Osprey Vacation Rentals

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Our top choices for Osprey vacation 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
$242 nightly
The price is $270
May 28 - May 29
Total with taxes and fees
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
$195 nightly
The price is $218
May 28 - May 29
Total with taxes and fees
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)
"Easy check in, clean and cozy."
United States
Robert J.
$130 nightly
The price is $144
May 28 - May 29
Total with taxes and fees
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
$314 nightly
The price is $355
Jun 2 - Jun 3
Total with taxes and fees
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
$503 nightly
The price is $539
May 28 - May 29
Total with taxes and fees
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
$117 nightly
The price is $132
May 28 - May 29
Total with taxes and fees
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.
$155 nightly
The price is $173
May 28 - May 29
Total with taxes and fees
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
$228 nightly
The price is $254
Jun 1 - Jun 2
Total with taxes and fees
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.
$361 nightly
The price is $370
May 31 - Jun 1
Total with taxes and fees
[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
$288 nightly
The price is $321
Jun 1 - Jun 2
Total with taxes and fees
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.
$244 nightly
The price is $272
May 28 - May 29
Total with taxes and fees
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.
$423 nightly
The price is $436
May 28 - May 29
Total with taxes and fees
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.
$451 nightly
The price is $502
Jun 15 - Jun 16
Total with taxes and fees
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, (129 reviews)
"Lovely spot. Clean and roomy. Host was easy to contact and accommodating. "
United States
April R.
$272 nightly
The price is $304
May 29 - May 30
Total with taxes and fees
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.
$286 nightly
The price is $319
Jun 6 - Jun 7
Total with taxes and fees
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.
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.
$194 nightly
The price is $216
Jun 6 - Jun 7
Total with taxes and fees
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.
$289 nightly
The price is $322
May 28 - May 29
Total with taxes and fees
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.
$274 nightly
The price is $306
Jun 1 - Jun 2
Total with taxes and fees
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
$371 nightly
The price is $419
May 31 - Jun 1
Total with taxes and fees
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 vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Osprey vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Osprey vacation 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 low season months. For more hustle and bustle, you may prefer to visit Osprey in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $132 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Osprey rentals

At Expedia, we put the best Osprey vacation 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 vacation.

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 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 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 Venice 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.