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  • The Penthouse at Madeira Beach 5 bedroom (sleeps 14) gorgeous Gulf views
    From $875 per night (USD)

    VRBO

    The Penthouse at Madeira Beach 5 bedroom (sleeps 14) gorgeous Gulf views

    Bedrooms:
    4
    Bathrooms:
    6
    Sleeps:
    12

    Come and enjoy spectacular views from this waterfront 5-bedroom penthouse situated directly on Madeira Beach. Situated i ...

    From $875 per night (USD)

    VRBO

    Details
  • ☀️Happy Home-Across Street from Beach-3BR-Madeira Beach-Great Location☀️
    Click For Pricing

    Expedia

    ☀️Happy Home-Across Street from Beach-3BR-Madeira Beach-Great Location☀️

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Top reasons to Book: * Steps away from restaurants, live entertainment, and the sugary white sands of Madeira Beach * ...

    Click For Pricing

    Expedia

    Details
  • Top Floor Overlooking the Marina. Close to Johns Pass. Spacious with Two Private Balconies!
    From $327 per night (USD)

    VRBO

    Top Floor Overlooking the Marina. Close to Johns Pass. Spacious with Two Private Balconies!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    With the Beach Access directly across the street and located just a block away from the shops, restaurants and vibrant a ...

    From $327 per night (USD)

    VRBO

    Details
  • The New Madeira Bay Resort I 1405 Marina View
    From $312 per night (USD)

    Expedia

    The New Madeira Bay Resort I 1405 Marina View

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    The brand new Madeira Bay Resort I #1405 is a two bedroom, two bathroom condo with a private balcony. King size bed in t ...

    From $312 per night (USD)

    Expedia

    Details
  • Beautiful spacious condo on located right on  Madeira Beach.
    Click For Pricing

    VRBO

    Beautiful spacious condo on located right on Madeira Beach.

    Bedrooms:
    4
    Bathrooms:
    3
    Sleeps:
    6

    Spacious condo can comfortably accommodate up to 4 adults and 2 children. It includes a full kitchen and dining area. 2 ...

    Click For Pricing

    VRBO

    Details
  • Madeira Bay Resort 209  Marina View w\/Beach Access
    From $256 per night (USD)

    Expedia

    Madeira Bay Resort 209 Marina View w\/Beach Access

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    5

    Madeira Bay Resort #209 is a two bedroom, one bathroom condo with a private balcony. Views of marina, sunrises, waterway ...

    From $256 per night (USD)

    Expedia

    Details
  • Madeira Bay Resort 316 Beach Access
    From $269 per night (USD)

    VRBO

    Madeira Bay Resort 316 Beach Access

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Madeira Bay Resort #316 is a two bedroom, two bathroom condo with a private balcony. The master bedroom has a king size ...

    From $269 per night (USD)

    VRBO

    Details
  • Stunning 3 bed\/2 bath beachfront condo in Madeira Beach, FL
    From $487 per night (USD)

    Expedia

    Stunning 3 bed\/2 bath beachfront condo in Madeira Beach, FL

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    The beachfront condo directly overlooks the glistening Gulf of Mexico and sparkling white, sandy beach of Madeira Beach, ...

    From $487 per night (USD)

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    Details
  • Sea Breeze 707 Gulf Front Balcony with Heated Pool
    From $377 per night (USD)

    VRBO

    Sea Breeze 707 Gulf Front Balcony with Heated Pool

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Hurricane Update: This unit was not damaged in the hurricanes, and we'd love to accommodate you! The building is current ...

    From $377 per night (USD)

    VRBO

    Details
  • Las Brisas 407 3BR 2BA Gulf Front
    From $423 per night (USD)

    Expedia

    Las Brisas 407 3BR 2BA Gulf Front

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    Hurricane Update: This unit was not damaged in the hurricanes, and we'd love to accommodate you! The building is current ...

    From $423 per night (USD)

    Expedia

    Details
  • Madeira Bay Resort 414 Beach Access
    From $276 per night (USD)

    VRBO

    Madeira Bay Resort 414 Beach Access

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Madeira Bay Resort #414 is a two bedroom, two bathroom condo with a private balcony. The master bedroom has a king size ...

    From $276 per night (USD)

    VRBO

    Details
  • Sea Breeze 505 Gulf Front Balcony with Heated Pool
    From $292 per night (USD)

    Expedia

    Sea Breeze 505 Gulf Front Balcony with Heated Pool

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Hurricane Update: This unit was not damaged in the hurricanes, and we'd love to accommodate you! The building is current ...

    From $292 per night (USD)

    Expedia

    Details
  • Madeira Bay Resort 313 Marina View w\/Beach Access
    From $282 per night (USD)

    VRBO

    Madeira Bay Resort 313 Marina View w\/Beach Access

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Madeira Bay Resort #313 is a two bedroom, two bathroom condo with a private balcony. View of marina, sunrises, waterway ...

    From $282 per night (USD)

    VRBO

    Details
  • Villa Madeira 601 Gulf Front Corner Unit Large Balcony
    From $408 per night (USD)

    Expedia

    Villa Madeira 601 Gulf Front Corner Unit Large Balcony

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Hurricane Update: This unit was not damaged in the hurricanes and we'd love to accommodate you! The elevator is operatio ...

    From $408 per night (USD)

    Expedia

    Details
  • Madeira Bay Resort 506 Gulf View w\/Beach Access
    From $285 per night (USD)

    VRBO

    Madeira Bay Resort 506 Gulf View w\/Beach Access

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Madeira Bay Resort #506 is a two bedroom, two bathroom condo with two private balconies. The master bedroom has a king s ...

    From $285 per night (USD)

    VRBO

    Details
  • Villa Madeira 610 Gulf Front Large Balcony
    From $374 per night (USD)

    Expedia

    Villa Madeira 610 Gulf Front Large Balcony

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Hurricane Update: This unit was not damaged in the hurricanes and we'd love to accommodate you! The elevator is operatio ...

    From $374 per night (USD)

    Expedia

    Details
  • Madeira Bay Resort 307 Marina View w\/Beach Access
    From $251 per night (USD)

    VRBO

    Madeira Bay Resort 307 Marina View w\/Beach Access

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Madeira Bay Resort #307 is a two bedroom, one bathroom condo with a private balcony. Views of marina, sunrises, waterway ...

    From $251 per night (USD)

    VRBO

    Details
  • Madeira Bay Resort 416 Beach Access
    From $261 per night (USD)

    Expedia

    Madeira Bay Resort 416 Beach Access

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Madeira Bay Resort #416 is a two bedroom, two bathroom condo with a private balcony. The master bedroom has a king size ...

    From $261 per night (USD)

    Expedia

    Details
  • Madeira Bay Resort 410
    From $257 per night (USD)

    VRBO

    Madeira Bay Resort 410

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Madeira Bay Resort #410 is a two bedroom, one bathroom condo with a private balcony. Views of marina, sunrises, waterway ...

    From $257 per night (USD)

    VRBO

    Details
  • Sea Breeze 508 Gulf Front Balcony with Heated Pool
    From $397 per night (USD)

    Expedia

    Sea Breeze 508 Gulf Front Balcony with Heated Pool

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Hurricane Update: This unit was not damaged in the hurricanes, and we'd love to accommodate you! The building is current ...

    From $397 per night (USD)

    Expedia

    Details
  • Sea Breeze 301 Gulf Front Balcony with Heated Pool
    From $374 per night (USD)

    VRBO

    Sea Breeze 301 Gulf Front Balcony with Heated Pool

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Hurricane Update: This unit was not damaged in the hurricanes, and we'd love to accommodate you! The building is current ...

    From $374 per night (USD)

    VRBO

    Details
  • Madeira Bay Resort 205 Beach Access
    From $237 per night (USD)

    Expedia

    Madeira Bay Resort 205 Beach Access

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Hurricane Update: This condo was not damaged in the hurricanes! We'd love to accommodate you. The heated pool and elevat ...

    From $237 per night (USD)

    Expedia

    Details
  • Madeira Bay Resort 413 Marina View w\/Beach Access
    From $224 per night (USD)

    VRBO

    Madeira Bay Resort 413 Marina View w\/Beach Access

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    4

    Madeira Bay Resort #413 is a two bedroom, two bathroom condo with two private balconies. Views of marina, sunrises, wate ...

    From $224 per night (USD)

    VRBO

    Details
  • Sea Breeze 703 Gulf Front Balcony with Heated Pool
    From $386 per night (USD)

    Expedia

    Sea Breeze 703 Gulf Front Balcony with Heated Pool

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Hurricane Update: This unit was not damaged in the hurricanes, and we'd love to accommodate you! The building is current ...

    From $386 per night (USD)

    Expedia

    Details
  • Madeira Bay Resort 301 Marina View w\/Beach Access
    From $242 per night (USD)

    VRBO

    Madeira Bay Resort 301 Marina View w\/Beach Access

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Madeira Bay Resort #301 is a one bedroom, one bathroom condo with a private balcony. Views of marina, sunrises, waterway ...

    From $242 per night (USD)

    VRBO

    Details
  • Madeira Bay Resort 207 Marina View w\/Beach Access
    From $259 per night (USD)

    Expedia

    Madeira Bay Resort 207 Marina View w\/Beach Access

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    4

    Madeira Bay Resort #207 is a two bedroom, one bathroom condo with a private balcony. View of marina, sunrises, waterway ...

    From $259 per night (USD)

    Expedia

    Details
  • Madeira Bay Resort 610 Gulf View w\/Beach Access
    From $377 per night (USD)

    VRBO

    Madeira Bay Resort 610 Gulf View w\/Beach Access

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Madeira Bay Resort #610 is a two bedroom, two bathroom condo with a private balcony. The master bedroom has a king size ...

    From $377 per night (USD)

    VRBO

    Details
  • Sea Breeze 402 Gulf Front Balcony with Heated Pool
    From $336 per night (USD)

    Expedia

    Sea Breeze 402 Gulf Front Balcony with Heated Pool

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Hurricane Update: This unit was not damaged in the hurricanes, and we'd love to accommodate you! The building is current ...

    From $336 per night (USD)

    Expedia

    Details
  • Sea Breeze 406 Gulf Front Balcony with Heated Pool
    From $385 per night (USD)

    VRBO

    Sea Breeze 406 Gulf Front Balcony with Heated Pool

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Hurricane Update: This unit was not damaged in the hurricanes, and we'd love to accommodate you! The building is current ...

    From $385 per night (USD)

    VRBO

    Details
  • Las Brisas 207 Gulf Front Large Balcony Sleeps 9
    From $426 per night (USD)

    Expedia

    Las Brisas 207 Gulf Front Large Balcony Sleeps 9

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    9

    Hurricane Update: This unit was not damaged in the hurricanes, and we'd love to accommodate you! The building is current ...

    From $426 per night (USD)

    Expedia

    Details
  • Sea Breeze 203 Gulf Front Balcony with Heated Pool
    From $327 per night (USD)

    VRBO

    Sea Breeze 203 Gulf Front Balcony with Heated Pool

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Hurricane Update: This unit was not damaged in the hurricanes, and we'd love to accommodate you! The building is current ...

    From $327 per night (USD)

    VRBO

    Details
  • Madeira Bay Resort 510 Gulf View w\/Beach Access
    From $284 per night (USD)

    Expedia

    Madeira Bay Resort 510 Gulf View w\/Beach Access

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Madeira Bay Resort #510 is a two bedroom, two bathroom condo with a private balcony. The master and second bedroom both ...

    From $284 per night (USD)

    Expedia

    Details
  • Madeira Bay Resort 206 Marina View w\/Beach Access
    From $256 per night (USD)

    VRBO

    Madeira Bay Resort 206 Marina View w\/Beach Access

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Madeira Bay Resort #206 is a two bedroom, one bathroom condo with private balcony. The master bedroom has a king size be ...

    From $256 per night (USD)

    VRBO

    Details
  • Villa Madeira 606 Gulf Front Large Balcony
    From $346 per night (USD)

    Expedia

    Villa Madeira 606 Gulf Front Large Balcony

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    5

    Hurricane Update: This unit was not damaged in the hurricanes and we'd love to accommodate you! The elevator is operatio ...

    From $346 per night (USD)

    Expedia

    Details
  • Madeira Bay Resort 611 ~ TOP FLOOR GREAT VIEWS OF THE BEACH AND CITY, CORNER UNIT FOR GREAT PRIVACY
    From $279 per night (USD)

    VRBO

    Madeira Bay Resort 611 ~ TOP FLOOR GREAT VIEWS OF THE BEACH AND CITY, CORNER UNIT FOR GREAT PRIVACY

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Madeira Bay Resort #611 is a TOP FLOOR CORNER UNIT, offering stunning views of both the beach and city. Its corner locat ...

    From $279 per night (USD)

    VRBO

    Details
  • Madeira Bay Resort 210 Marina View w\/Beach Access
    From $273 per night (USD)

    Expedia

    Madeira Bay Resort 210 Marina View w\/Beach Access

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Madeira Bay Resort #210 is a two bedroom, two bathroom condo with a private balcony. Corner balcony with access from liv ...

    From $273 per night (USD)

    Expedia

    Details
  • Madeira Bay Resort 602 Gulf View w\/Beach Access
    From $284 per night (USD)

    VRBO

    Madeira Bay Resort 602 Gulf View w\/Beach Access

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Madeira Bay Resort #602 is a two bedroom, two bathroom condo with two private balconies. The master bedroom has a king s ...

    From $284 per night (USD)

    VRBO

    Details
  • Madeira Bay Resort 402 Beach Access
    From $241 per night (USD)

    Expedia

    Madeira Bay Resort 402 Beach Access

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Madeira Bay Resort #402 is a one bedroom, one bathroom condo with a private balcony. This spacious floorplan is handicap ...

    From $241 per night (USD)

    Expedia

    Details
  • Madeira Bay Resort 412 Marina View w\/Beach Access
    From $245 per night (USD)

    VRBO

    Madeira Bay Resort 412 Marina View w\/Beach Access

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Madeira Bay Resort #412 is a two bedroom, one bathroom condo with a private balcony. Views of marina, sunrises, waterway ...

    From $245 per night (USD)

    VRBO

    Details
  • Madeira Bay Resort 208 Beach Access
    From $253 per night (USD)

    Expedia

    Madeira Bay Resort 208 Beach Access

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Madeira Bay Resort #208 is a two bedroom, two bathroom condo and private balcony. The master bedroom has a queen size be ...

    From $253 per night (USD)

    Expedia

    Details
  • Sea Breeze 305 Gulf Front Balcony with Heated Pool
    From $295 per night (USD)

    VRBO

    Sea Breeze 305 Gulf Front Balcony with Heated Pool

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Hurricane Update: This unit was not damaged in the hurricanes, and we'd love to accommodate you! The building is current ...

    From $295 per night (USD)

    VRBO

    Details
  • Madeira Bay Resort 504 Marina View w\/Beach Access
    From $357 per night (USD)

    Expedia

    Madeira Bay Resort 504 Marina View w\/Beach Access

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Madeira Bay Resort #504 is a three bedroom, two bathroom condo with two private balconies. Views of marina, sunrises, wa ...

    From $357 per night (USD)

    Expedia

    Details
  • Madeira Bay Resort 404 Beach Access
    From $271 per night (USD)

    VRBO

    Madeira Bay Resort 404 Beach Access

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    4

    Enjoy our updated Madeira Beach condo with a great location to beach and John's Pass! Madeira Bay Resort #404 is a two b ...

    From $271 per night (USD)

    VRBO

    Details
  • Madeira Bay Resort 608 Marina View w\/Beach Access
    From $293 per night (USD)

    Expedia

    Madeira Bay Resort 608 Marina View w\/Beach Access

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Madeira Bay Resort #608 is a two bedroom, two bathroom condo with two private balconies. Spacious corner unit with views ...

    From $293 per night (USD)

    Expedia

    Details
  • Villa Madeira 304 Gulf Front Large Balcony Sleeps 8
    From $504 per night (USD)

    VRBO

    Villa Madeira 304 Gulf Front Large Balcony Sleeps 8

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Hurricane Update: This unit was not damaged in the hurricanes and we'd love to accommodate you! The elevator is operatio ...

    From $504 per night (USD)

    VRBO

    Details
  • Chambre #301 Beach Front Balcony and Pool
    From $263 per night (USD)

    Expedia

    Chambre #301 Beach Front Balcony and Pool

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Hurricane Update: This unit was not damaged in the hurricanes, and we'd love to accommodate you! The pool is currently c ...

    From $263 per night (USD)

    Expedia

    Details
  • Madeira Bay Resort 408 Marina View w\/Beach Access
    From $238 per night (USD)

    VRBO

    Madeira Bay Resort 408 Marina View w\/Beach Access

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Madeira Bay Resort #408 is a two bedroom, one bathroom condo with a private balcony. Views of marina, sunrises, waterway ...

    From $238 per night (USD)

    VRBO

    Details
  • Madeira Bay Resort 314 Beach Access
    From $263 per night (USD)

    Expedia

    Madeira Bay Resort 314 Beach Access

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Hurricane Update: This condo was not damaged in the hurricanes! We'd love to accommodate you. The heated pool and elevat ...

    From $263 per night (USD)

    Expedia

    Details
  • Madeira Bay Resort 415 Beach Access
    From $272 per night (USD)

    VRBO

    Madeira Bay Resort 415 Beach Access

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Madeira Bay Resort #415 is a two bedroom, two bathroom condo with a private balcony. The master bedroom has a king size ...

    From $272 per night (USD)

    VRBO

    Details
  • Madeira Bay Resort 501 Gulf View w\/Beach Access
    From $250 per night (USD)

    Expedia

    Madeira Bay Resort 501 Gulf View w\/Beach Access

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Madeira Bay Resort #501 is a one bedroom, one bathroom condo with a private balcony. This spacious floorplan is handicap ...

    From $250 per night (USD)

    Expedia

    Details
  • Sea Breeze 403 Gulf Front Balcony with Heated Pool
    From $383 per night (USD)

    VRBO

    Sea Breeze 403 Gulf Front Balcony with Heated Pool

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Hurricane Update: This unit was not damaged in the hurricanes, and we'd love to accommodate you! The building is current ...

    From $383 per night (USD)

    VRBO

    Details
  • Madeira Bay Resort 505 Marina View w\/Beach Access
    From $346 per night (USD)

    Expedia

    Madeira Bay Resort 505 Marina View w\/Beach Access

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Madeira Bay Resort #505 is a three bedroom, two bathroom condo with two private balconies. Views of marina, sunrises, wa ...

    From $346 per night (USD)

    Expedia

    Details
  • Sea Breeze 206 Gulf Front Balcony with Heated Pool
    From $343 per night (USD)

    VRBO

    Sea Breeze 206 Gulf Front Balcony with Heated Pool

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Hurricane Update: This unit was not damaged in the hurricanes, and we'd love to accommodate you! The building is current ...

    From $343 per night (USD)

    VRBO

    Details
  • Madeira Bay Resort 502 Marina View w\/Beach Access
    From $278 per night (USD)

    Expedia

    Madeira Bay Resort 502 Marina View w\/Beach Access

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Madeira Bay Resort #502 is a two bedroom, two bathroom condo with a private balcony. Views of marina, sunrises, waterway ...

    From $278 per night (USD)

    Expedia

    Details
  • Madeira Bay Resort 604 Marina View w\/Beach Access
    From $363 per night (USD)

    VRBO

    Madeira Bay Resort 604 Marina View w\/Beach Access

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Madeira Bay Resort #604 is a three bedroom, two bathroom condo with two private balconies. Views of marina, sunrises, wa ...

    From $363 per night (USD)

    VRBO

    Details
  • Madeira Bay Resort 507 Marina View w\/Beach Access
    From $285 per night (USD)

    Expedia

    Madeira Bay Resort 507 Marina View w\/Beach Access

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Madeira Bay Resort #507 is a three bedroom, two bathroom condo with two private balconies. Views of marina, sunrises, wa ...

    From $285 per night (USD)

    Expedia

    Details
  • Large Family Condo with Outstanding View of the Beach
    From $437 per night (USD)

    VRBO

    Large Family Condo with Outstanding View of the Beach

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Hurricane Update: This unit was not damaged in the hurricanes, and we'd love to accommodate you! The building is current ...

    From $437 per night (USD)

    VRBO

    Details
  • Luxury Beachfront Corner Condo 3 BR 2 BA with a Pool - It’s 5 o’clock somewhere!
    From $405 per night (USD)

    Expedia

    Luxury Beachfront Corner Condo 3 BR 2 BA with a Pool - It’s 5 o’clock somewhere!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    6

    This newly remodeled Villa Madeira condo is a large north corner unit that has a screened in balcony facing the white sa ...

    From $405 per night (USD)

    Expedia

    Details
  • Sand Beach lifestyle and boardwalk vacation house
    From $892 per night (USD)

    VRBO

    Sand Beach lifestyle and boardwalk vacation house

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Welcome "Madeira Beach Area" - just steps from the beautiful white-sanded Beach and famous John's Pass Boardwalk! Great ...

    From $892 per night (USD)

    VRBO

    Details
  • Ocean Sands 1107: Amazing Gulf Front Retreat
    From $332 per night (USD)

    Expedia

    Ocean Sands 1107: Amazing Gulf Front Retreat

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Amazing 11th floor 2 bedroom 2, bath Gulf Front condo with upgrades galore and panoramic views from every window! There' ...

    From $332 per night (USD)

    Expedia

    Details
  • Stunning Top Floor Views and an Interior to Match. On the Beach. Close to Johns Pass Village.
    From $382 per night (USD)

    VRBO

    Stunning Top Floor Views and an Interior to Match. On the Beach. Close to Johns Pass Village.

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    This is the ultimate beachfront condo, complete with simply amazing views from the top floor of this immaculately mainta ...

    From $382 per night (USD)

    VRBO

    Details
  • Surf Song 236 Beach Vibes
    From $217 per night (USD)

    Expedia

    Surf Song 236 Beach Vibes

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    This one bedroom, one bathroom condo offers all the convenience of being beach side and even has a partial view of the G ...

    From $217 per night (USD)

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  • Surf Song 237 Florida Charm on Madeira Beach
    From $214 per night (USD)

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    Surf Song 237 Florida Charm on Madeira Beach

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Surf Song Resort #237 12960 Gulf Blvd, Madeira Beach, FL 33708 TRS office located just a block away: 13030 Gulf Blvd, Ma ...

    From $214 per night (USD)

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  • Madeira Beach Ground Floor One Bedroom Poolside
    From $205 per night (USD)

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    Madeira Beach Ground Floor One Bedroom Poolside

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Tropic Breeze 7 is a one-bedroom, one-bath condo with a pool view on the first floor. This condo has two Double beds, an ...

    From $205 per night (USD)

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  • Direct Beachfront Unit - Shores of Madeira #505
    From $162 per night (USD)

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    Direct Beachfront Unit - Shores of Madeira #505

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Shores of Madeira #505 - Please note that due to our hurricane season, there is no pool or patio at this time at The Sho ...

    From $162 per night (USD)

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  • Villa Madeira 202 Beautiful updates, breathtaking view, walk to John's Pass!
    From $285 per night (USD)

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    Villa Madeira 202 Beautiful updates, breathtaking view, walk to John's Pass!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    **Please note that due to damage from Hurricane Helene, this property temporarily has no access to the pool. Parking is ...

    From $285 per night (USD)

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  • 5⭐️  Coastal Luxury: 3BR, 3BA Condo with Heated Pool – Steps from the Beach
    From $548 per night (USD)

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    5⭐️ Coastal Luxury: 3BR, 3BA Condo with Heated Pool – Steps from the Beach

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    10

    Experience luxury & comfort in this stunning newly built 3BR/3BA condo. Perfectly located just a short walk from the be ...

    From $548 per night (USD)

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  • 2nd floor view of the gulf in Madeira Beach FL
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    2nd floor view of the gulf in Madeira Beach FL

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    This is the most adorable little place right on the beach and right across the street from John's Pass! If you are not f ...

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    Details
  • Madeira Bay Resort 606 Marina View w\/Beach Access
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    Madeira Bay Resort 606 Marina View w\/Beach Access

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Madeira Bay Resort #606 is newly remodeled 1,200 square foot Three-bedroom two-bathroom condo with a private double balc ...

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  • Coconut Paradise- Waterfront
    From $380 per night (USD)

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    Coconut Paradise- Waterfront

    Bedrooms:
    1
    Bathrooms:
    4
    Sleeps:
    8

    Top reasons to Book: • Direct waterfront views from your private dock! • The location- Walking distance to the sugary ...

    From $380 per night (USD)

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  • Las Brisas 203 Gulf Front Large Balcony Sleeps 8
    From $484 per night (USD)

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    Las Brisas 203 Gulf Front Large Balcony Sleeps 8

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Hurricane Update: This unit was not damaged in the hurricanes, and we'd love to accommodate you! The building is current ...

    From $484 per night (USD)

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  • Sunny condo with heated pool, two blocks from the beach - vacation ready
    From $439 per night (USD)

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    Sunny condo with heated pool, two blocks from the beach - vacation ready

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    7

    Mad Beach Hideaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...

    From $439 per night (USD)

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  • Villa Madeira 406 Gorgeous, Beach Front, Top Location!
    From $292 per night (USD)

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    Villa Madeira 406 Gorgeous, Beach Front, Top Location!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    5

    **Please note that due to damage from Hurricane Helene, this property temporarily has no access to the pool. Parking is ...

    From $292 per night (USD)

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  • Gulf Gardens Resort The Manatee.  No pool currently.
    From $156 per night (USD)

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    Gulf Gardens Resort The Manatee. No pool currently.

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    Quiet, clean 1 bedroom unit with the best view of the water in all of Gulf Gardens. Enjoy peek a boo views of the Gulf ...

    From $156 per night (USD)

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  • BEST BEACH DEALS! Beautiful Beach Front Condo!
    From $289 per night (USD)

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    BEST BEACH DEALS! Beautiful Beach Front Condo!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    This Kima unit has a beautiful sought after 2 bedroom 2 bathroom gulf front condo. Enjoy the gulf view and flat screen t ...

    From $289 per night (USD)

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  • Johns Pass Studio # 1 Fisherman's Cove and Cottages
    From $336 per night (USD)

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    Johns Pass Studio # 1 Fisherman's Cove and Cottages

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Only 150 steps into Johns Pass. Studio 1 - Newley Renovated Studio. No expense spared. Quality Linens, Smart Television, ...

    From $336 per night (USD)

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  • Luxury Beachhouse W\/ Direct Ocean Views Sleeps 11
    From $833 per night (USD)

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    Luxury Beachhouse W\/ Direct Ocean Views Sleeps 11

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    12

    Welcome to your perfect beachfront escape on Madeira Beach, Florida! Discover the allure of our modern 3-bedroom Beachho ...

    From $833 per night (USD)

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  • AWESOME Marina View\/BALCONY - 4th Floor @ John's Pass
    From $315 per night (USD)

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    AWESOME Marina View\/BALCONY - 4th Floor @ John's Pass

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Entire condo BRAND NEW Marina-front condo with balcony 2 bedroom 2 bath Master: King bed Bedroom: "Full-size" bunk beds ...

    From $315 per night (USD)

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  • Beach Front - John's Pass - Beach Place #210
    From $440 per night (USD)

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    Beach Front - John's Pass - Beach Place #210

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Beach Place #210 - This large 3 bedroom, 2 bath condo is right on the beach at John's Pass Village. This roomy vacation ...

    From $440 per night (USD)

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  • BEACHFRONT- 3BED\/3BATH TOP FLOOR
    From $661 per night (USD)

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    BEACHFRONT- 3BED\/3BATH TOP FLOOR

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    9

    WE ARE BACK!!!!!!!! We are so happy to host you again!!!! If you enjoy the beach and beautiful views this is your opport ...

    From $661 per night (USD)

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  • Madeira Bay Resort 309 Beach Access
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    Madeira Bay Resort 309 Beach Access

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Hurricane Update: This condo was not damaged in the hurricanes! We'd love to accommodate you. The heated pool and elevat ...

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  • BEST BEACH DEALS! Listen To The Waves 75ft to Ocean 55\TV Heated Pool Wifi
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    BEST BEACH DEALS! Listen To The Waves 75ft to Ocean 55\"TV Heated Pool Wifi

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    Kima Condominium is located at 14300 Gulf Blvd. at Madeira Beach, Florida, just 40 minutes from Tampa International Airp ...

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  • BEST BEACH DEALS! Gulf Front 75ft To Water And Waves! Heated Pool WIFI
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    BEST BEACH DEALS! Gulf Front 75ft To Water And Waves! Heated Pool WIFI

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    This condo has a "WOW" view factor! Enjoy this beautiful 2 bedroom 2 bathroom gulf/beach front condo on Madeira Beach Fl ...

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  • Las Brisas, Breathtaking view! Oceanfront, 3 Bedroom, 2 Bath, Sleeps 9
    From $479 per night (USD)

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    Las Brisas, Breathtaking view! Oceanfront, 3 Bedroom, 2 Bath, Sleeps 9

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    9

    Our Las Brisas three bedroom/two bath condominium rental is among the larger units available in the Tampa-St. Pete-Clear ...

    From $479 per night (USD)

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  • Quiet, Waterfront Top Floor Unit-Close to Beach & Dining, Private Screened In Balcony, Fishing Docks
    From $214 per night (USD)

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    Quiet, Waterfront Top Floor Unit-Close to Beach & Dining, Private Screened In Balcony, Fishing Docks

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    The Madeira Beach Yacht Club is located on the Bay, in a quiet and peaceful section of Madeira Beach. The gated communi ...

    From $214 per night (USD)

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  • Madeira Bay Resort 311 condo sleeps 7 with All Resort Amenities
    From $251 per night (USD)

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    Madeira Bay Resort 311 condo sleeps 7 with All Resort Amenities

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    7

    Unit 311 is a newly renovated condo with relaxing waterway views, high ceilings, and modern finishes and is directly acr ...

    From $251 per night (USD)

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  • Remodeled Top Floor Beachfront Condo
    From $476 per night (USD)

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    Remodeled Top Floor Beachfront Condo

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    If you would like a vacation rental that is in a perfect location, clean, on the beach, with a large balcony to start an ...

    From $476 per night (USD)

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  • Saltwater heated POOL! Walk to the beach! By John’s Pass Village Boardwalk!
    From $681 per night (USD)

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    Saltwater heated POOL! Walk to the beach! By John’s Pass Village Boardwalk!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    9

    Welcome to your own oasis with a private saltwater heated pool on the beautiful island in Madeira Beach! This home is ce ...

    From $681 per night (USD)

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  • OCEANFRONT condo directly overlooking the clear blue water of the Gulf of Mexico
    From $193 per night (USD)

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    OCEANFRONT condo directly overlooking the clear blue water of the Gulf of Mexico

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    A vacation home done right, and located where every need is met... including a WONDERFUL ice cream shop across the stree ...

    From $193 per night (USD)

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  • Heated Pool and Hot-Tub. Next to Johns Pass Village. Stroll over to Beach. Comfortable!
    From $303 per night (USD)

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    Heated Pool and Hot-Tub. Next to Johns Pass Village. Stroll over to Beach. Comfortable!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Welcome to this beautiful two bedroom condo, located just steps away from the beach! Comfortable Sleeping for six -Mas ...

    From $303 per night (USD)

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  • making memories at madeira
    From $541 per night (USD)

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    making memories at madeira

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    13

    Walk to the white sandy shore, beach access is directly across the street. Bring the entire family and friends. Home has ...

    From $541 per night (USD)

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  • Beachfront condo with gorgeous sunset views!
    From $467 per night (USD)

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    Beachfront condo with gorgeous sunset views!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Unparalleled beach and gulf views from your private balcony. Updated granite chef's kitchen with stainless appliances. T ...

    From $467 per night (USD)

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  • The Beach is Calling You! Sleeps 6, Coffee Bar\/Keurig
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    The Beach is Calling You! Sleeps 6, Coffee Bar\/Keurig

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Nestled along the Prestine shores of the Gulf Of Mexico, This centrally located condo in Maderia beach Yacht club offer ...

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  • 2br 2ba condo steps from the beach at the crosswalk monthly rental Feb-April
    From $208 per night (USD)

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    2br 2ba condo steps from the beach at the crosswalk monthly rental Feb-April

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Condo that is truly like being at home. Tastefully decorated with all the amenities you will need. Kitchen full stocked ...

    From $208 per night (USD)

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  • The Waterfront Relax House
    From $829 per night (USD)

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    The Waterfront Relax House

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

    Welcome to our charming property located in the beautiful coastal town of Madeira Beach, Florida. This delightful vacat ...

    From $829 per night (USD)

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  • Serene Shoreline Retreat
    From $348 per night (USD)

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    Serene Shoreline Retreat

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Welcome to your quiet beachfront condominium nestled on the pristine shores of the Gulf of Mexico, in the beautiful Made ...

    From $348 per night (USD)

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  • Madeira Beach Park Shore Suite 3
    From $307 per night (USD)

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    Madeira Beach Park Shore Suite 3

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Forget your worries in this spacious and serene space. This comfortable, convenient and stylish suite makes for the idea ...

    From $307 per night (USD)

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  • Sunset Beach Suites - Suite 5
    From $306 per night (USD)

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    Sunset Beach Suites - Suite 5

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    This cozy corner suite is situated on the ground floor, directly across the street from the scenic Madeira Beach. In jus ...

    From $306 per night (USD)

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  • Madeira Beach Park Shore Suite 1
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    Madeira Beach Park Shore Suite 1

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    The perfect beach getaway. Come and enjoy the tranquility of this suite near the beach. With a large open area that offe ...

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  • Adorable Beach Condo Located In Madeira Beach
    From $192 per night (USD)

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    Adorable Beach Condo Located In Madeira Beach

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Beautiful 1 bedroom condo located in Madeira Beach perfect for 2. Cross at crosswalk to miles of beautiful white sandy b ...

    From $192 per night (USD)

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