Villas Osprey

/ Home
/ Vacation Rentals
/ United States
/ Florida
/ Osprey
Book with confidence.

Updating...

age 0-16
37 Results

Relevance

Price: low to high

Price: high to low

Reviews

Why am I receiving these results?

37 villas

Why am I receiving these results?

LUX VILLAs close to sparkling Siesta Key Beach.

Osprey villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Rental types

All filters match

Price per night from

$160

Great rentals within 20 miles that match your search

Luxury Venice Florida 4 Bedroom home with Pool

Venice villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Rental types

All filters match

Price per night from

$286

ZILLI VILLA

Longboat Key villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 10

Match: Rental types

All filters match

Price per night from

$486

Serene Sarasota Getaway near shopping and golfing.

Fruitville villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Rental types

All filters match

Price per night from

$127

Little Palms Villa. A lakeside home with style.

Bradenton villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Excellent” Our stay at 4638 Runabout way was amazing. We loved that the house was very nice, spacious, and clean for my family and I. We loved swimming in the pool everyday. The service was excellent all around. We would definitely stay there again.

Match: Rental types

All filters match

Price per night from

$195

Sunset Point Siesta Key FL AWESOME RENTAL !!

Siesta Key villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Beautiful inside and out. Perfect location” My family and I stayed in this beautiful rental during February 2015. We could not have asked for a more perfect spot. The rental is just steps away from the beach and has a wonderful view of the beautiful sunsets. Siesta Key Village is an easy walk away and has great restaurants and shops. We are hoping to go back as soon as we can!

Responds fast! avg. 3 hours 50 minutes

Match: Rental types

All filters match

Price per night from

$801

2 bdrm Condo Villa in Birds Bay venice, florida

Venice villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Rental types

All filters match

Price per night from

$160

Siesta Key private beach access

Siesta Key villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

“Siesta Key Townhouse” This was a wonderful place to stay! The house was very clean and spacious and had everything we needed for a week at the beach.

Match: Rental types

All filters match

Price per night from

$508

Port Charlotte 3 bedroom, 2 bathroom heated pool villa

Port Charlotte villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Rental types

All filters match

Price per night from

$99

Addy's Villas: 2BR

Nokomis villa

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Match: Rental types

All filters match

Price per night from

$194

2Bd/2Bath NEW Remodeled Villa just steps away from Siesta Beach!

Siesta Key villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Rental types

All filters match

Price per night from

$233

Tranquil villa in the heart of Englewood, close to Beaches

Englewood villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

“Wonderful location and owner is super friendly” Amazing condo very well maintained. Great location to the beach and stores only min. away. We'll visit again!

Match: Rental types

All filters match

Price per night from

$206

Casey Key 1-Bed Villa #2

Nokomis villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Match: Rental types

All filters match

Price per night from

$172

Casey Key 1-Bedroom Dockside Villa #3

Nokomis villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Match: Rental types

All filters match

Price per night from

$229

SURF AND TURF ACTIVITY FILLED GOLF RESORT COMMUNITY

Venice villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 3 hours 31 minutes

Match: Rental types

All filters match

Price per night from

$86

Arnold Palmer Design 36 Holes - Lakewood National Resort

Lakewood Ranch villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Rental types

All filters match

Price per night from

$241

Match: Rental types

All filters match

Price per night from

$191

The Meadows golf course view villa

North Sarasota villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Rental types

All filters match

Price per night from

$122

Welcome to Paradise-6 miles from Anna Maria Island Beaches

Bradenton villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Rental types

All filters match

Price per night from

$205

Match: Rental types

All filters match

Price per night from

$148

Lido Beach Villa, 1.2k sf, 1 block to the beach

Lido Key villa

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Match: Rental types

All filters match

Price per night from

$183

Match: Rental types

All filters match

Price per night from

$972

Siesta Key/Derby Bay

Siesta Key villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Perfect!” Our family really enjoyed staying here! The villa was very well maintained and cleaned. It was stocked with everything you would need. The owner was very responsive to any concerns. We had a super nice neighbor and my boys loved fishing off the dock. I would recommend renting a golf cart to go to the beach if you have children (with toys etc) or elderly people with walking concerns. It is quite a walk to get to the beach (because you also have to walk down to the cross walk then across the street). The beach in front of the Aloha Kai property is very wide (great because it was never crowded like in front of other resorts) but it was an even farther walk to the water. We have always stayed beach front but needed more rooms than were available in my booking time frame this year. This property has changed the way I will book on siesta in the future. My boys LOVED fishing everyday off the dock. They caught lots of cool fish right off the back. The street that this villa is on was very quiet for our stay. Everyone was very kind & the property is very beautiful! We hope to come back very soon! It was a wonderful experience.

Match: Rental types

All filters match

Price per night from

$286

Sun and Sea: By Beachside Management

Siesta Key villa

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 40 minutes

Match: Rental types

All filters match

Price per night from

$285

Crescent Beach Villas - La Estrella: By Beachside Management

Siesta Key villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 40 minutes

Match: Rental types

All filters match

Price per night from

$274

Bianco Sands - 3 Bedroom 2 Bath: By Beachside Management

Siesta Key villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 40 minutes

Match: Rental types

All filters match

Price per night from

$308

Bianco Sands - 1 Bedroom 1 Bath: By Beachside Management

Siesta Key villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 1 hour 40 minutes

Match: Rental types

All filters match

Price per night from

$251

Crescent Beach Villas - La Perlita: By Beachside Management

Siesta Key villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 40 minutes

Match: Rental types

All filters match

Price per night from

$274

Siesta Beach House; by Beachside Management

Siesta Key villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 40 minutes

Match: Rental types

All filters match

Price per night from

$319

Bianco Sands - 2 Bedroom - Poolside: By Beachside Management

Siesta Key villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 1 hour 40 minutes

Match: Rental types

All filters match

Price per night from

$331

Match: Rental types

All filters match

Price per night from

$122

Siesta Key Villa

Siesta Key villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Rental types

All filters match

Price per night from

$332

Beautiful Location On Bay Side, Water View, Pool

Sarasota villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

Match: Rental types

All filters match

Price per night from

$229

Crystal Sands Villa #2

Siesta Key villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Rental types

All filters match

Price per night from

$239

Beechwood Villa

Gulf Gate Estates villa

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Match: Rental types

All filters match

Price per night from

$108

Casa Covella

Siesta Key villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Rental types

All filters match

Price per night from

$219

Crystal Sands Villa #4

Gulf Gate Estates villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Rental types

All filters match

Price per night from

$239

×

Also consider