Osprey Holidays from £659

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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.
Residence Inn By Marriott Tampa Downtown

Residence Inn By Marriott Tampa Downtown

3 out of 5
Downtown Tampa
per person
11 Sept - 18 Sept
found 1 day ago
Return flight included
London (LON) to Sarasota (SRQ)
8.4/10 Very Good! (1,009 reviews)
I enjoyed my stay here. Staff were all very nice and kind. Loved the amenities like the gym, computer area, pool and breakfast.

Reviewed on 16 Jul 2025

Hotel Alba, Tapestry Collection by Hilton

Hotel Alba, Tapestry Collection by Hilton

4 out of 5
Westshore
per person
11 Sept - 18 Sept
found 1 day ago
Return flight included
London (LON) to Sarasota (SRQ)
8.8/10 Excellent! (1,978 reviews)
It was a nice hotel the pool was bery nice and clean but the elevator wasnt working needed to use the stairs so carrying luggage down was hard

Reviewed on 19 Jul 2025

Sailport Waterfront Suites

Sailport Waterfront Suites

3.5 out of 5
Rocky Point
per person
11 Sept - 18 Sept
found 1 day ago
Return flight included
London (LON) to Sarasota (SRQ)
8.4/10 Very Good! (4,614 reviews)
Friendly and organized staff

Reviewed on 18 Jul 2025

The Westin Tampa Bay

The Westin Tampa Bay

4 out of 5
Rocky Point
per person
11 Sept - 18 Sept
found 1 day ago
Return flight included
London (LON) to Sarasota (SRQ)
8.2/10 Very Good! (1,010 reviews)
We enjoyed our stay!

Reviewed on 18 Jul 2025

Hotel Flor Tampa Downtown, Tapestry Collection by Hilton

Hotel Flor Tampa Downtown, Tapestry Collection by Hilton

4 out of 5
Downtown Tampa
per person
11 Sept - 18 Sept
found 1 day ago
Return flight included
London (LON) to Sarasota (SRQ)
8.2/10 Very Good! (518 reviews)
Bradley could be a little nicer, one of the managers I think..was rude, impatient.. He will keep me from staying there again.

Reviewed on 19 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
8.4/10 Very Good! (1,057 reviews)
"Ease of check in and nice facility."

Reviewed on 17 Jul 2025

Get rates
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! (4,139 reviews)
"It was clean and cute. We had to wait for our room to be available but the staff was apologetic and tried to male up for it. We were disappointed that the balcony didn't have what was pictured but it was a nice large space."

Reviewed on 17 Jul 2025

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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 £138 per night from 10 Aug to 11 Aug
£138
10 Aug - 11 Aug
includes taxes & fees
9.2/10 Wonderful! (4,769 reviews)
"Great location. Close to private beach and walking distance to awesome restaurants and nightlife. Very friendly staff."

Reviewed on 13 Jul 2025

Tropical Beach Resorts
See all 10,465 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

Private Luxury Boat Charter

Private Luxury Boat Charter

£276
per traveller
100% of travellers recommend
Private Luxury Boat Charter
Kayak Tour through Mangrove Tunnels

Mangroves, Manatees, and a Hidden Beach: Kayak Tour

£40
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.