Osprey Holiday Rentals

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Holiday Rentals in Osprey

Our top choices for Osprey holiday rentals

Charming Florida Beach Home w King Bed Patio

2.0 star property
10.0 out of 10, Exceptional, (2)
"The best place to stay! Super clean home and friendly service. I would stay here again. "
The price is AU$494
includes taxes & fees
30 Sept - 1 Oct
Charming Florida Beach Home w King Bed Patio

Tropical Beach Resorts

3.5 star property
9.4 out of 10, Exceptional, (4935)
"Wonderful resort "
The price is AU$275
includes taxes & fees
3 Sept - 4 Sept
Tropical Beach Resorts

Hibiscus Suites - Gateway to Siesta Key

2.5 star property
8.6 out of 10, Excellent, (2168)
"Bed comfort , great location, friendly staff. "
Hibiscus Suites - Gateway to Siesta Key

SeaSpray Resort

4.0 star property
9.2 out of 10, Wonderful, (31)
"Renovated resort, a block away from the beach, very clean and friendly staff. Would stay there again. "
The price is AU$395
includes taxes & fees
3 Sept - 4 Sept
SeaSpray Resort

The Ringling Beach House

3.5 star property
9.0 out of 10, Wonderful, (319)
"We loved the Villa!! It was spacious and stocked with every kitchen item you can imagine. "
The Ringling Beach House

Luxury Beach Home! Pool, Rooftop Deck & Fun Amenities! - Shell-Abrate Good Times

9.8 out of 10, Exceptional, (24)
"The house was in great condition and near everything. "
Luxury Beach Home! Pool, Rooftop Deck & Fun Amenities! - Shell-Abrate Good Times

Captiva Beach Resort

2.0 star property
9.0 out of 10, Wonderful, (1127)
"2nd time and excellent as always..close to the beach and great surroundings "
Captiva Beach Resort

Tiny House Siesta

2.0 star property
8.4 out of 10, Very good, (318)
"Super helpful staff."
The price is AU$210
includes taxes & fees
8 Sept - 9 Sept
Tiny House Siesta

Sea Club I Beach Resort

3.0 star property
9.0 out of 10, Wonderful, (320)
"just an amazing staff and clean rooms! it was paradise will go back next year for sure!!"
Sea Club I Beach Resort

Siesta Palms By the Beach

3.5 star property
9.2 out of 10, Wonderful, (127)
"An outstanding experience — a place that leaves you with a strong desire to return."
Siesta Palms By the Beach

Kon Tiki Inn

2.5 star property
10.0 out of 10, Exceptional, (227)
"We love everything about this place Debbie and her husband are awesome from check in to check out this is a 5 star resort and we will be back many more times"
Kon Tiki Inn

Bradenton Apartments by Landing

4.0 star property
7.4 out of 10, Good, (43)
"Absolutely beautiful location has everything you need n makes you feel like home"
Bradenton Apartments by Landing

The Residences at Siesta Key Beach by Hyatt Vacation Club

3.5 star property
9.8 out of 10, Exceptional, (285)
"Great location. Everyone was very friendly and accommodating!"
The price is AU$724
includes taxes & fees
2 Oct - 3 Oct
The Residences at Siesta Key Beach by Hyatt Vacation Club

Private Home Directly on Siesta Key Beach!

10.0 out of 10, Exceptional, (4)
"Beautiful place to stay… direct walk to the beach from your back door. Amazing view! Clean with all the amenities you need. "
Private Home Directly on Siesta Key Beach!

Siesta Key Island Rentals

3.0 star property
9.6 out of 10, Exceptional, (47)
"This place was incredible. We have traveled a lot with family and this was the best. Very comfortable and accommodating! I really cannot say enough good about this house. "
The price is AU$485
includes taxes & fees
3 Sept - 4 Sept
Siesta Key Island Rentals

Venice Beach Villas

3.0 star property
9.4 out of 10, Exceptional, (433)
"Clean and welcoming property"
Venice Beach Villas

The Inn On Siesta Key

3.5 star property
10.0 out of 10, Exceptional, (183)
"Great place to stay! "
The Inn On Siesta Key

Tropical Villas of Venice Beach

3.5 star property
9.6 out of 10, Exceptional, (239)
"Great Location !!"
Tropical Villas of Venice Beach

Tranquil Siesta Key Retreat ~ Walk to Beach ~ Pool

9.6 out of 10, Exceptional, (20)
"Close to beach. Easy to get to locations with the Frog Hop! Plenty of space for 8 of us!"
Tranquil Siesta Key Retreat ~ Walk to Beach ~ Pool

Beachfront 3-Bedroom Condo on Siesta Key – Steps to the Sand & Gulf Views

9.4 out of 10, Exceptional, (64)
"This is our second time staying here. Absolutely love this rental. Very clean and walking distance to the village "
Beachfront 3-Bedroom Condo on Siesta Key – Steps to the Sand & Gulf Views
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.
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Top Osprey Hotel Reviews

Find out more about Osprey

Find out more about Osprey

Everything you need to know about Osprey holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Osprey holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Osprey holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Osprey holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Osprey. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Osprey holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Osprey holiday rentals we have selected for you start as low as per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Osprey rentals

At Expedia, we put the best Osprey holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Osprey rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Osprey holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Osprey. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Osprey?

Yes, there are holiday rentals in Osprey close to Jim Neville Marine Preserve, or you can select a more secluded option if you're looking for a relaxing stay. Visitors to Osprey speak positively about the popular beaches and lively bars in this destination. While you're in the area, you can also enjoy the top-notch restaurants and shops.

What are some of the best holiday rentals that Osprey has to offer?

Charming Florida Beach Home w King Bed Patio: This highly rated holiday home rental in Osprey offers a garden and free WiFi to help you feel comfortable in your new surroundings. This holiday rental also comes with free parking to give you added peace of mind.

How many holiday rentals are there in Osprey?

With 31 Expedia holiday rentals, you're guaranteed to find just the right place for your Osprey stay.

What’s there to see and do in Osprey?

Family-friendly attractions include Jim Neville Marine Preserve and Nancy's Consignments, whereas Turtle Beach and Nokomis Beach are a couple of great spots to enjoy the outdoors. While in the area, you can also visit popular places such as Siesta Key Beach and Lido Beach.

What’s a holiday rental in Osprey like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Osprey. Holiday rentals feature extras such as kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, holiday rentals can provide a sense of security away from shared hotel lifts and lobbies bustling with people while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular choice for families.