Holiday Rentals in Osprey

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Our top choices for Osprey holiday rentals

Charming Osprey Home

Charming Osprey Home
2.0 star property
Bay Acres
10.0 out of 10, Exceptional, (1 review)
"Upon entering the property, we felt it was clean, bright and very welcoming. We loved the decor and the nice spaces in this two bedroom, two bath home. We thought the location was perfect, right across the main street is Walmart for quick grocery items, and we liked the amenities including a kettle for hot tea, a coffeemaker and a fully equipped kitchen! We would have liked to have more than two beach towels, but we made do with two. The laundry room was convenient for washing clothes and did...
United States
Van-Ha N.
The price is €334
includes taxes & fees
12 Jan - 13 Jan
Charming Osprey Home

Tiny House Siesta

Tiny House Siesta
2.0 star property
Sarasota
8.4 out of 10, Very good, (346 reviews)
"Enjoyable stay. "
United States
Lori
The price is €200
includes taxes & fees
13 Jan - 14 Jan
Tiny House Siesta

Charming cottage for 2 across warm mineral springs park

Charming cottage for 2 across warm mineral springs park
Warm Mineral Springs
9.2 out of 10, Wonderful, (10 reviews)
"Property was perfect for the price."
United States
William M.
The price is €147
includes taxes & fees
16 Jan - 17 Jan
Charming cottage for 2 across warm mineral springs park

Siesta Heron Suites & Villas

Siesta Heron Suites & Villas
3.5 star property
Siesta Key
8.6 out of 10, Excellent, (38 reviews)
"Clean pool great apartment could use more seating in living room. Beach chairs was cool patio was awesome parking good water pressure great bed clean and comfy "
United States
jason
The price is €329
includes taxes & fees
12 Jan - 13 Jan
Siesta Heron Suites & Villas

Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,215 reviews)
"Great place to stay. Very nice getaway. "
United States
Joyeeta
The price is €159
includes taxes & fees
12 Jan - 13 Jan
Tropical Beach Resorts

SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.4 out of 10, Exceptional, (84 reviews)
"Very clean very quiet and a great location to the beach."
United States
Dave
The price is €329
includes taxes & fees
20 Jan - 21 Jan
SeaSpray Resort

Chadwick Cove Resort & Marina

Chadwick Cove Resort & Marina
4.0 star property
Manasota Key
10.0 out of 10, Exceptional, (15 reviews)
"Great place and location "
United States
Cathy
The price is €508
includes taxes & fees
18 Jan - 19 Jan
Chadwick Cove Resort & Marina

Nestled in North Port. Updated 2 Bed / 1 Bath.

Nestled in North Port. Updated 2 Bed / 1 Bath.
North Port
10.0 out of 10, Exceptional, (15 reviews)
"Great place loved how clean and put together everything was would definitely stay here again"
United States
Jacob
Nestled in North Port. Updated 2 Bed / 1 Bath.

Kon Tiki Inn

Kon Tiki Inn
2.5 star property
Venice Island
10.0 out of 10, Exceptional, (250 reviews)
"Great place! "
United States
Michelle
The price is €283
includes taxes & fees
3 Feb - 4 Feb
Kon Tiki Inn

HAPPY FUN BLUE HOUSE for 8 people kids, pets friendly, 3 miles from the beach🏖️

HAPPY FUN BLUE HOUSE for 8 people kids, pets friendly, 3 miles from the beach🏖️
South Venice
9.8 out of 10, Exceptional, (48 reviews)
"Great place to stay especially if you have dogs "
United States
Erica R.
The price is €332
includes taxes & fees
11 Jan - 12 Jan
HAPPY FUN BLUE HOUSE for 8 people kids, pets friendly, 3 miles from the beach🏖️

Direct Beachfront 2BR Cottage on Casey Key!

Direct Beachfront 2BR Cottage on Casey Key!
Casey Key
9.2 out of 10, Wonderful, (69 reviews)
"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 €389
includes taxes & fees
11 Jan - 12 Jan
Direct Beachfront 2BR Cottage on Casey Key!

Myakka River

Myakka River
Venice
9.8 out of 10, Exceptional, (18 reviews)
"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 €400
includes taxes & fees
11 Jan - 12 Jan
Myakka River

Secluded Cottage with Hot Tub, Walking Distance to Benderson and UTC.

Secluded Cottage with Hot Tub, Walking Distance to Benderson and UTC.
The Meadows
10.0 out of 10, Exceptional, (19 reviews)
"Fun place "
United States
Maureen
The price is €223
includes taxes & fees
12 Jan - 13 Jan
Secluded Cottage with Hot Tub, Walking Distance to Benderson and UTC.

The Residences at Siesta Key Beach by Hyatt Vacation Club

The Residences at Siesta Key Beach by Hyatt Vacation Club
3.5 star property
South Village
9.6 out of 10, Exceptional, (306 reviews)
"The rooms were perfect, and the staff was great. The location was perfect and peaceful"
United States
Marybeth
The price is €373
includes taxes & fees
19 Jan - 20 Jan
The Residences at Siesta Key Beach by Hyatt Vacation Club

The Mermaid at Tiny House Siesta

The Mermaid at Tiny House Siesta
2.0 star property
Sarasota
10.0 out of 10, Exceptional, (2 reviews)
"It was exactly as listed on here. No problems with the check in it was very smooth as well as the check out process. Location was AMAZING, we were able to walk just 10 minutes to a longhorn to eat dinner and right next to it there was a bar near the beach and we were able to go back to the property just by walking. Really calm the area and the tiny house is very comfortable."
United States
Jackeline R.
The price is €184
includes taxes & fees
12 Jan - 13 Jan
The Mermaid at Tiny House Siesta

Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.

Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.
Southgate
10.0 out of 10, Exceptional, (69 reviews)
"Enjoyed our stay. Great location close to everything we needed"
United States
Christine M.
The price is €266
includes taxes & fees
12 Jan - 13 Jan
Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.

Old Floridian cottage in Historic Gulf Village

Old Floridian cottage in Historic Gulf Village
Olde Englewood Village
9.8 out of 10, Exceptional, (60 reviews)
"Very good, great location 👍👍"
United States
James M.
The price is €274
includes taxes & fees
11 Jan - 12 Jan
Old Floridian cottage in Historic Gulf Village

Waterfront Getaway, a Boating Paradise

Waterfront Getaway, a Boating Paradise
Englewood
10.0 out of 10, Exceptional, (49 reviews)
"Beautiful and immaculate property. Had everything we needed, uncluttered and so comfortable. Will definitely stay here again. "
United States
christine w.
Waterfront Getaway, a Boating Paradise

Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.6 out of 10, Excellent, (2,227 reviews)
"Very nice place !"
United States
Ivette
The price is €243
includes taxes & fees
9 Feb - 10 Feb
Hibiscus Suites - Gateway to Siesta Key

Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.

Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
South Village
9.6 out of 10, Exceptional, (81 reviews)
"Wonderful experience! It was perfect for a girls’ weekend which included me, my mother & my 12 yr old daughters. There was enough restaurants in walking distance, the beach was in walking distance and we appreciated the trolley and frog hopper to get to Turtle Beach for kayaking. "
United States
Michelle A.
The price is €264
includes taxes & fees
13 Jan - 14 Jan
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
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, apart-hotels, 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 €159 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 19 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.