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.
$350 nightly
The price is $390
Apr 22 - Apr 23
Total with taxes and fees
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.
$355 nightly
The price is $396
Apr 27 - Apr 28
Total with taxes and fees
Sunny Coastal Escape

Tiny House Siesta

Tiny House Siesta
2.0 star property
Sarasota
8.4 out of 10, Very Good, (362 reviews)
"super clean and comfortable. we were 4 people and had a very comfortable and lovely stay. i felt super at home and the location is very centralized to everything "
United States
Adanna
$207 nightly
The price is $233
Apr 27 - Apr 28
Total with taxes and fees
Tiny House Siesta

Mimosa Memories

Mimosa Memories
South Venice
9.6 out of 10, Exceptional, (37 reviews)
"Me and my significant other took a little mini vacation wonderful house. It was very clean very beautiful inside, I like the beach vibes beautiful bedrooms. I recommend anybody to book this place. If I had to go back, I’ll book again. "
United States
Alexus
$292 nightly
The price is $326
Apr 26 - Apr 27
Total with taxes and fees
Mimosa Memories

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
$538 nightly
The price is $579
Apr 22 - Apr 23
Total with taxes and fees
Chadwick Cove Resort & Marina

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, (124 reviews)
"We enjoyed our stay. Is as shown in pictures and description. "
United States
Erin M.
$288 nightly
The price is $321
May 10 - May 11
Total with taxes and fees
Lavish Corner Condo! IMG Academy 5 Min · Anna Maria Island · Pools & Hot Tubs

Entire Standalone Lido Beach Villa, 1.2k sf, 1 block to the beach

Entire Standalone Lido Beach Villa, 1.2k sf, 1 block to the beach
Lido Key
9.8 out of 10, Exceptional, (124 reviews)
"Super clean, perfect location, and cool decor - and, most important, veeerry comfortable beds! We loved our stay! "
United States
Kevin L.
$259 nightly
The price is $289
Apr 23 - Apr 24
Total with taxes and fees
Entire Standalone Lido Beach Villa, 1.2k sf, 1 block to the beach

Kon Tiki Inn

Kon Tiki Inn
2.5 star property
Venice Island
10.0 out of 10, Exceptional, (271 reviews)
"Wonderful place! Super friendly host! Very clean, affordable! Great place!!"
United States
Carolyn
$127 nightly
The price is $143
May 4 - May 5
Total with taxes and fees
Kon Tiki Inn

Siesta Key Village-Suite #1: A block to the Beach!

Siesta Key Village-Suite #1: A block to the Beach!
Siesta Key Village
9.8 out of 10, Exceptional, (47 reviews)
"The apartment is clean and comfortable! Location is amazing! The beach, restaurants, and bars are all very close. The beach is great and easily accessible. 100% would stay here again! "
United States
Alex
$348 nightly
The price is $375
Apr 27 - Apr 28
Total with taxes and fees
Siesta Key Village-Suite #1: A block to the Beach!

[lounge like locals] walk to siesta beach +bikes

[lounge like locals] walk to siesta beach +bikes
Siesta Key
9.8 out of 10, Exceptional, (33 reviews)
"The perfect beach vacation! Cute, quaint and quiet."
United States
amy l.
$289 nightly
The price is $294
Apr 22 - Apr 23
Total with taxes and fees
[lounge like locals] walk to siesta beach +bikes

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.
$304 nightly
The price is $340
Apr 22 - Apr 23
Total with taxes and fees
Cozy Beach House Just Minutes From Siesta Key

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, (118 reviews)
"Perfect spot and host "
United States
Dee B.
$279 nightly
The price is $311
May 3 - May 4
Total with taxes and fees
Lakefront Condo · IMG Academy 5 Min · Anna Maria Island 15 Min· Pools & Hot Tubs

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, (182 reviews)
"Maggie ,the hostess, was great. Responsive and very accommodating for our needs. "
United States
David S.
$340 nightly
The price is $379
Apr 26 - Apr 27
Total with taxes and fees
Paradise Retreat with HEATED POOL-- Need We Say More

Fantastic Shorewalk Vacation 2 bed/2 bath condo/Lake view/close to IMG, beaches

Fantastic Shorewalk Vacation 2 bed/2 bath condo/Lake view/close to IMG, beaches
Bradenton
10.0 out of 10, Exceptional, (68 reviews)
"Excellent stay. Great place that was nice, clean and quiet. "
United States
David S.
$343 nightly
The price is $383
Apr 22 - Apr 23
Total with taxes and fees
Fantastic Shorewalk Vacation 2 bed/2 bath condo/Lake view/close to IMG, beaches

Drift & Dune – Longboat Beachfront #101 RVA

Drift & Dune – Longboat Beachfront #101 RVA
Longboat Key
8.6 out of 10, Excellent, (79 reviews)
"Check in and out was easy, the pool and condo were great, and the location was awesome!"
United States
Bailey B.
$362 nightly
The price is $403
Apr 29 - Apr 30
Total with taxes and fees
Drift & Dune – Longboat Beachfront #101 RVA

Beachfront Studio – Cabana #5B by RVA

Beachfront Studio – Cabana #5B by RVA
Longboat Key
8.2 out of 10, Very Good, (77 reviews)
"Very nice place, clean and quiet. Staff very accommodating and professional. Definitely 5 star. "
United States
K M.
$269 nightly
The price is $301
Apr 23 - Apr 24
Total with taxes and fees
Beachfront Studio – Cabana #5B by RVA

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, (155 reviews)
"Very clean condo , we enjoyed closeness of the beaches."
United States
Joanna M.
$282 nightly
The price is $315
Apr 27 - Apr 28
Total with taxes and fees
Cozy 2BR Condo · IMG Academy 5 Min · Anna Maria Island 15 Min · Pools & Hot Tubs

Casa Azul 2Bed/1Bath

Casa Azul 2Bed/1Bath
Bayou Oaks
9.6 out of 10, Exceptional, (74 reviews)
"Very nice place beautiful home comfortable stay"
United States
Emanuel I.
$175 nightly
The price is $195
Apr 27 - Apr 28
Total with taxes and fees
Casa Azul 2Bed/1Bath

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, (23 reviews)
"Fun place "
United States
Maureen
$239 nightly
The price is $267
May 17 - May 18
Total with taxes and fees
Secluded Cottage with Hot Tub, Walking Distance to Benderson and UTC.

Siesta Cooler: Only Minutes Walk to Siesta Beach!

Siesta Cooler: Only Minutes Walk to Siesta Beach!
Siesta Key Village
9.6 out of 10, Exceptional, (71 reviews)
"Perfect little place for a long weekend away. Conveniently located by everything "
United States
Emily D.
$388 nightly
The price is $421
Apr 23 - Apr 24
Total with taxes and fees
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

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 $143 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 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 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.