISLAND RESORT NEAR DISNEY Welcome to this fully furnished 5 bedroom home in Davenport, FL, located in the hi...

  • 5 Beds
  • 6 Baths
  • Windsor Island Residence Ph 2a SubDv.
  • 33897 Zip Code
4045 Lana Avenue, Davenport image
4045 Lana Avenue, Davenport $678,000 ▼

Welcome to this beautifully maintained 7-bedroom, 5.5-bathroom home located in the highly sought-after Windsor Island Resort, where short-term rentals are permitted. Over...

  • 7 Beds
  • 5 Baths
  • Windsor Island Residence Ph 3 SubDv.
  • 33897 Zip Code
1191 Aloha Boulevard, Davenport image
1191 Aloha Boulevard, Davenport $675,000 ▼

Immaculately maintained and fully turnkey, this pristine 6-bedroom vacation pool home in the highly sought-after Windsor Island Resort shows like a model and is completel...

  • 6 Beds
  • 5 Baths
  • Windsor Island Residence SubDv.
  • 33897 Zip Code
3811 Lana Avenue, Davenport image
3811 Lana Avenue, Davenport $659,000 ▼

Welcome to 3811 Lana Ave in the highly sought-after Windsor Island Resort! This beautifully furnished home is turnkey and offers incredible potential as a short-term rent...

  • 5 Beds
  • 5 Baths
  • Windsor Island Residence Ph 2b SubDv.
  • 33897 Zip Code
3937 Lana Avenue, Davenport image
3937 Lana Avenue, Davenport $659,000 ▼

This professionally designed, fully furnished 7-bedroom, 5.5-bath vacation retreat offering over 3,200 square feet of upgraded living space in one of Central Florida’s mo...

  • 7 Beds
  • 6 Baths
  • Windsor Island Residence Ph 3 SubDv.
  • 33897 Zip Code
4070 Lana Avenue, Davenport image
4070 Lana Avenue, Davenport — 4070 $659,000 ▼

Immaculate five-bedroom, four-bath fully furnished vacation townhome in the prestigious Windsor Island Resort, just minutes from Disney! This 2,283-square-foot property f...

  • 5 Beds
  • 5 Baths
  • Windsor Island Residence SubDv.
  • 33897 Zip Code
3428 Lilac Way, Davenport image
3428 Lilac Way, Davenport $654,900 ▼

Discover an incredible opportunity to own a like-new 5-bedroom vacation home in the highly sought-after Windsor Island Resort! This fully furnished, turn-key property is ...

  • 5 Beds
  • 6 Baths
  • Windsor Island Residence Ph 2a SubDv.
  • 33897 Zip Code
3441 Lilac Way, Davenport image
3441 Lilac Way, Davenport $650,000

Welcome to this exceptional, fully furnished 7-bedroom, 5.5-bath vacation home in the highly desirable Windsor Island Resort, one of Central Florida's premier short-term ...

  • 7 Beds
  • 6 Baths
  • Windsor Island Resort Phase 2a Pb 187 Pg SubDv.
  • 33897 Zip Code
1177 Aloha Boulevard, Davenport image
1177 Aloha Boulevard, Davenport $649,000

Turnkey fully furnished vacation home located in the highly sought-after Windsor Island Resort community, just minutes from Walt Disney World, Margaritaville, ChampionsGa...

  • 5 Beds
  • 5 Baths
  • Windsor Island Residence SubDv.
  • 33897 Zip Code
2290 Lelani Circle, Davenport image
2290 Lelani Circle, Davenport $639,000

Nestled within the gated Windsor Island Resort in Davenport, 2290 Lelani Cir places you moments from shopping, restaurants, theme parks, major roads, and the airport. Thi...

  • 8 Beds
  • 6 Baths
  • Windsor Island Residence SubDv.
  • 33897 Zip Code
1697 Kona Lane, Davenport image
1697 Kona Lane, Davenport $630,000

**This home comes with a lender credit provided by seller's preferred lender, pending qualification.** Welcome to 1697 Kona Lane in Windsor Island Resort, a fully furnish...

  • 7 Beds
  • 5 Baths
  • Windsor Island Residence SubDv.
  • 33897 Zip Code
436 Aldridge Lane, Davenport image
436 Aldridge Lane, Davenport $630,000 ▼

Spacious 6-Bedroom Pool Home in Prime Davenport Location – Over $100,000 in Renovations! Welcome to your dream home in the heart of Davenport! This stunning two-story ...

  • 6 Beds
  • 5 Baths
  • Legacy Park Ph 02 SubDv.
  • 33897 Zip Code
3344 Lilac Way, Davenport image
3344 Lilac Way, Davenport $629,999 ▼

One or more photo(s) has been virtually staged. Discover Your Oasis at 3344 Lilac Way. Welcome to this exquisite 7-bedroom, 5.5-bathroom vacation home. A true gem nestled...

  • 7 Beds
  • 6 Baths
  • Windsor Island Residence Ph 2a SubDv.
  • 33897 Zip Code
1876 Summer Drive, Davenport image
1876 Summer Drive, Davenport $625,000

1876 Summer Drive at Windsor Island Resort is the turnkey, fully furnished vacation home investors and second-home buyers have been waiting for. Designed for both fun and...

  • 7 Beds
  • 6 Baths
  • Windsor Island Residence SubDv.
  • 33897 Zip Code
3401 Lilac Way, Davenport image
3401 Lilac Way, Davenport $625,000 ▼

Discover your perfect vacation retreat—an extraordinary, one-of-a-kind home crafted for unforgettable family fun and total relaxation. This seven-bedroom, five-and-a-half...

  • 7 Beds
  • 6 Baths
  • Windsor Island Res SubDv.
  • 33897 Zip Code
2201 Lelani Circle, Davenport image
2201 Lelani Circle, Davenport $619,900 ▼

Modern Elegance Meets Resort Living at Windsor Island Welcome to the ultimate blend of style, space, and resort-style living—perfectly situated in the sought-after Winds...

  • 6 Beds
  • 5 Baths
  • Windsor Island Residence SubDv.
  • 33897 Zip Code
3416 Lilac Way, Davenport image
3416 Lilac Way, Davenport $615,000 ▼

Turnkey opportunity in the highly sought-after Windsor Island Resort! This spacious and well-maintained home is located in a short-term rental / Airbnb-approved community...

  • 5 Beds
  • 5 Baths
  • Windsor Island Residence Ph 2a SubDv.
  • 33897 Zip Code
574 Tupelo Circle, Davenport image
574 Tupelo Circle, Davenport $615,000 ▼

This beautifully presented pool home delivers the perfect blend of comfort, functionality, and turnkey convenience. Bright, open living spaces welcome you inside, with a ...

  • 5 Beds
  • 5 Baths
  • Calabay Parc SubDv.
  • 33897 Zip Code
4106 Lana Avenue, Davenport image
4106 Lana Avenue, Davenport — 4106 $610,000

Welcome to Windsor Island Resort where everyday luxury meets vacation living! This immaculate 5-bedroom, 4.5-bath townhouse offers over 2,200 sq. ft. of thoughtfully de...

  • 5 Beds
  • 5 Baths
  • Windsor Island Residence Ph 3 SubDv.
  • 33897 Zip Code
2226 Lelani Circle, Davenport image
2226 Lelani Circle, Davenport $609,990 ▼

Welcome to this tastiflly furnished home located in the prestige Windsor Island Resort! Just minutes from Disney and world-class attractions, this home is fully furnishe...

  • 7 Beds
  • 6 Baths
  • Windsor Island Residence SubDv.
  • 33897 Zip Code
3859 Lana Avenue, Davenport image
3859 Lana Avenue, Davenport $609,000

Professionally designed and impeccably maintained, this exceptional 5-bedroom, 5-bathroom home offers luxury, comfort, and resort-style living. The beautifully appointed ...

  • 5 Beds
  • 5 Baths
  • Windsor Island Residence Ph 2b SubDv.
  • 33897 Zip Code
1180 Aloha Boulevard, Davenport image
1180 Aloha Boulevard, Davenport $609,000 ▼

Turnkey 5-Bedroom Pool Home in Windsor Island Resort — No Rear Neighbors & Close to Clubhouse! Welcome to this like-new, fully furnished 5-bedroom, 4-bath vacation hom...

  • 5 Beds
  • 4 Baths
  • Windsor Island Residence SubDv.
  • 33897 Zip Code
231 Belfry Drive, Davenport image
231 Belfry Drive, Davenport $599,999

Welcome to your dream Florida escape at 231 Belfry Drive! This fully furnished, 5-bedroom (With the possibility to convert the den into a 6th Bedroom), 5-bathroom home is...

  • 5 Beds
  • 5 Baths
  • Highlands Reserve SubDv.
  • 33897 Zip Code
1607 Kona Lane, Davenport image
1607 Kona Lane, Davenport $599,000

An Absolute MUST SEE!! This SPACIOUS 5 Bedroom 4 FULL Bath Private Pool Home is being offered FULLY FURNISHED! SUCCESSFUL VACATION RENTAL PROPERTY with over $60,000+ in ...

  • 5 Beds
  • 4 Baths
  • Windsor Island Residence SubDv.
  • 33897 Zip Code
1870 Summer Drive, Davenport image
1870 Summer Drive, Davenport $599,000 ▼

PREMIUM TURNKEY INVESTMENT- 100% RENTAL READY IN WINDSOR ISLAND! Avoid the massive upfront setup costs and months of delivery delays. This can be a 1031 exchange to immed...

  • 5 Beds
  • 6 Baths
  • Windsor Island Residence SubDv.
  • 33897 Zip Code
3413 Lilac, Davenport image
3413 Lilac, Davenport $596,000 ▼

MAJOR PRICE IMPROVEMENT AND BLOCKED FOR SHOWINGS! JUNE 7-18 & 22-30! BRING YOUR BUYERS!! Welcome to your dream vacation home in the highly sought-after Windsor Island ...

  • 6 Beds
  • 5 Baths
  • Windsor Island Resort Phase 2a SubDv.
  • 33897 Zip Code
4450 Kaipo Road, Davenport image
4450 Kaipo Road, Davenport $596,000 ▼

This is the one investors wait for — a proven, high-occupancy vacation home in Windsor Island Resort with professionally themed rooms, a sun-drenched south-facing pool, a...

  • 6 Beds
  • 5 Baths
  • Windsor Island Residence Ph 3 SubDv.
  • 33897 Zip Code
1721 Kona Lane Lane, Davenport image
1721 Kona Lane Lane, Davenport $589,900

Opportunity in Windsor Island Resort! Welcome to this beautifully furnished 5 bedroom, 4 bathroom home in one of the most desirable vacation communities in Central Florid...

  • 5 Beds
  • 4 Baths
  • Windsor Island Residence SubDv.
  • 33897 Zip Code
403 Corvina Drive, Davenport image
403 Corvina Drive, Davenport $589,000

welcome to your beautiful upgraded home in davenport, florida - a turnkey property that blends modern comfort with fun, resort-style living. this fully remodeled residenc...

  • 5 Beds
  • 4 Baths
  • Village At Tuscan Ridge SubDv.
  • 33897 Zip Code
108 Jetty Way, Davenport image
108 Jetty Way, Davenport — Jetty $585,000

Stylish former model home with private pool in the highly desirable Windsor Island Resort community! Located directly across from the clubhouse and resort amenities, this...

  • 5 Beds
  • 5 Baths
  • Windsor Island Residence SubDv.
  • 33897 Zip Code
167 Nazha Dr, Davenport image
167 Nazha Dr, Davenport $585,000

Beautifully renovated home located in the desirable Hampton Estates community in Davenport. This spacious residence features modern upgrades throughout, including updated...

  • 5 Beds
  • 4 Baths
  • Hampton Estates SubDv.
  • 33897 Zip Code
1187 Aloha Boulevard, Davenport image
1187 Aloha Boulevard, Davenport $584,000

Don’t miss this exceptional opportunity to own a stunning luxury vacation home in the highly sought-after Windsor Island Resort community! Built in 2022 and offered fully...

  • 5 Beds
  • 6 Baths
  • Windsor Island Resort SubDv.
  • 33897 Zip Code
630 Jasmine Lane, Davenport image
630 Jasmine Lane, Davenport — 630 $575,000

Welcome to this stunning, fully furnished vacation townhouse just minutes from Walt Disney World in the desirable Disney area. This modern and beautifully decorated prope...

  • 5 Beds
  • 5 Baths
  • Windsor Island SubDv.
  • 33897 Zip Code
996 Paradise Drive, Davenport image
996 Paradise Drive, Davenport — 996 $569,000

Available to view July 29 and 30. Ask y ou agent for viewing today!! Fully furnished Themed short term rental. LED lighting inside and out. Game room in the house! Open l...

  • 5 Beds
  • 5 Baths
  • Windsor Island Residence SubDv.
  • 33897 Zip Code
4322 Lana Avenue, Davenport image
4322 Lana Avenue, Davenport — Na $558,990

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
2116 Lelani Circle, Davenport image
2116 Lelani Circle, Davenport $550,000 ▼

Private backyard with firework view! Welcome to 2116 Lelani Circle in the prestige Windsor Island Resort. This elegant home has very tastiful design, very open and pleas...

  • 5 Beds
  • 4 Baths
  • Windsor Island SubDv.
  • 33897 Zip Code
4306 Lana Avenue, Davenport image
4306 Lana Avenue, Davenport — 4306 $549,990 ▼

ONE-OF-A-KIND TOWNHOME WITH LUXURY DESIGN! Experience the pinnacle of opulence and comfort in this remarkable 5-bedroom, 4.5-bathroom vacation haven situated within an ex...

  • 5 Beds
  • 5 Baths
  • Windsor Island Residence Ph 2b SubDv.
  • 33897 Zip Code
127 Jetty Way, Davenport image
127 Jetty Way, Davenport — N/A $549,900

Welcome to this beautifully remodeled and fully furnished 5-bedroom, 4.5-bathroom townhome in the highly sought-after Windsor Island Resort—one of Central Florida’s top d...

  • 5 Beds
  • 5 Baths
  • Windsor Island Residence SubDv.
  • 33897 Zip Code
227 Jetty Way, Davenport image
227 Jetty Way, Davenport — 227 $549,000

Amazing, income generating, turn-key ready vacation rental in the renowned Windsor Island Resort! 5 bedrooms, 4.5 bathrooms featuring 2 themed bedrooms, 2 king bedrooms ...

  • 5 Beds
  • 5 Baths
  • Windsor Island Residence SubDv.
  • 33897 Zip Code
4294 Lana Avenue, Davenport image
4294 Lana Avenue, Davenport — 581 $549,000 ▼

LUXURY ** PROFESSIONALLY DESIGNED BY TOP DECORATORS ** INCOME-READY 5BR VACATION HOME IN ORLANDO’S #1 RESORT ** PRE-BOOKED 2025 DATES. ...

  • 5 Beds
  • 5 Baths
  • Windsor Island Resort Phase 2b SubDv.
  • 33897 Zip Code
219 Plumoso Loop, Davenport image
219 Plumoso Loop, Davenport $545,000 ▼

Welcome to this stunning 6-bedroom, 4.5-bath home in the heart of Davenport, Florida! Perfectly situated in a highly convenient area, this spacious property offers the id...

  • 6 Beds
  • 5 Baths
  • Calabay Parc SubDv.
  • 33897 Zip Code
4358 Lana Avenue, Davenport image
4358 Lana Avenue, Davenport — - $540,000

This luxurious 5-bedroom, 4.5-bathroom vacation home is located in Windsor Island Resort, one of Orlando’s top vacation communities with the highest occupancy rates. Buil...

  • 5 Beds
  • 5 Baths
  • Windsor Island Residence Ph 2b SubDv.
  • 33897 Zip Code
200 Andover Drive, Davenport image
200 Andover Drive, Davenport $539,000 ▼

Virtually Staged. Luxury Pool New Home for Short-Term Rental nearby Disney Welcome to this beautifully updated 7-bedroom, 4.5-bath pool home in the sought-after Legacy ...

  • 7 Beds
  • 5 Baths
  • Legacy Park Ph 02 SubDv.
  • 33897 Zip Code
830 Paradise Drive, Davenport image
830 Paradise Drive, Davenport — Na $539,000

Welcome to 830 Paradise Drive, an exceptional professionally decorated vacation home located in the highly sought-after Windsor Island Resort. This spacious and beautifu...

  • 5 Beds
  • 5 Baths
  • Windsor Island Residence SubDv.
  • 33897 Zip Code
147 Troon Circle, Davenport image
147 Troon Circle, Davenport $525,000

WOW.... homes like this don't come along too often. Welcome Home!!! 147 Troon Circle is a fabulous 5 bed 3 bath pool home situated on the second hole of Highlands Reserve...

  • 5 Beds
  • 3 Baths
  • Highlands Reserve Ph 02 & 04 SubDv.
  • 33897 Zip Code
644 Montara Dr, Davenport image
644 Montara Dr, Davenport $525,000

Beautiful fully furnished turnkey 5-bedroom, 4-bath pool home in Calabay Parc! This spacious home features a flexible bonus room that can be used as an extra bedroom, off...

  • 5 Beds
  • 4 Baths
  • Calabay Parc - Unit One SubDv.
  • 33897 Zip Code
111 Aldridge Lane, Davenport image
111 Aldridge Lane, Davenport $525,000 ▼

SELLER MOTIVATED. One of the most popular floorplans in the Four Corners area, located on the highly sought-after community of The Retreat in Legacy Park just minutes fro...

  • 5 Beds
  • 5 Baths
  • Legacy Park Ph 02 SubDv.
  • 33897 Zip Code
100 Hollybrook Court, Davenport image
100 Hollybrook Court, Davenport $525,000 ▼

Stunning 5-Bedroom Pool Home Near Disney | New Roof 2024 | Over 2,800 Sq Ft Welcome to this meticulously maintained and beautifully presented home located along the desi...

  • 5 Beds
  • 4 Baths
  • Hampton Estates SubDv.
  • 33897 Zip Code
806 Paradise Drive, Davenport image
806 Paradise Drive, Davenport — Na $520,000 ▼

Welcome to your piece of Paradise on 806 Paradise Drive! This fully furnished 5-bedroom, 4.5-bathroom vacation home is located in the highly desirable Windsor Island Reso...

  • 5 Beds
  • 5 Baths
  • Windsor Island Residence SubDv.
  • 33897 Zip Code
3818 Lana Avenue, Davenport image
3818 Lana Avenue, Davenport — 2b $520,000 ▼

Welcome to 3818 Lana Ave, Davenport — an exceptional 5-bedroom, 4.5-bathroom home featuring a private screened-in pool, a game room, and professionally decorated themed b...

  • 5 Beds
  • 5 Baths
  • Windsor Island Resort SubDv.
  • 33897 Zip Code
448 Birkdale Street, Davenport image
448 Birkdale Street, Davenport $519,000

This completely renovated Florida-style home in Highlands Reserve offers 4 bedrooms, 3 bathrooms on a ¼-acre lot overlooking a golf course. Renovated in summer of 2024 it...

  • 4 Beds
  • 3 Baths
  • Highlands Reserve Ph 05 SubDv.
  • 33897 Zip Code
208 Troon Circle, Davenport image
208 Troon Circle, Davenport $516,000

Welcome to this beautifully remodeled 4-bedroom, 3-bathroom single-family home, where modern style meets comfort and versatility. Thoughtfully updated throughout, this mo...

  • 4 Beds
  • 3 Baths
  • Highlands Reserve Ph 02 & 04 SubDv.
  • 33897 Zip Code
4290 Lana Avenue, Davenport image
4290 Lana Avenue, Davenport — 4290 $515,000

Turnkey perfection meets resort-style luxury! Experience the ultimate Florida lifestyle in this beautifully maintained, fully furnished 5-bedroom, 4.5 bathroom townhome l...

  • 5 Beds
  • 4 Baths
  • Windsor Island Residence Ph 26 SubDv.
  • 33897 Zip Code
4310 Lana Avenue, Davenport image
4310 Lana Avenue, Davenport — 0000 $514,000 ▼

Welcome to this exquisite end-unit townhome in the prestigious Windsor Island Resort, Davenport's ultimate vacation destination! This 2023-built gem offers 5 bedrooms and...

  • 5 Beds
  • 5 Baths
  • Windsor Island Residence Ph 2b SubDv.
  • 33897 Zip Code
148 Belfry Drive, Davenport image
148 Belfry Drive, Davenport $510,000 ▼

Income Producing Property. 148 Belfry Dr is a bright 5 bedroom 3 bathroom pool home in the Highlands Reserve golf community in Davenport near Kissimmee, offering a comfor...

  • 5 Beds
  • 3 Baths
  • Highlands Reserve Ph 03a & 03b SubDv.
  • 33897 Zip Code
117 N Hampton Drive, Davenport image
117 N Hampton Drive, Davenport $499,999

Welcome to your Florida oasis at 117 N Hampton Dr in the highly sought-after Highlands Reserve community. This impeccably maintained golf course view 5-bedroom, 3-bathroo...

  • 5 Beds
  • 3 Baths
  • Highlands Reserve SubDv.
  • 33897 Zip Code
300 Kings Way, Davenport image
300 Kings Way, Davenport $499,990 ▼

This renovated Florida-style home in Highlands Reserve offers 5 bedrooms, 3 bathrooms, a flex room, and 2,076 sq ft of living space on a ¼-acre lot overlooking a golf cou...

  • 5 Beds
  • 3 Baths
  • Highlands Reserve Ph 05 SubDv.
  • 33897 Zip Code
Like or Share

Address Search

Realtor David MyersDavid Myers 407-801-3286
Your Orlando Vacation Home Expert

  • Orlando Vacation Properties Buyers Guide
  • Orlando Host Hub Blog

All Orlando Vacation Home Properties

  • Aviana Resort
  • Azur Resort
  • Bahama Bay Resort
  • Bella Piazza Resort
  • Bellavida Resort
  • Blue Heron Resort
  • Carib Cove Resort
  • Champions Gate Country Club
  • Champions Gate Omni Villas
  • Coral Cay Resort
  • Crestwynd Bay Resort
  • *NEW* Embassy Suites Sunset Walk
  • Emerald Island Resort
  • Encantada Resort
  • Enclave Suites Resort
  • Encore Resort
  • Festival Resort
  • Flats Resort - Under Construction
  • Floridays Resort
  • Fountains at Champions Gate
  • Galleria Palms Hotel
  • Greenpoint Kissimmee
  • Grove Resort & Spa
  • *NEW* Hub at Westside
  • Hawthorn Suites Lake Buena Vista
  • Lake Berkley Resort
  • Lake Buena Vista Resort
  • Lucaya Village Resort
  • Magic Village Views
  • Magic Village Yards
  • Margaritaville Resort
  • Melia Resort
  • Paradise Palms Resort
  • *NEW* Paradiso Grande
  • Parc Corniche Resort
  • Point Orlando Resort
  • Parkway Palms Resort
  • Regal Oaks at Old Town
  • Regal Palms Resort
  • Reunion Resort CONDOS
  • Reunion Resort HOMES
  • Runaway Beach Club
  • Solana Resort
  • Solara Resort
  • Solterra Resort
  • Stay Sky Suites Orlando
  • Storey Lake Resort
  • Summerville Resort
  • Terra Verde Resort
  • Tuscana Resort
  • Veranda Palms Resort
  • *NEW* Villa Domani Resort
  • Villas at 7 Dwarfs Lane
  • Villas of Somerset
  • Vista Cay Resort
  • Watersong Resort
  • West Lucaya Village
  • Windsor Cay Resort
  • Windsor Hills Resort
  • Windsor Island Resort
  • Windsor Palms Resort
  • Windsor at Westside
  • Worldquest Resort

Orlando STR Interactive Map Search

Orlando Short Term Rental Property Interactive Search Map

Popular Vacation Home Searches

  • 25 Latest Vacation Home Listings
  • 10+ Bedroom Orlando Vacation Homes
  • Orlando Vacation Home Foreclosures
  • Orlando Vacation Home New Construction
  • Orlando Vacation Home Waterfront Homes

Seach by Price

  • Orlando Vacation Homes Under $200K
  • Orlando Vacation Homes $200K to $300K
  • Orlando Vacation Homes $300K to $400K
  • Orlando Vacation Homes $400K to $500K
  • Orlando Vacation Homes $500K to $600K
  • Orlando Vacation Luxury Homes - $1M+

Your Ultimate How To Guide!
How to Buy an Orlando Vacation Home Guidebook

Search by Resort Type

  • Condotels
  • Condominiums
  • Homes
  • Townhomes

Search by Resort Amenities

  • Water Park
  • Golf Course
  • Putt Putt Course
  • Restaurant on Site

Search by Resort Area

  • Champions Gate Area
  • International Drive Area
  • Lake Buena Vista Area
  • East Hwy 192 Area
  • West Hwy 192 Area
  • Hwy 27 Area

Search by Maximum Owner Usage

Useful Resort Home Search Tools

  • Resort Vacation Home Mortgage Lenders
  • Orlando Vacation Property Buyers Guide
  • Condotel 3rd Party Restrictions
  • Featured Office Listings
  • Orlando Host Hub Blog
  • Orlando Vacation Home Valuation Tool
  • Visit Our Other Sites:
  • FloridaNeighborhoodRealty.com
  • NonaOrlandoProperties.com

David Myers - Broker Associate
My Orlando Vacation Home Team
Ziro Realty, LLC
549B Water Street
Celebration, FL 34747
Phone/Text: 407.801.3286
Web: MyOrlandoVacationHome.com
Stay Updated: Subscribe to Our Orlando Host Hub Blog RSS Feed

Realtor, MLS, and Equal Housing Opportunity logos

© Florida Neighborhood Realty LLC - All Rights Reserved

Site Support

  • About Us
  • Facebook
  • Terms of Use
  • Contact Us
  • Buyers Guide
  • Privacy Policy
  • Office Listings
  • Host Hub Blog
  • Data Disclaimer
IDX Real Estate Websites by
, an FNF RE Tech Company • Accessibility • Terms • Privacy