Osprey Holidays

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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

Top hotels in Osprey

Casey Key Resorts - Mainland

Casey Key Resorts - Mainland

2.5 out of 5
1650 South Tamiami Trail, Osprey, FL
Fully refundableReserve now, pay when you stay
The price is Rp2.018.703 per night from 31 Aug to 1 Sept
Rp2.018.703
Rp2.281.020 total
31 Aug - 1 Sept
includes taxes & fees
8.6/10 Excellent! (1,049 reviews)
"pool bar and patio was great noisy!"

Reviewed on 8 Aug 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! (4,224 reviews)
"Adorable little french boutique hotel. Simply underrated. Had a wonderful experience, highly recommended!!! :)"

Reviewed on 8 Aug 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 Rp2.271.244 per night from 1 Sept to 2 Sept
Rp2.271.244
Rp2.934.727 total
1 Sept - 2 Sept
includes taxes & fees
9.2/10 Wonderful! (4,846 reviews)
"We stayed here and found it last minute. Check-in was easy and the room is completely renovated"

Reviewed on 9 Aug 2025

Tropical Beach Resorts
See all 10,466 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.

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

Rp1.060.800
per adult
Siesta Key, FL - Clear Kayak LED Night Glass Bottom Tour
HydroCats

HydroCats - 2 Hour CraigCat Sightseeing Tour

Rp2.379.130
per adult
100% of travellers recommend
HydroCats - 2 Hour CraigCat Sightseeing Tour
Experience Parasailing in Sarasota

Experience Parasailing in Sarasota

Rp1.615.680
per adult
Experience Parasailing in Sarasota
See all activities in Osprey

Frequently asked questions

How much does an Osprey holiday package cost?
Offering great value package deals on Expedia, you'll be pleasantly surprised at how much a holiday to Osprey costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Osprey?
August, September and November are great times to look for cheap Osprey holiday packages. Travelling in less busy periods means you can usually find lower prices on hotels and flights.
How many days is enough for Osprey?
Dedicate at least 3 days for your Osprey holiday to really immerse yourself in everything that makes this place special. Stroll around popular areas, including Laurel and Casey Key. Then make a beeline for major sights such as Oscar Scherer State Park and The Oaks Club. With a clever itinerary, you'll be kept busy with room for some relaxation too. Want to venture beyond Osprey? Consider squeezing in a day trip or two.
Is it worth booking a holiday package to Osprey?
Osprey has everything you need for an amazing trip. Get your Osprey holiday off to a flying start by checking out major attractions like Oscar Scherer State Park.
How to find the best Osprey package deals?
Bagging a cheap Osprey package deal is easy with Expedia. After you've entered your preferred dates and destination under our "Packages" tab, set your budget range, apply some filters and browse what's available. You can personalise your search by "Property class," "Number of bedrooms," "Traveller experience" and more. Order the results by "Price: low to high" to view the most wallet-friendly Osprey package deals. Want a simple trick to score even more savings? Have some flexibility with your departure dates and consider travelling on a weekday, when prices are usually lower.
Is it cheaper to book an Osprey holiday as a package?
Expedia holiday packages are designed to give you more bang for your buck. Bundle your car rental, hotel and flight into one great-value price and you could save hundreds of dollars. You'll generally get a better deal than booking each component individually. And you'll still have the flexibility to create a customised Osprey holiday by choosing your favourite accommodation type, airline and car class.
When to book a holiday package to Osprey?
Score incredible bargains by reserving your flights ahead of time with Expedia. If spontaneity is more your style, snap up one of our last-minute deals for an impromptu Osprey getaway.
How to plan a trip to Osprey?

  1. Choose the ideal time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to visit Osprey.
  2. Budget wisely: On top of the cost of your hotel, you'll need to consider other expenses too. These include transportation, food and flights. Also, set aside a little extra for unexpected expenses that may crop up during your trip to Osprey.
  3. Decide how long to go away for: Now that you're more familiar with Osprey, you can work out the ideal length of your break. Put together a rough itinerary and allocate enough time for all the things you want to do.
  4. Bundle your hotel and flights: Awesome destination, check. Length of stay, check. Now all that's left is to choose an Osprey holiday package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.