Romantic Vacations in Caladesi Island State Park 2026

Photo by Fay Nicoll

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5* Romantic holidays in Caladesi Island State Park

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

The Ritz-Carlton, Sarasota

Central Sarasota

CA $2,613

per person

Sep 24 - Sep 30

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Tampa (TPA)

9.2/10 Wonderful! (1,017 reviews)

I had an excellent experience from the moment I arrived at the hotel. The staff were incredibly polite, friendly, and welcoming. I immediately felt comfortable and at home. Thank you for making my stay such a warm and pleasant experience!

Reviewed on Aug 21, 2026

The Gemma by Brightwild

CA $3,286

per person

Oct 26 - Oct 30

found 9 hours ago

Roundtrip flight included

Toronto (YYZ) to Tampa (TPA)

9.8/10 Exceptional! (6 reviews)

The Jade House is in an excellent location only a block from the beach and short walk to restaurants, shops, and bars. Communication with the management company was difficult through Expedia. Even when I called directly, one of the three client service agents was not helpful whatsoever. However, once I was given the number to text, communication was much better. The pool/ hot tub area is perfect. The house is very comfortable. Only decks are narrow (only stand); ocean view is from one of theses.

Reviewed on Jul 30, 2026

The St. Regis Longboat Key Resort

CA $8,251

per person

Nov 5 - Nov 12

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Tampa (TPA)

9.8/10 Exceptional! (88 reviews)

Great staff and close attention to detail. Helpful all around. Great restaurants.

Reviewed on Aug 14, 2026

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3 Night Romantic holidays in Caladesi Island State Park

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

The Hotel Zamora

CA $774

per person

Oct 2 - Oct 5

found 1 day ago

Roundtrip flight included

Detroit (DTW) to Tampa (TPA)

8.8/10 Excellent! (388 reviews)

The hotel is beautiful and very clean. Great amenities, close to great restaurants and beautiful stretch of the beach. Lovely service, staff weee friendly and very helpful. Rachel at the hotel restaurant was amazing. We had a beautiful weekend. Will definitely visit again.

Reviewed on Aug 21, 2026

CW Hotel

CA $827

per person

Nov 13 - Nov 16

found 16 hours ago

Roundtrip flight included

Toronto (YYZ) to Tampa (TPA)

9.6/10 Exceptional! (48 reviews)

Ocean Club Treasure Island Hotel

Sunshine Beach

CA $823

per person

Oct 1 - Oct 4

found 19 hours ago

Roundtrip flight included

Detroit (DTW) to Tampa (TPA)

9.6/10 Exceptional! (1,128 reviews)

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4 Night Romantic holidays in Caladesi Island State Park

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

ChartHouse Clearwater Beach Marina Hotel

CA $789

per person

Sep 23 - Sep 27

found 11 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Tampa (TPA)

9.6/10 Exceptional! (1,341 reviews)

Ocean Club Treasure Island Hotel

Sunshine Beach

CA $869

per person

Oct 31 - Nov 4

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Tampa (TPA)

9.6/10 Exceptional! (1,128 reviews)

Hibiscus Suites - Gateway to Siesta Key

CA $832

per person

Nov 12 - Nov 16

found 13 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Tampa (TPA)

8.6/10 Excellent! (2,412 reviews)

I loved that this property was on the edge of a quiet beautiful neighborhood for walking my dog. Very clean and cared for! Probably the best bed I’ve ever had in a rental. I would stay here again and recommend to others.

Reviewed on Aug 21, 2026

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What are some of the benefits of booking a romantic Caladesi Island State Park vacation?

When booking a romantic Caladesi Island State Park vacation, you'll find quite a few options to make the experience with your partner absolutely unforgettable. Luxury amenities like hot tubs and spa facilities are prominent, but a lot of romantic vacation getaways also make it easy to explore some of the best spots in St. Petersburg - Clearwater.

How can I find the best vacation packages for couples?

If you're looking for a romantic vacation getaway, all you have to do is implement the romantic search filter. That will automatically remove any property that isn't suitable for couples. Just put in your travel dates and the Caladesi Island State Park destination, and you'll be met with an array of options for you and your partner to enjoy.

Can I find cheap romantic vacations for 2 in Caladesi Island State Park?

Yes, there are several options for booking cheap romantic vacations that don't break the bank. You'll find prices as low as CA $774 and can enjoy savings of up to 4 when you book your hotel and flight together. Budget and luxury options are both available along with everything in between. Sorting your results by price will allow you to view the cheapest options first.

What do I need to consider when booking a romantic getaway in Caladesi Island State Park?

Romantic vacation getaways succeed based on catering to what you and your partner specifically want to do. Think about what your partner enjoys and what you want to do as a couple, then opt for something that is especially geared toward fulfilling your ideal romantic vacation getaway experience. Search filters for amenities and proximity to certain attractions throughout Caladesi Island State Park certainly come in handy here.

What amenities should I look for in a luxury romantic vacation?

If you and your partner are interested in luxury, you won't have to look far for a romantic vacation getaway that fits. In luxury accommodations, you can enjoy amenities like room service and a hot tub. Some accommodations may even have their own spa facilities complete with massage services that will add an extra touch of romance to your excursion to Caladesi Island State Park.

Can I book a romantic Caladesi Island State Park vacation with a hot tub?

Yes, and it's easy when you take advantage of available search filters. All you have to do is implement the hot tub filter from the amenities section into your search. This will automatically remove any stays from your search results that do not have hot tubs in them.

How can I find romantic vacation getaways that are all-inclusive?

An all-inclusive trip allows you to plan out your romantic vacation getaway in advance, letting you get a solid number on cost and a full itinerary before you set out. To start this kind of planning, simply apply the filter for all-inclusive trips in your Caladesi Island State Park search.

Can I book a romantic trip to Caladesi Island State Park that is fully refundable?

Several romantic Caladesi Island State Park vacations come with fully refundable reservations. You can filter for this specifically, but every accommodation will list its policy for cancellation in their policy section, which is visible after clicking on a search result. Always make sure to check their policy to determine the requirements.

Why should I book a romantic vacation with Expedia?

Booking your trip with Expedia makes the entire planning process that much easier, as we're your convenient, all-in-one stop for all your travel needs. You can book your stay and your flight, with special discounts potentially available for booking together. Additionally, you can enjoy more discounts by becoming an Expedia Rewards member and getting points to put toward your next booking. Becoming a member is free, so don't hesitate to take advantage.