Houses Osprey

Updating...

age 0-16
250 Results

Relevance

Price: low to high

Price: high to low

Reviews

250 houses

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

Bradenton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Rental types Trampoline

All filters match

Price per night from

$287

These homes match some but not all of your filters. Clear all filters

Lovely Brandnew Pool Villa w/ Private Beach, WiFi

Venice house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Trampoline, Rental types

1 of 2 filters match

Price per night from

$212

Stay near the heart of Sarasota

Sarasota house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Trampoline, Rental types

1 of 2 filters match

Price per night from

$115

New 6 Bedroom, Luxury Home in Gated Community

Siesta Key house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14

1 of 2 match: Trampoline, Rental types

1 of 2 filters match

Price per night from

$999

Vacation Home on Coral Sands Ct. Spring Special !

Venice house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Trampoline, Rental types

1 of 2 filters match

Price per night from

$155

Manasota Beachy Cottage

Manasota Key house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

“Our 2017 vacation” This was our first time ever renting a house. Peter was the best. This house had everything we need or wanted. It was super clean and beautiful. The screened porch was perfect to drink coffee in the morning. Didn't have to worry about the bugs or anything. Beach was a short walk around the corner over a bridge. The town was great and hardly no traffic. Safe for younger kids to play in the yard. Can't wait to rent again next year. Thank you!!

1 of 2 match: Trampoline, Rental types

1 of 2 filters match

Price per night from

$155

Quiet pool home with lake view, close to beaches

Venice house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Trampoline, Rental types

1 of 2 filters match

Price per night from

$229

Brand new villa with heated pool for swimmers

Venice house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Trampoline, Rental types

1 of 2 filters match

Price per night from

$189

Luxury Sarasota Golf Home

Sarasota house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 2 match: Trampoline, Rental types

1 of 2 filters match

Price per night from

$368

Siesta Vacation Home - 3 miles to beach

Venice house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Trampoline, Rental types

1 of 2 filters match

Price per night from

$211

1 of 2 match: Trampoline, Rental types

1 of 2 filters match

Price per night from

$149

****Walk to Beach-5min! Waterfront Canal! Private Pool~spa~Kayaks, Bikes!

Siesta Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Trampoline, Rental types

1 of 2 filters match

Price per night from

$454

Responds fast! avg. 0 minutes

1 of 2 match: Trampoline, Rental types

1 of 2 filters match

Price per night from

$229

Downtown Sarasota five star home

Sarasota house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Trampoline, Rental types

1 of 2 filters match

Price per night from

$195

Charming Artist's Cottage In Laurel Park

Sarasota house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Trampoline, 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: Trampoline, Rental types

1 of 2 filters match

Price per night from

$315

10- minute walk to downtown Sarasota

Sarasota house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Trampoline, Rental types

1 of 2 filters match

Price per night from

$98

A Comfortable getaway!

Sarasota house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Trampoline, Rental types

1 of 2 filters match

Price per night from

$115

Just a mile to downtown Sarasota!

Sarasota house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Trampoline, Rental types

1 of 2 filters match

Price per night from

$98

Stay near the beach and downtown

Sarasota house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Trampoline, Rental types

1 of 2 filters match

Price per night from

$69

Walk to the beach and downtown

Sarasota house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Trampoline, Rental types

1 of 2 filters match

Price per night from

$69

Stunning 2,550 Sq.ft House, FL

Bradenton house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Trampoline, Rental types

1 of 2 filters match

Price per night from

$286

Five star Downtown Sarasota tropical garden Cottage

Sarasota house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

“Paradise Found in Downtown Sarasota” Absolutely charming, fully redone/ upgraded bungalow close to everything Sarasota has to offer. This was the third year running my wife & I have stayed at the wonderful home located minutes from Sarasota's best beaches, restaurants & shopping. We fully intend to return again next year! The two bedroom home is in pristine condition. Beautifully decorated, lovely hardwood flooring throughout with a fully stocked (appliances, crockery, pots/pans, cutlery, etc...) kitchen & renovated bathroom. Everything you need is provided, just arrive & settle-in. A huge projection screen in the living room, should you want to have an at-home movie night (rental Dvd's a 5-minute walk away @ Publix). There's also a regular flat-screen TV in the living room, as well as a wall-mounted TV in the bedroom. The backyard is, personally, my favourite part of the home. A screen-in lanai to eat in & a beautifully manicured backyard to relax in under the tiki hut or under the palm trees. There are a few seating areas throughout the backyard. Find the space you like the best, sit-back & relax with a cool cocktail- very civilized & very beautiful. You'll feel like you're in the Caribbean, not Florida in this backyard. Maureen & Pat, your hosts who, very conveniently, live right next door have provided everything you need, including all the beach chairs, umbrellas, beach towels, etc...to take along with you to Sarasota's beautiful beaches. Maureen has also provided tons of literature about the area in the house- restaurant menus, local mags, maps- everything. Maureen & Pat are always happy to suggest restaurants, beaches, shopping, golf, etc. They know Sarasota well, are friendly & happy to help in any way they can to ensure you have a wonderful stay. My wife & I can honestly say we love this property, have encountered no negatives about the place in three years of week-long stays & look-forward to our time there each year. We recommend this lovely home to everyone.

1 of 2 match: Trampoline, Rental types

1 of 2 filters match

Price per night from

$189

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: Trampoline, Rental types

1 of 2 filters match

Price per night from

$103

Vacation Home on Alligator Drive . Winter 2025 Special !

Venice house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Trampoline, Rental types

1 of 2 filters match

Price per night from

$149

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: Trampoline, Rental types

1 of 2 filters match

Price per night from

$500

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: Trampoline, Rental types

1 of 2 filters match

Price per night from

$121

Three bedroom house directly on beach with gulf vi

Siesta Key house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 7

1 of 2 match: Trampoline, Rental types

1 of 2 filters match

Price per night from

$401

Luxury accommodation in Venetia, 3 months stay

Venice house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 2 match: Trampoline, 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: Trampoline, Rental types

1 of 2 filters match

Price per night from

$166

Charming Lido Key Beach House 5 min Walk to Beach!

Sarasota house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Trampoline, Rental types

1 of 2 filters match

Price per night from

$409

Lookout: By Beachside Management

Siesta Key house

  • 4 bedrooms
  • 6 bathrooms
  • sleeps 10

1 of 2 match: Trampoline, Rental types

1 of 2 filters match

Price per night from

$744

Whispering Lake House-Heated Pool, Wi-Fi, Lakeview

Venice house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

1 of 2 match: Trampoline, Rental types

1 of 2 filters match

Price per night from

$195

Private modern 3BR home, salt water pool

Bradenton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Trampoline, Rental types

1 of 2 filters match

Price per night from

$344

CKBH (Casey Key Beach House)

Osprey house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Trampoline, Rental types

1 of 2 filters match

Price per night from

$654

Downtown Sarasota Historic Burns Court Adorable Bungalow

Sarasota house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Trampoline, Rental types

1 of 2 filters match

Price per night from

$295

Heated pool home near Siesta Key

Sarasota house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Trampoline, Rental types

1 of 2 filters match

Price per night from

$263

2BR/2BA House Just Steps to Siesta Village & Siesta Key Beach

Siesta Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Great Location, Very Well Appointed” This house is perfectly located right in Siesta Key Village within an easy walk to shops and restaurants. It is also just a block from the beach. No parking hassles! The house is very well appointed. The owner has thoughtfully provided more than enough coffee for the Keurig, lots of towels, and all needed kitchen utensils, dishes, containers, and cooking supplies, in addition to a beach wagon and chairs. Although not luxurious, this is a very comfortable rental. We also liked the privacy of having our own house. The only negatives were the lack of towel racks in the bathrooms and the lack of hot water in the bathroom with the tub (it remained only warm, even after running for a very long time). The water in the other bathroom was fine.

1 of 2 match: Trampoline, Rental types

1 of 2 filters match

Price per night from

$315

Viewing 38 of 250
rentals in Osprey

×

Also consider