The Oaks Club Vacation Deals: The Oaks Club, Osprey Vacations

The Oaks Club vacation package deals

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

Venice Beach Villas

Save 100% on your flight

per person

Jun 17 - Jun 22

found 1 day ago

Roundtrip flight included

Boston (BOS) to Sarasota (SRQ)

This condo doesn't skimp on freebies - guests receive free WiFi and free self parking. Business travelers can take advantage of the express check-in. Enjoy the outdoor pool and conveniences like a terrace and laundry facilities.

Cedar Cove Resort and Cottages

Save 100% on your flight

per person

Jul 30 - Aug 3

found 1 day ago

Roundtrip flight included

Boston (BOS) to Sarasota (SRQ)

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a garden, and a snack bar/deli are also on offer.

Captiva Beach Resort

Save 100% on your flight

per person

Jun 19 - Jun 23

found 1 day ago

Roundtrip flight included

Boston (BOS) 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.

Barsala at Champions Walk

Save 100% on your flight

per person

Jun 20 - Jun 27

found 1 day ago

Roundtrip flight included

Boston (BOS) to Sarasota (SRQ)

This aparthotel features free WiFi in public areas, barbecue grills, and a virtual front desk.

Pelican Post at Anna Maria Island Inn

Save 100% on your flight

per person

Jul 30 - Aug 3

found 1 day ago

Roundtrip flight included

Boston (BOS) 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.

Legacy Hotel at IMG Academy

Save 100% on your flight

per person

Jun 20 - Jun 27

found 1 day ago

Roundtrip flight included

Boston (BOS) to Sarasota (SRQ)

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the 24-hour gym and perks like free self parking and free WiFi. You'll appreciate the area shuttle, valet parking, and coffee shop/cafe.

Frequently asked questions

How much are vacation packages to The Oaks Club?

If you love the idea of hassle-free planning and impressive savings, our $426 The Oaks Club vacation package will be perfect for you. With your hotel and flights sorted, organizing your trip around this fabulous attraction is easier than ever.

Where can I get the best vacation package deals for The Oaks Club?

Travelocity is the only place you need to go to score a great The Oaks Club package deal. Take your pick of 400 airlines and 1,000,000 properties across the globe and craft a travel itinerary that’s right for you. With so much choice, now’s the time to book your next big adventure.

Why should I book my The Oaks Club vacation bundle via Travelocity?

Whether you’re planning a weeks-long vacation or a last-minute weekend escape, we have plenty of tempting destinations to choose from at an affordable rate. What’s more, we offer 24/7 support, top-notch service and a Price Match Guarantee. Save yourself money and time and secure your dream vacation today.

Top The Oaks Club hotel deals

Charming Florida Beach Home w King Bed Patio

This vacation home doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden is also provided.

Renovated duplex near beach with central AC & private W/D-Dogs ok

This vacation home features laundry facilities.

Huge Pool, Close to Beaches, Restaurants, Shopping & More!

A water park and an outdoor pool are featured at this smoke-free vacation home. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available on site. Enjoy the hot tub and conveniences like a garden and laundry facilities.

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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.