A marina with docked boats, a wooden bridge, and a building with a red roof.

Osprey Vacation Rentals

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Check prices for these dates

In two weeks
31 Jul - 2 Aug
In two months
11 Sep - 13 Sep
In three months
9 Oct - 11 Oct
In four months
6 Nov - 8 Nov

Our top choices for Osprey vacation rentals

1 bedroom, desk, WiFi, bed sheets

Charming Secluded Tented Cabin in Sarasota, Florida

Charming Secluded Tented Cabin in Sarasota, Florida
Sarasota
The price is SAR 1,033
SAR 1,318 total
includes taxes & fees
14 Jul - 15 Jul
Charming Secluded Tented Cabin in Sarasota, Florida
1 bedroom, desk, WiFi, bed sheets

Enjoyable Secluded Tented Cabin with Fire Pit in Sarasota, Florida

Enjoyable Secluded Tented Cabin with Fire Pit in Sarasota, Florida
Sarasota
The price is SAR 1,033
SAR 1,318 total
includes taxes & fees
14 Jul - 15 Jul
Enjoyable Secluded Tented Cabin with Fire Pit in Sarasota, Florida
1 bedroom, desk, WiFi

Fantastic Tented Cabin with Fire Pit in Sarasota, Florida

Fantastic Tented Cabin with Fire Pit in Sarasota, Florida
Sarasota
The price is SAR 1,033
SAR 1,318 total
includes taxes & fees
14 Jul - 15 Jul
Fantastic Tented Cabin with Fire Pit in Sarasota, Florida
Property grounds

Incredible Tented Cabin with Stunning Forest Views in Sarasota, Florida

Incredible Tented Cabin with Stunning Forest Views in Sarasota, Florida
Sarasota
The price is SAR 1,033
SAR 1,318 total
includes taxes & fees
15 Jul - 16 Jul
Incredible Tented Cabin with Stunning Forest Views in Sarasota, Florida
Cabin (Tiny House - The Siesta) | Living area | Flat-screen TV, Netflix, streaming services

Tiny House Siesta

Tiny House Siesta
2.0 star property
Sarasota
8.4 out of 10, Very Good, (375 reviews)
"The house was clean and simple. Perfect for a couple to stay for a few nights. Not too far from the beach. Very quiet and safe area."
United States
bruno
The price is SAR 252
SAR 741 total
includes taxes & fees
16 Jul - 17 Jul
Tiny House Siesta
Microwave, oven, stovetop

Charming 2-bedroom house in lovely Sarasota with yard.

Charming 2-bedroom house in lovely Sarasota with yard.
Kensington Park
9.2 out of 10, Wonderful, (32 reviews)
"Great home with a wonderful back yard and very welcoming for pets. Very comfortable , great shower. I would stay here again!"
United States
Anonymous traveler
The price is SAR 321
SAR 789 total
includes taxes & fees
15 Jul - 16 Jul
Charming 2-bedroom house in lovely Sarasota with yard.
Living area

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, (25 reviews)
"Every part of this stay was perfect! "
United States
Stephen P.
The price is SAR 323
SAR 822 total
includes taxes & fees
14 Jul - 15 Jul
Nestled in North Port. Updated 2 Bed / 1 Bath.
Exterior

Chadwick Cove Resort & Marina

Chadwick Cove Resort & Marina
4.0 star property
Manasota Key
9.4 out of 10, Exceptional, (22 reviews)
"Nic place to stay and enjoy the area"
United States
isabel
The price is SAR 283
SAR 2,007 total
includes taxes & fees
15 Jul - 16 Jul
Chadwick Cove Resort & Marina
Dining

Lakeview Bradenton Rental Near Beaches & IMG

Lakeview Bradenton Rental Near Beaches & IMG
South Bradenton
10.0 out of 10, Exceptional, (3 reviews)
"Very clean and comfortable. "
United States
Dee F.
The price is SAR 398
SAR 927 total
includes taxes & fees
11 Aug - 12 Aug
Lakeview Bradenton Rental Near Beaches & IMG
Beach nearby, sun loungers, beach towels

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, (18 reviews)
"Great place. Clean with everything you need"
United States
Thomas Lee
The price is SAR 456
SAR 1,241 total
includes taxes & fees
14 Jul - 15 Jul
BAREFOOT BUNGALOW- 1O MINUTES TO SIESTA BEACH AND AMENITIES! PET FRIENDLY!
1 bedroom, desk, free WiFi, bed sheets

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, (42 reviews)
"It was a lovely quiet place to stay! Clean and homey, everything I needed was there! Highly recommended "
United States
Joyce H.
The price is SAR 282
SAR 648 total
includes taxes & fees
14 Jul - 15 Jul
Near to the Beach, UTC mall, SCF, IMG, Airport, Ringling Museum and much more
Outdoor pool, pool umbrellas, sun loungers

Cedar Run Resort - Roam Hospitality

Cedar Run Resort - Roam Hospitality
3.5 star property
South Bradenton
9.2 out of 10, Wonderful, (7 reviews)
"The room was very clean and well maintained/new. Staff was friendly and helpful. The air conditioner was great. The room we stayed at had lots of accessories for the beach like chairs and kid’s toys for the beach along with an umbrella. The surroundings are peaceful and beautiful. It was a great experience overall."
United States
Jose Luis Alberti
The price is SAR 518
SAR 2,350 total
includes taxes & fees
14 Jul - 15 Jul
Cedar Run Resort - Roam Hospitality
2 bedrooms, iron/ironing board, WiFi, bed sheets

[escape to paradise] siesta key beach getaway

[escape to paradise] siesta key beach getaway
Siesta Key
9.8 out of 10, Exceptional, (31 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 SAR 422
SAR 1,221 total
includes taxes & fees
14 Jul - 15 Jul
[escape to paradise] siesta key beach getaway
Beach nearby, beach towels

Resort Retreat Near IMG & Anna Maria Beaches ~ Pools & Hot Tubs ~ Private Lanai

Resort Retreat Near IMG & Anna Maria Beaches ~ Pools & Hot Tubs ~ Private Lanai
Bradenton
9.8 out of 10, Exceptional, (122 reviews)
"We loved the property, large pool & access to activities. "
United States
Mary Beth M.
The price is SAR 446
SAR 1,201 total
includes taxes & fees
6 Aug - 7 Aug
Resort Retreat Near IMG & Anna Maria Beaches ~ Pools & Hot Tubs ~ Private Lanai
Property grounds

Cabana Beach Club - Beachfront Stunning Ocean View *Snow Bird Promo* Winter 2027

Cabana Beach Club - Beachfront Stunning Ocean View *Snow Bird Promo* Winter 2027
Longboat Key
9.8 out of 10, Exceptional, (268 reviews)
"Great location for the price! Also, it was well equipped with everything you need."
United States
LJ G.
The price is SAR 822
SAR 2,099 total
includes taxes & fees
14 Jul - 15 Jul
Cabana Beach Club - Beachfront Stunning Ocean View *Snow Bird Promo* Winter 2027
5365 Calle Florida, Siesta Key, FL W/Pool | Private kitchen

Siesta Key Island Rentals

Siesta Key Island Rentals
3.0 star property
Siesta Key
9.6 out of 10, Exceptional, (72 reviews)
"Great location, very clean and spacious."
United States
Jason
The price is SAR 527
SAR 1,389 total
includes taxes & fees
15 Jul - 16 Jul
Siesta Key Island Rentals
On the beach

Beachfront Studio – Cabana #5B by RVA

Beachfront Studio – Cabana #5B by RVA
Longboat Key
8.2 out of 10, Very Good, (81 reviews)
"The cabana was a fantastic place to escape. It had easy access to both the beach and the pool. My kids loved every moment there."
United States
Roxana P.
The price is SAR 563
SAR 1,167 total
includes taxes & fees
15 Jul - 16 Jul
Beachfront Studio – Cabana #5B by RVA
Outdoor dining

Dolphin Villa - Pool - Steps to Siesta Key Village

Dolphin Villa - Pool - Steps to Siesta Key Village
Siesta Key Village
9.4 out of 10, Exceptional, (17 reviews)
"Great location to downtown, beach. Kitchen and furnishing updated and in great condition. Negatives would be the lock on the backdoor, air conditioning from the ceiling that could not be controlled from our apartment. The pool was great and had plenty of seating. Only issue with the Dolphin apartment is the many windows, which kind of made it feel like living in a fish bowl. That might not be an issues for others. "
United States
Sandra C.
The price is SAR 389
SAR 1,352 total
includes taxes & fees
14 Jul - 15 Jul
Dolphin Villa - Pool - Steps to Siesta Key Village
Exterior

Tropical, private, downtown

Tropical, private, downtown
Central Sarasota
9.6 out of 10, Exceptional, (92 reviews)
"Super cute place in a great location!"
United States
Lisa A.
The price is SAR 514
SAR 1,101 total
includes taxes & fees
14 Jul - 15 Jul
Tropical, private, downtown
On the beach

Jetties Pointe Cottage #1 - 408 “Casey Key”

Jetties Pointe Cottage #1 - 408 “Casey Key”
Casey Key
9.6 out of 10, Exceptional, (27 reviews)
"Great place to stay. Right on the beach! "
United States
William C.
The price is SAR 859
SAR 1,862 total
includes taxes & fees
14 Jul - 15 Jul
Jetties Pointe Cottage #1 - 408 “Casey Key”
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

Embassy Suites by Hilton Sarasota, FL

Embassy Suites by Hilton Sarasota, FL

10/10 Excellent
"The hotel is located at a perfect location with just 11 min to Sarasota International hotel, 8 min drive to a beautiful Lido beach and walking distance to a Wholefoods and different restaurants. Hotel offers a great breakfast with made to order omlets. Restaurant on site is a plus. The food was good. The room was clean and spacious. Loved the stay."
Ekaterina 5-night trip
Posted 2 hours ago
Embassy Suites by Hilton Sarasota, FL

Frequently asked questions

Can I find vacation rentals in Osprey?

Yes, we have vacation rentals in Osprey near Jim Neville Marine Preserve, or you can go with a more secluded option if you're looking for extra privacy while you relax. 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 vacation rentals in Osprey?

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

How many vacation rentals are there in Osprey?

With 14 Expedia vacation rentals, you're sure 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 like Siesta Key Beach and Lido Beach.

What’s a vacation rental in Osprey like?

Vacation rentals are private properties you can stay in for a long or short time in Osprey. Vacation rentals provide amenities such as WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of security away from shared hotel elevators and lobbies packed with people while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a hotel, which makes a vacation rental an attractive option for families.