Osprey Village Holiday Rentals

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Check prices for these dates

In two weeks
9 Jan - 11 Jan
In two months
20 Feb - 22 Feb
In three months
20 Mar - 22 Mar
In four months
17 Apr - 19 Apr

Our top choices for Osprey Village holiday rentals

Exterior
Kon Tiki Inn

Kon Tiki Inn

Kon Tiki Inn
2.5 star property
Venice Island
10.0 out of 10, Exceptional, (247)
"Lovely decor, very clean"
United States
Frederick
The price is S$339
includes taxes & fees
20 Jan - 21 Jan, 2026
Kon Tiki Inn
Property grounds
Tropical Beach Resorts

Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5170)
"Great place, easy beach access and property was beautiful. "
United States
Maria
The price is S$238
includes taxes & fees
7 Jan - 8 Jan, 2026
Tropical Beach Resorts
Outdoor pool, a heated pool, open 7:00 AM to 8:00 PM, pool loungers
Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.6 out of 10, Excellent, (2219)
"Very nice place !"
United States
Ivette
Hibiscus Suites - Gateway to Siesta Key
Front of property – evening/night
Captiva Beach Resort

Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1177)
"Clean room, snd friendly staff. Great location "
United States
Stephanie
Captiva Beach Resort
Private kitchen
Siesta Heron Suites & Villas

Siesta Heron Suites & Villas

Siesta Heron Suites & Villas
3.5 star property
Siesta Key
8.6 out of 10, Excellent, (38)
"It was perfect for my family of 4 for our beach vacation!!"
United States
Jesse
The price is S$541
includes taxes & fees
26 Dec - 27 Dec
Siesta Heron Suites & Villas
Living area
Tiny House Siesta

Tiny House Siesta

Tiny House Siesta
2.0 star property
Sarasota
8.4 out of 10, Very good, (346)
"Enjoyable stay. "
United States
Lori
The price is S$313
includes taxes & fees
7 Jan - 8 Jan, 2026
Tiny House Siesta
Front of property
The Ringling Beach House

The Ringling Beach House

The Ringling Beach House
3.5 star property
Siesta Key
9.0 out of 10, Wonderful, (347)
"great location, very clean, quiet"
United States
Joaquin
The Ringling Beach House
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 Village Hotel Reviews

Quality Inn Sarasota North Near Lido Key Beach

Quality Inn Sarasota North Near Lido Key Beach

10/10 Excellent
"Great"
Angela 1-night trip
Posted 4 days ago
Quality Inn Sarasota North Near Lido Key Beach

Frequently asked questions

Can I find a holiday rental in Osprey Village?

Yes, there are holiday rentals in Osprey Village close to Nancy's Consignments, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Osprey Village has to offer?

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

How many holiday rentals will I find in Osprey Village?

Expedia has 4 holiday rentals for your stay in Osprey Village.

What can I see and do in Osprey Village?

While exploring the area, visit family-friendly sights like Nancy's Consignments, or get outside and enjoy nature at Siesta Key Beach. Lido Beach and Oscar Scherer State Park are a couple of places you'll find in the wider area.

What are holiday rentals like in Osprey Village?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Osprey Village. Holiday rentals offer extras such as laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about a sanitised environment, a holiday rental can provide a sense of safety away from public hotel lifts and busy front desks while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular choice for a family trip.