Vacation Rentals & Condos in Madeira Beach

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1,325 condos

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Cottage By The Water With Boat Dock

Tarpon Springs cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3

“Awesome-perfect in every way” We cannot say enough possitive things about this home and the hosts. We have come to Tarpon for 30 years but this is the first time we ve used flipkey and we will only use flipkey from now on. From the welcoming hug to the perfect ammenities throughout, you could not beat this offering. Location is beautiful and perfect to access anything. The hosts were so nice and they had paid attention to so many details, we were overwhelmed. They had lots of suggestions and a great notebook filled with menus and things to do. Plus hints on specials, fishing and the area. As we ended our trip they even greeted us with a weather report--there was a storm headed our way. Thank you both for making sure this was the best time we ve ever had in this, our favorite, Florida location.

Responds fast! avg. 45 minutes

Match: Golf course on site or within 15 min walk Car not required

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Price per night from

$138

Responds fast! avg. 3 hours 8 minutes

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Price per night from

$287

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Price per night from

$171

beautiful condo with magnificent views of mandalay

Clearwater apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$153

Siesta Key Beach : 2 Bedroom, 3 Beds, 3 Bathroom Duplex & Heated Pool

Siesta Key apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$182

Luxurious Penthouse

Vista Cay condo

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

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Price per night from

$430

Book Today -Enjoy Perfect Weather

The Villages house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$148

Responds fast! avg. 2 hours 42 minutes

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Price per night from

$123

Luxury Condo, High Floor, Euro Design

Miami apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 2 hours 42 minutes

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Price per night from

$123

Luxurious Resort Condos minutes from Disney World with full access to all

Celebration condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 3 hours 8 minutes

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Price per night from

$103

Spacious modern pool home, Family & Golf trips - 4727

Hernando house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$315

Responds fast! avg. 2 hours 42 minutes

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Price per night from

$142

Naples 7min. to the beach - Play golf, tennis and pickle-ball 2 - WIFI

Naples apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Really nice, everything is new and immaculate.” The condo is perfect. It is immaculate, comfortable and pleasantly decorated. The owner made sure we had everything we needed, (well stocked kitchen, plenty of towels, laundry detergent etc.), for a wonderful vacation. The views from the balcony are beautiful and peaceful. The pool is just a few steps away from the condo where met very friendly residents.

Responds fast! avg. 1 hour 14 minutes

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Price per night from

$172

Spacious home with private pool & Jacuzzi

Hernando house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

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Price per night from

$315

Beautiful & Sunny Pool Home with Golf View

Hernando house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$275

Gorgeous Vacation Home Ciska

Hernando house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$281

Stunning & Serene +++ Minutes from Anna Maria Island, IMG Academy and more!

Bradenton apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 9 minutes

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Price per night from

$114

Family villa Bettina - recently remodeled

Hernando house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$224

Disney Dreams Luxury Home Private Water Park

Reunion villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

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Price per night from

$438

Cozy & Bright+++Minutes to Anna Maria Island, IMG Academy and more

Bradenton apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 9 minutes

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Price per night from

$117

Responds fast! avg. 3 hours 8 minutes

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Price per night from

$149

River Island - North - East - West Villages at Orange Lake

Kissimmee villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$245

Historic Pass-A-Grille, Literally Seconds to Beach

St. Pete Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

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Price per night from

$298

International Drive Luxury, LOCATION, LOCATION, LOCATION

Orlando condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$172

Sunny Sandy Escape! Steps 2 Famous Beach w/2 Bikes

St. Pete Beach cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 9 minutes

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Price per night from

$328

Island Beach cottage rental w/king+2bikes+smartTV

St. Pete Beach house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 9 minutes

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Price per night from

$224

Spacious, Serene, Private Studio Suite with Pool

Fort Pierce studio

  • Studio
  • 1 bathroom
  • sleeps 2

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Price per night from

$127

Close to all with a King-bed! Bikes included

St. Petersburg house

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Responds fast! avg. 1 hour 9 minutes

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Price per night from

$79

SPACIOUS 8 BEDROOM VILLA IN A GOLF COMMUNITY

ChampionsGate house

  • 9 bedrooms
  • 5 bathrooms
  • sleeps 21

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Price per night from

$361

Westgate vacation villa

Kissimmee villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$408

Tropical Escape Sarasota - Discover Real Florida Up-Close!

Lockwood Ridge house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 12

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Price per night from

$149

Tiny Home/Simple living+patio+BBQ+2bikes+Parking

St. Petersburg house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 1 hour 9 minutes

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Price per night from

$63

2 room PgaVillageResort by AmericanVacationLiving

Port Saint Lucie condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$455

7 Room PgaVillageResort by AmericanVacationLiving

Port Saint Lucie condo

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$539

Florida Beachfront Escape - Steps to Pool and Private Beach

Jensen Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Golf course on site or within 15 min walk Car not required

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Price per night from

$144

Weekly 2 bedroom Apartment for 8 guest all amenities included

Orlando apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 17 minutes

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Price per night from

$121

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Price per night from

$115

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DISNEY WORLD SWEETWATER CLUB CONDOMINIUM

Kissimmee condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Great vacation stay!!!!” EVERYTHING was above what I expected! The condo was very nice and comfortable I couldn't have stayed in a better area I give this vacation home a 10 all around! I will stay here again and again if/when I visit Florida again!!! THANKS MANNY

1 of 2 match: Car not required, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$75

Viewing 38 of 1,325
rentals in Madeira Beach

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