Keystone Beach Vacations
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Top Beach vacation packages in Keystone
Price found within the past 48 hours. Click for updated prices.
The Westin Tampa Bay
Rocky Point
Save 100% on your flight
Price was $1,053, price is now $690 per person
$690
per person
Mar 5 - Mar 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
8.4/10 Very Good! (1,047 reviews)
Staff was exceptional. Rooms were brand new and super clean. Pool is under construction, but other than that, the place was a gem!
Reviewed on Jan 7, 2026
The Westin Sarasota
Central Sarasota
Save 100% on your flight
Price was $2,380, price is now $1,447 per person
$1,447
per person
Mar 23 - Mar 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9/10 Wonderful! (1,131 reviews)
Nice place! Will stay again! Had a great NYE!
Reviewed on Jan 8, 2026
Saddlebrook Resort
Wesley Chapel South
Price was $1,107, price is now $784 per person
$784
per person
Feb 13 - Feb 16
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
No reviews
The resort is absolutely beautiful.We will definitely be staying here again.We actually decided to stay another night. What definitely recommended
Reviewed on Jan 1, 2026
Ocean Club Treasure Island Hotel
Sunshine Beach
Save 100% on your flight
Price was $1,451, price is now $1,063 per person
$1,063
per person
Mar 26 - Mar 29
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.6/10 Exceptional! (712 reviews)
Beautiful room, beautiful sunsets, diggers on the beach directly in view from hotel the entire time we stayed (moving pipes from hurricane beach repair) but we still got beautiful pictures, heated pool and hot tub was nice, enough long chairs around the pool, tether ball was fun for kids, walking path along beach front was very nice, walkable to beach and big Publix grocery store, room was spacious and nice, front desk very accommodating with all our needs, prompt service. Comfortable beds, nice bathrooms. Unit was clean and bright and quiet. Fun activities close by. Good fishing off the shoreline, soooo many shells, sand was beautiful, loved the professional sand sculptures, fireworks on beach at New Year’s was a nice treat. Lots of good restaurants near by. I wish the gym was bigger and had mirrors.
Reviewed on Jan 8, 2026
The Sarasota Modern, a Tribute Portfolio Hotel
Central Sarasota
Save 100% on your flight
Price was $1,981, price is now $1,466 per person
$1,466
per person
Mar 23 - Mar 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
8.2/10 Very Good! (515 reviews)
We stayed one night for a NY Eve dinner and thankfully it was only one night. The staff is super friendly; the facility was decorated for the holidays and is in a good location, that makes walking an option. The one issue we had was that there was no hot water in the shower and apparently had been going on for a couple of days. We should have been made aware of the problem and maybe given us free parking.
Reviewed on Jan 1, 2026
5* Beach vacations in Keystone
Price found within the past 48 hours. Click for updated prices.
The Adaline
Hyde Park
Save 100% on your flight
Price was $1,282, price is now $1,105 per person
$1,105
per person
Feb 10 - Feb 15
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
9.6/10 Exceptional! (53 reviews)
Really a great place. Everything was perfect.
Reviewed on Jan 1, 2026
The Ritz-Carlton, Sarasota
Central Sarasota
Save 100% on your flight
Price was $3,816, price is now $3,167 per person
$3,167
per person
Mar 23 - Mar 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (1,001 reviews)
Caitlyn came to our table last night and spent about 25 minutes with us, sharing her story about how she became a team member at The Ritz-Carlton. Even while taking the time to connect with us, she was still seamlessly managing the entire restaurant; truly impressive to watch. I don’t know where you found her, but you need about seven more like her across your properties. She’s far beyond first class; she’s in a league of her own. She truly elevated our evening and made our visit unforgettable. We will absolutely be back because of her.
Kimberly is an absolute standout; truly extraordinary. Her smile and laugh are so infectious that if you’re having a bad day, she’ll instantly turn it around. Whoever had the insight to place her at the front of the house is a genius, because her caring and loving nature shines through in every interaction. Her personal touch has a way of soothing even the most stressed guest and makes everyone feel genuinely welcome.
Reviewed on Dec 28, 2025
3 Night Beach vacations in Keystone
Price found within the past 48 hours. Click for updated prices.
Saddlebrook Resort
Wesley Chapel South
Price was $833, price is now $527 per person
$527
per person
Mar 13 - Mar 16
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
No reviews
The resort is absolutely beautiful.We will definitely be staying here again.We actually decided to stay another night. What definitely recommended
Reviewed on Jan 1, 2026
The Avalon Club
Save 100% on your flight
Price was $2,785, price is now $1,974 per person
$1,974
per person
Mar 12 - Mar 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.4/10 Exceptional! (481 reviews)
Overall, this is a great property with a lot going for it. The staff was friendly and helpful, and the rooftop bar was a really nice bonus—great atmosphere and a perfect place to unwind.
That said, I’m not sure how the property is marketed as a true two-bedroom. One of the rooms does not have a closet, which made it challenging for a family of four, especially with two teenage girls and limited space for clothing and belongings.
The unit does have a bath and a half, which can work well if you’re comfortable with teens essentially taking over the primary bathroom for showers and getting ready. Once we adjusted to that setup, it was manageable.
If you’re aware of the layout going in and don’t need traditional bedroom storage, this can be a great stay. Just something families should know when booking.
Reviewed on Jan 4, 2026
4 Night Beach vacations in Keystone
Price found within the past 48 hours. Click for updated prices.
Saddlebrook Resort
Wesley Chapel South
Save 100% on your flight
Price was $652, price is now $360 per person
$360
per person
Feb 22 - Feb 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
No reviews
The resort is absolutely beautiful.We will definitely be staying here again.We actually decided to stay another night. What definitely recommended
Reviewed on Jan 1, 2026
The Westin Tampa Bay
Rocky Point
Save 100% on your flight
Price was $1,053, price is now $690 per person
$690
per person
Mar 5 - Mar 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
8.4/10 Very Good! (1,047 reviews)
Staff was exceptional. Rooms were brand new and super clean. Pool is under construction, but other than that, the place was a gem!
Reviewed on Jan 7, 2026
Find your perfect Keystone beach vacation
How do I book the best Keystone beach vacation packages?
Life’s a beach when you dive into our brilliant Keystone beach vacation deals. Chuck a check in the filter boxes to find ocean views, pools, and resorts just a short saunter from the sizzling sands.
How can I find cheap beach vacations in Keystone?
A rental steps from the shore creates an amazingly affordable Keystone beach vacation. Seaside sojourns during low season start from $360. Prices and availability are subject to change. Additional terms may apply.
When should I book a Keystone beach holiday?
For a bustling beach break, book in . For a less crowded coast, is the time to turn up.
How can I book the best family beach vacations in Keystone?
With a flick of a finger, the family-friendly filter brings you the best breaks on offer for the whole brood. Look out for kids’ clubs, waterparks, and other incredible extras for a vacay the little ones will love.
How do I find a Keystone beachfront vacation?
Check the beachfront filter and, bam, the best available oceanside resorts will appear before your eyes. Along with the incredible view, when you book a beachfront resort, you can get from the lapping waves to your patio lounger in a matter of moments.
Can I book a package including a Keystone vacation beach house rental?
Hit up the vacation rental filter to book your dream beach house. Once you’ve selected the most alluring abode, add your flights and car rental for the perfect package deal.
Can I find Keystone beach vacation deals?
Sort your search results by deals to delight in amazing Keystone beach vacation offers. If you want more pizzazz for your pennies, travel outside the high season or stay a little further from the shoreline.
Can I book a Keystone beach trip with free cancellation and/or flexible dates?
Just like the Keystone tides, plans change. Filter by payment option to find trips with free cancellation. Buy now, pay later options are also available for full-on flexibility.
Why should I book my Keystone beach vacation with Expedia?
Relax long before you see the shore with simple search, fantastic filters, and more great deals than there are grains of sand in Keystone. (OK, maybe not that last part.)
Top Beach Keystone Hotels
Luxurious Home w/ Private Pool & Lanai Near Tampa!
Odessa FL
Stay at this villa in Odessa. Enjoy a garden, patios, and housekeeping. Popular attractions Keystone Lake and Brooker Creek Headwaters Nature Preserve are located ...
2 kitchens, Canoe, kayak on Sunset Lake + 700sqf apt Perfect for family getaways
Odessa FL
Book a stay at this family-friendly vacation home in Odessa. Enjoy free WiFi, a fitness center, and a garden. Popular attractions Keystone Lake and Silver Dollar ...
Truly enjoyed it.
We truly enjoyed our stay. It was wonderful. We loved taking the dogs out in the canoe on the lake. We grilled every night and even enjoyed a fire in the fire pit. It was so quiet and exactly the get away we needed.
Reviewed on May 30, 2023
Five Star Rating Lake/WaterFront Oasis Near Tampa/Orlando & Gulf Beaches
Odessa FL
Stay at this vacation home in Odessa. Enjoy a garden, laundry facilities, and patios. Popular attractions Keystone Lake and Brooker Creek Headwaters Nature Preserve ...
10/10 Exceptional! (38 reviews)
The Lake house is very peaceful and relaxing. The kitchen is the most well stocked of all the places we have stayed in.The hosts were eager to make our stay enjoyable.There is a Welcome book that is very well organized and informative. Before you do anything else, look at the Welcome book. It will ...
Reviewed on Jan 8, 2026
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.
More vacations you might like
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.