Osprey Vacation Rentals

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Our top choices for Osprey vacation rentals

Charming Osprey Home

Charming Osprey Home
Bay Acres
10.0 out of 10, Exceptional, (2 reviews)
"We had a positive experience staying at Linda’s duplex in Osprey. Linda was a lovely host and even furnished us with beach chairs and a cabana . The place was spotless & location was convenient for us as we explored most of the Sarasota, Venice & Naples area. Highly recommended staying at this lovely duplex. "
United States
Diane S.
The price is CA $202
CA $473 total
includes taxes & fees
Apr 30 - May 1
Charming Osprey Home

Sunny Coastal Escape

Sunny Coastal Escape
Bay Acres
10.0 out of 10, Exceptional, (6 reviews)
"Great location for exploring north & south! House was very clean and comfy. We appreciated the excellent communication with our nice host, Lynn."
United States
Kaja F.
The price is CA $259
CA $546 total
includes taxes & fees
May 20 - May 21
Sunny Coastal Escape

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, (23 reviews)
"Great place loved how clean and put together everything was would definitely stay here again"
United States
Jacob
The price is CA $118
CA $302 total
includes taxes & fees
May 3 - May 4
Nestled in North Port. Updated 2 Bed / 1 Bath.

Path to Paradise.

Path to Paradise.
Olde Englewood Village
The price is CA $146
CA $416 total
includes taxes & fees
May 1 - May 2
Path to Paradise.

Chadwick Cove Resort & Marina

Chadwick Cove Resort & Marina
4.0 star property
Manasota Key
10.0 out of 10, Exceptional, (17 reviews)
"Great place and location "
United States
Cathy
The price is CA $156
CA $788 total
includes taxes & fees
May 6 - May 7
Chadwick Cove Resort & Marina

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 CA $102
CA $258 total
includes taxes & fees
Apr 30 - May 1
Beautiful University Pines Studio in Sarasota

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, (74 reviews)
"Wonderful Stay"
United States
Christopher R.
The price is CA $112
CA $358 total
includes taxes & fees
May 3 - May 4
Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.

Kon Tiki Inn

Kon Tiki Inn
2.5 star property
Venice Island
10.0 out of 10, Exceptional, (271 reviews)
"Very clean & spacious pet friendly room. Would definitely stay there again."
United States
Brittany
The price is CA $171
CA $193 total
includes taxes & fees
May 6 - May 7
Kon Tiki Inn

Lakefront Condo · IMG Academy 5 Min · Anna Maria Island 15 Min· Pools & Hot Tubs

Lakefront Condo · IMG Academy 5 Min · Anna Maria Island 15 Min· Pools & Hot Tubs
Bradenton
9.8 out of 10, Exceptional, (120 reviews)
"Perfect spot and host "
United States
Dee B.
The price is CA $139
CA $410 total
includes taxes & fees
Apr 30 - May 1
Lakefront Condo · IMG Academy 5 Min · Anna Maria Island 15 Min· Pools & Hot Tubs

Sunset and beach view from your balcony Unit 403

Sunset and beach view from your balcony Unit 403
Longboat Key
9.8 out of 10, Exceptional, (113 reviews)
"Beach view with sunset!!"
United States
joseph l.
The price is CA $322
CA $660 total
includes taxes & fees
May 2 - May 3
Sunset and beach view from your balcony Unit 403

Cozy Beach House Just Minutes From Siesta Key

Cozy Beach House Just Minutes From Siesta Key
Sarasota
8.8 out of 10, Excellent, (14 reviews)
"Great location, family friendly! "
United States
Lyna T.
The price is CA $235
CA $471 total
includes taxes & fees
Apr 30 - May 1
Cozy Beach House Just Minutes From Siesta Key

Beautifully furnished condo

Beautifully furnished condo
Bradenton
9.8 out of 10, Exceptional, (157 reviews)
"Excellent host, great communication. Condo was clean, good quiet location. "
United States
Brandy E.
The price is CA $172
CA $410 total
includes taxes & fees
May 1 - May 2
Beautifully furnished condo

[escape to paradise] siesta key beach getaway

[escape to paradise] siesta key beach getaway
Siesta Key
9.8 out of 10, Exceptional, (30 reviews)
"Very clean and great location! Beds very comfortable and owner very responsive and accommodating! Highly recommend staying here!"
United States
Tim T.
The price is CA $149
CA $436 total
includes taxes & fees
May 3 - May 4
[escape to paradise] siesta key beach getaway

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, (81 reviews)
"Beautiful condo and perfect location for a relaxing beach getaway! We celebrated my husband’s 50th birthday and it was perfect! We will definitely book again! "
United States
Yasamin G.
The price is CA $271
CA $599 total
includes taxes & fees
May 3 - May 4
3 Bedroom- Beachfront Condo with Beautiful Views of the Gulf

Cozy 2BR Condo · IMG Academy 5 Min · Anna Maria Island 15 Min · Pools & Hot Tubs

Cozy 2BR Condo · IMG Academy 5 Min · Anna Maria Island 15 Min · Pools & Hot Tubs
Bradenton
9.8 out of 10, Exceptional, (156 reviews)
"Very clean condo , we enjoyed closeness of the beaches."
United States
Joanna M.
The price is CA $139
CA $410 total
includes taxes & fees
Apr 30 - May 1
Cozy 2BR Condo · IMG Academy 5 Min · Anna Maria Island 15 Min · Pools & Hot Tubs

Lavish Corner Condo! IMG Academy 5 Min · Anna Maria Island · Pools & Hot Tubs

Lavish Corner Condo! IMG Academy 5 Min · Anna Maria Island · Pools & Hot Tubs
Bradenton
10.0 out of 10, Exceptional, (127 reviews)
"We enjoyed our stay. Is as shown in pictures and description. "
United States
Erin M.
The price is CA $160
CA $439 total
includes taxes & fees
May 10 - May 11
Lavish Corner Condo! IMG Academy 5 Min · Anna Maria Island · Pools & Hot Tubs

Luxury House Walking Distance to Ocean - Sleeps 12

Luxury House Walking Distance to Ocean - Sleeps 12
Central Sarasota
9.8 out of 10, Exceptional, (16 reviews)
"Great place perfect location to the marina, and downtown area. Highly recommended thanks "
United States
Domingo B.
The price is CA $286
CA $651 total
includes taxes & fees
May 1 - May 2
Luxury House Walking Distance to Ocean - Sleeps 12

Paradise Retreat with HEATED POOL-- Need We Say More

Paradise Retreat with HEATED POOL-- Need We Say More
South Bradenton
10.0 out of 10, Exceptional, (183 reviews)
"Maggie ,the hostess, was great. Responsive and very accommodating for our needs. "
United States
David S.
The price is CA $219
CA $541 total
includes taxes & fees
May 10 - May 11
Paradise Retreat with HEATED POOL-- Need We Say More

Secluded Cottage with Hot Tub, Walking Distance to Benderson and UTC.

Secluded Cottage with Hot Tub, Walking Distance to Benderson and UTC.
The Meadows
10.0 out of 10, Exceptional, (24 reviews)
"Fun place "
United States
Maureen
The price is CA $149
CA $363 total
includes taxes & fees
May 17 - May 18
Secluded Cottage with Hot Tub, Walking Distance to Benderson and UTC.

Two Miles to Siesta Key

Two Miles to Siesta Key
Gulf Gate Estates
10.0 out of 10, Exceptional, (52 reviews)
"Easy location to find. Clean room"
United States
Jennifer
The price is CA $108
CA $194 total
includes taxes & fees
May 6 - May 7
Two Miles to Siesta Key
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

Find out more about Osprey

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Osprey. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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 free 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 19 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.