Osprey Holiday Rentals

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Our top choices for Osprey holiday rentals

Holiday Home in Bay Acres

Charming Osprey Home
2.0 star property
The price is NZ$659
includes taxes & fees
5 Jan - 6 Jan 2026
Charming Osprey Home

Mobile Home in Sarasota

Tiny House Siesta
2.0 star property
8.4 out of 10, Very good, (346)
"Enjoyable stay. "
United States
Lori
The price is NZ$411
includes taxes & fees
10 Jan - 11 Jan 2026
Tiny House Siesta
9.0 out of 10, Wonderful, (9)
"Property was very nice and exactly what I was looking for while working remote. Would absolutely recommend it to anyone and look forward to coming back in the future."
United States
Jake R.
The price is NZ$276
includes taxes & fees
29 Dec - 30 Dec
#3 Small house walking distance to Warm Mineral Spring

Aparthotel in South Village

Tropical Beach Resorts
3.5 star property
9.4 out of 10, Exceptional, (5181)
"Great location, value, clean, friendly staff. Will definitely stay there again. "
United States
JoAnna
The price is NZ$317
includes taxes & fees
4 Jan - 5 Jan 2026
Tropical Beach Resorts
9.2 out of 10, Wonderful, (10)
"Property was perfect for the price."
United States
William M.
The price is NZ$296
includes taxes & fees
1 Jan - 2 Jan 2026
Charming cottage for 2 across warm mineral springs park

Holiday Home in Siesta Key

Siesta Heron Suites & Villas
3.5 star property
8.6 out of 10, Excellent, (38)
"It was perfect for my family of 4 for our beach vacation!!"
United States
Jesse
The price is NZ$701
includes taxes & fees
4 Jan - 5 Jan 2026
Siesta Heron Suites & Villas

Aparthotel in Venice Island

Kon Tiki Inn
2.5 star property
10.0 out of 10, Exceptional, (248)
"Lovely decor, very clean"
United States
Frederick
The price is NZ$510
includes taxes & fees
20 Jan - 21 Jan 2026
Kon Tiki Inn

Condo in Manasota Key

Chadwick Cove Resort & Marina
4.0 star property
10.0 out of 10, Exceptional, (14)
"Great place and location "
United States
Cathy
The price is NZ$934
includes taxes & fees
7 Jan - 8 Jan 2026
Chadwick Cove Resort & Marina
2.5 star property
8.6 out of 10, Excellent, (2221)
"Very nice place !"
United States
Ivette
Hibiscus Suites - Gateway to Siesta Key
3.5 star property
9.6 out of 10, Exceptional, (302)
"The rooms were perfect, and the staff was great. The location was perfect and peaceful"
United States
Marybeth
The price is NZ$854
includes taxes & fees
27 Jan - 28 Jan 2026
The Residences at Siesta Key Beach by Hyatt Vacation Club

Holiday Home in South Venice

Mimosa Memories
9.4 out of 10, Exceptional, (30)
"Nice quiet home , very clean. "
United States
David M.
The price is NZ$567
includes taxes & fees
1 Jan - 2 Jan 2026
Mimosa Memories

Apartment in Olde Englewood Village

Newly renovated only minutes away from the beach!!
9.6 out of 10, Exceptional, (58)
"Clean, comfortable, everything you need! Owner is great!"
United States
Cheryl L.
The price is NZ$489
includes taxes & fees
31 Dec - 1 Jan 2026
Newly renovated only minutes away from the beach!!
9.2 out of 10, Wonderful, (36)
"Very nice place, easy check in, and communicative host"
United States
Cristopher M.
The price is NZ$296
includes taxes & fees
31 Dec - 1 Jan 2026
Near to the Beach, UTC mall, SCF, IMG, Airport, Ringling Museum and much more
9.2 out of 10, Wonderful, (69)
"The Cottage is simple and in need of a few updates, but it is a beach cottage and the salt air is not kind. Overall, the location is fantastic, the Cottage is clean and comfortable and our stay was great."
United States
Bob T.
The price is NZ$748
includes taxes & fees
29 Dec - 30 Dec
Direct Beachfront 2BR Cottage on Casey Key!

Holiday Home in Venice East

Venice Dove Shell
2.0 star property
The price is NZ$315
includes taxes & fees
27 Jan - 28 Jan 2026
Venice Dove Shell

Holiday Home in Venice

Myakka River
9.8 out of 10, Exceptional, (18)
"We loved everything about the property it’s nice and quiet. Nicely decorated and has a nice outdoor area and dock. The bed was a little firm for my taste but not terrible. 10/10 would stay here again "
United States
Ty
The price is NZ$782
includes taxes & fees
29 Dec - 30 Dec
Myakka River
9.8 out of 10, Exceptional, (35)
"Super clean rental… exactly as described, great location close to everything"
United States
Randy S.
The price is NZ$348
includes taxes & fees
1 Jan - 2 Jan 2026
Beautiful University Pines Studio in Sarasota

Condo in Casey Key

A Beach Retreat
2.5 star property
9.2 out of 10, Wonderful, (580)
"Great location, recent updates"
United States
Michael
A Beach Retreat
9.6 out of 10, Exceptional, (81)
"We loved our stay at the Drift Inn. Very clean, just the right amount of room for 4, easy access to the beach and pool. The beds were very comfortable. The owner was very quick to respond to questions from beginning to end. We would stay here again."
United States
Kimberly P.
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.

Holiday Home in South Bradenton

Lakeview Bradenton Rental Near Beaches & IMG
The price is NZ$422
includes taxes & fees
7 Jan - 8 Jan 2026
Lakeview Bradenton Rental Near Beaches & IMG
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

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 favorite 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 depends 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 NZ$317 per night. Entering your travel dates in the search wizard you might find 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 top-notch restaurants in this destination. While you're in the area, you can also enjoy the lively bars 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 20 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.