Keystone Vacations from $869

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Your Keystone Vacation

An easy way to experience this interesting city is with a tailor-made Keystone vacation package. Base yourself in the neighborhood of Lake Magdalene, which is great for shopping, families and hiking or choose someplace else — our packages are all about you. If sightseeing is on the cards during your trip to Keystone, check out popular attractions like TPC of Tampa Bay, Silver Dollar Golf Club and Crescent Lake. Whatever your travel plans or budget, organizing a tailored Keystone vacation is a piece of cake with Expedia.

The Latest Keystone vacation packages

Price found within the past 48 hours. Click for updated prices.
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Sunshine Beach
Save 100% on your flight
Price was $1,559, price is now $869 per person
$869
per person
Aug 25 - Sep 1
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.6/10 Exceptional! (1,004 reviews)
We have stayed at hotels, condos, and bnbs all over the country for years, and this has been the cleanest by far. We had a slight issue with our door and the staff immediately came to fix it. A maintenance worker goes around fixing up stuff and covering scuffs regularly. The staff was beyond accommodating and the bar tenders were great. Thank you for a great, easy vacation!!! We will be back!

Reviewed on Jun 18, 2026

CW Hotel

CW Hotel

4 out of 5
Price was $1,864, price is now $911 per person
$911
per person
Aug 25 - Sep 1
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
No reviews
The Don CeSar

The Don CeSar

4 out of 5
Save 100% on your flight
Price was $1,760, price is now $945 per person
$945
per person
Aug 25 - Sep 1
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (1,165 reviews)
I have one word, WOW!!! You need to go and experience this amazing place for yourself!!!!!!

Reviewed on Jun 19, 2026

Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
Price was $1,746, price is now $942 per person
$942
per person
Aug 28 - Sep 4
found 18 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (526 reviews)
Beautiful facility. Perfect for families close to all the beaches and fun. Can't wait to return for our next visit!

Reviewed on Jun 18, 2026

Villa Valentino Luxury 8BR Villa & Pool

Villa Valentino Luxury 8BR Villa & Pool

3 out of 5
Allen's Ridge
Save 100% on your flight
Price was $3,882, price is now $2,272 per person
$2,272
per person
Aug 22 - Aug 27
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
No reviews
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Stay near popular Keystone attractions

Lake Chunliff within Providence Rhode Island Roger Williams Park

Lake Rogers Park

8.8/5 (11 reviews)
Lake Rogers Park is just one of the places to see in Odessa, so why not enjoy the other things to explore during your travels? Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.
See properties

Keystone Hotel Deals

Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
100 Coronado Drive Clearwater Beach FL
Fully refundableReserve now, pay when you stay
$258 nightly
The price is $292 total per night from Jul 8 to Jul 9
$292 total
Jul 8 - Jul 9
Total with taxes and fees
9.4/10 Exceptional! (3,380 reviews)
"Very welcoming place. Staff is pleasant and attentive. Located within walking distance to local attractions."

Reviewed on Jun 18, 2026

Wyndham Grand Clearwater Beach
The Westin Tampa Bay

The Westin Tampa Bay

4 out of 5
7627 W Courtney Campbell Cswy Tampa FL
Fully refundableReserve now, pay when you stay
$151 nightly
The price is $172 total per night from Jun 29 to Jun 30
$172 total
Jun 29 - Jun 30
Total with taxes and fees
8.6/10 Excellent! (1,372 reviews)
"Swimming pool was closed for our stay."

Reviewed on Jun 15, 2026

The Westin Tampa Bay
Hilton Clearwater Beach Resort & Spa

Hilton Clearwater Beach Resort & Spa

4 out of 5
400 Mandalay Ave Clearwater Beach FL
Fully refundableReserve now, pay when you stay
$203 nightly
The price is $229 total per night from Jul 1 to Jul 2
$229 total
Jul 1 - Jul 2
Total with taxes and fees
8.2/10 Very Good! (2,695 reviews)
"Overall the hotel was very nice, the amenities were great, the staff were friendly. Check in was a little rough, but check out was a breeze. Cons: the air conditioner did not work very well, there was mold all over the corner of our room, and everything was incredibly expensive, especially for a ..."

Reviewed on Jun 19, 2026

Hilton Clearwater Beach Resort & Spa
See all 12,171 properties in Keystone
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.

Find the Best Keystone Vacation Packages

Keystone Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Tampa Intl. Airport (TPA)
Population
24,000

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Frequently asked questions

How much does a Keystone vacation package cost?
You'll find cheap prices from $869 on Expedia for your Keystone escape. However, a range of factors like your choice of hotel, the season and length of stay will determine how much your vacation to Keystone costs.
What are the cheapest months to go to Keystone?
April, June and September are great times to look for cheap Keystone vacation packages. Opting to travel in less busy months means you'll typically find better prices on accommodations and flights.
How many days is enough for Keystone?
We suggest planning a Keystone vacation for at least 2 days. This gives you enough time to tick off major attractions including Keystone Lake and Brooker Creek Headwaters Nature Preserve, and also explore neighborhoods like Cheval West and Cumberland Manors. You could even squeeze in a day trip or two from Keystone.
Is it worth booking a vacation package to Keystone?
During your Keystone vacation, you can look forward to enjoying some excellent hiking and nature. Leave enough room in your schedule to explore leading sights like Crescent Lake and Keystone Lake.
How to find the best Keystone package deals?
Finding a cheap Keystone package deal is a cinch with Expedia. After you've entered your trip dates and destination under our "Packages" tab, set your budget, add a couple of filters and browse what's available. You can personalize your search by "Popular locations," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to discover the most wallet-friendly Keystone package deals. Want a simple trick to get even more savings? Be flexible with your departure dates and consider traveling on a weekday, when prices are often lower.
Is it cheaper to book a Keystone vacation as a package?
You can enjoy significant savings on your Keystone escape by booking a tailored vacation package. Click on the "Package" heading, then enter your travel dates and destination to browse the best hotel and flight prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Keystone?
Land fantastic discounts by booking your flights ahead of time with Expedia. If being spontaneous is more your style, take advantage of our last-minute deals for a spur-of-the-moment Keystone break.
How to plan a trip to Keystone?

  1. Choose when to travel: Check your schedule and get your bags packed. Your favorite time of year and the available activities will also help you decide when to escape to Keystone.
  2. Figure out your budget: Make sure you have enough money to cover everything from transportation and food to flights and activities. Your accommodations will likely be the biggest expense during your trip to Keystone.
  3. Discover Keystone with Expedia's trip planning tool: Gain insights into the leading attractions and best hotels for your trip to Keystone. You can also save your favorite locations, collaborate with your group and organize all your plans in one place.
  4. Decide how long to go for: Now that you're up to speed on Keystone, you can figure out the right length of your break. Put together a draft itinerary and give yourself enough time to cover everything you want to see.
  5. Bundle your bookings: With your travel dates in place, you can combine your hotels, flights, car rental and more into a customized Keystone vacation package.
  6. Book any activities or day trips: Now to the fun part — organizing everything you want to see and do. Browse some of the incredible things to do in Keystone and reserve your tickets early to save time (and maybe some spending money too!).

Does Expedia offer Book Now, Pay Later Keystone vacation packages?
Jet off on your perfect escape to Keystone with our Book Now, Pay Later vacations. No need to save up or wait for the next payday — we've joined forces with online lender Affirm to give you more flexibility and choice. Our vacation packages with payment plans allow you to spread the total cost across 3, 6 or 12 months. With no hidden charges or late payment fees, it's a breeze to stay on budget and snap up travel deals while they last.

Explore a world of travel with Expedia

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