Osprey Holiday Rentals

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Our top choices for Osprey holiday 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 AU$490
includes taxes & fees
17 May - 18 May
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 AU$548
includes taxes & fees
17 May - 18 May
Sunny Coastal Escape

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
The price is AU$326
includes taxes & fees
28 Apr - 29 Apr
Tiny House Siesta

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 AU$198
includes taxes & fees
7 May - 8 May
Kon Tiki Inn

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
The price is AU$314
includes taxes & fees
29 Apr - 30 Apr
Nestled in North Port. Updated 2 Bed / 1 Bath.

Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,452 reviews)
"Really close to the beach, beautiful pool, friendly staff!"
United States
crystal
The price is AU$330
includes taxes & fees
25 May - 26 May
Tropical Beach Resorts

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
The price is AU$458
includes taxes & fees
27 May - 28 May
SeaSpray Resort

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
The price is AU$307
includes taxes & fees
28 Apr - 29 Apr
Captiva Beach Resort

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 AU$809
includes taxes & fees
28 Apr - 29 Apr
Chadwick Cove Resort & Marina

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
The price is AU$314
includes taxes & fees
18 May - 19 May
A Beach Retreat

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
The price is AU$619
includes taxes & fees
11 May - 12 May
The Inn On Siesta Key

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.
The price is AU$531
includes taxes & fees
28 Apr - 29 Apr
Paradise Retreat with HEATED POOL-- Need We Say More

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
The price is AU$180
includes taxes & fees
11 May - 12 May
Venice Beach Villas

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

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 AU$439
includes taxes & fees
28 Apr - 29 Apr
Cozy 2BR Condo · IMG Academy 5 Min · Anna Maria Island 15 Min · Pools & Hot Tubs

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

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 AU$439
includes taxes & fees
28 Apr - 29 Apr
Lakefront Condo · IMG Academy 5 Min · Anna Maria Island 15 Min· Pools & Hot Tubs

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
The price is AU$381
includes taxes & fees
11 May - 12 May
Bradenton condo short drive from GORGEOUS Anna Maria Island, near IMG

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 AU$580
includes taxes & fees
28 Apr - 29 Apr
Sunset and beach view from your balcony Unit 403

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 AU$438
includes taxes & fees
26 May - 27 May
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.
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Top Osprey Hotel Reviews

Find out more about Osprey

Everything you need to know about Osprey holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Osprey holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Osprey holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Osprey holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Osprey holiday rentals we have selected for you start as low as AU$198 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Osprey rentals

At Expedia, we put the best Osprey holiday 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 holiday.

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 holiday rentals in Osprey?

Yes, there are holiday rentals in Osprey close to Jim Neville Marine Preserve, or you can select a more secluded option if you're looking for a relaxing stay. 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 holiday rentals that Osprey has to offer?

Siesta Key Island Rentals: This holiday home rental outside of Osprey comes with free WiFi so that you can feel at home during your trip. This holiday rental also comes with free parking to give you added peace of mind.

How many holiday rentals are there in Osprey?

With 19 Expedia holiday rentals, you're guaranteed 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 such as Siesta Key Beach and Venice Beach.

What’s a holiday rental in Osprey like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Osprey. Holiday rentals feature extras such as kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, holiday rentals can provide a sense of security away from shared hotel lifts and lobbies bustling with people while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular choice for families.