Osprey Holidays from NZ$2,687

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The Latest Osprey Holiday Deals

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

Hotel Tampa Riverwalk

4 out of 5
Downtown Tampa
per person
16 Sept - 21 Sept
found 4 hours ago
Return flight included
Auckland (AKL) to Sarasota (SRQ)
7/10 Good! (1,602 reviews)
Our stay was great. The water view was beautiful. The staff very nice and helpful. We ate inside hotel food was good. Our server Linda was very helpful and polite. Hotel sit right on the Riverwalk with beautiful view and walkable dining and shops. I would diffently recommend here.

Reviewed on 10 Aug. 2025

The Barrymore Hotel Tampa Riverwalk

The Barrymore Hotel Tampa Riverwalk

3 out of 5
Downtown Tampa
per person
16 Sept - 21 Sept
found 4 hours ago
Return flight included
Auckland (AKL) to Sarasota (SRQ)
8.4/10 Very Good! (2,381 reviews)
I stayed here before taking the bar. The rooms were small but very comfortable. The parking was easy and with lots of spaces.

Reviewed on 10 Aug. 2025

Our guide on where to stay in Osprey

Find the best Osprey areas and neighborhoods for the activities you enjoy most. Learn more about Osprey
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Sorrento Shores

While Sorrento Shores may not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Oscar Scherer State Park and Nokomis Beach.

Find hotels in Sorrento Shores

Osprey Holiday

Our pick of the best Osprey Hotel Deals

Casey Key Resorts - Mainland

Casey Key Resorts - Mainland

2.5 out of 5
1650 South Tamiami Trail, Osprey, FL
Fully refundableReserve now, pay when you stay
The price is NZ$235 per night from 31 Aug to 1 Sept
NZ$235
31 Aug - 1 Sept
includes taxes & fees
8.6/10 Excellent! (1,051 reviews)
"Was very pleased that I choose to stay here for my first time, property and rooms clean, pool was very nice, staff was very accommodating, onsite restaurant was very good. I plan to return on future visits."

Reviewed on 10 Aug. 2025

Casey Key Resorts - Mainland
Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
965 University Pkwy, Sarasota, FL
Fully refundableReserve now, pay when you stay
9/10 Wonderful! (4,228 reviews)
"The hotel is nice, beautiful and super clean."

Reviewed on 10 Aug. 2025

Get rates
Kompose Boutique Hotel
Tropical Beach Resorts

Tropical Beach Resorts

3.5 out of 5
6717 Sara Sea Circle, Siesta Key, FL
Fully refundableReserve now, pay when you stay
The price is NZ$302 per night from 1 Sept to 2 Sept
NZ$302
1 Sept - 2 Sept
includes taxes & fees
9.2/10 Wonderful! (4,852 reviews)
"This is a beautiful place! The apartment was spotless, comfortable, and wonderfully quiet — a true relaxing getaway. The only downside (and I truly mean the only one) was the beach experience. While the beach itself is private and lovely, getting a spot with chairs and an umbrella was unnecessarily ..."

Reviewed on 10 Aug. 2025

Tropical Beach Resorts
See all 10,466 properties in Osprey
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.

What to do in Osprey

Private Luxury Boat Charter

Private Luxury Boat Charter

NZ$623
per traveller
100% of travellers recommend
Private Luxury Boat Charter
Great photo opportunity with this friendly Dolphin!

Dolphin and Manatee Adventure tour of Osprey with Florida History

NZ$108
per adult
Dolphin and Manatee Adventure tour of Osprey with Florida History
See all activities in Osprey

Frequently asked questions

How much does an Osprey holiday package cost?
Offering great value package deals from NZ$2,687 on Expedia, you'll be pleasantly surprised at how much a holiday to Osprey costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Osprey?
August, September and November are great times to look for cheap Osprey holiday packages. Travelling in less busy periods means you can usually find lower prices on hotels and flights.
How many days is enough for Osprey?
Dedicate at least 3 days for your Osprey holiday to really immerse yourself in everything that makes this place special. Stroll around popular areas, including Laurel and Casey Key. Then make a beeline for major sights such as Oscar Scherer State Park and The Oaks Club. With a clever itinerary, you'll be kept busy with room for some relaxation too. Want to venture beyond Osprey? Consider squeezing in a day trip or two.
Is it worth booking a holiday package to Osprey?
Osprey has everything you need for an amazing trip. Get your Osprey holiday off to a flying start by checking out major attractions like Oscar Scherer State Park.
How to find the best Osprey package deals?
Bagging a cheap Osprey package deal is easy with Expedia. After you've entered your preferred dates and destination under our "Packages" tab, set your budget range, apply some filters and browse what's available. You can personalise your search by "Property class," "Number of bedrooms," "Traveller experience" and more. Order the results by "Price: low to high" to view the most wallet-friendly Osprey package deals. Want a simple trick to score even more savings? Have some flexibility with your departure dates and consider travelling on a weekday, when prices are usually lower.
Is it cheaper to book an Osprey holiday as a package?
Expedia holiday packages are designed to give you more bang for your buck. Bundle your car rental, hotel and flight into one great-value price and you could save hundreds of dollars. You'll generally get a better deal than booking each component individually. And you'll still have the flexibility to create a customised Osprey holiday by choosing your favourite accommodation type, airline and car class.
When to book a holiday package to Osprey?
Score incredible bargains by reserving your flights ahead of time with Expedia. If spontaneity is more your style, snap up one of our last-minute deals for an impromptu Osprey getaway.
How to plan a trip to Osprey?

  1. Choose the ideal time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to visit Osprey.
  2. Budget wisely: On top of the cost of your hotel, you'll need to consider other expenses too. These include transportation, food and flights. Also, set aside a little extra for unexpected expenses that may crop up during your trip to Osprey.
  3. Decide how long to go away for: Now that you're more familiar with Osprey, you can work out the ideal length of your break. Put together a rough itinerary and allocate enough time for all the things you want to do.
  4. Bundle your hotel and flights: Awesome destination, check. Length of stay, check. Now all that's left is to choose an Osprey holiday package that brings all your bookings together.

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