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Our top choices for Osprey holiday rentals

Charming Osprey Home

Charming Osprey Home
Bay Acres
10.0 out of 10, Exceptional, (2 reviews)
"We had a positive experience staying at Linda’s duplex in Osprey. Linda was a lovely host and even furnished us with beach chairs and a cabana . The place was spotless & location was convenient for us as we explored most of the Sarasota, Venice & Naples area. Highly recommended staying at this lovely duplex. "
United States
Diane S.
The price is £307
includes taxes & fees
10 May - 11 May
Charming Osprey Home

Sunny Coastal Escape

Sunny Coastal Escape
Bay Acres
10.0 out of 10, Exceptional, (5 reviews)
"Great location for exploring north & south! House was very clean and comfy. We appreciated the excellent communication with our nice host, Lynn."
United States
Kaja F.
The price is £308
includes taxes & fees
10 May - 11 May
Sunny Coastal Escape

Tiny House Siesta

Tiny House Siesta
2.0 star property
Sarasota
8.4 out of 10, Very good, (362 reviews)
"super clean and comfortable. we were 4 people and had a very comfortable and lovely stay. i felt super at home and the location is very centralized to everything "
United States
Adanna
The price is £165
includes taxes & fees
27 Apr - 28 Apr
Tiny House Siesta

Coastal Quadruplex with private beach access & deck - dog-friendly

Coastal Quadruplex with private beach access & deck - dog-friendly
Manasota Key
8.2 out of 10, Very good, (17 reviews)
"Great place to stay. "
United States
Scott
The price is £287
includes taxes & fees
13 Apr - 14 Apr
Coastal Quadruplex with private beach access & deck - dog-friendly

Charming cottage for 2 across warm mineral springs park

Charming cottage for 2 across warm mineral springs park
Warm Mineral Springs
9.0 out of 10, Wonderful, (22 reviews)
"We liked how it was a quiet neighborhood and a short drive to stores and restaurants. "
United States
Luann F.
The price is £115
includes taxes & fees
13 Apr - 14 Apr
Charming cottage for 2 across warm mineral springs park

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, (21 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
11 Apr - 12 Apr
Nestled in North Port. Updated 2 Bed / 1 Bath.

Old Floridian cottage in Historic Gulf Village

Old Floridian cottage in Historic Gulf Village
Olde Englewood Village
9.8 out of 10, Exceptional, (61 reviews)
"Very good, great location 👍👍"
United States
James M.
The price is £208
includes taxes & fees
1 May - 2 May
Old Floridian cottage in Historic Gulf Village

Mimosa Memories

Mimosa Memories
South Venice
9.6 out of 10, Exceptional, (37 reviews)
"Me and my significant other took a little mini vacation wonderful house. It was very clean very beautiful inside, I like the beach vibes beautiful bedrooms. I recommend anybody to book this place. If I had to go back, I’ll book again. "
United States
Alexus
The price is £246
includes taxes & fees
13 Apr - 14 Apr
Mimosa Memories

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, (23 reviews)
"Fun place "
United States
Maureen
The price is £192
includes taxes & fees
10 May - 11 May
Secluded Cottage with Hot Tub, Walking Distance to Benderson and UTC.

Entire Standalone Lido Beach Villa, 1.2k sf, 1 block to the beach

Entire Standalone Lido Beach Villa, 1.2k sf, 1 block to the beach
Lido Key
9.8 out of 10, Exceptional, (122 reviews)
"Super clean, perfect location, and cool decor - and, most important, veeerry comfortable beds! We loved our stay! "
United States
Kevin L.
The price is £220
includes taxes & fees
23 Apr - 24 Apr
Entire Standalone Lido Beach Villa, 1.2k sf, 1 block to the beach

Chadwick Cove Resort & Marina

Chadwick Cove Resort & Marina
4.0 star property
Manasota Key
10.0 out of 10, Exceptional, (17 reviews)
"Great place and location "
United States
Cathy
The price is £291
includes taxes & fees
13 Apr - 14 Apr
Chadwick Cove Resort & Marina

Lakefront Condo · IMG Academy 5 Min · Anna Maria Beach 15 Min · Pools & Hot Tubs

Lakefront Condo · IMG Academy 5 Min · Anna Maria Beach 15 Min · Pools & Hot Tubs
Bradenton
9.8 out of 10, Exceptional, (118 reviews)
"Perfect spot and host "
United States
Dee B.
The price is £221
includes taxes & fees
3 May - 4 May
Lakefront Condo · IMG Academy 5 Min · Anna Maria Beach 15 Min · Pools & Hot Tubs

Paradise Retreat with HEATED POOL-- Need We Say More

Paradise Retreat with HEATED POOL-- Need We Say More
South Bradenton
10.0 out of 10, Exceptional, (181 reviews)
"Maggie ,the hostess, was great. Responsive and very accommodating for our needs. "
United States
David S.
The price is £274
includes taxes & fees
16 Apr - 17 Apr
Paradise Retreat with HEATED POOL-- Need We Say More

Beach to Bay! Heated Pool and Dock on the Bay! Walk to the Beach and Restaurants

Beach to Bay! Heated Pool and Dock on the Bay! Walk to the Beach and Restaurants
Manasota Key
9.8 out of 10, Exceptional, (33 reviews)
"We had a great time and a comfortable stay."
United States
Deb J.
The price is £296
includes taxes & fees
15 Apr - 16 Apr
Beach to Bay! Heated Pool and Dock on the Bay! Walk to the Beach and Restaurants

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, (72 reviews)
"Great location in Siesta Key Village, can walk to all the shops and restaurants as well as the beach "
United States
Erica S.
The price is £337
includes taxes & fees
12 Apr - 13 Apr
Siesta Key Village-Suite #3: A Block to the Beach!

2 Miles to Siesta Key

2 Miles to Siesta Key
Gulf Gate Estates
10.0 out of 10, Exceptional, (23 reviews)
"Had a great stay! "
United States
Keith K.
The price is £107
includes taxes & fees
13 Apr - 14 Apr
2 Miles to Siesta Key

[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 £305
includes taxes & fees
13 Apr - 14 Apr
[escape to paradise] siesta key beach getaway

Centrally Located, Sarasota Home Close To Amish Community

Centrally Located, Sarasota Home Close To Amish Community
Sarasota Springs
10.0 out of 10, Exceptional, (173 reviews)
"This home was amazing! Honestly felt at home the moment I walked in. Everything you could need for your stay was provided. Very clean, great host. I'll be back!"
United States
Maudi B.
The price is £292
includes taxes & fees
15 Apr - 16 Apr
Centrally Located, Sarasota Home Close To Amish Community

Best views of the beach from your balcony Unit 301

Best views of the beach from your balcony Unit 301
Longboat Key
9.8 out of 10, Exceptional, (89 reviews)
"Breathtaking view- super clean. Easy access. Perfect spot for a few days away with my husband."
United States
Ellen L.
The price is £313
includes taxes & fees
30 Apr - 1 May
Best views of the beach from your balcony Unit 301

Kon Tiki Inn

Kon Tiki Inn
2.5 star property
Venice Island
10.0 out of 10, Exceptional, (268 reviews)
"Wonderful place! Super friendly host! Very clean, affordable! Great place!!"
United States
Carolyn
The price is £107
includes taxes & fees
6 May - 7 May
Kon Tiki Inn
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 £107 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 free 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 17 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.