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  1. $781 to $3,018/night

    Arie Dam 503

    Arie Dam 503

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
  2. $412 to $1,825/night

    Madeira Bay Resort 306

    Madeira Bay Resort 306

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pets OK
  3. $729 to $2,946/night

    Arie Dam 102

    Arie Dam 102

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
  4. $374 to $1,698/night

    Madeira Bay Resort 204

    Madeira Bay Resort 204

    2 Bedrooms BathroomSleeps 6
    2 nights minstay
    Pets OK
  5. $181 to $328/night

    Beachfront Madeira Norte

    Beachfront Madeira Norte

    2 Bedrooms BathroomSleeps 6
    2 nights minstay
    Pool
  6. $600 to $2,319/night

    Sea Breeze 208

    Sea Breeze 208

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
  7. $142 to $424/night

    Trillium 4C Beach Front with Private Balcony/Updated/Pool!

    Trillium 4C Beach Front with Private Balcony/Updated/Poo...

    2 BedroomsBathroomsSleeps 4
    7 nights minstay
    Pool
  8. $142 to $424/night

    Trillium 1C Beach Front Condo with Private Balcony/Updated/Pool

    Trillium 1C Beach Front Condo with Private Balcony/Updat...

    2 BedroomsBathroomsSleeps 6
    7 nights minstay
    Pool
  9. $157 to $449/night

    Villa Madeira 201 South Corner/Huge Wrap Around Balcony!

    Villa Madeira 201 South Corner/Huge Wrap Around Balcony!...

    3 BedroomsBathroomsSleeps 5
    7 nights minstay
    Pool
  10. $132 to $400/night

    Villa Madeira 609 Top Floor Beach Front/Stunning Views/Pool

    Villa Madeira 609 Top Floor Beach Front/Stunning Views/P...

    2 BedroomsBathroomsSleeps 6
    7 nights minstay
    Pool
  11. $157 to $449/night

    Villa Madeira 301 Amazing updates/Corner/Wrap around balcony!

    Villa Madeira 301 Amazing updates/Corner/Wrap around bal...

    3 BedroomsBathroomsSleeps 6
    7 nights minstay
    Pool
  12. $650 to $2,511/night

    Arie Dam 204

    Arie Dam 204

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  13. $672 to $2,533/night

    Arie Dam 402

    Arie Dam 402

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
  14. $669 to $2,583/night

    Arie Dam 301

    Arie Dam 301

    2 BedroomsBathroomsSleeps 5
    2 nights minstay
    Pool Hot Tub
  15. $576 to $2,221/night

    Sea Breeze 705

    Sea Breeze 705

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
  16. $345 to $1,565/night

    Madeira Beach Yacht Club 250F

    Madeira Beach Yacht Club 250F

    2 Bedrooms BathroomSleeps 4
    2 nights minstay
  17. $201 to $347/night

    Sea Breeze 201

    Sea Breeze 201

    2 BedroomsBathroomsSleeps 6
    7 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  18. $99 to $197/night

    The Cottages at Madeira Beach/Sea Turtle

    The Cottages at Madeira Beach/Sea Turtle

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool Pets OK
  19. $99 to $197/night

    The Cottages at Madeira Beach/Sea Crab

    The Cottages at Madeira Beach/Sea Crab

    1 Bedroom BathroomSleeps 5
    3 nights minstay
    Pool Pets OK
  20. $99 to $197/night

    The Cottages at Madeira Beach/Star Fish

    The Cottages at Madeira Beach/Star Fish

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool Pets OK
  21. $89 to $179/night

    The Cottages at Madeira Beach/Seahorse

    The Cottages at Madeira Beach/Seahorse

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool Pets OK
  22. $216 to $412/night

    Las Brisas 105

    Las Brisas 105

    3 BedroomsBathroomsSleeps 8
    7 nights minstay
    Pool
    FREE CANCELLATION
  23. $175 to $329/night

    Ocean Sands I- 1208

    Ocean Sands I- 1208

    2 BedroomsBathroomsSleeps 4
    14 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  24. $142 to $424/night

    Trillium 4B Gulf Front Condo with Private Balcony/Amazing Views!

    Trillium 4B Gulf Front Condo with Private Balcony/Amazin...

    2 BedroomsBathroomsSleeps 6
    7 nights minstay
    Pool
  25. $132 to $400/night

    Villa Madeira 408 Walk to John's Pass/Great updates/AMAZING View

    Villa Madeira 408 Walk to John's Pass/Great updates...

    2 BedroomsBathroomsSleeps 6
    7 nights minstay
    Pool
  26. $142 to $429/night

    Villa Madeira 203 Great Updates/Pool/Walk to John's Pass!

    Villa Madeira 203 Great Updates/Pool/Walk to John's...

    3 BedroomsBathroomsSleeps 6
    7 nights minstay
    Pool
  27. $171 to $472/night

    Las Brisas 202 Beach Front/Very Spacious/Pool/BBQ!

    Las Brisas 202 Beach Front/Very Spacious/Pool/BBQ!

    3 BedroomsBathroomsSleeps 8
    3 nights minstay
    Pool
  28. $142 to $429/night

    Villa Madeira 504 Sleeps 6/Many updates/Walk to John's Pass!

    Villa Madeira 504 Sleeps 6/Many updates/Walk to John...

    2 BedroomsBathroomsSleeps 6
    7 nights minstay
    Pool
  29. $142 to $424/night

    Trillium 5A Gulf Front Condo with Private Balcony/Amazing Views!

    Trillium 5A Gulf Front Condo with Private Balcony/Amazin...

    2 BedroomsBathroomsSleeps 6
    7 nights minstay
    Pool
  30. $142 to $429/night

    Villa Madeira 505 Amazing updates/Stunning Beach View!

    Villa Madeira 505 Amazing updates/Stunning Beach View!

    3 BedroomsBathroomsSleeps 6
    7 nights minstay
    Pool
  31. $142 to $424/night

    Trillium 4A Beach Front Condo with Private Balcony/Amazing Views

    Trillium 4A Beach Front Condo with Private Balcony/Amazi...

    2 BedroomsBathroomsSleeps 6
    7 nights minstay
    Pool
  32. $142 to $424/night

    Trillium 5B Beach Front with Private Balcony/Amazing Gulf Views!

    Trillium 5B Beach Front with Private Balcony/Amazing Gul...

    2 BedroomsBathroomsSleeps 6
    7 nights minstay
    Pool
  33. $142 to $429/night

    Villa Madeira 204 Walk to John's Pass/Pool/Large balcony!

    Villa Madeira 204 Walk to John's Pass/Pool/Large ba...

    3 BedroomsBathroomsSleeps 6
    7 nights minstay
    Pool
  34. $132 to $400/night

    Villa Madeira 305 New kitchen/large balcony/walk to everything!

    Villa Madeira 305 New kitchen/large balcony/walk to ever...

    2 BedroomsBathroomsSleeps 5
    7 nights minstay
    Pool
  35. $672 to $2,533/night

    Sea Breeze 306

    Sea Breeze 306

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
  36. $550 to $2,125/night

    Madeira Bay Resort 508

    Madeira Bay Resort 508

    2 BedroomsBathroomsSleeps 8
    2 nights minstay
  37. $419 to $1,859/night

    Madeira Beach Yacht Club 329B

    Madeira Beach Yacht Club 329B

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
  38. $681 to $2,632/night

    Sea Breeze 608

    Sea Breeze 608

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  39. $771 to $2,908/night

    Arie Dam 403

    Arie Dam 403

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
  40. $663 to $2,559/night

    Sea Breeze 702

    Sea Breeze 702

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
  41. $89 to $179/night

    The Cottages at Madeira Beach/Octopus

    The Cottages at Madeira Beach/Octopus

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool Pets OK
  42. $89 to $179/night

    The Cottages at Madeira Beach/Manatee

    The Cottages at Madeira Beach/Manatee

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool Pets OK
  43. $142 to $400/night

    Villa Madeira 208 Walk to John's Pass/Beachfront Condo/Balcony

    Villa Madeira 208 Walk to John's Pass/Beachfront Co...

    2 BedroomsBathroomsSleeps 6
    28 nights minstay
    Pool
  44. $140 to $227/night

    Madeira Bay Resort 512

    Madeira Bay Resort 512

    1 BedroomBathroomsSleeps 3
    7 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  45. $132 to $400/night

    Villa Madeira 502 Bright/Updated/BeachFRONT/Wood and tile floors

    Villa Madeira 502 Bright/Updated/BeachFRONT/Wood and til...

    3 BedroomsBathroomsSleeps 6
    7 nights minstay
    Pool
  46. $142 to $424/night

    Trillium 2C Beach Front Condo with Private Balcony/Pool!

    Trillium 2C Beach Front Condo with Private Balcony/Pool!...

    2 BedroomsBathroomsSleeps 6
    7 nights minstay
    Pool
  47. $142 to $424/night

    Trillium 5C Beach Front/Private Balcony with Amazing Views/Pool!

    Trillium 5C Beach Front/Private Balcony with Amazing Vie...

    2 BedroomsBathroomsSleeps 6
    7 nights minstay
    Pool
  48. $132 to $395/night

    Trillium 1B Beach Views from ALL rooms/Very unique/Top location!

    Trillium 1B Beach Views from ALL rooms/Very unique/Top l...

    2 BedroomsBathroomsSleeps 6
    7 nights minstay
    Pool
  49. $142 to $424/night

    Trillium 1A South Corner/Amazing Remodel/Stunning View!

    Trillium 1A South Corner/Amazing Remodel/Stunning View!

    2 BedroomsBathroomsSleeps 6
    7 nights minstay
    Pool
  50. $128 to $370/night

    Arie Dam 202 Amazing Sunsets/Beach Front/Walk to John's Pass

    Arie Dam 202 Amazing Sunsets/Beach Front/Walk to John�...

    2 BedroomsBathroomsSleeps 6
    7 nights minstay
    Pool Hot Tub
  51. $142 to $424/night

    Trillium 2A Desired South Corner/Large Balcony/Beach Views!

    Trillium 2A Desired South Corner/Large Balcony/Beach Vie...

    2 BedroomsBathroomsSleeps 6
    7 nights minstay
    Pool
  52. $102 to $296/night

    Madeira Norte 304 WALK to John's Pass / Beach Access!!

    Madeira Norte 304 WALK to John's Pass / Beach Acces...

    2 BedroomsBathroomsSleeps 5
    7 nights minstay
    Pool
  53. $132 to $400/night

    Villa Madeira 206 Beach Front/Pool/Balcony/Great updates!

    Villa Madeira 206 Beach Front/Pool/Balcony/Great updates...

    3 BedroomsBathroomsSleeps 6
    7 nights minstay
    Pool
  54. $142 to $429/night

    Villa Madeira 506 Amazing updates/Walk everywhere/Large balcony!

    Villa Madeira 506 Amazing updates/Walk everywhere/Large ...

    2 BedroomsBathroomsSleeps 6
    7 nights minstay
    Pool
  55. $142 to $429/night

    Villa Madeira 404 Beautiful updates/Amazing decor/Beach FRONT!

    Villa Madeira 404 Beautiful updates/Amazing decor/Beach ...

    3 BedroomsBathroomsSleeps 6
    7 nights minstay
    Pool
  56. $132 to $400/night

    Villa Madeira 410 Corner Condo/Amazing Beach View/Large Balcony!

    Villa Madeira 410 Corner Condo/Amazing Beach View/Large ...

    2 BedroomsBathroomsSleeps 6
    7 nights minstay
    Pool
  57. $142 to $429/night

    Villa Madeira 307 Amazing Updates/Pool/Walk to everything!

    Villa Madeira 307 Amazing Updates/Pool/Walk to everythin...

    2 BedroomsBathroomsSleeps 6
    7 nights minstay
    Pool
  58. $142 to $424/night

    Trillium 2B Beach View from ALL rooms/Very unique/Top location!

    Trillium 2B Beach View from ALL rooms/Very unique/Top lo...

    2 BedroomsBathroomsSleeps 6
    7 nights minstay
    Pool
  59. $139 to $251/night

    The Cottages at Madeira Beach/Dolphin

    The Cottages at Madeira Beach/Dolphin

    2 Bedrooms BathroomSleeps 6
    3 nights minstay
    Pool Pets OK
  60. $142 to $400/night

    Arie Dam 304 Beachfront with AMAZING views/Near John's Pass!

    Arie Dam 304 Beachfront with AMAZING views/Near John...

    2 BedroomsBathroomsSleeps 6
    7 nights minstay
    Pool Hot Tub
  61. $348 to $1,545/night

    Madeira Beach Yacht Club 250G

    Madeira Beach Yacht Club 250G

    2 Bedrooms BathroomSleeps 6
    2 nights minstay