Osprey Holidays

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Our guide on where to stay in Osprey

Find the best Osprey areas and neighborhoods for the activities you enjoy most. Learn more about Osprey
An aerial view of a coastal area with a sandy beach, a road, and scattered buildings.

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.

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A river with boats, a bridge, and a cityscape with tall buildings.

Bay Acres

When in Bay Acres, you can plan a visit to Oscar Scherer State Park and Jim Neville Marine Preserve, some noteworthy sights in the nearby area.

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Rivendell

Though Rivendell may not have many top sights, you can venture to the surrounding area to see attractions like Oscar Scherer State Park and Jim Neville Marine Preserve.

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Osprey Holiday

Our pick of the best Osprey Hotel Deals

Casey Key Resorts - Mainland

Casey Key Resorts - Mainland

1650 South Tamiami Trail Osprey FL
Fully refundableReserve now, pay when you stay
NZ$196
12 Aug - 13 Aug
includes taxes & fees
Casey Key Resorts - Mainland
Kompose Boutique Hotel

Kompose Boutique Hotel

965 University Pkwy Sarasota FL
Fully refundableReserve now, pay when you stay
NZ$125
12 Aug - 13 Aug
includes taxes & fees
Kompose Boutique Hotel
Tropical Beach Resorts

Tropical Beach Resorts

6717 Sara Sea Circle Siesta Key FL
Fully refundableReserve now, pay when you stay
NZ$303
19 Aug - 20 Aug
includes taxes & fees
9.4/10 Exceptional! (5,748 reviews)
"Clean room, friendly staff and great location."

Reviewed on 10 Aug 2026

Tropical Beach Resorts
See all 11,414 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.

Stay near popular Osprey attractions

A forest with tall trees and a dirt path.
Photo by Frank Methling

Oscar Scherer State Park

8.8/10 (83 reviews)
A sanctuary for endangered Florida scrub-jays, Oscar Scherer State Park offers trails through diverse ecosystems. Paddle South Creek or swim in Lake Osprey after spotting wildlife in the scrubby flatwoods.
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A white wooden chapel with a triangular roof, surrounded by trees.
Photo by Jessica M Dobbins

Historic Spanish Point

9.0/10 (42 reviews)
This 30-acre outdoor museum showcases Florida history through shell middens and pioneer buildings. Stroll through Bertha Palmer's bayfront gardens while exploring archaeological treasures spanning millennia.
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Nancy's Consignments

6.8/10 (11 reviews)
Nancy's Consignments showcases gently used designer clothing and estate jewellery in a well-organized boutique setting. Browse high-end fashion at affordable prices while staff help you uncover hidden treasures.
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What to do in Osprey

Taking in the views of another epic Siesta Key sunset!

Siesta Key Electric Bike Sunset Tour

NZ$124
per adult
98% of travellers recommend
Siesta Key Electric Bike Sunset Tour
HydroCats - 2 Hour CraigCat Sightseeing Tour

HydroCats - 2 Hour CraigCat Sightseeing Tour

NZ$227
per adult
100% of travellers recommend
HydroCats - 2 Hour CraigCat Sightseeing Tour
Mangroves, Manatees & a Hidden Beach Kayak Tour

Mangrove Tunnel & Manatee Kayak Eco-Tour

NZ$102
per adult
94% of travellers recommend
Mangrove Tunnel & Manatee Kayak Eco-Tour
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.

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