Search Deals on
The Oaks Club Vacation Packages

The Oaks Club Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Travelodge by Wyndham Venice

Travelodge by Wyndham Venice

3.5 out of 5
per person
Jan 10 - Jan 14
found 5 hours ago
Roundtrip flight included
Philadelphia (PHL) to Sarasota (SRQ)
Book a stay at this business-friendly hotel in Venice. Enjoy free WiFi, free parking, and a rooftop terrace. Popular attractions Manasota Beach and Caspersen Beach are located nearby.
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
per person
Jan 16 - Jan 22
found 1 day ago
Roundtrip flight included
New York (JFK) to Sarasota (SRQ)
Stay at this 3-star beach hotel in Holmes Beach. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Bradenton Beach and Cortez Beach are located nearby.
Barsala at Champions Walk

Barsala at Champions Walk

4 out of 5
Save 100% on your flight
per person
Dec 27 - Jan 3
found 5 hours ago
Roundtrip flight included
Baltimore (BWI) to Sarasota (SRQ)
Stay at this 4-star aparthotel in Bradenton. Enjoy free WiFi, in-room washers/dryers, and in-room soaking tubs. Popular attractions Coquina Beach and Smugglers Cove Adventure Golf are located nearby.
Legacy Hotel at IMG Academy

Legacy Hotel at IMG Academy

4 out of 5
Save 100% on your flight
per person
Dec 29 - Jan 3
found 14 hours ago
Roundtrip non-stop flight included
Nashville (BNA) to Sarasota (SRQ)
Stay at this 4-star spa hotel in Bradenton. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Coquina Beach and Cortez Beach are located nearby.
Captiva Beach Resort

Captiva Beach Resort

2 out of 5
Save 100% on your flight
per person
Jan 16 - Jan 22
found 1 day ago
Roundtrip flight included
New York (JFK) to Sarasota (SRQ)
Book a stay at this beach condo in Siesta Key. Enjoy free WiFi, free parking, and a private beach. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Siesta Key Beach and Lido Beach are located nearby.
Escape Resort & Marina

Escape Resort & Marina

2.5 out of 5
Save 100% on your flight
per person
Jan 16 - Jan 22
found 1 day ago
Roundtrip flight included
New York (JFK) to Sarasota (SRQ)
Stay at this hotel in Nokomis. Enjoy free WiFi, a marina, and daily housekeeping. Our guests praise the helpful staff in our reviews. Popular attractions Nokomis Beach and Venice Beach are located nearby.
The Residences at Siesta Key Beach by Hyatt Vacation Club

The Residences at Siesta Key Beach by Hyatt Vacation Club

3.5 out of 5
Save 100% on your flight
per person
Jan 16 - Jan 22
found 1 day ago
Roundtrip flight included
New York (JFK) to Sarasota (SRQ)
Stay at this 3.5-star beach aparthotel in Siesta Key. Enjoy free breakfast, free WiFi, and free valet parking. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Siesta Key Beach and Lido Beach are located nearby.
Casey Key Resorts - Beachfront

Casey Key Resorts - Beachfront

2 out of 5
Save 100% on your flight
per person
Jan 16 - Jan 22
found 1 day ago
Roundtrip flight included
New York (JFK) to Sarasota (SRQ)
Book a stay at this beach hotel in Nokomis. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Nokomis Beach and Venice Beach are located nearby.
Turtle Beach Resort and Inn

Turtle Beach Resort and Inn

3.5 out of 5
Save 100% on your flight
per person
Jan 16 - Jan 22
found 1 day ago
Roundtrip flight included
New York (JFK) to Sarasota (SRQ)
Book a stay at this spa hotel in Siesta Key. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions Siesta Key Beach and Turtle Beach are located nearby.
Beachside of the Village by Beachside

Beachside of the Village by Beachside

4 out of 5
Save 100% on your flight
per person
Jan 8 - Jan 13
found 1 hour ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Sarasota (SRQ)
Stay at this 4-star vacation home in Siesta Key. Enjoy laundry facilities, furnished balconies, and in-room washers/dryers. Popular attractions Siesta Key Beach and Lido Beach are located nearby.
Siesta Heron Suites & Villas

Siesta Heron Suites & Villas

3.5 out of 5
Save 100% on your flight
per person
Jan 16 - Jan 22
found 1 day ago
Roundtrip flight included
New York (JFK) to Sarasota (SRQ)
Stay at this 3.5-star vacation home in Siesta Key. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Siesta Key Beach and Turtle Beach are located nearby.
Twin Palms at Siesta

Twin Palms at Siesta

3 out of 5
per person
Jan 10 - Jan 14
found 5 hours ago
Roundtrip flight included
Philadelphia (PHL) to Sarasota (SRQ)
Stay at this 3-star beach hotel in Siesta Key. Enjoy free WiFi, free parking, and private pools. Our guests praise the helpful staff in our reviews. Popular attractions Siesta Key Beach and Lido Beach are located nearby.

3-4 Night Vacations in The Oaks Club

Price found within the past 48 hours. Click for updated prices.
Travelodge by Wyndham Venice

Travelodge by Wyndham Venice

3.5 out of 5
South Venice
per person
Jan 10 - Jan 14
found 5 hours ago
Roundtrip flight included
Philadelphia (PHL) to Sarasota (SRQ)
Barsala at Champions Walk

Barsala at Champions Walk

4 out of 5
per person
Jan 17 - Jan 20
found 4 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) to Sarasota (SRQ)
Legacy Hotel at IMG Academy

Legacy Hotel at IMG Academy

4 out of 5
per person
Dec 27 - Dec 30
found 1 day ago
Roundtrip flight included
New York (JFK) to Sarasota (SRQ)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
per person
Jan 17 - Jan 20
found 4 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) to Sarasota (SRQ)

5-7 Night Vacations in The Oaks Club

Price found within the past 48 hours. Click for updated prices.
Captiva Beach Resort

Captiva Beach Resort

2 out of 5
Save 100% on your flight
per person
Jan 16 - Jan 22
found 1 day ago
Roundtrip flight included
New York (JFK) to Sarasota (SRQ)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
per person
Jan 16 - Jan 22
found 1 day ago
Roundtrip flight included
New York (JFK) to Sarasota (SRQ)
Barsala at Champions Walk

Barsala at Champions Walk

4 out of 5
Save 100% on your flight
per person
Dec 27 - Jan 3
found 5 hours ago
Roundtrip flight included
Baltimore (BWI) to Sarasota (SRQ)
Legacy Hotel at IMG Academy

Legacy Hotel at IMG Academy

4 out of 5
Save 100% on your flight
per person
Dec 29 - Jan 3
found 14 hours ago
Roundtrip non-stop flight included
Nashville (BNA) to Sarasota (SRQ)

The Oaks Club Last Minute Hotel Deals

Casey Key Resorts - Mainland
Casey Key Resorts - Mainland
3 out of 5
1650 South Tamiami Trail, Osprey, FL
Stay at this 3-star business-friendly hotel in Osprey. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the pool and the restaurant ...
Casey Key Resorts - Mainland
Turtle Beach Resort and Inn
Turtle Beach Resort and Inn
3.5 out of 5
9049 Midnight Pass Road, Siesta Key, FL
Book a stay at this spa hotel in Siesta Key. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular ...
Turtle Beach Resort and Inn
Siesta Heron Suites & Villas
Siesta Heron Suites & Villas
3.5 out of 5
8254 Midnight Pass Rd, Siesta Key, FL
Stay at this 3.5-star vacation home in Siesta Key. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Siesta Key Beach and Turtle Beach ...
Siesta Heron Suites & Villas
Spark by Hilton Sarasota Siesta Key Gateway
Spark by Hilton Sarasota Siesta Key Gateway
3 out of 5
6600 S Tamiami Trl, Sarasota, FL
Stay at this 3-star business-friendly hotel in Sarasota. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the pool ...
Spark by Hilton Sarasota Siesta Key Gateway
Tropical Beach Resorts
Tropical Beach Resorts
3.5 out of 5
6717 Sara Sea Circle, Siesta Key, FL
Stay at this 3.5-star beach aparthotel in Siesta Key. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the pool and the helpful staff ...
Tropical Beach Resorts
Siesta Key Palms Resort
Siesta Key Palms Resort
4 out of 5
1800 Stickney Point Rd, Sarasota, FL
Stay at this 4-star hotel in Sarasota. Enjoy 2 outdoor pools, free bicycles on site, and a garden. Our guests praise the pool and the helpful staff in our reviews. ...
Siesta Key Palms Resort
Siesta Key Inn
Siesta Key Inn
2 out of 5
1125 Point of Rocks Rd, Siesta Key, FL
Stay at this hotel in Siesta Key. Enjoy free WiFi, free parking, and a garden. Popular attractions Siesta Key Beach and Lido Beach are located nearby.
Siesta Key Inn
Captiva Beach Resort
Captiva Beach Resort
2 out of 5
6772 Sara Sea Circle, Siesta Key, FL
Book a stay at this beach condo in Siesta Key. Enjoy free WiFi, free parking, and a private beach. Our guests praise the helpful staff and the clean rooms in ...
Captiva Beach Resort
See all 7,433 properties in The Oaks Club
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.

Book the perfect getaway to The Oaks Club

With Hotwire, booking your next trip to Osprey is a breeze. When it comes to planning a show-stopping vacay, you’re the reigning champion of doing it on a dime. You love to plan exciting destination adventures while saving money on a budget.

Hotwire is here to help you plan a smooth sailing trip to The Oaks Club while saving some major cash. Doubling up on vacation expenses like hotel and car rentals and fun-filled excursions can save you money—especially when you book one of Hotwire’s vacation packages.

If your trip to is spur-of-the-moment and you’re leaving soon, Hotwire can save you up to 60% off your rentals with Hotwire Hot Rate deals. Book with Hotwire to grab a stellar The Oaks Club flight and hotel package for as low as $370.

Living it up in Osprey means getting there in style and staying in a hotel that matches your mood. Book one of Hotwire’s The Oaks Club, Osprey vacation packages to enjoy the best of both worlds. Flight and hotel packages typically include roundtrip non-stop flights and multi-day hotel stays. Packages are priced per person and are perfect for flying solo or traveling with a group of friends or family. Conveniently choose from Hotwire’s inventory of hotels in The Oaks Club for some of the best accommodations and flight deals.

FAQs about cheap The Oaks Club packages:

How to get cheap vacation deals to The Oaks Club?

Save up to 60% off vacation deals with Hotwire Hot Rates. Just plug in your general preferences and let Hotwire choose matching hotels for as low as $143.

How much are The Oaks Club packages?

Vacation packages to The Oaks Club vary in price. They are priced per person and include discounted hotel and flight costs. With Hotwire, you can score a vacation package for as low as $370.

How to find cheap car rentals near The Oaks Club?

Hotwire partners with some of the most reliable car rental companies in Osprey to bring you the best car rental deals in The Oaks Club for as low as . Select a rental from Hotwire’s extensive inventory of cars for every travel style. If you plan on bringing friends or family along, opt for a spacious SUV. If you’re visiting on business but still plan to make time for off-the-clock adventures, Hotwire offers sleek luxury and convertible rentals.

Is it safe to travel to The Oaks Club now?

With recent COVID-19 closures and reopenings, many people are wondering, “Is it safe to travel to The Oaks Club right now?” When it’s time to book your vacation, check out the most up-to-date information on all safety measures, any restrictions, and guidance on traveling during the coronavirus pandemic.