Keystone Romantic Vacations
Book a Romantic Hotel + Flight or Car together to unlock savings
Photo by Travel Ginger
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Romantic vacation packages in Keystone
Price found within the past 48 hours. Click for updated prices.
SkyBeach Resort
Greater Pinellas Point
Save 100% on your flight
Price was $941, price is now $665 per person
$665
per person
Jun 22 - Jun 27
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
8.6/10 Excellent! (679 reviews)
It was okay. Resort fees provided nothing we would use. On top of resort fees, you must pay for parking, and pay to reserve/use the cabanas.
Our last day, the maids didn't even service our room. And the one night we ordered room service, it was kind of a nightmare...once we got the food, it was not good.
All that aside, it is an older resort, that is maintained in pretty good shape. Great launching pad to explore Tampa and surrounding beaches.
Reviewed on May 12, 2026
Ocean Club Treasure Island Hotel
Sunshine Beach
Save 100% on your flight
Price was $1,941, price is now $1,202 per person
$1,202
per person
Aug 1 - Aug 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.6/10 Exceptional! (932 reviews)
The room was fabulous! Spotless, modern and spacious. The kitchen came equipped with everything we needed. The air conditioning was perfect. The balcony overlooked the pool and the beach which was just a short walk away. The hotel is in a great location with the beach so close, a Publix just 1 km away, lots of nearby restaurants to choose from, and walking distance to the village in John’s Pass. The staff were super friendly and helpful and always around doing something. We would totally recommend the Ocean Club Treasure island hotel!
Reviewed on May 13, 2026
Wyndham Grand Clearwater Beach
Save 100% on your flight
Price was $1,580, price is now $1,075 per person
$1,075
per person
Jun 17 - Jun 22
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.4/10 Exceptional! (3,211 reviews)
We had a fabulous Mother’s Day weekend at Wyndham Grand Clearwater Beach. It also happened to be Country Weekend, which made the experience even more fun and memorable. The entertainment was a huge plus and created such an amazing atmosphere throughout the weekend.
The lobby bar staff and pool staff were absolutely amazing. Everyone was so attentive, friendly, and welcoming, especially on Mother’s Day. They truly went above and beyond to make all the moms feel special and taken care of.
From the beautiful property to the great energy and outstanding customer service, the entire experience exceeded our expectations. Thank you to the whole team for making our Mother’s Day celebration so enjoyable and unforgettable. We will definitely be back!
Reviewed on May 12, 2026
The Avalon Club
Save 100% on your flight
Price was $2,360, price is now $1,624 per person
$1,624
per person
Jun 17 - Jun 22
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.4/10 Exceptional! (534 reviews)
Great experience! The staff is very kind. The only issue was the living room sofa was very noisy. Would definitely stay again!
Reviewed on May 12, 2026
5* Romantic vacations in Keystone
Price found within the past 48 hours. Click for updated prices.
The Adaline
Hyde Park
Price was $1,117, price is now $990 per person
$990
per person
Jul 13 - Jul 18
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.6/10 Exceptional! (70 reviews)
Beautiful property and in such a charming and walkable neighborhood. Will plan to stay here again.
Reviewed on Apr 29, 2026
The Ritz-Carlton, Sarasota
Central Sarasota
Price was $1,322, price is now $1,155 per person
$1,155
per person
Jun 19 - Jun 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (1,001 reviews)
Club level is definitely worth the upgrade excellent place to stay
Reviewed on May 10, 2026
3 Night Romantic vacations in Keystone
Price found within the past 48 hours. Click for updated prices.
Wyndham Grand Clearwater Beach
Save 100% on your flight
Price was $994, price is now $735 per person
$735
per person
Jul 15 - Jul 18
found 4 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
9.4/10 Exceptional! (3,211 reviews)
We had a fabulous Mother’s Day weekend at Wyndham Grand Clearwater Beach. It also happened to be Country Weekend, which made the experience even more fun and memorable. The entertainment was a huge plus and created such an amazing atmosphere throughout the weekend.
The lobby bar staff and pool staff were absolutely amazing. Everyone was so attentive, friendly, and welcoming, especially on Mother’s Day. They truly went above and beyond to make all the moms feel special and taken care of.
From the beautiful property to the great energy and outstanding customer service, the entire experience exceeded our expectations. Thank you to the whole team for making our Mother’s Day celebration so enjoyable and unforgettable. We will definitely be back!
Reviewed on May 12, 2026
Ocean Club Treasure Island Hotel
Sunshine Beach
Save 100% on your flight
Price was $1,118, price is now $792 per person
$792
per person
Jul 13 - Jul 16
found 1 day ago
Roundtrip flight included
New York (JFK) to Tampa (TPA)
9.6/10 Exceptional! (932 reviews)
The room was fabulous! Spotless, modern and spacious. The kitchen came equipped with everything we needed. The air conditioning was perfect. The balcony overlooked the pool and the beach which was just a short walk away. The hotel is in a great location with the beach so close, a Publix just 1 km away, lots of nearby restaurants to choose from, and walking distance to the village in John’s Pass. The staff were super friendly and helpful and always around doing something. We would totally recommend the Ocean Club Treasure island hotel!
Reviewed on May 13, 2026
The Avalon Club
Save 100% on your flight
Price was $1,591, price is now $1,137 per person
$1,137
per person
Jul 15 - Jul 18
found 4 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
9.4/10 Exceptional! (534 reviews)
Great experience! The staff is very kind. The only issue was the living room sofa was very noisy. Would definitely stay again!
Reviewed on May 12, 2026
4 Night Romantic vacations in Keystone
Price found within the past 48 hours. Click for updated prices.
ChartHouse Clearwater Beach Marina Hotel
Save 100% on your flight
Price was $861, price is now $607 per person
$607
per person
Jul 13 - Jul 17
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.6/10 Exceptional! (976 reviews)
Great service and very clean room.
Reviewed on May 13, 2026
Ocean Club Treasure Island Hotel
Sunshine Beach
Save 100% on your flight
Price was $1,706, price is now $1,226 per person
$1,226
per person
Jul 1 - Jul 5
found 24 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.6/10 Exceptional! (932 reviews)
The room was fabulous! Spotless, modern and spacious. The kitchen came equipped with everything we needed. The air conditioning was perfect. The balcony overlooked the pool and the beach which was just a short walk away. The hotel is in a great location with the beach so close, a Publix just 1 km away, lots of nearby restaurants to choose from, and walking distance to the village in John’s Pass. The staff were super friendly and helpful and always around doing something. We would totally recommend the Ocean Club Treasure island hotel!
Reviewed on May 13, 2026
BeachTrail Lodging
Save 100% on your flight
Price was $939, price is now $676 per person
$676
per person
Jul 19 - Jul 23
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Tampa (TPA)
9.8/10 Exceptional! (100 reviews)
The cottage was well stocked with a snack basket and a super dog basket. The kitchen was stocked with all needed essentials and the parking also worked out well.
Reviewed on Apr 14, 2026
How to find a romantic Keystone vacation
How can I find the best Keystone vacation packages for couples?
To win over the love of your life, first choose where and when you want to bring the romance. Now flirt with the filters to add ocean views, spa, pools, and anything else that gets your heart racing.
How can I find cheap Keystone romantic packages for two?
For dollar-friendly delights, sort your search results by price or deals. You can also filter by budget to find romantic retreats at prices you’ll love. For an affordable and alluring adventure, try self-catering.
How can I plan a great romantic trip to Keystone?
Find what fills you with joy and dive right in, whether you thrill in a little adventure or lust for long lazy days by the pool, handcrafted cocktails in hand. Fire cupid’s arrow at our filters and build your dream trip for two.
How much is a trip for two to Keystone?
Put a price on love with stunning deals for duos starting at just $607. Prices and availability are subject to change. Additional terms may apply.
Can I book Keystone spa packages for couples?
Check the filter box for a seductive stay at a spa. Sort your results by price, deals, rating, and more to guarantee the perfect match.
How can I book romantic weekend getaway packages in Keystone?
To book a loved-up break in Keystone, enter your travel dates and sort by price, deals, rating—whatever matters most to you and your partner. Now, you can add some adult-only amenities, like a hot tub or full-service spa for total R, R, & R (that’s romance, rest, and recuperation).
Can I book a romantic trip to Keystone with free cancellation and/or flexible dates?
The course of true love should always run smooth, but we get that there are hiccups. So, filter by payment option to search for romantic stays with free cancellation and buy now, pay later options.
Why should I book my Keystone romantic holiday with Expedia?
If you’ve only got eyes for excellent escapes, book your loved-up break with Expedia. Fling the filters to find accommodation you’ll adore. And what’s more attractive than ATOL protection?
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.
