Osprey Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
May 15 - May 17
In two months
Jun 26 - Jun 28
In three months
Jul 24 - Jul 26
In four months
Aug 21 - Aug 23

Our top choices for Osprey vacation rentals

Beach towels

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.
$312 nightly
The price is $347
Apr 28 - Apr 29
Total with taxes and fees
Charming Osprey Home
Beach

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
May 1 - May 2
Total with taxes and fees
Sunny Coastal Escape
Cabin (Tiny House - The Siesta) | Living area | Flat-screen TV, Netflix, streaming services

Tiny House Siesta

Tiny House Siesta
2.0 star property
Sarasota
8.4 out of 10, Very Good, (362 reviews)
"Cute place perfect for our holiday beach stay."
United States
Shelly
$207 nightly
The price is $233
Apr 28 - Apr 29
Total with taxes and fees
Tiny House Siesta
Terrace/patio

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
$127 nightly
The price is $143
May 28 - May 29
Total with taxes and fees
Kon Tiki Inn
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, (22 reviews)
"Great place loved how clean and put together everything was would definitely stay here again"
United States
Jacob
$195 nightly
The price is $218
Apr 28 - Apr 29
Total with taxes and fees
Nestled in North Port. Updated 2 Bed / 1 Bath.
Property grounds

Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,451 reviews)
"Really close to the beach, beautiful pool, friendly staff!"
United States
crystal
$209 nightly
The price is $236
May 25 - May 26
Total with taxes and fees
Tropical Beach Resorts
Deluxe Suite, 2 Bedrooms | In-room safe, iron/ironing board, free WiFi

SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (115 reviews)
"Amazing staff, and beautiful property. Very nice place to visit and kid friendly."
United States
Ahmad
$296 nightly
The price is $335
May 10 - May 11
Total with taxes and fees
SeaSpray Resort
Front of property - evening/night

Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,241 reviews)
"Wonderful spot to stay! Traveled solo and Captiva was perfect "
United States
Angela
$207 nightly
The price is $232
Apr 28 - Apr 29
Total with taxes and fees
Captiva Beach Resort
Exterior

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 28 - Apr 29
Total with taxes and fees
Chadwick Cove Resort & Marina
Beachside One Bedroom Suite | Premium bedding, pillowtop beds, individually decorated

A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (628 reviews)
"Love this place"
United States
Marialis
$221 nightly
The price is $249
May 18 - May 19
Total with taxes and fees
A Beach Retreat
Beach nearby, white sand, beach umbrellas, beach towels

The Inn On Siesta Key

The Inn On Siesta Key
3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (198 reviews)
"The room was clean and spacious with all the amenities. The location was perfect. I would highly recommend!"
United States
Amanda
$285 nightly
The price is $322
Apr 28 - Apr 29
Total with taxes and fees
The Inn On Siesta Key
Beach

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.
$339 nightly
The price is $378
Apr 28 - Apr 29
Total with taxes and fees
Paradise Retreat with HEATED POOL-- Need We Say More
Lobby

Venice Beach Villas

Venice Beach Villas
3.0 star property
Venice Island
9.4 out of 10, Exceptional, (478 reviews)
"Exceptional location both to the beach and restaurants. The facility has everything you need to augment your stay: bikes, beach chairs and umbrellas, coolers and pool floats. The room is immaculate too."
United States
Kathy
$129 nightly
The price is $146
May 11 - May 12
Total with taxes and fees
Venice Beach Villas
Interior

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
Mimosa Memories
Beach

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.
$266 nightly
The price is $297
Apr 28 - Apr 29
Total with taxes and fees
Cozy 2BR Condo · IMG Academy 5 Min · Anna Maria Island 15 Min · Pools & Hot Tubs
5365 Calle Florida, Siesta Key, FL W/Pool | Private kitchen

Siesta Key Island Rentals

Siesta Key Island Rentals
3.0 star property
Siesta Key
9.6 out of 10, Exceptional, (66 reviews)
"Excellent location , minute walk to local bars and supermarket. Right across from beautiful siesta key beach."
United States
Alessandra
Siesta Key Island Rentals
Beach

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.
$266 nightly
The price is $297
Apr 28 - Apr 29
Total with taxes and fees
Lakefront Condo · IMG Academy 5 Min · Anna Maria Island 15 Min· Pools & Hot Tubs
Beach

Bradenton condo short drive from GORGEOUS Anna Maria Island, near IMG

Bradenton condo short drive from GORGEOUS Anna Maria Island, near IMG
Bradenton
9.6 out of 10, Exceptional, (25 reviews)
"Perfect for our weekend getaway Full kitchen / easy for cooking in Pool was nice for us"
United States
Carolyn
$212 nightly
The price is $237
Apr 28 - Apr 29
Total with taxes and fees
Bradenton condo short drive from GORGEOUS Anna Maria Island, near IMG
Smart TV

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.
$382 nightly
The price is $420
Apr 28 - Apr 29
Total with taxes and fees
Sunset and beach view from your balcony Unit 403
Sun loungers, beach towels

Beautifully furnished condo

Beautifully furnished condo
Bradenton
9.8 out of 10, Exceptional, (156 reviews)
"Excellent host, great communication. Condo was clean, good quiet location. "
United States
Brandy E.
$267 nightly
The price is $298
May 1 - May 2
Total with taxes and fees
Beautifully furnished condo
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Osprey Hotel Reviews

Azul Resort Siesta Key

Azul Resort Siesta Key

10/10 Excellent
"The location is great short walk distance to to beach, stores and restaurants. The room I stayed in didn’t have microwave I stayed for only one night but if I was going to stay longer it will be a down point to me. The room was clean and well maintained. I arrived after the reception was closed but check in was easy I was give my door code after a short phone call. Definitely recommend this property. "
alessandra 1-night trip
Posted 5 hours ago
Azul Resort Siesta Key

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.

Explore a world of travel with Expedia

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.