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

Filter by Region:


Filter by Amenities:


Filter by Entertainment:


Close Filters
  1. HOUSE
    40 Picadilly House

    40 Picadilly House

    Kissimmee, FL

    4 Bedroom / 2.5 Bathroom (1,910 sqft)Two StoryGated CommunityNorth Facing Private Pool Electric Pool Heat is an additional cost.Living Room (Back): SOFA/TVLiving Room (Front): Seating AreaDining Area - Seats 4Breakfast Bar - Seats 4aster Bedroom 1:...

    Pool
    FREE CANCELLATION

    $95 to $136/night

  2. HOUSE
    40 Woodsong House

    40 Woodsong House

    Clermont, FL

    3 Bedroom / 2 Bathroom (1,192 sqft)Single StoryNorth Facing Private Pool Electric Pool Heat is an additional costLiving Room: HD TV/DVD PLAYERDining Area - Seats 4Breakfast Table - Seats 3Master Bedroom 1: QUEEN/ TV Bedroom 2:FULL Bedroom 3: Twins...

    Pool
    FREE CANCELLATION

    $89 to $113/night

  3. HOUSE
    18 Reserve House

    18 Reserve House

    Davenport, FL

    3 Bedroom / 3 Bathroom (1,512 sqft)Single Story Gated Community South Facing Private Pool Electric Pool Heat is an additional cost.Living Room: TV / DVD / Playstation2 / Dining Area - Seats 6Master Bedroom 1: King / TV / Pool AccessMaster Bedroom 2:...

    Pool
    FREE CANCELLATION

    $89 to $130/night

  4. HOUSE
    35 Fresh House

    35 Fresh House

    Clermont, FL

    4 Bedroom / 2 Bathroom (1,412 sqft)Single StoryNorth Facing Private Pool and SPA Electric Pool Heat is an additional cost.Living Room : TV / DVD / VCR / StereoDining Area - Seats 6Breakfast Bar - Seats 2Master Bedroom 1 : King / TV / Garden Tub /...

    Pool
    FREE CANCELLATION

    $101 to $154/night

  5. HOUSE
    34 Thousand House

    34 Thousand House

    Davenport, FL

    4 Bedroom / 2 Bathoom (1,673 sqft)Single Story South-East Facing Private Pool Electric Pool Heat is an additional cost.Living Room: TV / DVD / VCR / Stereo / ComputerDining Area - Seats 6Kitchen Table - Seats 4Master Bedroom: QueenBedroom 2:...

    Pool
    FREE CANCELLATION

    $95 to $136/night

  6. CONDOMINIUM
    Seagate 406- Indian Shores Condo

    Seagate 406- Indian Shores Condo

    Indian Shores, FL

    This property has Saturday to Saturday check in - check out requirement. Extraordinary Beach Front Condo Completely Renovated from Top to Bottom in 2017! Journey from the everyday to the exceptional at Sea Gate 406. Lovingly remodeled by the...

    Pool

    $792 to $3,212/night

  7. CONDOMINIUM
    Sea Breeze 306 Condominium

    Sea Breeze 306 Condominium

    Madeira Beach, FL

    Stunning Sunsets, Powdery Sand and Classic Beach Boardwalk in Madeira Beach! The Sea Breeze Condominium is one of the most desirable complexes in Madeira Beach. Each unit sports a roomy balcony overlooking the powdery white sand and emerald...

    Pool Hot Tub

    $625 to $2,533/night

  8. HOUSE
    Sunset Sea-esta House

    Sunset Sea-esta House

    Treasure Island, FL

    Decadent Treasure Island Home Overlooking Beach with Private Pool and Kayaks! A little piece of paradise awaits you at this upscale 2 story home just steps from the beach. The second floor balcony has a direct ocean view where you can delight in...

    Pool Pets OK

    $888 to $3,598/night

  9. CONDOMINIUM
    Reef Club 507 Condominium

    Reef Club 507 Condominium

    Indian Rocks Beach, FL

    Experience Beachfront Bliss in Central Indian Rocks Beach! We proudly announces its partnership with Rich and Diana, who are actively purchasing and renovating properties in the award-winning St. Pete/Clearwater area! Rich and Diana are committed...

    Pool Hot Tub Pets OK

    $724 to $2,934/night

  10. CABIN
    Beach Haven Cabin C6

    Beach Haven Cabin C6

    Treasure Island, FL

    Fantastic Oceanfront Condo Hidden in the Dunes of Treasure Island! You will feel as if you've slipped away to times past in this modern beach front property with a classic coastal feel. Only steps from the ocean, this property truly is a Treasure...

    Pets OK

    $738 to $2,994/night

  11. CONDOMINIUM
    Sea Gate 507 Condominium

    Sea Gate 507 Condominium

    Indian Shores, FL

    Stunning Gulf Views in this Modern and Spacious Gulf Getaway! This spacious condo provides plenty of room for family and friends without giving up the amenities our guests expect for an exceptional beachside experience! Perched above the radiant...

    Pool

    $726 to $2,945/night

  12. CONDOMINIUM
    Reef Club Condominium 107

    Reef Club Condominium 107

    Indian Rocks Beach, FL

    Spectacular and Completely Renovated Oceanfront Condo with Luxury Amenities! This property offers the full package for those seeking a convenient, upscale vacation experience. The entire condo has been renovated and features contemporary...

    Pool

    $703 to $2,848/night

  13. CONDOMINIUM
    Sea Breeze 608 Condominium

    Sea Breeze 608 Condominium

    Madeira Beach, FL

    You will not want to miss out on this delightful vacation spot. Unit 608 at the Sea Breeze Condominium has it all. It is situated directly on the powdery sands on the Gulf of Mexico where you can sit on the balcony and watch the most unbelievable...

    Pool Hot Tub

    $649 to $2,632/night

  14. CONDOMINIUM
    Beach Haven Condominium B4

    Beach Haven Condominium B4

    Treasure Island, FL

    Beachside Bliss and Natural Beauty Meet in Treasure Island Gem! We are pleased to present Jeff and Gina's newest Gulf Coast treasure! Their signature style is both relaxed and modern beach chic offering high quality furnishings and thoughtful...

    Pets OK

    $1,022 to $4,144/night

  15. CONDOMINIUM
    Sea Breeze 702 Condominium

    Sea Breeze 702 Condominium

    Madeira Beach, FL

    Unit 702 at the Sea Breeze Condominium in Madeira Beach depicts the true essence of getting away from it all. This luxurious condo has all the comforts of home but includes the brilliant view of the emerald, sparkling waters of the Gulf of Mexico....

    Pool Hot Tub

    $631 to $2,559/night

  16. CONDOMINIUM
    Sea Gate Condominium 104

    Sea Gate Condominium 104

    Indian Shores, FL

    *Elevator will be out of service Oct. 22-Nov. 19.* Savor the Beautiful Sunsets at this Sunny Indian Shores Beachfront! Soak up those breathtaking Gulf of Mexico sunsets from your delightful balcony in this roomy 3-bedroom condo. Savor the pristine...

    Pool

    $709 to $2,873/night

  17. CONDOMINIUM
    Holiday Villas III 201

    Holiday Villas III 201

    Indian Shores, FL

    Relish the Magnificent Ocean Views in Carefree Indian Shores! Holiday Villas is the essence of a laid back rental property. The exquisite view of the pristine Gulf and the central location allow guests to fully embrace these award winning beaches...

    Pool

    $560 to $2,269/night

  18. CONDOMINIUM
    Pointe Condo 104 Condominium

    Pointe Condo 104 Condominium

    Indian Shores, FL

    You'll feel as though you can reach right out and touch the shimmering shores of the Gulf of Mexico from this intimate retreat overlooking turquoise waters. Soak in stunning evening sunsets from the corner balcony offering panoramic views,...

    $620 to $2,511/night

  19. HOUSE
    Street South House #54587

    Street South House #54587

    Bradenton Beach, FL

    105 A 12th Street South, Bradenton Beach, Anna Maria Island Unit A - Back ... Lovely 2 bedroom, 1 bath unit within walking distance to both beach and bay. Comfortably furnished with private, lushly landscaped courtyard. High speed internet, nice...

    Pool
    FREE CANCELLATION

    $173 to $294/night

  20. CONDOMINIUM
    Sunset Beach Condo #54455

    Sunset Beach Condo #54455

    Holmes Beach, FL

    2716 Gulf Drive, Holmes Beach, Anna Maria Island Sunset Beach Condo # 202 ... Direct gulf front 2 bedrooms, 2 bath unit with screened porches overlooking the beach. Smaller complex with lush landscaping, private pool, and covered parking. Amenities...

    Pool
    FREE CANCELLATION

    $234 to $381/night

  21. COTTAGE
    301 23rd St- Cha Cha Cottage #68392

    301 23rd St- Cha Cha Cottage #68392

    BRADENTON BEACH, FL

    Glimpses of the water are one of the special features from this adorable coastal cottage. Lives large is what you'll say as you enter the living area with lots of windows to let the outside in. Dining area off the perfectly appointed new kitchen....

    FREE CANCELLATION

    $191 to $363/night

  22. HOUSE
    Street South House #54586

    Street South House #54586

    Bradenton Beach, FL

    105 B 12th Street South, Bradenton Beach, Anna Maria Island Unit B - Front ... Lovely 2 bedroom, 1 bath unit within walking distance to both the beach and bay. Comfortably furnished with private, lushly landscaped courtyard. High speed internet,...

    Pool
    FREE CANCELLATION

    $173 to $294/night

  23. HOUSE
    526 72nd St (2 Bedroom- Home)

    526 72nd St (2 Bedroom- Home)

    Holmes Beach, FL

    Gorgeous, recently renovated two bedroom, two bath canal front home. This ground level home located in Bay Palms Subdivision was just updated with brand new furnishings, paint and an updated kitchen and bathrooms. Very bright interior with tons of...

    FREE CANCELLATION

    $260 to $277/night

  24. CABIN
    TORTUGA COTTAGE

    TORTUGA COTTAGE

    BRADENTON BEACH, FL

    "Tortuga Cottage"..... Charming & quaint, historic cottage ideally situated just a few steps to the beach AND the bay. This classic cottage was built in 1915 but offers all of today's updated amenities. 2 bedrooms and 2 bathrooms with a tasteful...

    Pool
    FREE CANCELLATION

    $260 to $450/night

  25. HOUSE
    504 Bay Drive Upstairs House #54612

    504 Bay Drive Upstairs House #54612

    Bradenton Beach, FL

    504 Bay Drive South, Bradenton Beach, Anna Maria Island Dock on the Bay ... Exceptional direct bay front 2 bedroom, 1 bath. This is the upstairs of a two unit building that was just completely remodeled. New bathroom with deep jet tub and separate...

    Hot Tub
    FREE CANCELLATION

    $200 to $294/night

  26. HOUSE
    Barefoot Villas W #54496

    Barefoot Villas W #54496

    Holmes Beach, FL

    Barefoot Villas West ... Adorable duplex located just steps to the beach. Each side has 2 bedrooms, 1 bath with open porches. Artistic decor, phone, cable, and microwave. Wonderful private outdoor shower with hot and cold water. Each side sleeps 4....

    Pets OK
    FREE CANCELLATION

    $151 to $277/night

  27. COTTAGE
    203 76Th St- Upstairs Cottage #54631

    203 76Th St- Upstairs Cottage #54631

    Holmes Beach, FL

    Lime in De Coconut - Upstairs..... Adorable, one bedroom, one bath in a 2 unit cottage. Cheery beach decor and a shared heated pool in a tropically landscaped courtyard. Flat screen TV, wireless internet access, washer & dryer, and a gas grill...

    Pool
    FREE CANCELLATION

    $173 to $329/night

  28. DUPLEX
    Vacationer's Duplex #54505

    Vacationer's Duplex #54505

    Holmes Beach, FL

    211 58th Street, Holmes Beach, Anna Maria Island Vacationer's Duplex ... Newly furnished, 2 bedroom, 2 bath elevated duplex located in a quiet residential neighborhood. Offers phone, cable, dishwasher, washer & dryer, microwave. Just one block from...

    Pets OK
    FREE CANCELLATION

    $148 to $277/night

  29. HOUSE
    Palm Cay 9 House #54482

    Palm Cay 9 House #54482

    Holmes Beach, FL

    Holmes Beach, Anna Maria Island Palm Cay # 9 ... Updated 1 bedroom, 1 bath unit located in small complex with heated pool located west of Gulf Drive just 2 houses to the beach for easy beach access. Enjoy peeks of the beach from the balcony....

    Pool
    FREE CANCELLATION

    $139 to $294/night

  30. VILLA
    SANDBOX 203 71ST ST EAST

    SANDBOX 203 71ST ST EAST

    HOLMES BEACH, FL

    Quiet and quaint is this cute 2 Bedroom/1 Bath Duplex with a large shared HEATED POOL in a lush tropical landscaped setting. Centrally located in Holmes Beach and only 75 yards to one of the best beaches on the Gulf Coast! You will feel right at...

    Pool
    FREE CANCELLATION

    $242 to $484/night