Welcome to Florida, land of perpetual sunshine! Here you'll find sandy beaches, crystal springs, Walt Disney World, and sun-soaked vacation rentals to call home. A weekend on Panama City Beach could be just the ticket and we have vacation homes/condos galore. Use the blue location links below to select the region you'd like to explore or filter your preferences using the panel to the side. RedAwning offers easy, instant, hotel-style reservations and a simplified booking process that will have your vacation buttoned up in no time!
Photo Credit Ann Caron

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  1. HOUSE
    Windsor At Westside- 2135 Tripoli Court

    Windsor At Westside- 2135 Tripoli Court

    Kissimmee, FL

    Welcome to this stunning vacation home built in 2016 and located in the heart of Windsor at Westside. This incredible 9 bedroom, 6 bathroom home features luxurious finishes and beautiful features. This home is a part of the Grand Collection, meaning...

    Pool
    FREE CANCELLATION

    $472 to $860/night

  2. TOWNHOUSE
    Windsor Hills- 2540 Renshaw Street

    Windsor Hills- 2540 Renshaw Street

    Kissimmee, FL

    Welcome to Windsor Hills – this wonderful townhome is a great way to vacation with family and friends. Whether it’s a family vacation or a guys or girls getaway, this community and home will not disappoint. Complete with 3 bedrooms and 3...

    Pool
    FREE CANCELLATION

    $120 to $285/night

  3. HOUSE
    Windsor Hills- 2572 Archfeld Blvd

    Windsor Hills- 2572 Archfeld Blvd

    Kissimmee, FL

    Book your Orlando rental home now at this beautiful and professionally decorated 6 bedrooms and 4 bathrooms ''Grand'' 2 story 2812 sq. ft.home with west facing pool and spa. The home features a 50 inch flat screen TV in the living room. The dining...

    Pool
    FREE CANCELLATION

    $265 to $495/night

  4. HOUSE
    Windsor Hills- 7739 Comrow Street

    Windsor Hills- 7739 Comrow Street

    Kissimmee, FL

    Our villa accommodates 8 people, and is equipped with everything needed to make your stay enjoyable. Only a short walk to the clubhouse, it is conveniently located and, with no rear neighbors, privacy is optimal. There are four bedrooms complete...

    Pool
    FREE CANCELLATION

    $204 to $359/night

  5. TOWNHOUSE
    Paradise Palms- 3069 Beach Palm Ave.

    Paradise Palms- 3069 Beach Palm Ave.

    Kissimee, FL

    Welcome to this lovely 4 bedroom, 3 bathroom townhome in the stunning resort community of Paradise Palms. There are 32 inch LED flat screen TV’s in all the bedrooms and a 40-inch flat screen TV in living room. This unit is tastefully decorated and...

    Pool
    FREE CANCELLATION

    $135 to $325/night

  6. HOUSE
    Windsor Palms- 8154 Fan Palm Way

    Windsor Palms- 8154 Fan Palm Way

    Kissimmee, FL

    This 4bdrm/3bth home located in the gated Windsor Palms just minutes away from disney has many ammenities and upgrades. This home features a large screen TV in the living room, and a gameroom. The home also has unlimited long distance and...

    Pool Hot Tub
    FREE CANCELLATION

    $176 to $314/night

  7. HOUSE
    Windsor Palms- 8038 King Palm Circle

    Windsor Palms- 8038 King Palm Circle

    Kissimmee, FL

    2450 sq. ft, 5 bedroom – 3.5 bath (2 story) Welcome to this elegant, professionally decorated Orlando vacation pool home. This 5 bedroom, 3.5 bath home has a screened-in pool and spa. The fun game room has a pool table and foosball table . The...

    Pool Hot Tub
    FREE CANCELLATION

    $186 to $357/night

  8. HOUSE
    2514 Dharma Circle

    2514 Dharma Circle

    Kissimmee, Florida

    This spacious home-away-from-home offers a luxurious and well-designed living space – with professionally furnished and decorated rooms and decor. Relax and enjoy all this space and comfort for a fraction of the cost of staying in a hotel!...

    Pool Hot Tub
    FREE CANCELLATION
  9. HOUSE
    Windsor Palms- 8167 Sun Palm Drive

    Windsor Palms- 8167 Sun Palm Drive

    Kissimmee, FL

    We invite you to enjoy our home on your next trip to Orlando. Absolutely perfect for family groups, this property features all the comforts of home and more! Book your vacation now at this beautiful home with south facing pool and spa. Attention to...

    Pool
    FREE CANCELLATION

    $212 to $407/night

  10. HOUSE
    Windsor Palms- 8208 Fan Palm Way

    Windsor Palms- 8208 Fan Palm Way

    Kissimmee, FL

    This beautifull 4 bedroom 3 bath home located in the Resort style gated community just minutes away from disney offers many ammenities for the whole family. Bedding: 1 king bed, 1 queen bed, 4 twin beds, and a sleeper sofa. Large screen TV - 50", 1...

    Pool
    FREE CANCELLATION

    $176 to $314/night

  11. HOUSE
    Paradise Palms- 2960 Buccaneer Palm Road

    Paradise Palms- 2960 Buccaneer Palm Road

    Kissimmee, FL

    Welcome to this gorgeous 6 bedroom, 5 bathroom rental home in the stunning resort community of Paradise Palms. The fully equipped kitchen features stainless steel appliances, granite counter tops and upgraded tile and cabinetry. For your dining...

    Pool
    FREE CANCELLATION

    $260 to $465/night

  12. HOUSE
    Champions Gate- 1471 Myrtlewood Street

    Champions Gate- 1471 Myrtlewood Street

    Davenport, FL

    Welcome to this stunning 6 Bedroom, 6 Bathroom pool home. One of the benefits of staying in a rental home is that everyone can have their own bedroom for privacy. The unique feature of this beautiful rental home is that there are 6 bathrooms to go...

    Pool
    FREE CANCELLATION

    $297 to $582/night

  13. HOUSE
    Fan Palm Way House 8127

    Fan Palm Way House 8127

    Kissimmee, FL

    This spacious 4 bedroom, 3 bathroom home is located in the gated Windsor Palms community just minutes from Disney! This home has been recently upgraded and features a king master, queen room, two twin rooms and a screened in pool area with new patio...

    Pool
    FREE CANCELLATION

    $176 to $314/night

  14. HOUSE
    Manesty House- 2709

    Manesty House- 2709

    Kissimmee, FL

    "Home away from home" is the perfect way to describe this 5 bedroom, 4 bathroom home located in the gated community of Windsor Hills. A warm and inviting atmosphere greets you in every room. The living room is perfectly decorated with cozy couches...

    Pool
    FREE CANCELLATION

    $231 to $434/night

  15. HOUSE
    Solterra- 4204 Oak Tree Drive

    Solterra- 4204 Oak Tree Drive

    Davenport, FL

    This stunning vacation home boasts 7 bedrooms along with 5 large bathrooms and sleeps 16 - ideal for large family groups. The kitchen has upgraded stainless steel appliances and granite counter tops. The entire home is beautifully decorated and each...

    Pool
    FREE CANCELLATION

    $296 to $603/night

  16. HOUSE
    7787 Bassnett Circle

    7787 Bassnett Circle

    Kissimmee, FL

    A few miles from all the Orlando entertainment lies this gorgeous 5 bedroom, 5 bathroom home in Windsor Hills. This gated community home sleeps up to 10 guests perfectly where everyone will find their own space on vacation, with 1 king bedroom, 2...

    Pool Hot Tub
    FREE CANCELLATION

    $231 to $434/night

  17. HOUSE
    Windsor Hills- 2604 Daulby Street

    Windsor Hills- 2604 Daulby Street

    Kissimmee, FL

    We invite you to enjoy our home on your next trip to Orlando. Absolutely perfect for family groups, this property features all the comforts of home and more! Book your vacation now at this beautiful home with pool and spa located in the Windsor...

    Pool
    FREE CANCELLATION

    $231 to $434/night

  18. HOUSE
    Champions Gate- 1412 Thunderbird Road

    Champions Gate- 1412 Thunderbird Road

    Davenport, FL

    We invite you to enjoy our home on your next trip to Orlando. Absolutely perfect for family groups, this property features all the comforts of home and more! Book your vacation now at this beautiful home with pool located in the ChampionsGate...

    Pool
    FREE CANCELLATION

    $339 to $664/night

  19. TOWNHOUSE
    Paradise Palms- 8944 Majesty Palm Road

    Paradise Palms- 8944 Majesty Palm Road

    Kissimmee, FL

    This 4-bedroom, 3-bathroom, 1.914 sq. ft. townhome can accommodate 8 in spacious living. This townhome features upgraded furniture and all of the bedrooms are eye catching indeed with a flat screen TV in each for your enjoyment. The bedrooms...

    Pool
    FREE CANCELLATION

    $135 to $325/night

  20. HOUSE
    Archfeld Blvd House 2601

    Archfeld Blvd House 2601

    Kissimmee, FL

    Welcome to Windsor Hills. When you come to sunny central Florida, be sure to stay in this magnificent home. This opulent 6 bedroom, 4 bathroom home is what vacation is all about. As a part of the Grand Collection, this home is top of the line in...

    Pool Hot Tub
    FREE CANCELLATION

    $265 to $495/night

  21. HOUSE
    2617 Archfeld Blvd House

    2617 Archfeld Blvd House

    Kissimmee, FL

    If you’re looking to go on a vacation, then look no further than Windsor Hills in sunny Orlando. Accommodating up to 10 guests with 5 bedrooms and 5 bathrooms, this vacation rental is perfect for you. As a part of the Grand Collection, this home...

    Pool
    FREE CANCELLATION

    $276 to $434/night

  22. TOWNHOUSE
    Windsor Palms- 2332 Silver Palm Drive

    Windsor Palms- 2332 Silver Palm Drive

    Kissimmee, FL

    This wonderful 1.416 sq. ft. 3 bedroom town home features two master bedrooms each one with private bathroom, and one twin Mickey Mouse themed kids’ bedroom with private bathroom, a private lounge pool and patio, with a beautiful view to a...

    Pool
    FREE CANCELLATION

    $113 to $271/night

  23. HOUSE
    Champions Gate- 9165 Wedge Drive

    Champions Gate- 9165 Wedge Drive

    Champions Gate, FL

    Welcome to the beautiful resort community of Champions Gate. Champions Gate, located in the heart of the Orlando theme park area, is the perfect location for your vacationing needs. This vacation home is sure to bring your getaway to the next level!...

    Pool
    FREE CANCELLATION

    $233 to $424/night

  24. HOUSE
    Windsor Palms- 8008 King Palm Circle

    Windsor Palms- 8008 King Palm Circle

    Kissimmee, FL

    Solar-Power/Carbon Zero! Amazing 6 Bedroom Pool Home just 3 Miles from Disney Just installed: All new modern Solar-Power PV panels and efficient cooling systems give this home a super low carbon footprint! Our wonderful, 5-star pool home is fully...

    Pool Hot Tub
    FREE CANCELLATION

    $212 to $407/night

  25. HOUSE
    Windsor Hills- 7744 Comrow Street

    Windsor Hills- 7744 Comrow Street

    Kissimmee, FL

    Welcome to our stunning 2,966 sq. ft. 5 bedroom, 5 bathroom (with 3 suites) vacation home located in Windsor Hills. This home is professionally decorated and painted with a stone accent wall in the dining room and features 2 king suites with 40"...

    Pool
    FREE CANCELLATION

    $231 to $434/night

  26. HOUSE
    2995 Buccaneer Palm Road

    2995 Buccaneer Palm Road

    Kissimmee, FL

    Rest and relaxation meet here to create this gorgeous home located in the resort community of Paradise Palms. With lush greenery surrounding the home and Mediterranean architecture, you will feel transported to a new paradise. Bright and airy are...

    Pool
    FREE CANCELLATION

    $229 to $407/night

  27. CONDOMINIUM
    Windsor Palms- 2303 Butterfly Palm Way, U102

    Windsor Palms- 2303 Butterfly Palm Way, U102

    Kissimmee, FL

    This stunning 2 bedroom, 2 Bathroom (1206 sq. ft.) rental located near the theme parks in Orlando, Florida.  This vacation rental has all the comforts of home and more.  The kitchen is fully furnished and ideal for those times when it makes sense...

    Pool
    FREE CANCELLATION

    $91 to $194/night

  28. HOUSE
    Champions Gate- 1638 Moon Valley Drive

    Champions Gate- 1638 Moon Valley Drive

    Davenport, FL

    Begin your dream vacation by booking this spectacular vacation home located in the resort community of Champions Gate. As you enter this home, rich colors and opulence surround you. The first floor living area is roomy yet cozy with a dark leather...

    Pool
    FREE CANCELLATION

    $297 to $582/night

  29. HOUSE
    Windsor Hills- 2659 Dinville Street

    Windsor Hills- 2659 Dinville Street

    Kissimmee, FL

    You need to see for yourself why guests rate Windsor Hills a 4.5 out of 5 on Trip Advisor… the closest Orlando vacation home resort to Walt Disney World (1.5mi or 2.4km)! This 6 bedroom, 4 bathroom, 2,812 sq. foot executive pool home sleeps up to...

    Pool
    FREE CANCELLATION

    $265 to $495/night

  30. HOUSE
    Champions Gate- 9151 Caddie Way

    Champions Gate- 9151 Caddie Way

    Champions Gate, FL

    Welcome to Champions Gate Resort featuring the stunning world-class Oasis clubhouse. The lovely, open floor plan is professionally decorated and includes a stunning furniture package with two 58-inch flat-screen TV’s and 2 bluray DVD players....

    Pool
    FREE CANCELLATION

    $450 to $864/night