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  • Waterfront Treasure Island Florida Beach Condo
    From $206 per night (USD)

    VRBO

    Waterfront Treasure Island Florida Beach Condo

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    This Blind Pass Lagoons condo on Treasure Island is on the third floor with an elevator. It has views of water from almo ...

    From $206 per night (USD)

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    Details
  • Beautiful Gulf Front Condo
    From $314 per night (USD)

    VRBO

    Beautiful Gulf Front Condo

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    This condo is located directly on the shores of the Gulf of Mexico in beautiful Madeira Beach, 1.5 miles north of the fa ...

    From $314 per night (USD)

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    Details
  • Beachfront Treasure Island Condo  Gulf Views  Heated Pool  Sleeps 6
    From $375 per night (USD)

    VRBO

    Beachfront Treasure Island Condo Gulf Views Heated Pool Sleeps 6

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Stunning 5th Floor Gulf-View Condo at Sunset Vistas Beachfront Suites Wake up to breathtaking views of the Gulf of Mexi ...

    From $375 per night (USD)

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  • Fabulous Waterfront  Home. CLEARWATER BEACH. Bayfront. Large private dock
    From $885 per night (USD)

    Expedia

    Fabulous Waterfront Home. CLEARWATER BEACH. Bayfront. Large private dock

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    7

    This home is actually on the island of CLEARWATER BEACH and ON THE WATER with a large private dock. CLEARWATER BEACH ha ...

    From $885 per night (USD)

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    Details
  • Lovely condo steps to beach…wow sunsets..
    From $333 per night (USD)

    VRBO

    Lovely condo steps to beach…wow sunsets..

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Gulf Views! Remodeled 2 bedroom, 2 bath. VERY PRIVATE WITH AN IDEAL LOCATION ON THE GULF SIDE OF GULF BOULEVARD WITH BE ...

    From $333 per night (USD)

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    Details
  • Tierra Palms - Pool View, Garage, Nearby Beaches
    From $217 per night (USD)

    VRBO

    Tierra Palms - Pool View, Garage, Nearby Beaches

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Beautifully decorated 2-bedroom condo in idyllic Tierra Verde. Experience life on "The Island" and live like a local, ju ...

    From $217 per night (USD)

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    Details
  • SPECTACULAR BEACH CONDO. 2/2 PLUS DEN. HEATED POOL - EMAIL US.
    From $347 per night (USD)

    VRBO

    SPECTACULAR BEACH CONDO. 2/2 PLUS DEN. HEATED POOL - EMAIL US.

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    SPECTACULAR, Beach condo. 2 BEDROOM, 2 BATH, PLUS DEN. Spacious 1,400 sq. feet, offers comfort and luxury in one of the ...

    From $347 per night (USD)

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    Details
  • Beach Front Complex - Madeira Norte #106
    From $170 per night (USD)

    Expedia

    Beach Front Complex - Madeira Norte #106

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Madeira Norte 106 - Please note that the pool is scheduled to undergo repairs beginning in May 2026 and will be unavaila ...

    From $170 per night (USD)

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    Details
  • Cozy Affordable Beach Condo
    From $252 per night (USD)

    VRBO

    Cozy Affordable Beach Condo

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    There is a big discount when you stay by the week vs nightly rates. Our goal is to provide comforts of home in a peacef ...

    From $252 per night (USD)

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    Details
  • Scenic Beach View - Balcony - Madeira Norte #213
    From $201 per night (USD)

    Expedia

    Scenic Beach View - Balcony - Madeira Norte #213

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Madeira Norte 213 - Please note that the pool is scheduled to undergo repairs beginning in May 2026 and will be unavaila ...

    From $201 per night (USD)

    Expedia

    Details
  • Large 1B1B Unit - Pool Side - Surf Song #229
    From $222 per night (USD)

    VRBO

    Large 1B1B Unit - Pool Side - Surf Song #229

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Surf Song #229 - Very spacious 1 bedroom, 1 bathroom condo is the only one bedroom unit near the pool at Surf Song. This ...

    From $222 per night (USD)

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    Details
  • Beachfront Complex - 2b 2b - Beach Place #304
    From $250 per night (USD)

    Expedia

    Beachfront Complex - 2b 2b - Beach Place #304

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    Beach Place #304 - This condo is spacious with tons of natural light, a beautiful 2 bedroom, 2 bath retreat ready for f ...

    From $250 per night (USD)

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    Details
  • 3br Luxury 1400 sq ft - Oceanfront - Crimson #301
    From $298 per night (USD)

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    3br Luxury 1400 sq ft - Oceanfront - Crimson #301

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Crimson on the Gulf #301 - Beautiful and completely updated 3 bedroom 2 bathroom beachfront condo in popular Crimson On ...

    From $298 per night (USD)

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    Details
  • Direct Beach View Studio 2nd Fl - Surf Song #226
    From $213 per night (USD)

    Expedia

    Direct Beach View Studio 2nd Fl - Surf Song #226

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Surf Song #226 - This beachfront Studio Efficiency is perfect for couples looking for a memorable Florida vacation alon ...

    From $213 per night (USD)

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    Details
  • Exquisitely Decorated-Beach Views Crimson #205
    From $191 per night (USD)

    VRBO

    Exquisitely Decorated-Beach Views Crimson #205

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Crimson on the Gulf #205 - Enjoy Southern Madeira Beach at its best from this spacious, gulf view, newly renovated 2 bed ...

    From $191 per night (USD)

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    Details
  • Corner Unit Views John's Pass - Beach Place #204
    From $271 per night (USD)

    Expedia

    Corner Unit Views John's Pass - Beach Place #204

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    Beach Place #204 - Spacious, comfortable and relaxing are three words that describe 204 Beach Place. This 2 bedroom 2 ba ...

    From $271 per night (USD)

    Expedia

    Details
  • Direct Beachfront Balcony - Beach Place #309
    From $267 per night (USD)

    VRBO

    Direct Beachfront Balcony - Beach Place #309

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    This is a very nice 1 bedroom, 1 bathroom condo with beach front view in southern Madeira Beach that sleeps up to four! ...

    From $267 per night (USD)

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    Details
  • 1br 1b Beach View - Surf Song #332
    From $181 per night (USD)

    Expedia

    1br 1b Beach View - Surf Song #332

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Surf Song #332 - Nice floor plan, complete with gulf views in this 1 bedroom, 1 bath condo in popular Surf Song Resort. ...

    From $181 per night (USD)

    Expedia

    Details
  • Direct Oceanfront Views -  Madeira Norte #110
    From $241 per night (USD)

    VRBO

    Direct Oceanfront Views - Madeira Norte #110

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Madeira Norte #110 - Please note that the pool is scheduled to undergo repairs beginning in May 2026 and will be unavail ...

    From $241 per night (USD)

    VRBO

    Details
  • Beach View Balcony 1b 1b - King - Surf Song #239
    From $214 per night (USD)

    Expedia

    Beach View Balcony 1b 1b - King - Surf Song #239

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Surf Song #239 - Great beach getaway at popular Surf Song Resort! This is a 1 bedroom, 1 bathroom condo with side view b ...

    From $214 per night (USD)

    Expedia

    Details
  • Beachfront Complex - 2b 2b - Beach Place #302
    From $275 per night (USD)

    VRBO

    Beachfront Complex - 2b 2b - Beach Place #302

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Beach Place #302 - This is a cute and comfortable 2 bedroom, 2 bath condo offering terrific views of popular John's Pass ...

    From $275 per night (USD)

    VRBO

    Details
  • 2b 2b Ground Floor Poolside - Surf Song #120
    From $229 per night (USD)

    Expedia

    2b 2b Ground Floor Poolside - Surf Song #120

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Surf Song #120 - Relax in this bright and airy 2 bedroom, 2 bath poolside condo, complete with brand new kitchen, new fu ...

    From $229 per night (USD)

    Expedia

    Details
  • Beach View - Balcony - 3b 2b - Beach Place #505
    From $307 per night (USD)

    VRBO

    Beach View - Balcony - 3b 2b - Beach Place #505

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Views? Check! Spacious rental condo with all the amenities? Check! Near beaches, pool and John's Pass Village? Check! He ...

    From $307 per night (USD)

    VRBO

    Details
  • Large 1,225 sq ft Unit Beach Views Crimson #204
    From $202 per night (USD)

    Expedia

    Large 1,225 sq ft Unit Beach Views Crimson #204

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Crimson on the Gulf #204 - This condo is a popular vacation 2 bedroom 2 bathroom retreat that is near it all: beaches, h ...

    From $202 per night (USD)

    Expedia

    Details
  • Beachfront Complex - 2b 2b - Beach Place #401
    From $270 per night (USD)

    VRBO

    Beachfront Complex - 2b 2b - Beach Place #401

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    Beach Place 401 - Need lots of room not to mention incredible views? Look no further than this popular vacation rental a ...

    From $270 per night (USD)

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    Details
  • Awesome Florida Cottage - 2b 1b - Surf Song #113
    From $338 per night (USD)

    Expedia

    Awesome Florida Cottage - 2b 1b - Surf Song #113

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Surf Song #113 - This is a 2 bedroom 1 bath Surf Song Cottage - Ground floor. The cottage is a separate building apart f ...

    From $338 per night (USD)

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    Details
  • Beachfront Complex - 2b 2b - Beach Place #501
    From $269 per night (USD)

    VRBO

    Beachfront Complex - 2b 2b - Beach Place #501

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    What more could you want in a vacation property? Here at Beach Place #501 we have a terrific 2 bedroom, 2 bath condo jus ...

    From $269 per night (USD)

    VRBO

    Details
  • Direct Beachfront Unit- 3b 2b - Las Brisas #104
    From $362 per night (USD)

    Expedia

    Direct Beachfront Unit- 3b 2b - Las Brisas #104

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Wake up to breathtaking Gulf views, cool ocean breezes, and the sound of the waves at Las Brisas #104, a beautifully app ...

    From $362 per night (USD)

    Expedia

    Details
  • Beach View 1b 1b - Balcony - King - Surf Song #347
    From $212 per night (USD)

    VRBO

    Beach View 1b 1b - Balcony - King - Surf Song #347

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Surf Song #347 - Great opportunity to rent a beach view property in popular Surf Song Resort in Madeira Beach! This 1 be ...

    From $212 per night (USD)

    VRBO

    Details
  • Direct Beachfront 3B2B - Beach Place #310
    From $412 per night (USD)

    Expedia

    Direct Beachfront 3B2B - Beach Place #310

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Ready to soak up some sun? How about a vacation retreat with prime ocean and pool views? If so, 310 Beach Place is ready ...

    From $412 per night (USD)

    Expedia

    Details
  • 1b Direct Beachfront - Balcony - Beach Place #409
    From $272 per night (USD)

    VRBO

    1b Direct Beachfront - Balcony - Beach Place #409

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Views, views and more views are all here in this 1 bedroom, 1 bath condo in Madeira Beach. This updated 940 square foot ...

    From $272 per night (USD)

    VRBO

    Details
  • Beachfront Complex - 2b 2b - Beach Place #503
    From $261 per night (USD)

    Expedia

    Beachfront Complex - 2b 2b - Beach Place #503

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Too many words can describe this 2 bedroom, 2 bath condo including: Big! Updated! Location! Step inside this 1,140 squar ...

    From $261 per night (USD)

    Expedia

    Details
  • 2b 2b Direct Beachfront - Surf Song #121
    From $286 per night (USD)

    VRBO

    2b 2b Direct Beachfront - Surf Song #121

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Surf Song #121 - A Great opportunity to rent a beachfront property in popular Surf Song Resort in Madeira Beach! This 2 ...

    From $286 per night (USD)

    VRBO

    Details
  • Beach View 1b 1b - Balcony - King - Surf Song #345
    From $212 per night (USD)

    Expedia

    Beach View 1b 1b - Balcony - King - Surf Song #345

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Surf Song #345 - Reserve this bright and spacious 1 bedroom, 1 bath condo if you desire a relaxing Florida vacation clos ...

    From $212 per night (USD)

    Expedia

    Details
  • Prime Beachfront Balcony - Madeira Norte #311
    From $247 per night (USD)

    VRBO

    Prime Beachfront Balcony - Madeira Norte #311

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Madeira Norte #311 - Please note that the pool is scheduled to undergo repairs beginning in May 2026 and will be unavail ...

    From $247 per night (USD)

    VRBO

    Details
  • Stunning Beach & Gulf Views - Madeira Norte #214
    From $202 per night (USD)

    Expedia

    Stunning Beach & Gulf Views - Madeira Norte #214

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Madeira Norte #214 - Please note that the pool is scheduled to undergo repairs beginning in May 2026 and will be unavail ...

    From $202 per night (USD)

    Expedia

    Details
  • Beach View 2b 2.5b Townhouse - Surf Song #342
    From $250 per night (USD)

    VRBO

    Beach View 2b 2.5b Townhouse - Surf Song #342

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Surf Song #342 - Great 2 bedroom and 2 1/2 bath condo with two floors of living including large dining area, living room ...

    From $250 per night (USD)

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    Details
  • Coastal Decor - Top Floor View - Crimson #303
    From $285 per night (USD)

    Expedia

    Coastal Decor - Top Floor View - Crimson #303

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Crimson on the Gulf #303 - This is a wonderful 3 bedroom, 3 bathroom condo. With gulf views, this spacious, beautifully ...

    From $285 per night (USD)

    Expedia

    Details
  • Poolside 2b 2b Unit - 2nd Floor - Surf Song #224
    From $196 per night (USD)

    VRBO

    Poolside 2b 2b Unit - 2nd Floor - Surf Song #224

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Surf Song #224 - Very nice 2 bedroom, 2 bath poolside condo at popular Surf Song Resort. Located just steps from the la ...

    From $196 per night (USD)

    VRBO

    Details
  • 2b 2b Ground Floor - Near Pool - Surf Song #114
    From $238 per night (USD)

    Expedia

    2b 2b Ground Floor - Near Pool - Surf Song #114

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Surf Song #114 - A quaint, adorable ground floor 2 bedroom, 2 bath unit, just steps away from the relaxing, heated swim ...

    From $238 per night (USD)

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    Details
  • Beachfront Complex - 2b 2b - Beach Place #303
    From $250 per night (USD)

    VRBO

    Beachfront Complex - 2b 2b - Beach Place #303

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Beach Place #303 - Here is your perfect home away from home! Enjoy a memorable vacation in this beautiful 2 bedroom, 2 b ...

    From $250 per night (USD)

    VRBO

    Details
  • Studio Unit Facing Beach 2nd Fl - Surf Song #227
    From $175 per night (USD)

    Expedia

    Studio Unit Facing Beach 2nd Fl - Surf Song #227

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Surf Song #227 - Terrific opportunity to enjoy poolside and beach views from this Studio Efficiency in popular Surf Song ...

    From $175 per night (USD)

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    Details
  • Beach View 1b 1b Balcony Quiet - Surf Song #238
    From $203 per night (USD)

    VRBO

    Beach View 1b 1b Balcony Quiet - Surf Song #238

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    Surf Song #238 - Lovely 1 bedroom, 1 bath condo close to all of the popular attractions in south Madeira Beach. Bright a ...

    From $203 per night (USD)

    VRBO

    Details
  • Direct Oceanfront - 4 Queen Beds - Surf Song #241
    From $345 per night (USD)

    Expedia

    Direct Oceanfront - 4 Queen Beds - Surf Song #241

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Surf Song #241 - Beautiful! Spacious! Great views! First class! Just a few of the words you will say when entering this ...

    From $345 per night (USD)

    Expedia

    Details
  • Luxury Direct Ocean Front 1315 sq ft. - Hot Tub & Pool
    From $321 per night (USD)

    VRBO

    Luxury Direct Ocean Front 1315 sq ft. - Hot Tub & Pool

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Crimson on The Gulf #101 - Enjoy oceanfront and pool views from this bright and well appointed 3 bedroom, 2 bath condomi ...

    From $321 per night (USD)

    VRBO

    Details
  • Direct Beach Front Views - Surf Song #222
    From $290 per night (USD)

    Expedia

    Direct Beach Front Views - Surf Song #222

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Surf Song #222 - Here is your home away from home! Relaxing and comfortable 2 bedroom, 2 bathroom vacation retreat at th ...

    From $290 per night (USD)

    Expedia

    Details
  • Studio Efficiency Ground Floor - Surf Song #117
    From $179 per night (USD)

    VRBO

    Studio Efficiency Ground Floor - Surf Song #117

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Surf Song #117 - This unit is a ground floor non-smoking Studio Efficiency overlooking the pool and the beautiful gulf w ...

    From $179 per night (USD)

    VRBO

    Details
  • Direct Beachfront - Gulf Views - Beach Place #407
    From $360 per night (USD)

    Expedia

    Direct Beachfront - Gulf Views - Beach Place #407

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Unit 407 is a large, 3 bedroom, 2 bath condo with direct beach front balcony view in popular Beach Place Condos is ready ...

    From $360 per night (USD)

    Expedia

    Details
  • Beachfront Complex - 2b 2b - Beach Place #202
    From $250 per night (USD)

    VRBO

    Beachfront Complex - 2b 2b - Beach Place #202

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Beach Place #202 is a 2 bedroom, 2 bath condo centrally located to beaches, pool and popular John's Pass Village is read ...

    From $250 per night (USD)

    VRBO

    Details
  • Beach View 1b 1b - Balcony - King - Surf Song #346
    From $203 per night (USD)

    Expedia

    Beach View 1b 1b - Balcony - King - Surf Song #346

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Surf Song #346 - Beautiful and completely updated 1 bedroom 1 bathroom condo in popular Surf Song Resort is ready for yo ...

    From $203 per night (USD)

    Expedia

    Details
  • Beach View - Balcony - 2 Queen - Surf Song #350
    From $241 per night (USD)

    VRBO

    Beach View - Balcony - 2 Queen - Surf Song #350

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Surf Song #350 - This is a wonderful opportunity to vacation near all the amenities of southern Madeira Beach! Here you ...

    From $241 per night (USD)

    VRBO

    Details
  • Awesome Beach & Gulf Views - Madeira Norte #111
    From $222 per night (USD)

    Expedia

    Awesome Beach & Gulf Views - Madeira Norte #111

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Madeira Norte #111 - Please note that the pool is scheduled to undergo repairs beginning in May 2026 and will be unavail ...

    From $222 per night (USD)

    Expedia

    Details
  • Best Value, 2nd Floor 2b 2b Near Pool - Surf Song #230
    From $229 per night (USD)

    VRBO

    Best Value, 2nd Floor 2b 2b Near Pool - Surf Song #230

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Surf Song #230 - Delightful, nicely appointed 2 bedroom, 2 bathroom condo in popular Surf Song Resort! Located near the ...

    From $229 per night (USD)

    VRBO

    Details
  • Top Floor Direct Beachfront - Madeira Norte #510
    From $246 per night (USD)

    Expedia

    Top Floor Direct Beachfront - Madeira Norte #510

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Madeira Norte #510 - Please note that the pool is scheduled to undergo repairs beginning in May 2026 and will be unavail ...

    From $246 per night (USD)

    Expedia

    Details
  • Beachfront Complex - 2b 2b - Beach Place #403
    From $250 per night (USD)

    VRBO

    Beachfront Complex - 2b 2b - Beach Place #403

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    Beach Place #403 - Find out why guests come back over and over again to Beach Place Condos! Close to everything, includi ...

    From $250 per night (USD)

    VRBO

    Details
  • Cozy Bungalow With Private Pool Near Beaches & Pinellas Bike Trail
    From $358 per night (USD)

    VRBO

    Cozy Bungalow With Private Pool Near Beaches & Pinellas Bike Trail

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Situated in an award winning neighborhood off the Gulf and minutes from downtown Dunedin our 3 bedroom-2 bathroom bungal ...

    From $358 per night (USD)

    VRBO

    Details
  • Top Floor Beach & Gulf Views - Madeira Norte #516
    From $212 per night (USD)

    VRBO

    Top Floor Beach & Gulf Views - Madeira Norte #516

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Madeira Norte #516 - Please note that the pool is scheduled to undergo repairs beginning in May 2026 and will be unavail ...

    From $212 per night (USD)

    VRBO

    Details
  • Clear Beach Views  - Balcony - Madeira Norte #414
    From $203 per night (USD)

    Expedia

    Clear Beach Views - Balcony - Madeira Norte #414

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Madeira Norte #414 - Please note that the pool is scheduled to undergo repairs beginning in May 2026 and will be unavail ...

    From $203 per night (USD)

    Expedia

    Details
  • Luxury Updated Unit w/ Balcony - Crimson #105
    From $212 per night (USD)

    VRBO

    Luxury Updated Unit w/ Balcony - Crimson #105

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Crimson on the Gulf #105 - This is a well maintained 2 bedroom, 2 bathroom condo in sought after southern Madeira Beach ...

    From $212 per night (USD)

    VRBO

    Details
  • 2b 2b Ground Floor Poolside - Surf Song #118
    From $238 per night (USD)

    Expedia

    2b 2b Ground Floor Poolside - Surf Song #118

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Surf Song #118 - Enjoy this wonderful 2 bedroom, 2 bath poolside condo in sought after Madeira Beach. Nicely furnished ...

    From $238 per night (USD)

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    Details
  • Beach View - John's Pass - Madeira Norte #208
    From $199 per night (USD)

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    Beach View - John's Pass - Madeira Norte #208

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Madeira Norte #208 - Please note that the pool is scheduled to undergo repairs beginning in May 2026 and will be unavail ...

    From $199 per night (USD)

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    Details
  • Coastal Property - Johns Pass Beach Place #201
    From $270 per night (USD)

    Expedia

    Coastal Property - Johns Pass Beach Place #201

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Beach Place #201 - The unit is a 2 bedroom, 2 bath rental property that offers terrific views of popular John's Pass Vil ...

    From $270 per night (USD)

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    Details
  • Direct Beach Front 1b 1b Balcony - Surf Song #240
    From $219 per night (USD)

    VRBO

    Direct Beach Front 1b 1b Balcony - Surf Song #240

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Surf Song #240 - Well laid out 1 bedroom, 1 bathroom condo allows you to vacation near it all in Madeira Beach! Enjoy vi ...

    From $219 per night (USD)

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    Details
  • Beachfront Complex - 2b 2b - Beach Place #504
    From $270 per night (USD)

    Expedia

    Beachfront Complex - 2b 2b - Beach Place #504

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Beach Place #504 is a lovely 2 bedroom, 2 bath condo close to all of the popular attractions in south Madeira Beach. Bri ...

    From $270 per night (USD)

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    Details
  • Corner Unit John's Pass View- Beach Place #101
    From $263 per night (USD)

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    Corner Unit John's Pass View- Beach Place #101

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    Beach Place #101 - Get away from it all in this delightful 2 bedroom, 2 bath condominium in exclusive southern Madeira B ...

    From $263 per night (USD)

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    Details
  • Beautiful luxury 2 bedroom private   Cottage
    From $255 per night (USD)

    Expedia

    Beautiful luxury 2 bedroom private Cottage

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Beautifully decorated 2 bedroom cottage sleeps four one queen bed one full bed ,full kitchen, dining, outside seating, c ...

    From $255 per night (USD)

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    Details
  • Studio Efficiency Ground Floor - Surf Song #116
    From $181 per night (USD)

    VRBO

    Studio Efficiency Ground Floor - Surf Song #116

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Surf Song #116 - This cozy ground floor Studio efficiency is directly facing the beach and offers every amenity for a on ...

    From $181 per night (USD)

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    Details
  • Beach Front 1B1B Balcony 2 Beds - Surf Song #349
    From $234 per night (USD)

    Expedia

    Beach Front 1B1B Balcony 2 Beds - Surf Song #349

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Surf Song #349 - Rain or shine, enjoy spectacular beach views from the covered balcony in this delightful 1 bedroom, 1 b ...

    From $234 per night (USD)

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    Details
  • Beachfront Complex - 2b 2b - Beach Place #301
    From $270 per night (USD)

    VRBO

    Beachfront Complex - 2b 2b - Beach Place #301

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Beach Place #301- This is a recently remodeled charming 2 bedroom, 2 bathroom condo with views of John's Pass waterway, ...

    From $270 per night (USD)

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    Details
  • Luxury Direct Beachfront Views - Crimson #201
    From $268 per night (USD)

    Expedia

    Luxury Direct Beachfront Views - Crimson #201

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Crimson on the Gulf #201 - See why guests come back year after year to this beachfront condo. Crimson #201 is a highly p ...

    From $268 per night (USD)

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    Details
  • Beachfront 1b 1b Suite - Beach Place #209
    From $270 per night (USD)

    VRBO

    Beachfront 1b 1b Suite - Beach Place #209

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Beach Place #209 - Planning a Vacation? Have a young family? What better place to soak up some sun than this large 1 be ...

    From $270 per night (USD)

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    Details
  • 1br 1b - 3rd Floor - King - Surf Song #335
    From $181 per night (USD)

    Expedia

    1br 1b - 3rd Floor - King - Surf Song #335

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Surf Song 335 - Enjoy your stay at Madeira Beach in your home away from home! Here you will find a 1 bedroom, 1 bath con ...

    From $181 per night (USD)

    Expedia

    Details
  • Beach View - Balcony - 3b 2b - Beach Place #405
    From $330 per night (USD)

    VRBO

    Beach View - Balcony - 3b 2b - Beach Place #405

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    This is a very cute and updated 3 bedroom, 2 bath home is available at popular Beach Place Condos. This 1,360 square foo ...

    From $330 per night (USD)

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    Details
  • Quality stay at a cheaper price!
    From $455 per night (USD)

    VRBO

    Quality stay at a cheaper price!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    7

    St. Petersburg is where you'll find your ideal holiday house. This charming 2-bedroom property offers a cozy and comfort ...

    From $455 per night (USD)

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    Details
  • Top Floor John's Pass Village Views - Madeira Norte #503
    From $172 per night (USD)

    VRBO

    Top Floor John's Pass Village Views - Madeira Norte #503

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Madeira Norte #503 - Please note that the pool is scheduled to undergo repairs beginning in May 2026 and will be unavail ...

    From $172 per night (USD)

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    Details
  • SMACK ON THE BEACH! OCEANSIDE CONDO. (9/14-9/25/26 Pool Closed)
    From $333 per night (USD)

    VRBO

    SMACK ON THE BEACH! OCEANSIDE CONDO. (9/14-9/25/26 Pool Closed)

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    POOL CLOSED 9/14 - /25/26 STUNNING BEACH VIEWS! Beautiful direct 2 bedroom 2 bath condo with AMAZING views and a grea ...

    From $333 per night (USD)

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    Details
  • Endless Beach Views 2b 1.5b - Madeira Norte #513
    From $203 per night (USD)

    VRBO

    Endless Beach Views 2b 1.5b - Madeira Norte #513

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Madeira Norte #513 - Please note that the pool is scheduled to undergo repairs beginning in May 2026 and will be unavail ...

    From $203 per night (USD)

    VRBO

    Details
  • Picturesque Setting Directly on The Beach!!
    From $265 per night (USD)

    VRBO

    Picturesque Setting Directly on The Beach!!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Welcome to your laid-back Indian Shores escape—where you get the best of both worlds with sweeping Gulf views out front ...

    From $265 per night (USD)

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    Details
  • Bella Sol - Beautiful Beach Front Condominium on Indian Rocks Beach
    From $319 per night (USD)

    VRBO

    Bella Sol - Beautiful Beach Front Condominium on Indian Rocks Beach

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    *****************************POOL AND ELEVATOR FUNCTIONING POST HURRICANE*************************************** Welcom ...

    From $319 per night (USD)

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    Details
  • Spectacular Views & Endless Views! (Bldg. Construction-See Descrpt)
    From $229 per night (USD)

    VRBO

    Spectacular Views & Endless Views! (Bldg. Construction-See Descrpt)

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    The Seaside Real Estate Store & Property Shoppe proudly presents this beautiful Vacation Rental with Endless Views!!! * ...

    From $229 per night (USD)

    VRBO

    Details
  • Gulf Front Private Home. Dogs Welcome (under 50#). 2 Bedroom, 1 Bath-Sleeps 6
    From $309 per night (USD)

    VRBO

    Gulf Front Private Home. Dogs Welcome (under 50#). 2 Bedroom, 1 Bath-Sleeps 6

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Direct Beach Front cottage located on the Gulf of America! An Indian Rocks Beach original 1930's Bungalow. If you want ...

    From $309 per night (USD)

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    Details
  • HGTV Worthy! 1BR/1BA Coastal Boutique Cottage. Sleeps 4. Steps to the Beach!!
    From $416 per night (USD)

    VRBO

    HGTV Worthy! 1BR/1BA Coastal Boutique Cottage. Sleeps 4. Steps to the Beach!!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    It's the one you've been dreaming of!! Bright, modern and adorable cottage located in the quieter North section of Clea ...

    From $416 per night (USD)

    VRBO

    Details
  • Take a step closer to paradise! SEAGATE - Apt. 302
    From $437 per night (USD)

    VRBO

    Take a step closer to paradise! SEAGATE - Apt. 302

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Take a step closer to paradise! SEAGATE - Apt. 302 !!! This 3 bedroom with 2 full baths is located on the third floor an ...

    From $437 per night (USD)

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    Details
  • A Beachfront Paradise
    From $215 per night (USD)

    VRBO

    A Beachfront Paradise

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    5

    Located directly on the Gulf of Mexico in prestigious Belleair Beach, this convenient and totally updated condo offers t ...

    From $215 per night (USD)

    VRBO

    Details
  • Paradise Villa at MADEIRA NORTE - Awesome Beach Front Unit
    From $320 per night (USD)

    VRBO

    Paradise Villa at MADEIRA NORTE - Awesome Beach Front Unit

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Note: As of July 1st the pool is undergoing unscheduled maintenance. We believe our Unit "Paradise Villa" at Madeira ...

    From $320 per night (USD)

    VRBO

    Details
  •  5 star condo on Main Street!
    From $214 per night (USD)

    Expedia

    5 star condo on Main Street!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Top Rated Downtown Dunedin condo! Do you love downtown Dunedin? If so, be part of the downtown with this 2 bedroom apart ...

    From $214 per night (USD)

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  • Relaxing Family Home minutes from beach.
    From $321 per night (USD)

    VRBO

    Relaxing Family Home minutes from beach.

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    10

    Visit this lovely family home close to the wonderful gulf beaches, there are lots of restaurants and shopping places eve ...

    From $321 per night (USD)

    VRBO

    Details
  • Spectacular Sunsets!!!
    From $391 per night (USD)

    Expedia

    Spectacular Sunsets!!!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    This unit has direct access to walk right out onto the soft, white sands of Indian Rocks Beach from your own private pat ...

    From $391 per night (USD)

    Expedia

    Details
  • Cozy Cottage With A Sensational Sunset View
    From $296 per night (USD)

    VRBO

    Cozy Cottage With A Sensational Sunset View

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    This cottage has been recently renovated. It has a fully equipped kitchen, washer/dryer, central heat and air, WiFi, 3 H ...

    From $296 per night (USD)

    VRBO

    Details
  • Fantastic Beachside Cottage<br>Professional Baseball,Football and Hockey,  Golf
    From $290 per night (USD)

    Expedia

    Fantastic Beachside Cottage<br>Professional Baseball,Football and Hockey, Golf

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    VRBO member since 2004 This 2-bedroom Owners Cottage really convinces you that you are on vacation at the beach. Janie' ...

    From $290 per night (USD)

    Expedia

    Details
  • 2 bedroom, 2 bath condo with  view of  Gulf.  Condo not wheelchair accessible.
    From $269 per night (USD)

    VRBO

    2 bedroom, 2 bath condo with view of Gulf. Condo not wheelchair accessible.

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    New living room and dining room furniture. King size bed in master and two twins in guest room. Floors are new and entir ...

    From $269 per night (USD)

    VRBO

    Details
  • Tranquility at the Beach
    From $476 per night (USD)

    VRBO

    Tranquility at the Beach

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    4

    Situated just steps away from the Gulf Coast Beaches, The Location provides great access to everything Tampa/St. Petersb ...

    From $476 per night (USD)

    VRBO

    Details
  • Professional cottage on 1/2 acre lot in quiet country setting
    From $256 per night (USD)

    VRBO

    Professional cottage on 1/2 acre lot in quiet country setting

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    This is a newly renovated, cozy, yet professional cottage situated on a 1/2 acre lot in a quiet, safe neighborhood. It ...

    From $256 per night (USD)

    VRBO

    Details
  • family friendly, gated community, two pools, lake outside back door.
    From $194 per night (USD)

    VRBO

    family friendly, gated community, two pools, lake outside back door.

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Light, spacious, 930 sq. ft. condo, with bedrooms situated on opposite sides of unit. Two screened lanais, four patio do ...

    From $194 per night (USD)

    VRBO

    Details
  • Steps to Sand! Gulf Views, Private Balcony, Beach Gear - FREE Activities & Parking - 2 Piper's Nest
    From $321 per night (USD)

    VRBO

    Steps to Sand! Gulf Views, Private Balcony, Beach Gear - FREE Activities & Parking - 2 Piper's Nest

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Piper's Nest is a small, intimate complex with direct access to the beach, convenient for romantic evening walks or days ...

    From $321 per night (USD)

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    Details
  • Updated Condo! Heated Pool & Hot Tub, Grill, FREE Parking, FREE Activities! ~ 707 Sandcastle
    From $351 per night (USD)

    VRBO

    Updated Condo! Heated Pool & Hot Tub, Grill, FREE Parking, FREE Activities! ~ 707 Sandcastle

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Beautifully Updated Beach Lovers Paradise! This Indian Shores condo has been completely remodeled from top to bottom wit ...

    From $351 per night (USD)

    VRBO

    Details
  • Sun, Sand & Serenity: Your Fully Renovated Pass-A-Grille Beach Retreat Awaits
    From $366 per night (USD)

    VRBO

    Sun, Sand & Serenity: Your Fully Renovated Pass-A-Grille Beach Retreat Awaits

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Welcome to Pass-A-Grille Beach, FL. Whether you’re looking for a month-long escape or a seasonal getaway, our beachside ...

    From $366 per night (USD)

    VRBO

    Details
  • Direct Beach Front! Amazing New Remodel!!  Holiday Villas II #213
    From $485 per night (USD)

    VRBO

    Direct Beach Front! Amazing New Remodel!! Holiday Villas II #213

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    We just purchased this beautiful condo in May 2017. Did a complete remodel in the fall of 2017, looks amazing. Enjoy t ...

    From $485 per night (USD)

    VRBO

    Details
  • Beachfront End Unit, Pool, Hot Tub, Tennis, Grill, Free Wi-Fi & Cable, W/D ~ 1208 Lighthouse Towers
    From $245 per night (USD)

    VRBO

    Beachfront End Unit, Pool, Hot Tub, Tennis, Grill, Free Wi-Fi & Cable, W/D ~ 1208 Lighthouse Towers

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    NOTE: There is an application required for rental of this property that must be submitted 15 days in advance and approve ...

    From $245 per night (USD)

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  • Pets Allowed! Waterfront Pool! Prime Location! ~ FREE Parking and FREE Activities ~ 404 Bay Harbor
    From $272 per night (USD)

    VRBO

    Pets Allowed! Waterfront Pool! Prime Location! ~ FREE Parking and FREE Activities ~ 404 Bay Harbor

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    This contemporary 3 BR, 3BA condo overlooking the marina in Clearwater Beach features upscale amenities and all the conv ...

    From $272 per night (USD)

    VRBO

    Details