Orange, FL Homes

• 

  

  

  /65

  $324,900

  • 2 Beds
  • 2 Baths
  • 1,557 Sq Ft

  2026 Key Bay Trail, Kissimmee, FL 34747

  >> Unbelievable opportunity now offered at a new price, are you ready to live the Florida lifestyle? Do you visit Florida so much that you thought, doesn't it just make more sense to have a second home here; and one that's turn-key, in a guard gated community, already furnished and with all of the exterior maintenance included.....well you are right indeed! Only lived-in part time by the

  

  Steven Horner

  RE/MAX PRIME PROPERTIES

  (321) 386-2456

  2026 Key Bay Trail, Kissimmee, FL 34747
• Selling your home? Sell it faster and for more with a Homes.com Boost.

  Learn More
• 

  

  

  /20

  $2,200 per month

  • 1 Bed
  • 1 Bath
  • 844 Sq Ft
  • Condo for Rent

  825 Laura Oaks Blvd Unit . 9, Unit 203, Kissimmee, FL 34747

  Property Id: 1701068Come stay at an amazing place, and make it your temporary home! 15 minutes to Disney and endless Kissimmee attractions. Right at the junction of 3 main highways. Convenience is here. Golfing, biking, parks, adult games, everything is here. Also a great selection of restaurants to choose from.Brand new building. Has never been lived in. Clean and

  825 Laura Oaks Blvd Unit . 9, Unit 203, Kissimmee, FL 34747
• 

  

  /2

  $459,900 Sold Jul 14, 2025

  • 1,662 Sq Ft
  • $277/SF
  • 11 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1998

  7905 Golden Pond Cir, Kissimmee, FL 34747

  Welcome to this charming home located in Rolling Hills Estates, just a short drive to your favorite Disney gate! With a newer roof, A/C, pool heater, and brand new water heater, this property has been thoughtfully updated throughout. Featuring four bedrooms and three full bathrooms, and offering a spacious layout with an inviting living area, granite countertops, white shaker cabinets, and

  Benjamin Gilbert KELLER WILLIAMS REALTY AT THE PARKS

  7905 Golden Pond Cir, Kissimmee, FL 34747
• 

  

  

  /33

  Est $454,841 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 1,724 Sq Ft

  2952 On the Rocks Point, Kissimmee, FL 34747

  2952 On the Rocks Point, Kissimmee, FL 34747
• 

  

  

  /36

  $335,000

  • 3 Beds
  • 2 Baths
  • 1,246 Sq Ft

  2774 Almaton Loop Unit 101, Kissimmee, FL 34747

  ***TURNKEY & THEMED CONDO*** Come see this TASTEFULLY FURNISHED & THEMED condo in beautiful WINDSOR HILLS RESORT! This condo has been renovated by the current owners to stand out in the short-term rental market and is ready to hit the ground running for the new owner! FULLY FURNISHED & meticulously maintained by the current owner this unit has had upgrades such as newer cabinets & touches of Star

  

  Brandon Ramirez

  REAL BROKER, LLC

  (321) 510-4565

  2774 Almaton Loop Unit 101, Kissimmee, FL 34747
• 

  

  /76

  $3,000 per month

  • 2 Beds
  • 2.5 Baths
  • 1,380 Sq Ft
  • Townhouse for Rent

  2906 Castaway Ln, Kissimmee, FL 34747

  Currently Leased ~ AVAILABLE FOR MOVE IN ON 8/18/25 – MAKE IT YOURS NOW! GORGEOUS FULLY FURNSIHED TOWNHOME AVAILABLE FOR LONG TERM RENTAL AT MARGARITAVILLE RESORT ORLANDO! Spacious 2 Bed, 2.5 Baths, PLUS an ADDITIONAL BONUS ROOM! Half Bath and Laundry Downstairs, Kitchen with Quartz Countertops, Island with Seating, "WOOD" Tile Floors, Full Size Washer and Dryer Included. The Door from the

  Suzanne Docobo EXP REALTY LLC

  2906 Castaway Ln, Kissimmee, FL 34747
• 

  /2

  $385,000 Sold Jul 11, 2025

  • 1,440 Sq Ft
  • $267/SF
  • 90 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 2005

  7666 Sir Kaufmann Ct, Kissimmee, FL 34747

  END UNIT Townhome with Private PoolDiscover this inviting 3-bedroom, 2-bathroom townhome nestled in the sought-after Windsor Hills Resort. Located at 7666 Sir Kaufmann Ct in Kissimmee, this rental-ready property offers both comfort and convenience.The home features an open-concept main floor with a spacious kitchen flowing into the living area, perfect for gathering. A guest

  Deanna Meredith LUXE PROPERTIES LLC

  7666 Sir Kaufmann Ct, Kissimmee, FL 34747
• 

  /2

  Est $559,762 Not Listed For Sale

  • 6 Beds
  • 4.5 Baths
  • 2,709 Sq Ft

  8030 Acadia Estates Ct, Kissimmee, FL 34747

  8030 Acadia Estates Ct, Kissimmee, FL 34747
• 

  

  /26

  $330,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,410 Sq Ft

  2821 Almaton Loop Unit 105, Kissimmee, FL 34747

  Under contract-accepting backup offers. Turnkey Short-Term Rental Near Disney – Ground Floor Condo with Resort Style Amenities! Welcome to your FULLY FURNISHED, INCOME-PRODUCING property just minutes from Walt Disney World in the sought-after Windsor Hills Resort! This beautifully maintained 3-bedroom, 2-bath ground floor condo is not only vacation-ready—it’s guest-loved and booking-ready. Step

  

  Ariel Vargas

  EXP REALTY LLC

  (321) 655-2006

  2821 Almaton Loop Unit 105, Kissimmee, FL 34747
• 

  

  /20

  $2,200 per month

  • 1 Bed
  • 1 Bath
  • Condo for Rent

  775 Laura Oaks Blvd Unit Building 9 Apt.203, Kissimmee, FL 34747

  Property Id: 1701535Come stay at an amazing place and make it your temporary home!15 minutes to Disney and endless Kissimmee attractions. Right at the junction of 3 main highways, convenience is here.Golfing, biking, parks, adult games, everything at your finger tips. Also, a great selection of restaurants to choose from.Brand new building. Built in October of

  775 Laura Oaks Blvd Unit Building 9 Apt.203, Kissimmee, FL 34747
• 

  /2

  $330,000 Sold Jul 11, 2025

  • 1,557 Sq Ft
  • $212/SF
  • 466 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2019

  1777 Flora Pass Place, Kissimmee, FL 34747

  Welcome to 1777 Flora Pass Place, Kissimmee. This is a beautiful Sandpiper Villa with two bedroom, two full bath and an office/den/3rd BR. Features are: screened in lanai with super screens and shades, tray ceilings in the living room, crown molding, wainscoting in the hallway and on the large Island, both bedrooms have LVP floring and the two car garage floor is finished beautifully. Also

  Sue Rinaldi VIVA ORLANDO REALTY INC.

  1777 Flora Pass Place, Kissimmee, FL 34747
• 

  /2

  Est $491,114 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,029 Sq Ft

  7890 Stoney Bay Loop Unit 443, Kissimmee, FL 34747

  7890 Stoney Bay Loop Unit 443, Kissimmee, FL 34747
• 

  

  /47

  $379,900 Pending

  • 3 Beds
  • 2 Baths
  • 1,246 Sq Ft

  7650 Comrow St Unit 403, Kissimmee, FL 34747

  Under contract-accepting backup offers. In all of Windsor Hills, there is only one corner, penthouse condominium that overlooks the pool and clubhouse... This is the one! This crown jewel delivers the kind of views and lifestyle most people only dream about. Perched on the top floor, this rare 3-bed, 2-bath gives you front-row seats to the best sights in the resort. Step inside, the open layout

  

  Cathy Starkweather

  LA ROSA REALTY LLC

  (321) 341-6487

  7650 Comrow St Unit 403, Kissimmee, FL 34747
• 

  

  /89

  $3,000 per month

  • 3 Beds
  • 3 Baths
  • 1,545 Sq Ft
  • Townhouse for Rent

  2967 Castaway Ln, Kissimmee, FL 34747

  Currently Leased ~ AVAIALBLE FOR MOVE IN ON 9/12/25 - LOCK IN YOUR FUTURE HOME NOW! AMAZING VILLA AVAILABLE FOR LONG-TERM RENTAL AT MARGARITAVILLE RESORT ORLANDO. This Villa has 3 Bedrooms and 3 Baths, High-End Quartz Countertops, Upgraded "Wood" Tile Flooring and Appliances. Kitchen has Island with Seating, Large Counter Space and Windows with Lots of Natural Light. Master Bedroom Located

  Suzanne Docobo EXP REALTY LLC

  2967 Castaway Ln, Kissimmee, FL 34747
• 

  /2

  $770,000 Sold Jul 09, 2025

  • 1,818 Sq Ft
  • $424/SF
  • 24 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 2018

  3020 Parrot Head Place, Kissimmee, FL 34747

  Spectacular ONE-OF-A-KIND Phase 1 Premium Waterfront Cottage at Margaritaville! LARGE 3 Bedroom, 3.5 Bathroom 1818-A Model with UNIQUE ONE OF A KIND CUSTOM BUILT TIKI THEMED LOFT - THE ONLY ONE IN THE ENTIRE RESORT! Loft is a Magnificent Tranquil Hideaway with "Pirates of the Caribbean" Pinball Machine and Cocktail Table Style Arcade Game with Hundreds of Games! Cottage is Located on a Corner Lot

  Suzanne Docobo EXP REALTY LLC

  3020 Parrot Head Place, Kissimmee, FL 34747
• 

  

  /36

  Est $670,110 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 2,360 Sq Ft

  7786 Four Seasons Blvd, Kissimmee, FL 34747

  7786 Four Seasons Blvd, Kissimmee, FL 34747
• 

  

  /43

  $698,000

  • 7 Beds
  • 4 Baths
  • 2,812 Sq Ft

  7801 Basnett Cir, Kissimmee, FL 34747

  Discover this exceptional 7-bedroom, 4-bathroom fully furnished home in the highly sought-after Windsor Hills Resort, just 4 miles from Walt Disney World! This property offers a rare advantage—no rear neighbor and a spacious open view of lush green space and trees, creating a serene and private setting. Perfect as a vacation retreat or short-term rental investment, this spacious home boasts a

  

  Cui Li

  RATIO REAL ESTATE, LLC

  (321) 472-3117

  7801 Basnett Cir, Kissimmee, FL 34747
• 

  

  /17

  $3,095 per month

  • 5 Beds
  • 3.5 Baths
  • 2,618 Sq Ft
  • House for Rent

  7962 Magnolia Bend Ct, Kissimmee, FL 34747

  Beautiful, pet-friendly home coming soon! Apply now, Move-In is available on or after the listed date. Upon approval, $500 reservation deposit to reserve (applied to security deposit and/or refundable). Application fee: $50 per adult. Security Deposit: one month?s rent. Pet fees: $250 + $35/mo per pet. Some homes may include pool ($150/mo), septic ($15/mo), and/or HOA fees; other fees may apply.

  7962 Magnolia Bend Ct, Kissimmee, FL 34747
• 

  /2

  $479,000 Sold Jul 08, 2025

  • 1,422 Sq Ft
  • $337/SF
  • 22 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 2018

  3062 Pirate Way, Kissimmee, FL 34747

  # Tropical Paradise in Margaritaville of OrlandoDiscover this exquisite 3-bedroom, 3.5-bath SPA home nestled in the coveted first phase of Margaritaville of Orlando. Located just 200 steps from the resort amenities, this prime property has a beach sand playground right in your backyard – perfect for building sandcastles or hosting holiday cookouts with neighbors!Step inside to

  Deanna Meredith LUXE PROPERTIES LLC

  3062 Pirate Way, Kissimmee, FL 34747
• 

  /2

  Est $605,075 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 2,445 Sq Ft

  2280 Seagrass Point Unit 448, Kissimmee, FL 34747

  2280 Seagrass Point Unit 448, Kissimmee, FL 34747
• 

  

  /51

  $279,000

  • 3 Beds
  • 2 Baths
  • 1,484 Sq Ft

  3107 Sun Lake Ct Unit B, Kissimmee, FL 34747

  Turn Your Florida Dream Into Reality! Step into this fullyfurnished, spacious condo nestled in the heart of Kissimmee—justminutes from the magic of Animal Kingdom park! Whether you'relooking for a permanent residence, a lucrative investment, or yournext vacation getaway, this gem checks every box.Featuring an open layout with tile and laminate flooring (nocarpet!), high

  

  JAY Caballer

  HOMETRUST REALTY GROUP

  (321) 450-4304

  3107 Sun Lake Ct Unit B, Kissimmee, FL 34747
• 

  

  /97

  $3,900 per month

  • 4 Beds
  • 4.5 Baths
  • 2,066 Sq Ft
  • House for Rent

  8044 Lost Shaker Ln, Kissimmee, FL 34747

  Currently Occupied ~ Available for Move in 9/1/25. GORGEOUS 1990-A Model 3-Story Cottage in Margaritaville Resort Orlando with Convenient Central Resort Location! Home Features 4 Bedrooms and 4.5 Bathrooms. There are Primary Suites Located on Second and Third Floors with En-Suite Bathrooms. Another Bedroom has 2 Beds with En Suite Bathroom. Both Second and Third Floors have Large Balconies to Sit

  Suzanne Docobo EXP REALTY LLC

  8044 Lost Shaker Ln, Kissimmee, FL 34747
• 

  /2

  $520,000 Sold Jul 08, 2025

  • 2,618 Sq Ft
  • $199/SF
  • 35 Days On Market

  • 5 Beds
  • 3.5 Baths
  • Built 1998

  7916 Golden Pond Cir, Kissimmee, FL 34747

  Welcome to this stunning 5-bedroom, single-family home with its welcoming luxurious interior and playful charm. Recently updated, this home offers the perfect blend of modern amenities and high end design, making it the ultimate retreat for family and friends. As you step inside, you'll be greeted with an open views of your private conservation water views. Notice the new flooring throughout and

  Michael Steward EXP REALTY LLC

  7916 Golden Pond Cir, Kissimmee, FL 34747
• 

  

  /14

  Est $536,870 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,189 Sq Ft

  2296 Seagrass Point Unit 450, Kissimmee, FL 34747

  2296 Seagrass Point Unit 450, Kissimmee, FL 34747
• 

  

  /28

  $360,000

  • 3 Beds
  • 2 Baths
  • 1,450 Sq Ft

  7675 Comrow St Unit 404, Kissimmee, FL 34747

  Discover this beautifully updated 3-bedroom, 2-bath Santa Anna floor plan—the largest available in the highly sought-after Windsor Hills Resort. This stunning 3-bedroom, 2-bathroom Santa Anna floor plan—the largest condo layout in the community—offers top-floor privacy, modern upgrades, and unbeatable resort-style living just minutes from Walt Disney World.Step inside to discover a

  Claudia Villarroel ROBERT SLACK LLC

  7675 Comrow St Unit 404, Kissimmee, FL 34747
• 

  

  /42

  $2,100 per month

  • 3 Beds
  • 3 Baths
  • 1,490 Sq Ft
  • Townhouse for Rent

  7663 Sir Kaufmann Ct, Kissimmee, FL 34747

  Beautiful 3 bedrooms with 3 in-suite bathrooms, open concept kitchen/living room exiting to a private splash pool 11x11x4 with the fenced/screened patio. Located in a quiet, comfortable, gated and life-guarded, prestigious Windsor Hills Resort, all the amenities it offers. Bedrooms location: 1 bedroom with in-suit bathroom on main floor and 2 bedrooms with 2 in-suit bathrooms on the 2nd

  7663 Sir Kaufmann Ct, Kissimmee, FL 34747
• 

  /2

  $565,000 Sold Jul 07, 2025

  • 2,848 Sq Ft
  • $198/SF
  • 43 Days On Market

  • 5 Beds
  • 5 Baths
  • Built 2006

  2710 Manesty Ln, Kissimmee, FL 34747

  WELCOME to your DREAM vacation home! Located only 0.4 miles (away short 7-10 minute walk) to the the insane water park and community amenity center. Windsor Hills has everything you could want from water slides, to community events, movie theater, arcade and more! But you don’t even need to leave your home to enjoy the Movie and arcade experience since the garage has been professionally

  Kira Woods SANDS REALTY GROUP LLC

  2710 Manesty Ln, Kissimmee, FL 34747
• 

  /2

  Est $401,495 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,545 Sq Ft

  3148 Caribbean Soul Dr, Kissimmee, FL 34747

  3148 Caribbean Soul Dr, Kissimmee, FL 34747
• 

  

  /62

  $625,000

  • 5 Beds
  • 5 Baths
  • 2,342 Sq Ft

  2616 Bowring St, Kissimmee, FL 34747

  Book your Appointment now! Welcome to this well maintained pool home, perfectly situated on one of the most private streets in the highly desirable Windsor Hills Community. With a strong history as a short-term rental and future bookings already in place, this property is both a charming retreat and a smart investment.Step inside and you’ll find a warm, inviting space with five spacious

  Kimberley Beaudry ORLANDO REGIONAL REALTY

  2616 Bowring St, Kissimmee, FL 34747
• 

  

  /34

  $2,750 per month

  • 4 Beds
  • 2 Baths
  • 1,778 Sq Ft
  • House for Rent

  Unlisted Address

  Beautiful fully furnished pool home. Has natural gas for the water heater, pool heater, clothes dryer and range. Available for seasonal rental, from 2 months to 2 years. Tenant may do rental arbitrage. It used to be a short term rental between 2016 to 2020. No HOA, and Osceola County allows it. Beautiful community park with community pool, tennis court

  Ricardo De Lara LA ROSA REALTY KISSIMMEE

  Unlisted Address
• 

  /2

  $600,000 Sold Jul 07, 2025

  • 2,342 Sq Ft
  • $256/SF
  • 134 Days On Market

  • 5 Beds
  • 5 Baths
  • Built 2009

  2549 Archfeld Blvd, Kissimmee, FL 34747

  Welcome to a completely furnished 5bedroom and 5 bathrooms pool home in the Windsor Hills community resort. This well-decorated home with luxury vinyl planking and tile throughout the house, features a spacious and beautifully furnished living room, where you can relax and unwind with your family and friends. The living room has a large TV, comfortable sofas and chairs, and plenty of light

  Long Nguyen ALLIANCE REAL ESTATE GROUP

  2549 Archfeld Blvd, Kissimmee, FL 34747
• 

  

  /56

  Est $440,189 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 1,804 Sq Ft

  2637 Sunrise Shores Dr, Kissimmee, FL 34747

  2637 Sunrise Shores Dr, Kissimmee, FL 34747
• 

  

  /85

  $325,000

  • 2 Beds
  • 2 Baths
  • 1,557 Sq Ft

  1890 Flora Pass Place, Kissimmee, FL 34747

  Imagine waking up each morning to breathtaking views of the 16th hole of Mystic Dunes Golf & Country Club, right in your backyard! This stunning 2 bedroom, 2 bathroom villa with a versatile den that could easily serve as a third bedroom invites you to experience the best of maintenance free living in the highly sought-after 55+ gated community of Four Seasons at Orlando. Perfectly located just

  Stella Tornabene COMPASS FLORIDA LLC

  1890 Flora Pass Place, Kissimmee, FL 34747
• 

  

  /25

  $2,399 per month

  • 4 Beds
  • 3 Baths
  • 1,650 Sq Ft
  • House for Rent

  3139 Sun Lake Ct, Kissimmee, FL 34747

  Fully furnished and professionally decorated 4 bed/3 bath home only 2 miles from Disney's Animal Kingdom. New flooring and updated kitchen and bathrooms. Gorgeous lakeview from the screened in patio. Walking distance to lots of shopping and restaurants as well as Margaritaville and the H20 waterpark. Neighborhood has a pool and hot tub.

  3139 Sun Lake Ct, Kissimmee, FL 34747
• 

  /2

  $385,000 Sold Jul 02, 2025

  • 2,076 Sq Ft
  • $185/SF
  • 60 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1987

  7691 Indian Ridge Trail S, Kissimmee, FL 34747

  Take a dive into serenity, look at this beautiful spacious Pool Home - Short Term Approved! 4 bedroom, 2 bath, 2 car garage with pool and large corner lot! Many upgrades and ready for its new owners. The Kitchen features closet pantry and tile flooring, Formal dining room, split bedroom plan. The Master bath includes dual sinks and shower/no tub. Close to Disney Parks, shopping & dining. Don't

  Antonios Kappos TRANSCEND REALTY

  7691 Indian Ridge Trail S, Kissimmee, FL 34747
• 

  

  /32

  Est $662,657 Not Listed For Sale

  • 5 Beds
  • 5.5 Baths
  • 1,908 Sq Ft

  8016 Lost Shaker Ln, Kissimmee, FL 34747

  8016 Lost Shaker Ln, Kissimmee, FL 34747
• 

  

  /31

  $399,000

  • 3 Beds
  • 3 Baths
  • 1,440 Sq Ft

  7663 Fitzclarence St, Kissimmee, FL 34747

  Welcome investors, to your dream vacation home at 7663 Fitzclarence Street in Kissimmee, Florida. Located just 1.5 miles from the gates of Walt Disney World, this fully furnished 3-bedroom, 3-bathroom pool home is nestled within the highly desirable Windsor Hills Resort community. Whether you're searching for the perfect family getaway or a high-performing short-term rental, this property offers

  Ty McTague RE/MAX VANTAGE

  7663 Fitzclarence St, Kissimmee, FL 34747
• 

  

  /19

  $2,500 per month

  • 3 Beds
  • 2 Baths
  • 1,484 Sq Ft
  • Condo for Rent

  3133 Sun Lake Ct Unit A, Kissimmee, FL 34747

  Amazing first floor condo, recently remodeled, very spacious, quiet place, fully furniture, condo is located close to heated pool, gym and pool table; walking distance to the new H2O water park and Margaritaville mall and resort, 10 minutes to Disney theme parks and walking distance to restaurants, mini golf course, supermarkets and pharmacies, bus stop is right outside the condo, close to other

  Kirvio Peralta LOKATION

  3133 Sun Lake Ct Unit A, Kissimmee, FL 34747
• 

  /2

  $665,000 Sold Jun 30, 2025

  • 2,812 Sq Ft
  • $236/SF
  • 6 Days On Market

  • 6 Beds
  • 4 Baths
  • Built 2005

  2609 Dinville St, Kissimmee, FL 34747

  Windsor Hills- just minutes to Disney! Check out the entertainment in this busy short term rental! Large home perfect for large families or rental guests. Windsor Hills amenities: lagoon-style pool, waterpark with slides, movie theater, fitness center, clubhouse, playgrounds, RV parking. Perfect for your personal vacation home, amazing primary, or income producing rental. Seller is providing a

  Holly Hudson EXP REALTY LLC

  2609 Dinville St, Kissimmee, FL 34747
• 

  /2

  Est $643,337 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,970 Sq Ft

  1975 Flora Pass Place, Kissimmee, FL 34747

  1975 Flora Pass Place, Kissimmee, FL 34747

Showing Results 41 - 80, Page 2 of 18