Osprey Holidays from £708

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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.

Top Osprey Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Hotel Alba, Tapestry Collection by Hilton

Hotel Alba, Tapestry Collection by Hilton

4 out of 5
Westshore
per person
17 Sept - 24 Sept
found 12 hours ago
Return flight included
London (LGW) to Sarasota (SRQ)
8.8/10 Excellent! (2,016 reviews)
My recent stay at the Hilton Hotel in Tampa was an all-around great experience. The hotel itself is clean, stylish, and in a prime location close to downtown, restaurants, and the waterfront. My room was spotless, spacious, and very comfortable — a perfect place to unwind after a busy day.

Reviewed on 4 Aug 2025

Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
per person
18 Sept - 21 Sept
found 1 day ago
Return flight included
London (LON) to Sarasota (SRQ)
9.2/10 Wonderful! (452 reviews)
Such a Beautiful Resort and the rooms are so clean and beautiful , located on the beach steps from the bluest Ocean water ,which was a dream come true.. The staff was amazing, everything you need they have for you, so helpful...we didn't want to leave..we will be back

Reviewed on 2 Aug 2025

Landing Apartments near Sun City Center and Riverview

Landing Apartments near Sun City Center and Riverview

4 out of 5
per person
17 Sept - 24 Sept
found 12 hours ago
Return flight included
London (LGW) to Sarasota (SRQ)
No reviews
Hotel Tampa Riverwalk

Hotel Tampa Riverwalk

4 out of 5
Downtown Tampa
per person
17 Sept - 24 Sept
found 12 hours ago
Return flight included
London (LGW) to Sarasota (SRQ)
7/10 Good! (1,550 reviews)
Not a fan of the room, especially with no microwave or updates. Booked 4 months in advance just to get an okay experience. Received an email 1hour prior to check in with unexpected expenses that were not listed in the booking. A/C in hallway 2nd floor was non existent. Bed was uncomfortable and room not sound proof. The pool party, views of the water and valet staff were THE only highlights of my trip.

Reviewed on 3 Aug 2025

Legacy Hotel at IMG Academy

Legacy Hotel at IMG Academy

4 out of 5
per person
17 Sept - 24 Sept
found 14 hours ago
Return flight included
London (LGW) to Sarasota (SRQ)
9/10 Wonderful! (859 reviews)
The location was awesome. We stayed in the Villas. For the price I truly expect more. The villa was huge but a lot of old and outdated furniture and appliances. The floors were worn down, Tiles cracked, the walls was nasty (like a little kid blew his nose on the wall)! I informed the staff but it was just an ok. Nothing else. The front porch and back porch had big wasp nests over the doors.

Reviewed on 27 Jul 2025

Where to stay in Osprey

Find the best Osprey areas and neighborhoods for the activities you enjoy most. Learn more about Osprey
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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

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

Top hotels in Osprey

Casey Key Resorts - Mainland

Casey Key Resorts - Mainland

3 out of 5
1650 South Tamiami Trail, Osprey, FL
Fully refundableReserve now, pay when you stay
The price is £105 per night from 31 Aug to 1 Sept
£105
31 Aug - 1 Sept
includes taxes & fees
8.6/10 Excellent! (1,050 reviews)
"."

Reviewed on 31 Jul 2025

Casey Key Resorts - Mainland
Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
965 University Pkwy, Sarasota, FL
Fully refundableReserve now, pay when you stay
9/10 Wonderful! (4,204 reviews)
"I spent 2 nights here with my best friend for a birthday getaway and it exceeded our expectations. Every aspect of our stay was a 10 +! The front desk & housekeeping were all smiles at every interaction! Would most definitely recommend and I would stay there again if I am back in the area."

Reviewed on 30 Jul 2025

Get rates
Kompose Boutique Hotel
Tropical Beach Resorts

Tropical Beach Resorts

3.5 out of 5
6717 Sara Sea Circle, Siesta Key, FL
Fully refundableReserve now, pay when you stay
The price is £136 per night from 1 Sept to 2 Sept
£136
1 Sept - 2 Sept
includes taxes & fees
9.2/10 Wonderful! (4,825 reviews)
"The hotel is an good location close to restaurants and bars.the beach is an waliking distance. What we don't like.. we found a roach on our room.."

Reviewed on 3 Aug 2025

Tropical Beach Resorts
See all 10,455 properties in Osprey
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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

What to do in Osprey

Siesta Key, FL - Clear Kayak LED Night Glass Bottom Tour

Siesta Key, FL - Clear Kayak LED Night Glass Bottom Tour

£48
per adult
Siesta Key, FL - Clear Kayak LED Night Glass Bottom Tour
HydroCats

HydroCats - 2 Hour CraigCat Sightseeing Tour

£108
per adult
100% of travellers recommend
HydroCats - 2 Hour CraigCat Sightseeing Tour
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

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.

* 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.