Houses Osprey

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260 houses

Anna Maria Island/ IMG Academy/ Beach/ HotTub/ Bikes/ Kayaks/ Golf/ Fishing

Bradenton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Rental types Swing set or jungle gym

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Price per night from

$287

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GUEST HOUSE

Fruitville guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 29 minutes

1 of 2 match: Rental types, Swing set or jungle gym

1 of 2 filters match

Price per night from

$107

+++ Clean & Bright +++ Minutes to Anna Maria Island

Bradenton apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 9 minutes

1 of 2 match: Rental types, Swing set or jungle gym

1 of 2 filters match

Price per night from

$178

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

1 of 2 match: Rental types, Swing set or jungle gym

1 of 2 filters match

Price per night from

$114

Just Minutes from the White Sandy Siesta Beach

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“It was very cozy and comfortable apartment!” We loved to spend our vacation at this place. Really close to the beach, to different restaurants, and all kind of stores.

1 of 2 match: Rental types, Swing set or jungle gym

1 of 2 filters match

Price per night from

$115

LUX VILLAs close to sparkling Siesta Key Beach.

Osprey villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Rental types, Swing set or jungle gym

1 of 2 filters match

Price per night from

$161

Seaplace Condo - 1975 GMD 104

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Rental types, Swing set or jungle gym

1 of 2 filters match

Price per night from

$192

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

1 of 2 match: Rental types, Swing set or jungle gym

1 of 2 filters match

Price per night from

$117

Gorgeous Direct Gulf/Beach Front 2 Bedroom Condo on Siesta Key, Amazing views!

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 1 minutes

1 of 2 match: Rental types, Swing set or jungle gym

1 of 2 filters match

Price per night from

$267

Responds fast! avg. 11 minutes

1 of 2 match: Rental types, Swing set or jungle gym

1 of 2 filters match

Price per night from

$132

2 Bedroom, 2 Bathroom condo / Heated pool / 7 minute walk to beach

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Rental types, Swing set or jungle gym

1 of 2 filters match

Price per night from

$178

Charming Artist's Cottage In Laurel Park

Sarasota house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Swing set or jungle gym, Rental types

1 of 2 filters match

Price per night from

$144

Convenient + Cozy + Quite + Comfortable :-)

Sarasota house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 2 hours 17 minutes

1 of 2 match: Swing set or jungle gym, Rental types

1 of 2 filters match

Price per night from

$316

Lovely Brandnew Pool Villa w/ Private Beach, WiFi

Venice house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Rental types

1 of 2 filters match

Price per night from

$213

New 6 Bedroom, Luxury Home in Gated Community

Siesta Key house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14

1 of 2 match: Swing set or jungle gym, Rental types

1 of 2 filters match

Price per night from

$1,001

Vacation Home on Coral Sands Ct. Spring Special !

Venice house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Swing set or jungle gym, Rental types

1 of 2 filters match

Price per night from

$155

Manasota Beach Vacation Rental

Englewood house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Rental types

1 of 2 filters match

Price per night from

$270

Quiet pool home with lake view, close to beaches

Venice house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Swing set or jungle gym, Rental types

1 of 2 filters match

Price per night from

$230

Brand new villa with heated pool for swimmers

Venice house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Rental types

1 of 2 filters match

Price per night from

$190

Luxury Sarasota Golf Home

Sarasota house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 2 match: Swing set or jungle gym, Rental types

1 of 2 filters match

Price per night from

$369

Siesta Vacation Home - 3 miles to beach

Venice house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Rental types

1 of 2 filters match

Price per night from

$211

1 of 2 match: Swing set or jungle gym, Rental types

1 of 2 filters match

Price per night from

$150

Venice Island Bellagio Home w/ 3BR & 3BA

Venice house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

“Great Vacation” Thanks for allowing us to stay in your beautiful home in Venice Florida. It was very comfortable and had all the convenience of home. Everything we needed was close by (restaurants and grocery store). We really liked the bike trails along the canal since we brought our bikes. We would rent your house again.

1 of 2 match: Swing set or jungle gym, Rental types

1 of 2 filters match

Price per night from

$104

Vacation Home on Alligator Drive . Winter 2025 Special !

Venice house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Swing set or jungle gym, Rental types

1 of 2 filters match

Price per night from

$150

A Siesta Tropical Retreat - Island Pool Oasis in Village & 2 blocks to Beach

Siesta Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

“Your best choice for location!” We stayed for 10 lovely days in this home and I have to say It was an even better location than I expected. Everything you could want to do is in walking distance or you can walk to the village (maybe a 3 minute walk)and hop in a free taxi . The house is well appointed and beds are very comfortable. We traveled with a 10 yr.old, 11yr. old , and 15 yr. old my 15 yr. old niece slept in the trundle bed and commented on how comfortable the bed was. In the kitchen you will find a drawer full of menus for the many nearby restaurants and information for water activities. I highly recommend parasailing while your there ! Considering how close everything is the street is very quiet and the owners were great to deal with. Thanks Kathi and Grant!

1 of 2 match: Swing set or jungle gym, Rental types

1 of 2 filters match

Price per night from

$501

A Wonderful Pool House on a lake full of wildlife.

Sarasota house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Location location” Great house convincent , clean , close to everything

1 of 2 match: Swing set or jungle gym, Rental types

1 of 2 filters match

Price per night from

$122

Three bedroom house directly on beach with gulf vi

Siesta Key house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 7

1 of 2 match: Swing set or jungle gym, Rental types

1 of 2 filters match

Price per night from

$402

Luxury accommodation in Venetia, 3 months stay

Venice house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 2 match: Swing set or jungle gym, Rental types

1 of 2 filters match

Price per night from

$192

Lovely 3 BR Home with Office & Heated Pool at Tara

Bradenton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Rental types

1 of 2 filters match

Price per night from

$167

Charming Lido Key Beach House 5 min Walk to Beach!

Sarasota house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Swing set or jungle gym, Rental types

1 of 2 filters match

Price per night from

$410

Stunning 2,550 Sq.ft House, FL

Bradenton house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Swing set or jungle gym, Rental types

1 of 2 filters match

Price per night from

$286

Oceanfront home w/sunset views of Sarasota Bay

Sarasota house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Swing set or jungle gym, Rental types

1 of 2 filters match

Price per night from

$630

Seaside Vacation Home w/office

South Venice house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Rental types

1 of 2 filters match

Price per night from

$211

Captiva Paradise Home close to IMG Academy & Siesta Key Beach

Bradenton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

Responds fast! avg. 9 minutes

1 of 2 match: Swing set or jungle gym, Rental types

1 of 2 filters match

Price per night from

$373

Lakefront Oasis 3 Bdrm House with Heated Pool minutes from village and beach

Siesta Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Swing set or jungle gym, Rental types

1 of 2 filters match

Price per night from

$689

Another Day in Paradise

Siesta Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 3 hours 1 minutes

1 of 2 match: Swing set or jungle gym, Rental types

1 of 2 filters match

Price per night from

$545

1 of 2 match: Swing set or jungle gym, Rental types

1 of 2 filters match

Price per night from

$132

Venice Immaculate RemodeledHome-2 Bdr/2 Bath-Pool-WIFl&CABLE-2 Miles to Beach

South Venice house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Rental types

1 of 2 filters match

Price per night from

$172

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