Osprey Holidays from £675

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Your Osprey Holiday

When a getaway to the city is calling, answer it with a Osprey holiday package. The neighbourhood of Main Street Merchants, which is great for cafes, markets and shopping, makes a fantastic base for your adventures. Siesta Key Beach, Turtle Beach and Nokomis Beach are just a few of the sights worth exploring during your trip to Osprey. Check out Expedia's extensive range of travel options and book your dream holiday to Osprey now.

The Latest Osprey Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Legacy Hotel at IMG Academy

Legacy Hotel at IMG Academy

4 out of 5
per person
13 Sept - 20 Sept
found 9 hours ago
Return flight included
London (LON) to Sarasota (SRQ)
9/10 Wonderful! (830 reviews)
For anyone attending IMG, this is the only place to stay. It is the equivalent of a Holiday in express with the exception of the bar and restaurant. The staff there are exceptional and the food is first rate.

Reviewed on 29 Jun 2025

Hotel Alba, Tapestry Collection by Hilton

Hotel Alba, Tapestry Collection by Hilton

4 out of 5
Westshore
per person
9 Sept - 16 Sept
found 1 day ago
Return direct flight included
London (LHR) to Sarasota (SRQ)
8.8/10 Excellent! (1,945 reviews)
Only 1 elevator we were on 3rd floor and my husband has a walking problem

Reviewed on 2 Jul 2025

The Pointe Condos by Barsala

The Pointe Condos by Barsala

4.5 out of 5
Port Tampa City
per person
17 Sept - 22 Sept
found 21 hours ago
Return direct flight included
London (LHR) to Sarasota (SRQ)
9/10 Wonderful! (149 reviews)
The insulation was awful. We could hear everything going on above us. It sounded like they were stomping and moving furniture. When the air conditioner kicked on you had to turn the tv up quite a bit to hear it

Reviewed on 10 Jun 2025

Residence Inn By Marriott Tampa Downtown

Residence Inn By Marriott Tampa Downtown

3 out of 5
Downtown Tampa
per person
9 Sept - 16 Sept
found 1 day ago
Return direct flight included
London (LHR) to Sarasota (SRQ)
8.4/10 Very Good! (1,007 reviews)
I recently stayed at this hotel and had a pretty mixed experience. Pros: The location is definitely the highlight. It's super convenient—within walking distance to great restaurants and bars. The Hub was my personal favorite! It’s also close to the Riverwalk and has easy access to the freeway, which made getting around town really simple. Cons: Unfortunately, the rest of the stay didn’t go as smoothly. Parking was a nightmare—there were barely any available spaces, and to make matters worse, my car was towed for no reason. Dealing with that was a major headache. On top of that, there was no hot water during my stay, and the air conditioning barely worked, which made the room super uncomfortable. Overall, while the location was great, the basic comforts and amenities really missed the mark. Probably wouldn’t stay here again unless those issues were addressed.

Reviewed on 23 Jun 2025

Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
per person
14 Aug - 17 Aug
found 15 hours ago
Return direct flight included
London (LHR) to Sarasota (SRQ)
9.2/10 Wonderful! (445 reviews)
My family and I had a wondeful stay here, beds were comfortable, ac worked well, friendly and attentive staff, etc. Definitely recommend staying here and will be back soon.

Reviewed on 20 Jun 2025

Courtyard by Marriott Tampa Downtown

Courtyard by Marriott Tampa Downtown

3 out of 5
Downtown Tampa
per person
9 Sept - 16 Sept
found 1 day ago
Return direct flight included
London (LHR) to Sarasota (SRQ)
8.4/10 Very Good! (1,004 reviews)
I was greeted upon my arrival. The staff were very friendly and polite. I will definitely be staying here again!

Reviewed on 22 Jun 2025

Osprey Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Sarasota-Bradenton Intl. Airport (SRQ)
Population
6,100
Max Temp Winter
21ºC
Max Temp Summer
32ºC
Top Sights
Siesta Key Beach, Lido Beach and Venice Beach

Our guide on where to stay in Osprey

Check out a few of the areas and neighbourhoods we love in Osprey Learn more about Osprey
Default Image

Sorrento Shores

While Sorrento Shores may not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Oscar Scherer State Park and Nokomis Beach.

Find hotels in Sorrento Shores

All Inclusive Holidays

All Inclusive Holidays

Beach Holidays

Beach Holidays

Family Friendly Holidays

Family Friendly Holidays

Frequently asked questions

Why should I book my Osprey holiday with Expedia?
Choose Expedia to arrange your next big break easily and all in one convenient place. Our top tip for getting a great deal on an Osprey retreat? Bundle your accommodation, airfares and/or hire car into a package holiday. Then throw in a couple of awesome tours and activities. Many bookings also come with flexible cancellation policies, so there's no need to worry if you have to change plans. Round-the-clock help with cancelling and amending your trip is available via our Customer Service Portal link.
When is the best time of year to holiday in Osprey?
Osprey is a bustling place in January, February and March. If you're not into large crowds and prefer a more relaxed pace, book your escape for May, June and September. Plan your escape to Osprey according to what style of holiday you're looking for. January is the coolest time of year, when daytime temperatures average 17ºC. In July, the warmest month, you can expect temperatures of around 28ºC during the day.
What are the top hotels for my holiday in Osprey?
If you're planning to stay in the Osprey Village neighbourhood, Casey Key Resorts - Mainland and Enjoy the fall in our Lovely 2 bed 2 bath condo - Jan 2024 is available are fabulous options. Bay Acres is another favourite Osprey area. We recommend Pool, Hot tub, Close to Beaches, Shopping, More! or Gorgeous Updated Heated Saltwater Pool Home, WiFi, Dog Friendly, Kayak Launch & Park, Garage if you prefer this part of town.
How do I get a cheap holiday to Osprey?
Browse and lock in everything in one place with our Osprey holidays. We have incredible bargains on hotels, flights and more that'll keep your wallet happy and your adventurous side busy. And, with more than 400 airlines and 321,000 hotel options around the world to select from, you'll have endless opportunities to mix and match your own way. Learn more about how you can save money on your holiday when you combine your flight and hotel bookings with Expedia.
What should I do on my Osprey holiday?
Ensure your holiday in Osprey is a memorable one by visiting its top attractions. Siesta Key Beach, Venice Beach, Turtle Beach and Nokomis Beach are some of the things worth discovering while you're here.
What is the best area to stay in when on holiday in Osprey?
There's so much to see in Osprey, so stay near its top sights and treat yourself to more time sightseeing. Oscar Scherer State Park is one place to put on your to-do list.
Do I need a visa for my Osprey holiday?
Visa requirements for Osprey vary depending on your nationality and the purpose of your visit. Remember to check official government websites to determine if you need a visa for your trip. This is also a good place to find the most up-to-date information, including details about application procedures or supporting documentation you may need. Enquire about your visa requirements in advance to ensure a smooth travel experience. Finally, make sure your passport is valid for at least six months from your date of return.
What should I wear on my Osprey holiday?
Though everyone's style varies, it can be useful to have some guidelines for what to bring during your holiday in Osprey. Consider looking up style blogs before you leave to get inspiration for local fashion trends. Be sure to look at the local weather forecast so you can pack your bags accordingly. The warmest time of year in Osprey is July, with average daily temperatures of 28ºC. If you're visiting during the coolest month of January, the mercury hovers around 17ºC during the day.
What does an Expedia Osprey holiday include?
Expedia has all you need to organise your Osprey trip, but what your package looks like is your choice. Choose from a combination of hotels, hire cars and flights. In search of a few activities to keep you on the move? Once you've made your booking, you can add them too. No matter your style or budget, there's a deal to match your needs. Private holiday homes and condos are two sought-after property types in Osprey. Whatever your preference or size of your group, you can rely on Expedia for the flexibility to customise your next dream escape.
Does Expedia offer Book Now, Pay Later Osprey holidays?
Expedia has teamed up with online lender Klarna to make booking your next getaway easier on your bank balance. Paying by instalment means you can spread the costs of your next big holiday, leaving you with more cash to splash while you're away. Klarna has several payment plans to choose from, so you're sure to find something that suits your budget. Take a look at these flexible payment options:

  • Pay monthly holidays: If paying across multiple transactions works for you, Klarna can help. Paying in several transactions will make your holiday dreams come true.
  • No-deposit holidays: Clicking the "book now" button is much easier with this payment plan. With no upfront fee for your holiday, you can Book Now, Pay Later and start packing your bags.

Can I choose my airline with an Osprey Expedia holiday?
Yes, and with over 400 airlines to pick from across the globe, it's all about choice. Scroll through the available options and see which airline suits your needs and budget.

Unmissable things to do in Osprey

Private Luxury Boat Charter

Private Luxury Boat Charter

£277
per traveller
100% of travellers recommend
Private Luxury Boat Charter
Kayak Tour through Mangrove Tunnels

Mangroves, Manatees, and a Hidden Beach: Kayak Tour

£41
per adult
88% of travellers recommend
Mangroves, Manatees, and a Hidden Beach: Kayak Tour
See all activities in Osprey

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.