Osprey Holidays

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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 Annual Holiday Sale

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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

Things to do in and around Osprey

Osprey, Florida, is an ideal destination for beach lovers, families, and outdoor enthusiasts. Visitors can enjoy a range of activities, including golf at local courses, exploring recreational areas, and embarking on weekend getaways. With its exciting attractions and opportunities for easy adventures, Osprey promises a delightful Mediterranean experience, perfect for those seeking theatre breaks and memorable excursions.

Shopping

The closest shopping option is Sarasota Square, just 4.8km from Osprey, offering a vibrant mix of entertainment and family-friendly stores. The Gulf Gate Mall is a mere 8.0km away, featuring similar vibes. For a unique experience, drive 11.3km to Siesta Key Farmers Market for local produce and crafts.

Recreation

Experience the serene Pelican Pointe Golf and Country Club, where you can enjoy a round of golf amidst beautiful landscapes. For a touch of luxury, visit The Oaks Club, perfect for unwinding in a sophisticated atmosphere. Don’t miss the Venice Theater for a delightful evening of culture and entertainment.

Adventure

Experience the scenic Sarasota BayWalk, an invigorating hiking trail located 17.7km from Osprey, perfect for outdoor enthusiasts. Enjoy a thrilling game at Payne Park Tennis Center, situated 16.1km away, offering adventurous vibes. Explore the Canopy Walkway and Boylston Nature Trail, a captivating treetop walk 19.3km from Osprey.

Nightlife

Osprey offers a charming nightlife with venues like the picturesque Casey Key Fish House, where you can savour fresh seafood and cocktails by the water. For a lively atmosphere, visit the nearby Sarasota, boasting vibrant bars and live music, creating a delightful evening experience.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions near Osprey

Osprey, Florida, is an ideal destination for beach, outdoor, and family holidays. Visitors can explore a variety of attractions, including beautiful beaches, urban parks, and scenic jetties. This charming locale caters perfectly to those seeking outdoor adventures and family-friendly experiences, making it a delightful spot for travellers looking to unwind and enjoy nature.

  • Siesta Key Beach: Located 9.7km from Osprey, Siesta Key Beach is renowned for its powdery white sands and crystal-clear waters, making it an idyllic spot for sunbathing and swimming. The relaxed beach vibes invite visitors to unwind and enjoy stunning sunsets.
  • The Landings: Also 9.7km away, The Landings offers a vibrant town atmosphere with a variety of shops, restaurants, and local art. It's a great place to explore the community and experience the lively city vibes.
  • Turtle Beach: Just 4.8km from Osprey, Turtle Beach is a quieter alternative, perfect for those seeking a more secluded experience. With its natural beauty and tranquil beach vibes, it's ideal for relaxation and nature walks.

Best time to go to Osprey

The best time to visit Osprey is dependent on what kind of holiday you are seeking. August is its hottest month on average. At this time, visitor numbers are average and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly sunny with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January62.6°F (17.0°C)Light RainMostly SunnyAverageAverage
February65.1°F (18.4°C)No RainMostly SunnyAverageSlightly High
March68.0°F (20.0°C)No RainSunnySlightly HighSlightly High
April73.4°F (23.0°C)Light RainMostly SunnySlightly HighSlightly High
May77.7°F (25.4°C)Light RainMostly SunnyAverageAverage
June81.7°F (27.6°C)Light RainMostly SunnyAverageAverage
July82.9°F (28.3°C)Light RainMostly SunnyAverageAverage
August83.3°F (28.5°C)Light RainMostly SunnyAverageSlightly Low
September81.5°F (27.5°C)Light RainMostly SunnySlightly HighSlightly Low
October77.2°F (25.1°C)Light RainMostly SunnySlightly LowAverage
November70.7°F (21.5°C)No RainMostly SunnySlightly LowSlightly Low
December66.6°F (19.2°C)No RainMostly SunnySlightly LowAverage

Tips to save on your trip to Osprey

  • Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
  • Consider traveling to Osprey during the low season (August to September and November) for more affordable options.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

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

4 out of 5
1650 South Tamiami Trail Osprey FL
Fully refundableReserve now, pay when you stay
The price is £160 per night from 8 Mar to 9 Mar
£160
8 Mar - 9 Mar
includes taxes & fees
8.8/10 Excellent! (1,147 reviews)
This place has been updated but poorly done. It’s an average property. I think for the price I paid I could have found a better property.

Reviewed on 5 Mar 2026

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
9.2/10 Wonderful! (5,095 reviews)
Didn’t like the way the room was laid out

Reviewed on 5 Mar 2026

Kompose Boutique Hotel
Golden Host Resort - Sarasota

Golden Host Resort - Sarasota

3 out of 5
4675 N Tamiami Trl Sarasota FL
Fully refundable
The price is £86 per night from 5 Apr to 6 Apr
£86
5 Apr - 6 Apr
includes taxes & fees
8.4/10 Very Good! (2,323 reviews)
I am a fan of this property. Kat is great and made the check-in process a breeze. The bartenders in the Tiki Bar were also very nice and overall it is a nice, clean property with a great location! However, the room furnishing are really starting to show its age. Baseboards and doors are looking beat-up ...

Reviewed on 5 Mar 2026

Golden Host Resort - Sarasota
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

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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. Flight-inclusive packages are ATOL protected.