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Our top choices for Osprey holiday rentals

Path to Paradise.

Path to Paradise.
Olde Englewood Village
8.0 out of 10, Very good, (1 review)
"Comfortable stay, just what we wanted."
United States
Matthew
The price is £201
includes taxes & fees
27 May - 28 May
Path to Paradise.

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, (24 reviews)
"Great place loved how clean and put together everything was would definitely stay here again"
United States
Jacob
The price is £167
includes taxes & fees
28 May - 29 May
Nestled in North Port. Updated 2 Bed / 1 Bath.

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, (24 reviews)
"Great little place! Wish we could have spent more time"
United States
Tricia W.
The price is £110
includes taxes & fees
8 Jun - 9 Jun
Charming cottage for 2 across warm mineral springs park

Cedar Run Resort - Roam Hospitality

Cedar Run Resort - Roam Hospitality
3.5 star property
South Bradenton
10.0 out of 10, Exceptional, (2 reviews)
"Every room is very well equipped, I had to communicate with the host for some issues and it was really easy and helpful, I would recommend this place!"
United States
Liz
The price is £260
includes taxes & fees
27 May - 28 May
Cedar Run Resort - Roam Hospitality

Chadwick Cove Resort & Marina

Chadwick Cove Resort & Marina
4.0 star property
Manasota Key
9.6 out of 10, Exceptional, (19 reviews)
"Great place and location "
United States
Cathy
The price is £391
includes taxes & fees
28 May - 29 May
Chadwick Cove Resort & Marina

Kon Tiki Inn

Kon Tiki Inn
2.5 star property
Venice Island
10.0 out of 10, Exceptional, (278 reviews)
"Property is super cute and clean and has everything you need!"
United States
Vanessa
The price is £98
includes taxes & fees
27 May - 28 May
Kon Tiki Inn

Near to the Beach, UTC mall, SCF, IMG, Airport, Ringling Museum and much more

Near to the Beach, UTC mall, SCF, IMG, Airport, Ringling Museum and much more
Bayshore Gardens
9.2 out of 10, Wonderful, (41 reviews)
"The host was excellent and the place was clean and just as expected."
United States
Jim M.
The price is £131
includes taxes & fees
30 May - 31 May
Near to the Beach, UTC mall, SCF, IMG, Airport, Ringling Museum and much more

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, (25 reviews)
"The perfect place and the best rental I’ve stayed in!! All the descriptions are perfect. If you’re looking for a private getaway that’s close and cozy, this is it."
United States
Emma
The price is £196
includes taxes & fees
31 May - 1 Jun
Secluded Cottage with Hot Tub, Walking Distance to Benderson and UTC.

[escape to paradise] siesta key beach getaway

[escape to paradise] siesta key beach getaway
Siesta Key
9.8 out of 10, Exceptional, (30 reviews)
"Very clean and great location! Beds very comfortable and owner very responsive and accommodating! Highly recommend staying here!"
United States
Tim T.
The price is £277
includes taxes & fees
31 May - 1 Jun
[escape to paradise] siesta key beach getaway

BAREFOOT BUNGALOW- 1O MINUTES TO SIESTA BEACH AND AMENITIES! PET FRIENDLY!

BAREFOOT BUNGALOW- 1O MINUTES TO SIESTA BEACH AND AMENITIES! PET FRIENDLY!
Ridge Wood Heights
10.0 out of 10, Exceptional, (17 reviews)
"Great place. Clean with everything you need"
United States
Thomas Lee
The price is £247
includes taxes & fees
2 Jun - 3 Jun
BAREFOOT BUNGALOW- 1O MINUTES TO SIESTA BEACH AND AMENITIES! PET FRIENDLY!

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, (75 reviews)
"Wonderful Stay"
United States
Christopher R.
The price is £212
includes taxes & fees
8 Jun - 9 Jun
Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.

Waterfront Condo Walkable to Everything with Beach Access

Waterfront Condo Walkable to Everything with Beach Access
Manasota Key
9.6 out of 10, Exceptional, (50 reviews)
"Property managers were very helpful to work with and will still stay again despite a hiccup. "
United States
Jennifer J.
The price is £347
includes taxes & fees
28 May - 29 May
Waterfront Condo Walkable to Everything with Beach Access

IMG Lake & Beach Home with Pool White Sand Beaches MAY 16-10, Oct, Nov SPECIALS!

IMG Lake & Beach Home with Pool White Sand Beaches MAY 16-10, Oct, Nov SPECIALS!
South Bradenton
9.8 out of 10, Exceptional, (140 reviews)
"Beautiful pool, nice kitchen, and close to Anna Marie Island."
United States
Gary B.
The price is £374
includes taxes & fees
15 Jun - 16 Jun
IMG Lake & Beach Home with Pool White Sand Beaches MAY 16-10, Oct, Nov SPECIALS!

Upscale 2BR Condo w/ Lanai · Two Pools & Hot Tubs · IMG Academy · Gulf Beaches

Upscale 2BR Condo w/ Lanai · Two Pools & Hot Tubs · IMG Academy · Gulf Beaches
Bradenton
10.0 out of 10, Exceptional, (128 reviews)
"Lovely spot. Clean and roomy. Host was easy to contact and accommodating. "
United States
April R.
The price is £236
includes taxes & fees
29 May - 30 May
Upscale 2BR Condo w/ Lanai · Two Pools & Hot Tubs · IMG Academy · Gulf Beaches

2BR Corner Condo w/ Lanai · Dual Pools & Hot Tubs · IMG Academy · Gulf Beaches

2BR Corner Condo w/ Lanai · Dual Pools & Hot Tubs · IMG Academy · Gulf Beaches
Bradenton
9.8 out of 10, Exceptional, (156 reviews)
"Very clean condo , we enjoyed closeness of the beaches."
United States
Joanna M.
The price is £229
includes taxes & fees
27 May - 28 May
2BR Corner Condo w/ Lanai · Dual Pools & Hot Tubs · IMG Academy · Gulf Beaches

Siesta Key Village-Suite #3: A Block to the Beach!

Siesta Key Village-Suite #3: A Block to the Beach!
Siesta Key Village
9.2 out of 10, Wonderful, (75 reviews)
"Perfect location, super clean.comfortable"
United States
matthew w.
The price is £302
includes taxes & fees
31 May - 1 Jun
Siesta Key Village-Suite #3: A Block to the Beach!

Beautiful University Pines Studio in Sarasota

Beautiful University Pines Studio in Sarasota
Sarasota
9.8 out of 10, Exceptional, (41 reviews)
"Perfect area, close to all the stores and restaurants"
United States
Maria B.
The price is £161
includes taxes & fees
8 Jun - 9 Jun
Beautiful University Pines Studio in Sarasota

Affordable Beach Studio – Silver Sands #257A by RVA

Affordable Beach Studio – Silver Sands #257A by RVA
Longboat Key
9.6 out of 10, Exceptional, (78 reviews)
"Right on beach-perfect for a short stay"
United States
Sean P.
The price is £241
includes taxes & fees
27 May - 28 May
Affordable Beach Studio – Silver Sands #257A by RVA

2BR Corner Condo w/ Lanai · Dual Pools & Hot Tubs · IMG Academy · Gulf Beaches

2BR Corner Condo w/ Lanai · Dual Pools & Hot Tubs · IMG Academy · Gulf Beaches
Bradenton
9.8 out of 10, Exceptional, (122 reviews)
"Perfect spot and host "
United States
Dee B.
The price is £235
includes taxes & fees
1 Jun - 2 Jun
2BR Corner Condo w/ Lanai · Dual Pools & Hot Tubs · IMG Academy · Gulf Beaches

Siesta Key Island Rentals

Siesta Key Island Rentals
3.0 star property
Siesta Key
9.6 out of 10, Exceptional, (68 reviews)
"Excellent location , minute walk to local bars and supermarket. Right across from beautiful siesta key beach."
United States
Alessandra
Siesta Key Island Rentals
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 £98 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 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?

Siesta Key Island Rentals: This holiday home rental outside of Osprey comes with WiFi so that you can feel at home during your trip. This holiday rental also comes with free parking to give you added peace of mind.

How many holiday rentals are there in Osprey?

With 14 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 Venice 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.