
Pinellas Area Rentals
- 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)VRBO
- 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)VRBO
- 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)VRBO
- 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)Expedia
- 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)VRBO
- 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)VRBO
- 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)VRBO
- 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)Expedia
- 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)VRBO
- 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
- 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)VRBO
- 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)Expedia
- From $298 per night (USD)
VRBO
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)VRBO
- 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)Expedia
- 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)VRBO
- 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
- 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)VRBO
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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)VRBO
- 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)Expedia
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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)VRBO
- 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
- 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
- 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)Expedia
- 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
- 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)Expedia
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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)Expedia
- From $199 per night (USD)
VRBO
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)VRBO
- 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)Expedia
- 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)VRBO
- 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)Expedia
- From $263 per night (USD)
VRBO
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)VRBO
- 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)Expedia
- 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)VRBO
- 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)Expedia
- 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)VRBO
- 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)Expedia
- 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)VRBO
- 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
- 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)VRBO
- 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)VRBO
- 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)VRBO
- 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)VRBO
- 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
- 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)VRBO
- 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)VRBO
- 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
- 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)VRBO
- 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
- 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)VRBO
- 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
- 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
- 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)Expedia
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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)VRBO
- 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
- 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
- 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
- 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)VRBO
- 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




































































































