Deals on vacations and trips to Osprey
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Osprey flight + hotel vacation packages
Price found within the past 48 hours. Click for updated prices.
Captiva Beach Resort
Save 100% on your flight
per person
Jun 12 - Jun 17
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Sarasota (SRQ)
A private beach and an outdoor pool are featured at this smoke-free condo. Guests will appreciate free perks like free self parking and WiFi in public areas. A picnic area, laundry facilities, and barbecue grills are also on offer.
Pelican Post at Anna Maria Island Inn
Save 100% on your flight
per person
Jul 10 - Jul 13
found 20 hours ago
Roundtrip flight included
Detroit (DTW) to Sarasota (SRQ)
This apartment features an outdoor pool and a hot tub. Guests will appreciate free perks like free self parking and WiFi in public areas. A garden and barbecue grills are also provided.
Fairfield Inn & Suites by Marriott Sarasota Lakewood Ranch
Save 100% on your flight
per person
Jun 15 - Jun 22
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Sarasota (SRQ)
This hotel features an outdoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the hot tub and free perks like continental breakfast and free self parking.
Top Osprey hotels deals
Casey Key Resorts - Mainland
1650 South Tamiami Trail, Osprey, FL
Free Cancellation
Reserve now, pay when you stay
$170 nightly
The price is $193 total per night
$193 total
May 11 - May 12
Total includes taxes and fees
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Relax with a drink at the poolside bar and enjoy perks like free self parking.
Pool
Pet friendly
Kompose Boutique Hotel
965 University Pkwy, Sarasota, FL
Free Cancellation
Reserve now, pay when you stay
$85 nightly
The price is $96 total per night
$96 total
May 11 - May 12
Total includes taxes and fees
This hotel features an outdoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the hot tub and perks like free self parking.
Pool
Hot Tub
Golden Host Resort - Sarasota
4675 N Tamiami Trl, Sarasota, FL
Free Cancellation
$79 nightly
The price is $90 total per night
$90 total
May 11 - May 12
Total includes taxes and fees
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Business travelers can take advantage of the free WiFi in public areas. Free self parking, a terrace, and a garden are also offered.
Pool
Parking included
Spark by Hilton Sarasota Siesta Key Gateway
6600 S Tamiami Trl, Sarasota, FL
Free Cancellation
Reserve now, pay when you stay
$100 nightly
The price is $113 total per night
$113 total
May 20 - May 21
Total includes taxes and fees
This hotel features an outdoor pool, a hot tub, and a restaurant. Business travelers can take advantage of the free WiFi in public areas. Relax with a drink at the bar/lounge and enjoy free perks like continental breakfast and free self parking.
Pool
Hot Tub
Tropical Beach Resorts
6717 Sara Sea Circle, Siesta Key, FL
Free Cancellation
Reserve now, pay when you stay
$175 nightly
The price is $197 total per night
$197 total
May 26 - May 27
Total includes taxes and fees
This aparthotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Spend a day at the beach surfing, or relax with sun loungers and beach umbrellas. There's an outdoor pool on site, and laundry facilities and concierge services are also offered.
Pool
Kitchen
Hyatt Regency Sarasota
1000 Blvd Of The Arts, Sarasota, FL
Free Cancellation
Reserve now, pay when you stay
$209 nightly
The price is $236 total per night
$236 total
May 27 - May 28
Total includes taxes and fees
A marina, a 24-hour gym, and a restaurant are all featured at this eco-certified hotel. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and valet parking. Enjoy the outdoor pool and unwind at the bar/lounge and poolside bar.
Pool
Hot Tub
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.
Popular places to visit
Oscar Scherer State Park
4/5(9 reviews)
You can take time to visit Oscar Scherer State Park during your travels to Osprey. Attend a sporting event or simply enjoy the lively bars while you're in the area.
Historic Spanish Point
You can spend time exploring the galleries in Historic Spanish Point in Osprey. Attend a sporting event or simply enjoy the lively bars while you're in the area.
The Oaks Club
Enjoy a round of golf in Osprey at The Oaks Club. Wander the area's beautiful beaches or simply enjoy one of its lively bars.
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