Cottages Anna Maria Island

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626 cottages

Siesta Key Beach Cottages on Crescent

Siesta Key cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Rental types Private outdoor pool (heated)

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Price per night from

$224

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Perfect house for your dream vacation

St. Pete Beach house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 52 minutes

1 of 2 match: Rental types, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$210

Condo wOcean view on Siesta

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 40 minutes

1 of 2 match: Rental types, Private outdoor pool (heated)

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Price per night from

$402

Coastal Paradise! 5 mi to beaches! Heated Pool! Sleep up to 14

Bradenton Beach house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 12

1 of 2 match: Rental types, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$1,255

Remodeled 4BR Pool Home / Golf View/Near Beaches

South Bradenton house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 14

1 of 2 match: Rental types, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$516

FantaSea

Anna Maria house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 2 match: Rental types, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$1,490

THE LIDO RESIDENCE

Lido Key house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 12

1 of 2 match: Rental types, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$778

Glorious Daze 4bedroom/4bath beachfront home with golf cart & elevator!

Holmes Beach house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 2 match: Rental types, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$1,374

Anna Maria Islands best location Heated pool Best prices!

Anna Maria Island house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Rental types, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$860

Beautiful home- Private getaway-Heated Pool/HotTub IMG 5 Close to Beaches

Palma Sola house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 22

1 of 2 match: Rental types, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$831

Responds fast! avg. 50 minutes

1 of 2 match: Rental types, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$157

Hibiscus Hideaway Condo Walk to Historic Bridge St

Bradenton Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 1 hour 39 minutes

1 of 2 match: Rental types, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$298

SS119 2BR 2BA

Madeira Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Rental types, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$178

SS343 2BR 2BA

Madeira Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Rental types, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$210

SS115 2BR 2BA

Madeira Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Rental types, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$178

SS348 1BR 1BA

Madeira Beach condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Rental types, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$185

SS237 1BR 1BA

Madeira Beach condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Rental types, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$172

SS344 1BR 1BA

Madeira Beach condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Rental types, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$157

Gulf Winds 108 Gulf View Studio Condo

St. Pete Beach studio

  • Studio
  • 1 bathroom
  • sleeps 2

1 of 2 match: Rental types, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$125

SS236 1BR 1BA

Madeira Beach condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Rental types, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$161

SS223 2BR 2BA

Madeira Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Rental types, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$178

Tropic Terrace #38 - Beachfront Resort

Treasure Island studio

  • Studio
  • 1 bathroom
  • sleeps 2

1 of 2 match: Rental types, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$117

Tropic Terrace #12 - Beachfront Resort

Treasure Island condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Rental types, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$117

Siesta Key - Gulf-Front Retreat - 2 BR – Free Boat Docks - Upscale

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Excellent location for a great vacation!” This is the fifth time we have had the pleasure of vacationing at El Galeon. We love the location with the beautiful beach access and walking to restaurants. We love the Manasota Key and have been vacationing there for the last seventeen years. El Galeon Gulf Unit 2 is our favorite place to stay with plenty of space and everything we need for a wonderful stay. We have already reserved "our place" for 2015.

1 of 2 match: Rental types, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$266

BEACHFRONT CONDO - THREE BEDROOM - HEATED POOL - FREE BOAT DOCKS - RENOVATED

Siesta Key apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

“Trip to paradise” Renting unit was very easy. Unit was the best layout was great. Amenities within we're well thought, out and for us anything we wanted was there including beach chairs. View of ocean was breath taking along with sunsets. I will come back again.

1 of 2 match: Rental types, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$311

Siesta Key - Beachfront Condo - 2 BR – Free Boat Docks - Turtle Beach

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Romantic place. Perfect for young families with small kids” Firshermans Cove is on a shore side. The views are amazing as well as beach which is clean and not crowded at all. Easy check in/out and very quiet place, was ideal in our case, young family with 1,5 old boy. It was nice stay and we hopefully come back again.

1 of 2 match: Rental types, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$266

Fishermans Cove FC Unit 310B 2

Gulf Gate Estates condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Rental types, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$311

Siesta Key - Beachfront Condo - 2 BR – Free Boat Docks - Renovated!

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Great Experience” This condo is well kept, clean and looks directly onto the Gulf of Mexico. We liked it because the furniture is up to date and replaced when it becomes worn. We also love the fact it is within walking distance of a good restaurant. In fact there is nothing about this rental that we don't like and that is why we return there year after year. A great choice for you to start a great experience!

1 of 2 match: Rental types, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$266

Fishermans Cove FC Unit 205B *

Gulf Gate Estates condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Rental types, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$266

Turtle Beach - Gulf-Front Condo - 2BR - Free Boat Docks - Siesta Key

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Rental types, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$266

Siesta Key - 2BR - Beachfront Condo on Crescent Beach - Heated Pool - Tennis Ct

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Rental types, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$303

Beachfront Condo - 3 BR- Heated Pool - Free Boat Docks – Upscale – Siesta Key

Siesta Key apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

“Great location!” The unit was just as described and pictures matched. The view of the ocean and bay were gorgeous. The kitchen was well equipped and there were lots of toys and chairs for the beach.

1 of 2 match: Rental types, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$311

Beachfront Condo - 3 BR- Heated Pool - Free Boat Docks – Upscale – Siesta Key

Siesta Key apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Rental types, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$311

Executive Waterfront Home

St. Petersburg house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Rental types, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$258

Anna Maria Island Beach Paradise 10

Holmes Beach studio

  • Studio
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 3 hours 20 minutes

1 of 2 match: Rental types, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$227

Anna Maria Island Martinique On The Beach

Holmes Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 3 hours 20 minutes

1 of 2 match: Rental types, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$780

Anna Maria Island Beach Sands

Bradenton Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

“Paradise” We loved this place, felt right at home the minute we walked in the door. Had a view minor problems and the service to deal with them was awesome. Thanks Terry for a great experience, being our first time here on anna Maria Island. If we didn't need the extra bedroom, we would have booked for next yr. Location~~!! wow, close to great restaurants Love the view...can't say enough of the sunsets and of course the dolphins, got chills every time I seen them, almost daily...first class...thanks...

Responds fast! avg. 3 hours 20 minutes

1 of 2 match: Rental types, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$336

Anna Maria Island Beach Palms 8B

Cortez condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 20 minutes

1 of 2 match: Rental types, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$193

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rentals in Anna Maria Island

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