Osprey Rentals

Updating...

age 0-16
36 Results

Relevance

Price: low to high

Price: high to low

Reviews

36 Houses

Oceanfront home w/sunset views of Sarasota Bay

Sarasota house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Sea view

All filters match

Price per night from

$629

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

Match: Sea view

All filters match

Price per night from

$266

Sea Shell Condo-Right On Crescent Beach-Siesta Key

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 23 minutes

Match: Sea view

All filters match

Price per night from

$390

Gulfview/Bayfront Condo with Million Dollar Views on Siesta Key

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

Match: Sea view

All filters match

Price per night from

$109

Amazing Beachfront Condo, Siesta Key,

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Sea view

All filters match

Price per night from

$344

Renovated Beach Front 2BR/2BA Condo, Steps to beach, Gulf of Mexico Views

Siesta Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Sea view

All filters match

Price per night from

$277

Monthly Rental, 2 bed, 2 bath, Ocean view.

Sarasota condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Sea view

All filters match

Price per night from

$115

“Clean comfortable Siesta Key Condo with all the comforts of home...Perfect!” The condo is walking distance to shops, restaurants and quaint local tiki bar! The beach is a short walk across the street and through the beach-front section of the complex with lounge chairs and umbrellas available, very nice! I didn't mention the 2 pools (one beachside) and nice gym facilities also just downstairs of the unit. The covered parking space was an added plus! The condo was clean and very comfortable with all of the amenities of home which is greatly appreciated! You can even enjoy the view of the bayside inlet and beautiful landscaping from the kitchen through the entire wall of glass doors in the living/dining room! We had a wonderful week! The property owner Vic supplied more than enough information on the condo, local businesses and area maps! He was such a pleasure to work with! Thanks again Vic! We are already planning our next trip to Siesta Key in May!!

Match: Sea view

All filters match

Price per night from

$144

Match: Sea view

All filters match

Price per night from

$144

Match: Sea view

All filters match

Price per night from

$284

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: Sea view

All filters match

Price per night from

$602

Beautiful Crescent Beach on Siesta Key One of the

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Sea view

All filters match

Price per night from

$300

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

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Sea view

All filters match

Price per night from

$271

3BR/4BA TOWNHOUSE - POOL VIEW PARADISE - PRIVATE BEACH ACCESS

Siesta Key townhouse

  • 2 bedrooms
  • 4 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 38 minutes

Match: Sea view

All filters match

Price per night from

$430

Ten35 Seaside - Direct Gulf View: Residence 405

Siesta Key condo

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

Match: Sea view

All filters match

Price per night from

$859

Ten35 Seaside - Direct Gulf View: Residence 303

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Sea view

All filters match

Price per night from

$859

Ten35 Seaside - Direct Gulf View: Residence 403

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Sea view

All filters match

Price per night from

$859

Ten35 Seaside - Direct Gulf View: Residence 301

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Sea view

All filters match

Price per night from

$859

Casey Key 1-Bedroom Dockside Villa #3

Nokomis villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Match: Sea view

All filters match

Price per night from

$229

Ten35 Seaside - Direct Gulf View: Residence 501

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Sea view

All filters match

Price per night from

$950

Crescent Condos; by Beachside Management

Siesta Key condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Sea view

All filters match

Price per night from

$515

Buttonwood 442

Gulf Gate Estates condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Sea view

All filters match

Price per night from

$290

Magnificent Bayfront Condo - Resort Living on the Bay

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Sea view

All filters match

Price per night from

$161

Oceanfront home

Gulf Gate Estates house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

Match: Sea view

All filters match

Price per night from

$686

Casey Key 2-Bed Dockside Penthouse

Nokomis penthouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Match: Sea view

All filters match

Price per night from

$205

Ten35 Seaside - North Water View: Residence 506

Siesta Key condo

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Sea view

All filters match

Price per night from

$778

Ten35 Seaside - Direct Gulf View: Residence 307

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Sea view

All filters match

Price per night from

$859

Ten35 Seaside - North Water View: Residence 606

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Sea view

All filters match

Price per night from

$778

Ten35 Seaside - North Water View: Residence 310

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Sea view

All filters match

Price per night from

$630

Ten35 Seaside - South Water View: Residence 602

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Sea view

All filters match

Price per night from

$687

Ten35 Seaside - North Water View: Residence 410

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Sea view

All filters match

Price per night from

$630

Ten35 Seaside - South Water View: Residence 302

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Sea view

All filters match

Price per night from

$607

Beach House Residence - Penthouse; by Beachside Management

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Sea view

All filters match

Price per night from

$435

Ten35 Seaside - South Water View: Residence 502

Siesta Key condo

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Sea view

All filters match

Price per night from

$756

Crystal Sands - 803 Tower; By Beachside Management

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Sea view

All filters match

Price per night from

$297

Beach House Residence - 301; by Beachside Management

Siesta Key apartment

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Match: Sea view

All filters match

Price per night from

$630

×

Also consider