Osprey Vacation Rentals

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Check prices for these dates

In two weeks
Apr 24 - Apr 26
In two months
Jun 5 - Jun 7
In three months
Jul 3 - Jul 5
In four months
Jul 31 - Aug 2

Our top choices for Osprey vacation rentals

Beach towels

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.
$358 nightly
The price is $400
May 10 - May 11
Total with taxes and fees
Charming Osprey Home
Beach

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.
$370 nightly
The price is $412
May 11 - May 12
Total with taxes and fees
Sunny Coastal Escape
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, (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
$195 nightly
The price is $220
Apr 27 - Apr 28
Total with taxes and fees
Tiny House Siesta
Beach nearby

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
$344 nightly
The price is $381
Apr 12 - Apr 13
Total with taxes and fees
Coastal Quadruplex with private beach access & deck - dog-friendly
Interior

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.
$135 nightly
The price is $150
Apr 12 - Apr 13
Total with taxes and fees
Charming cottage for 2 across warm mineral springs park
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, (21 reviews)
"Great place loved how clean and put together everything was would definitely stay here again"
United States
Jacob
$197 nightly
The price is $220
Apr 11 - Apr 12
Total with taxes and fees
Nestled in North Port. Updated 2 Bed / 1 Bath.
Beach nearby, beach towels

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.
$251 nightly
The price is $280
May 1 - May 2
Total with taxes and fees
Old Floridian cottage in Historic Gulf Village
Interior

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
$292 nightly
The price is $326
Apr 12 - Apr 13
Total with taxes and fees
Mimosa Memories
Fridge, microwave, oven, stovetop

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
$217 nightly
The price is $242
May 10 - May 11
Total with taxes and fees
Secluded Cottage with Hot Tub, Walking Distance to Benderson and UTC.
Beach nearby, sun loungers, beach towels

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.
$255 nightly
The price is $285
Apr 23 - Apr 24
Total with taxes and fees
Entire Standalone Lido Beach Villa, 1.2k sf, 1 block to the beach
Exterior

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
$354 nightly
The price is $396
Apr 15 - Apr 16
Total with taxes and fees
Chadwick Cove Resort & Marina
Property grounds

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.
$262 nightly
The price is $292
May 3 - May 4
Total with taxes and fees
Lakefront Condo · IMG Academy 5 Min · Anna Maria Beach 15 Min · Pools & Hot Tubs
Beach

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.
$315 nightly
The price is $353
Apr 16 - Apr 17
Total with taxes and fees
Paradise Retreat with HEATED POOL-- Need We Say More
Property grounds

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.
$362 nightly
The price is $401
Apr 15 - Apr 16
Total with taxes and fees
Beach to Bay! Heated Pool and Dock on the Bay! Walk to the Beach and Restaurants
Beach nearby, sun loungers, beach towels

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.
$409 nightly
The price is $446
Apr 12 - Apr 13
Total with taxes and fees
Siesta Key Village-Suite #3: A Block to the Beach!
1 bedroom, free WiFi, bed sheets

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.
$126 nightly
The price is $140
May 5 - May 6
Total with taxes and fees
2 Miles to Siesta Key
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, (30 reviews)
"Very clean and great location! Beds very comfortable and owner very responsive and accommodating! Highly recommend staying here!"
United States
Tim T.
$363 nightly
The price is $372
Apr 15 - Apr 16
Total with taxes and fees
[escape to paradise] siesta key beach getaway
Microwave, oven, stovetop, dishwasher

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.
$354 nightly
The price is $394
Apr 15 - Apr 16
Total with taxes and fees
Centrally Located, Sarasota Home Close To Amish Community
Beach nearby

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.
$380 nightly
The price is $418
Apr 30 - May 1
Total with taxes and fees
Best views of the beach from your balcony Unit 301
Terrace/patio

Kon Tiki Inn

Kon Tiki Inn
2.5 star property
Venice Island
10.0 out of 10, Exceptional, (269 reviews)
"Wonderful place! Super friendly host! Very clean, affordable! Great place!!"
United States
Carolyn
$127 nightly
The price is $143
May 4 - May 5
Total with taxes and fees
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

Cirque St. Armands Beachside

Cirque St. Armands Beachside

10/10 Excellent
"Amazing stay! Will definitely be returning!"
Payton 4-night trip
Posted 1 hour ago
Cirque St. Armands Beachside

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 $143 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.

Explore a world of travel with Expedia

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 19 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.