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.
$422 nightly
The price is $470
Mar 31 - Apr 1
Total with taxes and fees
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.
$446 nightly
The price is $497
Mar 31 - Apr 1
Total with taxes and fees
Charming Osprey Home

Mobile Home in Sarasota

Tiny House Siesta
2.0 star property
8.4 out of 10, Very Good, (352 reviews)
"Clean room, easy check in, beach nearby 15 minute walk, Florida Fun Rides scooter rental place nearby"
United States
Justice
$219 nightly
The price is $247
Mar 7 - Mar 8
Total with taxes and fees
Tiny House Siesta
9.2 out of 10, Wonderful, (13 reviews)
"Property was very nice and exactly what I was looking for while working remote. Would absolutely recommend it to anyone and look forward to coming back in the future."
United States
Jake R.
$150 nightly
The price is $167
Mar 1 - Mar 2
Total with taxes and fees
#3 Small house walking distance to Warm Mineral Spring
9.0 out of 10, Wonderful, (14 reviews)
"Property was perfect for the price."
United States
William M.
$145 nightly
The price is $161
Mar 1 - Mar 2
Total with taxes and fees
Charming cottage for 2 across warm mineral springs park

Vacation Home in South Venice

Mimosa Memories
9.4 out of 10, Exceptional, (34 reviews)
"Nice quiet home , very clean. "
United States
David M.
$292 nightly
The price is $326
Mar 2 - Mar 3
Total with taxes and fees
Mimosa Memories
10.0 out of 10, Exceptional, (18 reviews)
"Great place loved how clean and put together everything was would definitely stay here again"
United States
Jacob
$234 nightly
The price is $262
Mar 1 - Mar 2
Total with taxes and fees
Nestled in North Port. Updated 2 Bed / 1 Bath.
9.8 out of 10, Exceptional, (39 reviews)
"Perfect area, close to all the stores and restaurants"
United States
Maria B.
$173 nightly
The price is $193
Mar 11 - Mar 12
Total with taxes and fees
Beautiful University Pines Studio in Sarasota
9.2 out of 10, Wonderful, (37 reviews)
"Very nice place, easy check in, and communicative host"
United States
Cristopher M.
$155 nightly
The price is $173
Mar 21 - Mar 22
Total with taxes and fees
Near to the Beach, UTC mall, SCF, IMG, Airport, Ringling Museum and much more
8.2 out of 10, Very Good, (74 reviews)
"Very nice place, clean and quiet. Staff very accommodating and professional. Definitely 5 star. "
United States
K M.
$274 nightly
The price is $306
Mar 3 - Mar 4
Total with taxes and fees
Beachfront Studio – Cabana #5B by RVA

Condo in Bayou Oaks

Riverside Oasis 1Bed/1Bath
9.2 out of 10, Wonderful, (45 reviews)
"Excellent place to stay"
United States
garry s.
$140 nightly
The price is $156
Mar 22 - Mar 23
Total with taxes and fees
Riverside Oasis 1Bed/1Bath
9.8 out of 10, Exceptional, (27 reviews)
"Everything was great!"
United States
Lisa and Colin M.
$351 nightly
The price is $393
Mar 4 - Mar 5
Total with taxes and fees
Enjoy Coastal Townhome w/ sunset views! Near The Gulf’s most popular beaches!
9.8 out of 10, Exceptional, (27 reviews)
"Clean and comfortable. "
United States
Laney
$369 nightly
The price is $378
Mar 8 - Mar 9
Total with taxes and fees
[escape to paradise] siesta key beach getaway
9.6 out of 10, Exceptional, (14 reviews)
"We had a lovely week in this property and even saw some dolphins swimming by!"
United States
Hilda H.
$597 nightly
The price is $666
Mar 1 - Mar 2
Total with taxes and fees
Manatee at Coastal Breeze | Stunning Bay Views | Walk to Beach | Dock Access | Fishing | Beach Gear

Apartment in Gulf Gate Estates

2 Miles to Siesta Key
10.0 out of 10, Exceptional, (22 reviews)
"Had a great stay! "
United States
Keith K.
$139 nightly
The price is $154
Mar 3 - Mar 4
Total with taxes and fees
2 Miles to Siesta Key
7.8 out of 10, Good, (11 reviews)
"Amazing property with direct beach access. "
United States
maria m.
$312 nightly
The price is $348
Mar 3 - Mar 4
Total with taxes and fees
Beachfront- Longboat Key efficiency condo w/ king size bed, steps to sand.
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.
$355 nightly
The price is $396
Mar 28 - Mar 29
Total with taxes and fees
Beach Retreat - Completely Renovated!!Half Duplex, WIFI/TV,1mile to Beach.
8.8 out of 10, Excellent, (74 reviews)
"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: The condo was clean and had all that we needed for our two night stay. Loved it will be back again... just a little walk to the beach and some he pool was very nice as well."
United States
Nancy C.
$327 nightly
The price is $364
Mar 10 - Mar 11
Total with taxes and fees
Newly Renovated 1BR – Cabana Beach #5 RVA

Apartment in Gulf Gate Estates

Two Miles to Siesta Key
10.0 out of 10, Exceptional, (46 reviews)
"Terry was a great host. The apartment was very comfortable and had everything we needed for our short stay in Sarasota. Would stay here again."
United States
Robert C.
$139 nightly
The price is $154
Mar 11 - Mar 12
Total with taxes and fees
Two Miles to Siesta Key
7.8 out of 10, Good, (7 reviews)
"Great locale right on the beach "
United States
Carole
$329 nightly
The price is $367
Mar 11 - Mar 12
Total with taxes and fees
Beachfront Bliss on Longboat Key- Steps to the sand
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

Everything you need to know about Osprey vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Osprey vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Osprey vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Osprey vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Osprey. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Osprey in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $247 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Osprey rentals

At Expedia, we put the best Osprey vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Osprey rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Osprey vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Osprey. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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 Heron Suites & Villas: This vacation home rental near Osprey is located on the waterfront and has an outdoor pool, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a full-sized fridge, a stovetop, and a microwave.

How many vacation rentals are there in Osprey?

With 18 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.