Osprey Rentals

Updating...

age 0-16
207 Results

Relevance

Price: low to high

Price: high to low

Reviews

207 Houses

Sarasota Stoneybrook Golf Condo, overlooking #3 Hole, near Siesta Key

Osprey condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Elevator access

All filters match

Price per night from

$161

Great rentals within 20 miles that match your search

Amazing Beachfront Condo, Siesta Key,

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Elevator access

All filters match

Price per night from

$344

FANTASTIC VACATION! STEPS FROM THE POOL AND BEACH, VERY CLEAN CONDO!

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Elevator access

All filters match

Price per night from

$271

New 6 Bedroom, Luxury Home in Gated Community

Siesta Key house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14

Match: Elevator access

All filters match

Price per night from

$999

Match: Elevator access

All filters match

Price per night from

$284

Luxury Romantic Oceanfront Siesta Beach Condo #304

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“What a View!” This is a very nicely decorated 1 bedroom and bath on Siesta Key Beach. You have an unobstructed view of the beach the minute you look into the condo. There's a great view from the bedroom as well! Very easy walk fo the beach..chairs and umbrella provided as well as all the amenities of home. We'd stay here again!

Match: Elevator access

All filters match

Price per night from

$184

St.Armands Circle condo ( Kingston Arms )

Sarasota apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 3 hours 25 minutes

Match: Elevator access

All filters match

Price per night from

$258

Amazing views, 11th flr, On the beach

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Elevator access

All filters match

Price per night from

$409

4 Bedroom with Gulf View Siesta Key FL Beach Fun

Siesta Key apartment

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

“Fantastic Location and Beautiful Accomodations” Our daughters and their families stayed here in February. The condo was everything we expected and more. It has a breathtaking view of the Gulf from the screened in lani which runs the width of the unit. The four bedrooms were perfect for our group of nine and the kitchen / dining area was well stocked with appliances , pots & pans , dishes , glassware , etc. Condo has easy access to heated pool and ample parking. Owner made the rental process smooth as silk , and we all felt right at home as soon as we had checked in. Right across street from world famous Siesta Beach. Would highly recommend.

Match: Elevator access

All filters match

Price per night from

$514

GULF FRONT ON #1 Beach! Siesta Dunes (by owner)

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Perfect, Perfect, Perfect” Nice condo with everything close by! Owners were great to deal with and as stated it would be . We plan on visiting again and would recommend this place to anyone.

Match: Elevator access

All filters match

Price per night from

$271

Siesta Key - 2bdrm on the beach - amazing views!!

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

“Escape from reality” We had an amazing vacation. Accommodations were great and very comfortable. Breakfast on the lanai and sunset fishing on the beach were 2 of our families favorite things to do. You also have the bay right behind you where you can kayak or paddle board. The community was quiet which was prefect for our getaway. We will definitely be staying here again.

Match: Elevator access

All filters match

Price per night from

$602

Jamaica Royale - Beachfront Tower: By Beachside Management

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Elevator access

All filters match

Price per night from

$377

BEACH RESIDENCES on Siesta, aka The Hyatt – 3 Bed/3 Bath Luxury Penthouse

Siesta Key hotel apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Elevator access

All filters match

Price per night from

$515

Gulfview/Bayfront Condo with Million Dollar Views on Siesta Key

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

Match: Elevator access

All filters match

Price per night from

$109

Arnold Palmer Design 36 Holes - Lakewood National Resort

Lakewood Ranch villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Elevator access

All filters match

Price per night from

$241

Amazing Gulf Beech Rental with Fantastic FREE Amenities!!!

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Elevator access

All filters match

Price per night from

$435

Gulf and Bay Club 3bdrm “E” Luxury END CORNER Unit - RIGHT ON BEACH

Siesta Key condo

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Elevator access

All filters match

Price per night from

$903

Lakeside Point 2 bedrooms condo with golf and lake view

Lakewood Ranch apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 3 hours 36 minutes

Match: Elevator access

All filters match

Price per night from

$138

Serenity Shore

Lakewood Ranch apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 36 minutes

Match: Elevator access

All filters match

Price per night from

$287

Sunny Daze

Lakewood Ranch apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 36 minutes

Match: Elevator access

All filters match

Price per night from

$252

Endless Summer

Lakewood Ranch apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 3 hours 36 minutes

Match: Elevator access

All filters match

Price per night from

$252

Lakeview Oasis

Lakewood Ranch condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 36 minutes

Match: Elevator access

All filters match

Price per night from

$252

Golf Haven

Lakewood Ranch apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 3 hours 36 minutes

Match: Elevator access

All filters match

Price per night from

$252

Skyline Resort

Lakewood Ranch apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 3 hours 36 minutes

Match: Elevator access

All filters match

Price per night from

$252

Eagles Nest

Lakewood Ranch apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 3 hours 36 minutes

Match: Elevator access

All filters match

Price per night from

$252

Beach condo

Longboat Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Elevator access

All filters match

Price per night from

$516

*** SUPER SPECIAL RATES at Harbor Towers ***

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 56 minutes

Match: Elevator access

All filters match

Price per night from

$114

Paradise Palms Resort at Lakewood National

Lakewood Ranch apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 3 hours 36 minutes

Match: Elevator access

All filters match

Price per night from

$252

180 Panoramic beach View and amazing Sunset.

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

Match: Elevator access

All filters match

Price per night from

$457

Sunsets on Beach Siesta Key top floor #402

Siesta Key condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Match: Elevator access

All filters match

Price per night from

$229

Sea~N~Blue

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Elevator access

All filters match

Price per night from

$401

Beachplace Building 3 unit 302

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Elevator access

All filters match

Price per night from

$187

SUNSET VISTA ON LONGBOAT KEY

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Elevator access

All filters match

Price per night from

$287

Siesta Dunes #300: By Beachside Management

Siesta Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Elevator access

All filters match

Price per night from

$331

Crystal Sands - 206 Tower: By Beachside Management

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Elevator access

All filters match

Price per night from

$263

Palm Bay Club - G46: By Beachside Management

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

Match: Elevator access

All filters match

Price per night from

$286

Crystal Sands - 803 Tower; By Beachside Management

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Elevator access

All filters match

Price per night from

$297

Sea Shell Cottage

Sarasota house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Match: Elevator access

All filters match

Price per night from

$172

Viewing 38 of 207
rentals in Osprey

×

Also consider