Osprey Vacation Rentals

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Check prices for these dates

In two weeks
Jun 5 - Jun 7
In two months
Jul 17 - Jul 19
In three months
Aug 14 - Aug 16
In four months
Sep 11 - Sep 13

Our top choices for Osprey vacation rentals

Fridge, microwave, oven, stovetop

Path to Paradise.

Path to Paradise.
Olde Englewood Village
The price is ￥12,724
￥43,377 total
includes taxes & fees
May 25 - May 26
Path to Paradise.
Interior

Charming cottage for 2 across warm mineral springs park

Charming cottage for 2 across warm mineral springs park
Warm Mineral Springs
9.2 out of 10, Wonderful, (24 reviews)
"Great little place! Wish we could have spent more time"
United States
Tricia W.
The price is ￥7,943
￥22,923 total
includes taxes & fees
May 28 - May 29
Charming cottage for 2 across warm mineral springs park
Living area

Nestled in North Port. Updated 2 Bed / 1 Bath.

Nestled in North Port. Updated 2 Bed / 1 Bath.
North Port
10.0 out of 10, Exceptional, (24 reviews)
"Great place loved how clean and put together everything was would definitely stay here again"
United States
Jacob
The price is ￥13,679
￥34,611 total
includes taxes & fees
May 24 - May 25
Nestled in North Port. Updated 2 Bed / 1 Bath.
Exterior

Chadwick Cove Resort & Marina

Chadwick Cove Resort & Marina
4.0 star property
Manasota Key
9.6 out of 10, Exceptional, (19 reviews)
"Great place and location "
United States
Cathy
The price is ￥15,422
￥88,822 total
includes taxes & fees
May 30 - May 31
Chadwick Cove Resort & Marina
Interior

Charming 2 bedroom 2 bathroom home with pool in Sarasota with central location.

Charming 2 bedroom 2 bathroom home with pool in Sarasota with central location.
Kensington Park
9.4 out of 10, Exceptional, (34 reviews)
"Nice place to stay "
United States
Kari O.
The price is ￥27,163
￥64,926 total
includes taxes & fees
May 31 - Jun 1
Charming 2 bedroom 2 bathroom home with pool in Sarasota with central location.
1 bedroom, desk, free WiFi, bed sheets

Near to the Beach, UTC mall, SCF, IMG, Airport, Ringling Museum and much more

Near to the Beach, UTC mall, SCF, IMG, Airport, Ringling Museum and much more
Bayshore Gardens
9.2 out of 10, Wonderful, (41 reviews)
"The host was excellent and the place was clean and just as expected."
United States
Jim M.
The price is ￥11,914
￥27,410 total
includes taxes & fees
May 26 - May 27
Near to the Beach, UTC mall, SCF, IMG, Airport, Ringling Museum and much more
Microwave, oven, stovetop

Charming 2-bedroom house in lovely Sarasota with yard.

Charming 2-bedroom house in lovely Sarasota with yard.
Kensington Park
9.0 out of 10, Wonderful, (25 reviews)
"Great little place. Very clean. Convenient location. All the niceties. "
United States
Ryan M.
The price is ￥13,582
￥32,885 total
includes taxes & fees
May 26 - May 27
Charming 2-bedroom house in lovely Sarasota with yard.
Terrace/patio

BAREFOOT BUNGALOW- 1O MINUTES TO SIESTA BEACH AND AMENITIES! PET FRIENDLY!

BAREFOOT BUNGALOW- 1O MINUTES TO SIESTA BEACH AND AMENITIES! PET FRIENDLY!
Ridge Wood Heights
10.0 out of 10, Exceptional, (17 reviews)
"Great place. Clean with everything you need"
United States
Thomas Lee
The price is ￥20,015
￥53,624 total
includes taxes & fees
May 26 - May 27
BAREFOOT BUNGALOW- 1O MINUTES TO SIESTA BEACH AND AMENITIES! PET FRIENDLY!
Fridge, microwave, coffee/tea maker, electric kettle

Beautiful University Pines Studio in Sarasota

Beautiful University Pines Studio in Sarasota
Sarasota
9.8 out of 10, Exceptional, (40 reviews)
"Perfect area, close to all the stores and restaurants"
United States
Maria B.
The price is ￥11,580
￥29,883 total
includes taxes & fees
May 24 - May 25
Beautiful University Pines Studio in Sarasota
Beach

Cozy Beach House Just Minutes From Siesta Key

Cozy Beach House Just Minutes From Siesta Key
Sarasota
9.0 out of 10, Wonderful, (16 reviews)
"Great location, family friendly! "
United States
Lyna T.
The price is ￥27,383
￥54,769 total
includes taxes & fees
May 26 - May 27
Cozy Beach House Just Minutes From Siesta Key
Dining

Retro Sarasota Haven: Private Yard| BBQ |Downtown

Retro Sarasota Haven: Private Yard| BBQ |Downtown
Southgate
The price is ￥7,498
￥36,676 total
includes taxes & fees
May 26 - May 27
Retro Sarasota Haven: Private Yard| BBQ |Downtown
On the beach, sun loungers, beach towels

3 Bedroom- Beachfront Condo with Beautiful Views of the Gulf

3 Bedroom- Beachfront Condo with Beautiful Views of the Gulf
Manasota Key
9.4 out of 10, Exceptional, (86 reviews)
"Beautiful condo!! The owner was very responsive and attentive. We will definitely recommend this place to anyone!"
United States
Kay C.
The price is ￥31,452
￥69,061 total
includes taxes & fees
May 24 - May 25
3 Bedroom- Beachfront Condo with Beautiful Views of the Gulf
Fridge, microwave, oven, stovetop

[lounge like locals] walk to siesta beach +bikes

[lounge like locals] walk to siesta beach +bikes
Siesta Key
9.8 out of 10, Exceptional, (34 reviews)
"Only 10 mins walking from the Village, so easy to check in, great communication, super clean. "
United States
John
The price is ￥17,834
￥52,277 total
includes taxes & fees
May 26 - May 27
[lounge like locals] walk to siesta beach +bikes
Fridge, microwave, oven, stovetop

Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.

Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.
Southgate
10.0 out of 10, Exceptional, (75 reviews)
"Wonderful Stay"
United States
Christopher R.
The price is ￥17,315
￥45,180 total
includes taxes & fees
Jun 6 - Jun 7
Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.
House, Lakeside | Living area | 39-inch flat-screen TV with digital channels, TV, streaming services

Siesta Heron Suites & Villas

Siesta Heron Suites & Villas
3.5 star property
Siesta Key
8.4 out of 10, Very Good, (43 reviews)
"Clean rooms, convenient location, nice property and amenities. Simple check-in and check-out"
United States
Christopher Robert
The price is ￥18,668
￥53,046 total
includes taxes & fees
May 25 - May 26
Siesta Heron Suites & Villas
Terrace/patio

Kon Tiki Inn

Kon Tiki Inn
2.5 star property
Venice Island
10.0 out of 10, Exceptional, (278 reviews)
"Property is super cute and clean and has everything you need!"
United States
Vanessa
The price is ￥17,466
￥19,736 total
includes taxes & fees
Jun 1 - Jun 2
Kon Tiki Inn
Beach nearby, beach towels

Gulf Coast 2BR Condo · IMG Academy 5 min · Anna Maria Island 15 Min · Two Pools

Gulf Coast 2BR Condo · IMG Academy 5 min · Anna Maria Island 15 Min · Two Pools
Bradenton
9.8 out of 10, Exceptional, (122 reviews)
"Perfect spot and host "
United States
Dee B.
The price is ￥17,871
￥47,080 total
includes taxes & fees
Jun 1 - Jun 2
Gulf Coast 2BR Condo · IMG Academy 5 min · Anna Maria Island 15 Min · Two Pools
Beach nearby, sun loungers, beach towels

Two Miles to Siesta Key

Two Miles to Siesta Key
Gulf Gate Estates
10.0 out of 10, Exceptional, (53 reviews)
"Easy location to find. Clean room"
United States
Jennifer
The price is ￥11,914
￥21,845 total
includes taxes & fees
Jun 15 - Jun 16
Two Miles to Siesta Key
Pool

Sleeps 10 - Pool w/ Slide - Games - 6 Min to IMG

Sleeps 10 - Pool w/ Slide - Games - 6 Min to IMG
South Bradenton
The price is ￥34,947
￥84,573 total
includes taxes & fees
May 26 - May 27
Sleeps 10 - Pool w/ Slide - Games - 6 Min to IMG
Beach nearby, sun loungers, beach towels

Luxury Gulf Coast Condo · Anna Maria Beaches 15 Min · IMG 5 Min · Resort Pools

Luxury Gulf Coast Condo · Anna Maria Beaches 15 Min · IMG 5 Min · Resort Pools
Bradenton
10.0 out of 10, Exceptional, (128 reviews)
"Lovely spot. Clean and roomy. Host was easy to contact and accommodating. "
United States
April R.
The price is ￥16,759
￥46,005 total
includes taxes & fees
May 24 - May 25
Luxury Gulf Coast Condo · Anna Maria Beaches 15 Min · IMG 5 Min · Resort Pools
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Osprey Hotel Reviews

Kompose Boutique Hotel

Kompose Boutique Hotel

8/10 Good
"Good value for money spent. The breakfast buffet was good. Staff were very helpful."
richard 1-night trip
Posted 1 hour ago
Kompose Boutique Hotel

Find out more about Osprey

Search for holiday rentals in Osprey on Expedia! You can easily find your home rentals, villas, holiday apartments in Osprey using one of the methods below:

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Frequently asked questions

Can I find vacation rentals in Osprey?

Yes, we have vacation rentals in Osprey near Jim Neville Marine Preserve, or you can go with a more secluded option if you're looking for extra privacy while you relax. Visitors to Osprey speak positively about the popular beaches and lively bars in this destination. While you're in the area, you can also enjoy the top-notch restaurants and shops.

What are some of the best vacation rentals in Osprey?

Siesta Key Island Rentals: This vacation home rental near Osprey comes with WiFi so you can feel at home during your trip. This vacation rental also comes with free parking to give you added peace of mind.

How many vacation rentals are there in Osprey?

With 16 Expedia vacation rentals, you're sure to find just the right place for your Osprey stay.

What’s there to see and do in Osprey?

Family-friendly attractions include Jim Neville Marine Preserve and Nancy's Consignments, whereas Turtle Beach and Nokomis Beach are a couple of great spots to enjoy the outdoors. While in the area, you can also visit popular places like Siesta Key Beach and Venice Beach.

What’s a vacation rental in Osprey like?

Vacation rentals are private properties you can stay in for a long or short time in Osprey. Vacation rentals provide amenities such as WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of security away from shared hotel elevators and lobbies packed with people while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a hotel, which makes a vacation rental an attractive option for families.