Osprey Vacation Rentals from ￥21,665: Search Short-Term Rentals

Q: 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.

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Our top choices for Osprey vacation rentals

Charming Osprey Home

Bay Acres

Diane S.

￥63,052 total

includes taxes & fees

May 15 - May 16

Sunny Coastal Escape

Bay Acres

Kaja F.

￥63,052 total

includes taxes & fees

May 15 - May 16

Nestled in North Port. Updated 2 Bed / 1 Bath.

North Port

Jacob

￥34,608 total

includes taxes & fees

Apr 17 - Apr 18

Mimosa Memories

South Venice

Alexus

￥52,041 total

includes taxes & fees

Apr 27 - Apr 28

Paradise Retreat with HEATED POOL-- Need We Say More

South Bradenton

David S.

￥58,008 total

includes taxes & fees

Apr 17 - Apr 18

Old Floridian cottage in Historic Gulf Village

Olde Englewood Village

James M.

￥44,571 total

includes taxes & fees

May 1 - May 2

Beach nearby, sun loungers, beach towels

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

Lido Key

Kevin L.

￥45,196 total

includes taxes & fees

Apr 23 - Apr 24

Chadwick Cove Resort & Marina

Manasota Key

Cathy

￥91,891 total

includes taxes & fees

Apr 19 - Apr 20

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Top Osprey Hotel Reviews

Spark by Hilton Sarasota Siesta Key Gateway

10/10 Excellent

"very good "

Tropical Breeze Resort

10/10 Excellent

"The location of this property is just amazing. You are in very close walking distance to both the beach (which the beach location is amazing and there is a sandbar to walk out to) and to Siesta Key Village loaded with restaurants and other conveniences. The room was decent. All that one really needs to have on a beach trip however the cleanliness was just ok. I realized this after I accidentally kicked one of my shoes under the bed and I found a pacifier.... clearly, I didn't have children with me on this trip. I also found a bottle of used water under the bed. I accidentally spilled some coffee on the bed sheets, so I took them off and the mattress cover had a lot of unknown hair on it. They should really use a lint brush to clean it off before the next guests arrive and replace it if it's bad. But I am a world traveler, and I know that it can't always be perfect, so I am more obliged to outweigh the positives versus negatives. I can say that the facilities such as the pools and the free bikes were great to use. The pools were nice and clean but the hot tub needed some attendance when we went so I didn't go in. Aside from that, I would recommend this place to anyone. Again, the location is amazing. The clientele was also great. There were no problems with the obnoxiousness that one can experience on spring break in Florida! So, I hope you find this review insightful and we will be back again! "

Zota Beach Resort

6/10 Okay

"Services in room, replenishment, toiletries, towels etc not done. The older was rundown. Moving to the newer tower was an up charge of $175 per night. .Restaurant evening service poor. Vanessa pool side service was excellent! Beautiful beach could have had more amenities than just towels and umbrellas. For example food and drink service on the beach. We would not stay at that location again and we would consider other Opal properties. "

Find out more about Osprey

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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 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.

Osprey Vacation Rentals

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Check prices for these dates

Our top choices for Osprey vacation rentals

Charming Osprey Home

Sunny Coastal Escape

Nestled in North Port. Updated 2 Bed / 1 Bath.

Mimosa Memories

Paradise Retreat with HEATED POOL-- Need We Say More

Old Floridian cottage in Historic Gulf Village

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

Chadwick Cove Resort & Marina

Centrally Located, Sarasota Home Close To Amish Community

Siesta Key Village-Suite #3: A Block to the Beach!

Luxury House Walking Distance to Ocean - Sleeps 12

Kon Tiki Inn

Secluded Cottage with Hot Tub, Walking Distance to Benderson and UTC.

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

Beachfront Studio – Cabana #5B by RVA

[escape to paradise] siesta key beach getaway

Best views of the beach from your balcony Unit 301

Tropical Treehouse · Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

Lavish Condo! Heated Pools & Hot Tubs · IMG Academy 5 Min · Anna Maria Island

Ground Floor, Steps to Sand – Silver Sands #243A by RVA

Find vacation rentals that suit your style

Top Osprey Hotel Reviews

Spark by Hilton Sarasota Siesta Key Gateway

Find out more about Osprey

Explore a world of travel with Expedia

Frequently asked questions

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