Osprey Vacation Rentals

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Our top choices for Osprey vacation rentals

Vacation Home in Bay Acres

Sunny Coastal Escape
10.0 out of 10, Exceptional, (4 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 $302
CA $604 total
includes taxes & fees
Apr 12 - Apr 13
Sunny Coastal Escape

Vacation Home in Bay Acres

Charming Osprey Home
10.0 out of 10, Exceptional, (1 review)
"Upon entering the property, we felt it was clean, bright and very welcoming. We loved the decor and the nice spaces in this two bedroom, two bath home. We thought the location was perfect, right across the main street is Walmart for quick grocery items, and we liked the amenities including a kettle for hot tea, a coffeemaker and a fully equipped kitchen! We would have liked to have more than two beach towels, but we made do with two. The laundry room was convenient for washing clothes and did...
United States
Van-Ha N.
The price is CA $338
CA $648 total
includes taxes & fees
Apr 7 - Apr 8
Charming Osprey Home

Mobile Home in Sarasota

Tiny House Siesta
2.0 star property
8.4 out of 10, Very good, (356 reviews)
"So cute, with clear instructions "
United States
Jair
The price is CA $152
CA $339 total
includes taxes & fees
Mar 25 - Mar 26
Tiny House Siesta
10.0 out of 10, Exceptional, (19 reviews)
"Great place loved how clean and put together everything was would definitely stay here again"
United States
Jacob
The price is CA $184
CA $390 total
includes taxes & fees
Mar 16 - Mar 17
Nestled in North Port. Updated 2 Bed / 1 Bath.
9.2 out of 10, Wonderful, (17 reviews)
"Property was perfect for the price."
United States
William M.
The price is CA $82
CA $213 total
includes taxes & fees
Mar 26 - Mar 27
Charming cottage for 2 across warm mineral springs park

Vacation Home in Olde Englewood Village

Old Floridian cottage in Historic Gulf Village
9.8 out of 10, Exceptional, (61 reviews)
"Very good, great location 👍👍"
United States
James M.
The price is CA $226
CA $463 total
includes taxes & fees
Apr 1 - Apr 2
Old Floridian cottage in Historic Gulf Village

Vacation Home in South Venice

Mimosa Memories
9.4 out of 10, Exceptional, (35 reviews)
"Nice house. Very clean. Comfortable bed and linens. Easy check in and out. Convenient location "
United States
Kelly
The price is CA $171
CA $481 total
includes taxes & fees
Apr 12 - Apr 13
Mimosa Memories
9.8 out of 10, Exceptional, (39 reviews)
"Perfect area, close to all the stores and restaurants"
United States
Maria B.
The price is CA $112
CA $274 total
includes taxes & fees
Mar 16 - Mar 17
Beautiful University Pines Studio in Sarasota
9.2 out of 10, Wonderful, (71 reviews)
"Second time staying here. Great location. "
United States
Nathan H.
The price is CA $285
CA $641 total
includes taxes & fees
Mar 29 - Mar 30
Siesta Key Village-Suite #3: A Block to the Beach!
9.2 out of 10, Wonderful, (37 reviews)
"Very nice place, easy check in, and communicative host"
United States
Cristopher M.
The price is CA $103
CA $237 total
includes taxes & fees
Mar 21 - Mar 22
Near to the Beach, UTC mall, SCF, IMG, Airport, Ringling Museum and much more
9.8 out of 10, Exceptional, (24 reviews)
"Nice place "
United States
Viktoriia
The price is CA $401
CA $791 total
includes taxes & fees
Mar 22 - Mar 23
Chic cottage, Vamo area, close to beaches, pet friendly, kayaks

Aparthotel in Venice Island

Kon Tiki Inn
2.5 star property
10.0 out of 10, Exceptional, (259 reviews)
"Great place! "
United States
Michelle
The price is CA $186
CA $211 total
includes taxes & fees
Apr 1 - Apr 2
Kon Tiki Inn
9.4 out of 10, Exceptional, (35 reviews)
"Our stay was lovely and beautiful l. Everything was nice and clean and anywhere we went was only 5 minutes away so the location and neighborhood was great! "
United States
Chelsey H.
The price is CA $236
CA $536 total
includes taxes & fees
Mar 28 - Mar 29
Beach Retreat - Completely Renovated!!Half Duplex, WIFI/TV,1mile to Beach.
9.4 out of 10, Exceptional, (30 reviews)
" Great location, office staff are very pleasant, room was very spacious with everything you need"
United States
GLENNA M.
Silver Sands Serenity – Unit 234 by RVA
9.4 out of 10, Exceptional, (75 reviews)
"Nicely decorated the host was easy to communicate with! Would definitely stay here again!"
United States
Tara H.
The price is CA $369
CA $726 total
includes taxes & fees
Mar 25 - Mar 26
3 Bedroom- Beachfront Condo with Beautiful Views of the Gulf
10.0 out of 10, Exceptional, (10 reviews)
"What a wonderful house to stay in! In a great location, very comfortable. Would definitely stay there again."
United States
Robert
The price is CA $287
CA $365 total
includes taxes & fees
Apr 9 - Apr 10
Modern Sarasota Retreat ★ 10 Min to Beach ★ Family Friendly no cleaning fee

Condo in Bayou Oaks

Riverside Oasis 1Bed/1Bath
9.2 out of 10, Wonderful, (49 reviews)
"Excellent place to stay"
United States
garry s.
The price is CA $100
CA $195 total
includes taxes & fees
Mar 22 - Mar 23
Riverside Oasis 1Bed/1Bath
9.8 out of 10, Exceptional, (31 reviews)
"Fantastic place! Host was excellent no issues. Would stay here again."
United States
David B.
The price is CA $247
CA $617 total
includes taxes & fees
Mar 17 - Mar 18
[lounge like locals] walk to siesta beach +bikes

Condo in Manasota Key

Chadwick Cove Resort & Marina
4.0 star property
10.0 out of 10, Exceptional, (17 reviews)
"Great place and location "
United States
Cathy
The price is CA $319
CA $975 total
includes taxes & fees
Apr 13 - Apr 14
Chadwick Cove Resort & Marina
9.6 out of 10, Exceptional, (65 reviews)
"Host was great, clean room, balcony was nice. It’s on the Main Street so not quite until the bars closed. Overall a great place to visit. "
United States
Brandon N.
The price is CA $300
CA $661 total
includes taxes & fees
Mar 31 - Apr 1
Siesta Cooler: Only Minutes Walk to Siesta Beach!
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 top-notch restaurants in this destination. While you're in the area, you can also enjoy the lively bars 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 17 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 Lido 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.