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Osprey Rentals

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Osprey Rentals

1,840 Houses

Welcome to the Paradise

Osprey house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$170

1 / 17

NEW! Siesta Key Condo w/Pool-Walk to Turtle Beach!

Osprey condo

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 10 minutes

Price per night from

$110

1 / 24

Sarasota Condo w/Deck - 1/2 mile to Turtle Beach!

Osprey apartment

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 48 minutes

Price per night from

$141

1 / 24

LUX VILLAs close to sparkling Siesta Key Beach.

Osprey villa

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$99

1 / 29

Spacious Sarasota Waterfront Pool Home with Dock - Amazing Sunsets Included

Osprey condo

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$280

1 / 24

Sunny 3BR Oasis w/ New Appliances & Furnishings—Near Coast, Dining

Osprey house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$97

1 / 24

Price per night from

$175

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Fisherman's Cove - A207

Osprey apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 58 minutes

Price per night from

$143

1 / 14

Responds fast! avg. 8 minutes

Price per night from

$64

1 / 33

Sarasota 05

Osprey house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$132

1 / 33

Osprey 01

Osprey condo

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$95

1 / 25

Tortoise Estates

Osprey house

5 bedrooms / 4 bathrooms / sleeps 12

Price per night from

$600

1 / 25

Beautiful South Sarasota Bay Home in Harbor Front Community

Osprey house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$75

1 / 16

2 BR / 2 BA Condo in Stoneybrook Golf & County Club - Sarasota & Siesta Key

Osprey condo

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$60

1 / 15

Sarasota 38

Osprey house

3 bedrooms / 3 bathrooms / sleeps 7

Price per night from

$124

1 / 32

Pelican Cove - Sarasota

Osprey condo

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$31

1 / 25

Condo with breathtaking View of Sarasota Bay

Osprey condo

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$68

1 / 18

CKBH (Casey Key Beach House)

Osprey house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$501

1 / 15

Great rentals within 20 miles that match your search

Jamaica Royale #92 on the #1 Beach in the USA!

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 50 minutes

Price per night from

$248

1 / 12

Luxury Venice Home with (heated) Private Pool and Lake View

Venice house

4 bedrooms / 3 bathrooms / sleeps 8

“I wish I was there right now :) !!!” My family and I had a wonderful time while at this beautiful, brand new, and completely furnished home. This was our first vacation since our daughter was born, and this place was the perfect retreat for the entir

Price per night from

$193

1 / 34

The Top Location on Siesta Key - Gertrude's Village House

Siesta Key house

3 bedrooms / 2 bathrooms / sleeps 10

“Location, location, location!” This little gem is the perfect get-a-way for a family or group of friends. I went with my daughter and her friends for her bachelorette weekend, and the fact that we were walking distance to ALL restaurants and shops was

Responds fast! avg. 50 minutes

Price per night from

$227

1 / 50

Sandy Toes Siesta Key Florida (6798)

Siesta Key house

2 bedrooms / 2 bathrooms / sleeps 6

“Very good” It's was great stay ,close to the beach (3-5)min walk,private,quite for vacation location. Car was parked in the garage and we loved it !!! Also you have everything you possibly need in a kitchen !! And condo has everything you need to go t

Responds fast! avg. 56 minutes

Price per night from

$240

1 / 37

Honeymoon Suite - Gulf views - next to Siesta Key Beach

Siesta Key apartment

1 bedroom / 2 bathrooms / sleeps 4

Responds fast! avg. 1 hour 16 minutes

Price per night from

$197

1 / 21

Oceanfront 1250 sq ft Townhome

Siesta Key villa

2 bedrooms / 3 bathrooms / sleeps 4

“Absolutely Perfect---one Kodak sunset after another” This townhome was gorgeous! We totally enjoyed our 3 week stay and hated to leave. Kelley (owner) could have not been more helpful. We fished off the dock and enjoyed watching the birds fish then

Price per night from

$158

1 / 15

Heated Pool 2 Bed 3 Bath near Siesta Key

Sarasota house

2 bedrooms / 3 bathrooms / sleeps 4

“Florida Trip” We rented this lovely home through Flipkey. This was a great rental for two couples and had everything you could possibly want at your fingertips. Just like home. Location was great and is located in a nice quiet neighborhood. Monica, th

Responds fast! avg. 44 minutes

Price per night from

$183

1 / 46

Beachfront Ground Level Suite - Remodeled - 2 king bedrooms

Siesta Key condo

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 58 minutes

Price per night from

$154

1 / 42

Island Oasis - steps to the Gulf & Bay, heated swimming pool

Manasota Key house

3 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$204

1 / 14

Top in Siesta Village at Best Beaches, Food & Entertainment! - Casa Van Lopik(J)

Siesta Key house

3 bedrooms / 2 bathrooms / sleeps 10

“Location, Location, Location!” Great house. Just as pictured and described. Dan and Jon are super-easy hosts. I like the little things - that the house is set up and fully ready. Abundance of supplies and towels, even beach chairs await! This having

Responds fast! avg. 50 minutes

Price per night from

$207

1 / 49

Nice in Nokomis

Nokomis house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$119

1 / 22

2 BR plus Den Condo. Golf Course & Water View

Sarasota apartment

3 bedrooms / 2 bathrooms / sleeps 6

“Wonderful” Fantastic place and owner Robin C very accomadating and very helpful everything here is all we need, so relaxed. This condo is near any kind of shopping, restaurants you could possibly be interested in! We don’t want our time to end!

Price per night from

$67

1 / 24

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 uni

Price per night from

$353

1 / 14

Beachy Villa, Pool, Bikes & Kayaks

Venice villa

3 bedrooms / 2 bathrooms / sleeps 7

“Great vacation home, Strongly recommend to fellow travlers” We Had a great time at this vacation Rental home. The pool was clean and very well maintained. The House was very clean and very well equiept with everything you would need. The Beds are eve

Responds fast! avg. 2 hours 21 minutes

Price per night from

$193

1 / 29

Comfortable Sarasota Villa

Sarasota villa

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$108

1 / 47

Beach Condo across from Siesta Beach

Sarasota condo

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$126

1 / 24

Two-Story Condo with Roof Deck

Englewood condo

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 2 hours 57 minutes

Price per night from

$142

1 / 37

Charming Siesta Key Village Unbeatable Location

Siesta Key condo

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 59 minutes

Price per night from

$126

1 / 22

Lovely 3 BR Home with Office & Heated Pool at Tara

Bradenton house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$124

1 / 16

Siesta Key Beach with gorgeous sunsets in Siesta Key

Sarasota condo

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$104

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