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

Osprey Vacation Rentals

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Our top choices for Osprey vacation 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 CA $282
CA $626 total
includes taxes & fees
Aug 2 - Aug 3
Charming Osprey Home

Enjoyable Secluded Tented Cabin with Fire Pit in Sarasota, Florida

Enjoyable Secluded Tented Cabin with Fire Pit in Sarasota, Florida
Sarasota
The price is CA $392
CA $499 total
includes taxes & fees
Aug 3 - Aug 4
Enjoyable Secluded Tented Cabin with Fire Pit in Sarasota, Florida

Fantastic Tented Cabin with Fire Pit in Sarasota, Florida

Fantastic Tented Cabin with Fire Pit in Sarasota, Florida
Sarasota
The price is CA $392
CA $499 total
includes taxes & fees
Aug 3 - Aug 4
Fantastic Tented Cabin with Fire Pit in Sarasota, Florida

Charming Secluded Tented Cabin in Sarasota, Florida

Charming Secluded Tented Cabin in Sarasota, Florida
Sarasota
The price is CA $392
CA $499 total
includes taxes & fees
Aug 3 - Aug 4
Charming Secluded Tented Cabin in Sarasota, Florida

Incredible Tented Cabin with Stunning Forest Views in Sarasota, Florida

Incredible Tented Cabin with Stunning Forest Views in Sarasota, Florida
Sarasota
The price is CA $392
CA $499 total
includes taxes & fees
Aug 3 - Aug 4
Incredible Tented Cabin with Stunning Forest Views in Sarasota, Florida

Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,700 reviews)
"Great location, very close to the beach, very nice and helpful front desk."
United States
Airida
The price is CA $215
CA $279 total
includes taxes & fees
Aug 23 - Aug 24
Tropical Beach Resorts

Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.6 out of 10, Excellent, (2,386 reviews)
"Staff was helpful, and room were very clean"
United States
Doris Isabel
The price is CA $179
CA $203 total
includes taxes & fees
Aug 11 - Aug 12
Hibiscus Suites - Gateway to Siesta Key

Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,292 reviews)
"Very helpful staff and excellent beach!"
United States
Vania
The price is CA $220
CA $272 total
includes taxes & fees
Aug 10 - Aug 11
Captiva Beach Resort

A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (655 reviews)
"The beach is right there, very clean and nice place."
United States
Maryna
The price is CA $260
CA $294 total
includes taxes & fees
Aug 27 - Aug 28
A Beach Retreat

SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (155 reviews)
"We love the hotel the cleaners the facility was amazing"
United States
yisel
The price is CA $356
CA $403 total
includes taxes & fees
Aug 26 - Aug 27
SeaSpray Resort

Tiny House Siesta

Tiny House Siesta
2.0 star property
Sarasota
8.4 out of 10, Very good, (382 reviews)
"Great place"
United States
Mario
The price is CA $109
CA $218 total
includes taxes & fees
Aug 3 - Aug 4
Tiny House Siesta

The Ringling Beach House

The Ringling Beach House
3.5 star property
Siesta Key
9.0 out of 10, Wonderful, (374 reviews)
"In resume the property is amazing"
United States
Lazaro
The Ringling Beach House

Siesta Key Island Rentals

Siesta Key Island Rentals
3.0 star property
Siesta Key
9.6 out of 10, Exceptional, (74 reviews)
"Great location, very clean and spacious."
United States
Jason
The price is CA $218
CA $545 total
includes taxes & fees
Aug 2 - Aug 3
Siesta Key Island Rentals

Casey Key Beachfront Escape: Charming 1BR Cottage

Casey Key Beachfront Escape: Charming 1BR Cottage
Casey Key
9.4 out of 10, Exceptional, (128 reviews)
"We loved the cottage on the beach. The view was wonderful. Very peaceful location. The cottage was clean and had everything we needed. Highly recommend!"
United States
Virginia W.
The price is CA $350
CA $769 total
includes taxes & fees
Aug 14 - Aug 15
Casey Key Beachfront Escape: Charming 1BR Cottage

2BR Beach Style w Pool Beach Club Siesta 204C RVA

2BR Beach Style w Pool Beach Club Siesta 204C RVA
South Village
8.8 out of 10, Excellent, (80 reviews)
"Beautiful place"
United States
Chad
The price is CA $281
CA $664 total
includes taxes & fees
Aug 2 - Aug 3
2BR Beach Style w Pool Beach Club Siesta 204C RVA

Walk to the Beach and More from this Fully Renovated Unit W/ Heated Pool

Walk to the Beach and More from this Fully Renovated Unit W/ Heated Pool
Siesta Key
9.4 out of 10, Exceptional, (99 reviews)
"Great location"
United States
Daphane
The price is CA $351
CA $590 total
includes taxes & fees
Jul 30 - Jul 31
Walk to the Beach and More from this Fully Renovated Unit W/ Heated Pool

The Beach Club at Siesta Key #106D Resort by RVA

The Beach Club at Siesta Key #106D Resort by RVA
South Village
9.4 out of 10, Exceptional, (62 reviews)
"Great!"
United States
Douglas
The price is CA $292
CA $682 total
includes taxes & fees
Aug 9 - Aug 10
The Beach Club at Siesta Key #106D Resort by RVA

Couple’s Escape-Beach Club at Siesta Key 106C by RVA

Couple’s Escape-Beach Club at Siesta Key 106C by RVA
South Village
9.4 out of 10, Exceptional, (104 reviews)
"Awesome location and the staff was great!"
United States
John F.
The price is CA $215
CA $470 total
includes taxes & fees
Aug 3 - Aug 4
Couple’s Escape-Beach Club at Siesta Key 106C by RVA

Siesta Key, Walk to Beach. POOL VIEW. King Bed. Daily Rentals

Siesta Key, Walk to Beach. POOL VIEW. King Bed. Daily Rentals
South Village
9.6 out of 10, Exceptional, (49 reviews)
"Everything was very clean, great location, perfect for a couple and enjoyed the pool area too"
United States
Dirk T
The price is CA $227
CA $476 total
includes taxes & fees
Jul 31 - Aug 1
Siesta Key, Walk to Beach. POOL VIEW. King Bed. Daily Rentals

House of The Sun on Crescent Beach: Beachfront Bliss w/ Heated Pool, Tennis & Free VIP Perks Daily!

House of The Sun on Crescent Beach: Beachfront Bliss w/ Heated Pool, Tennis & Free VIP Perks Daily!
South Village
9.2 out of 10, Wonderful, (141 reviews)
"Accommodations were perfect for our family of 6. Extremely convenient to have private beach access along with chairs and ability to get umbrellas for shade."
United States
James N.
The price is CA $392
CA $1,239 total
includes taxes & fees
Aug 6 - Aug 7
House of The Sun on Crescent Beach: Beachfront Bliss w/ Heated Pool, Tennis & Free VIP Perks Daily!
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Osprey. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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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.