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Check prices for these dates

In two weeks
12 Sep - 14 Sep
In one month
26 Sep - 28 Sep
In two months
24 Oct - 26 Oct
In three months
21 Nov - 23 Nov

Top Holiday Rentals in Osprey Village

Our top choices for Osprey Village holiday rentals

Tropical Beach Resorts
Outdoor pool, a heated pool, open 8 AM to 10 PM, pool umbrellas

Tropical Beach Resorts

3.5 star property
9.4 out of 10, Exceptional, (4913)
"Wonderful resort "
The price is 3.667.056 ₫
4.737.973 ₫ total
includes taxes & fees
9 Sept - 10 Sept
Tropical Beach Resorts
Hibiscus Suites - Gateway to Siesta Key
Outdoor pool, a heated pool, open 7:00 AM to 8:00 PM, pool loungers

Hibiscus Suites - Gateway to Siesta Key

2.5 star property
8.6 out of 10, Excellent, (2165)
"Bed comfort , great location, friendly staff. "
Hibiscus Suites - Gateway to Siesta Key
SeaSpray Resort
Deluxe Suite, 2 Bedrooms | Living area

SeaSpray Resort

4.0 star property
9.4 out of 10, Exceptional, (24)
"Renovated resort, a block away from the beach, very clean and friendly staff. Would stay there again. "
The price is 5.508.822 ₫
6.224.968 ₫ total
includes taxes & fees
1 Sept - 2 Sept
SeaSpray Resort
The Ringling Beach House
Front of property

The Ringling Beach House

3.5 star property
9.0 out of 10, Wonderful, (319)
"We loved the Villa!! It was spacious and stocked with every kitchen item you can imagine. "
The Ringling Beach House
Captiva Beach Resort
Front of property – evening/night

Captiva Beach Resort

2.0 star property
9.0 out of 10, Wonderful, (1124)
"Everything was great and a walking distance to the beach❤️❤️❤️❤️❤️. Everyone was very friendly and kind, thank you so much."
Captiva Beach Resort
Tiny House Siesta
Cabin (Tiny House - The Siesta) | Living area | Flat-screen TV, Netflix, streaming services

Tiny House Siesta

2.0 star property
8.4 out of 10, Very good, (314)
"Super helpful staff."
The price is 1.894.032 ₫
3.626.545 ₫ total
includes taxes & fees
4 Sept - 5 Sept
Tiny House Siesta
Sea Club I Beach Resort
On the beach, white sand

Sea Club I Beach Resort

3.0 star property
9.0 out of 10, Wonderful, (320)
"just an amazing staff and clean rooms! it was paradise will go back next year for sure!!"
Sea Club I Beach Resort
Kon Tiki Inn
Exterior

Kon Tiki Inn

2.0 star property
10.0 out of 10, Exceptional, (227)
"We love everything about this place Debbie and her husband are awesome from check in to check out this is a 5 star resort and we will be back many more times"
The price is 3.661.269 ₫
4.137.233 ₫ total
includes taxes & fees
9 Sept - 10 Sept
Kon Tiki Inn
Siesta Palms By the Beach
Garden

Siesta Palms By the Beach

3.5 star property
9.2 out of 10, Wonderful, (126)
"An outstanding experience — a place that leaves you with a strong desire to return."
Siesta Palms By the Beach
Venice Beach Villas
Terrace/patio

Venice Beach Villas

3.0 star property
9.4 out of 10, Exceptional, (429)
"Outstanding stay. Great room and amenities with a great locatio. We will return!! "
Venice Beach Villas
Bradenton Apartments by Landing
Exterior

Bradenton Apartments by Landing

4.0 star property
7.4 out of 10, Good, (43)
"Absolutely beautiful location has everything you need n makes you feel like home"
Bradenton Apartments by Landing
Siesta Key Island Rentals
322 Calle Miramar, Siesta Key, FL W/pool | Private kitchen

Siesta Key Island Rentals

3.0 star property
9.6 out of 10, Exceptional, (46)
"This place was incredible. We have traveled a lot with family and this was the best. Very comfortable and accommodating! I really cannot say enough good about this house. "
The price is 4.135.834 ₫
8.630.235 ₫ total
includes taxes & fees
3 Sept - 4 Sept
Siesta Key Island Rentals
The Residences at Siesta Key Beach by Hyatt Vacation Club
Property amenity

The Residences at Siesta Key Beach by Hyatt Vacation Club

3.5 star property
9.8 out of 10, Exceptional, (283)
"Great location. Everyone was very friendly and accommodating!"
The price is 13.679.802 ₫
16.798.481 ₫ total
includes taxes & fees
28 Aug - 29 Aug
The Residences at Siesta Key Beach by Hyatt Vacation Club
The Inn On Siesta Key
Outdoor pool, a heated pool, open 8:00 AM to 8:00 PM, pool umbrellas

The Inn On Siesta Key

3.5 star property
10.0 out of 10, Exceptional, (183)
"Great place to stay! "
The price is 6.357.813 ₫
8.643.771 ₫ total
includes taxes & fees
27 Aug - 28 Aug
The Inn On Siesta Key
Tropical Villas of Venice Beach
Beach nearby, beach umbrellas, beach towels

Tropical Villas of Venice Beach

3.5 star property
9.6 out of 10, Exceptional, (238)
"Great Location !!"
Tropical Villas of Venice Beach
Siesta Heron Suites & Villas
Condo, Pool View | Private kitchen | Full-sized fridge, microwave, oven, stovetop

Siesta Heron Suites & Villas

3.5 star property
8.4 out of 10, Very good, (35)
"It was perfect for my family of 4 for our beach vacation!!"
The price is 5.510.055 ₫
15.708.886 ₫ total
includes taxes & fees
31 Aug - 1 Sept
Siesta Heron Suites & Villas
Casey Key Resort - Gulf Shores
Deluxe Studio, Bay View | View from room

Casey Key Resort - Gulf Shores

3.0 star property
8.4 out of 10, Very good, (261)
"Cute place and property! Cozy, quiet and clean. The property manager was very nice. We enjoyed the private beach on the property. It is walking distance to 2 restaurants. Would def go back, we had a nice relaxing weekend. "
Casey Key Resort - Gulf Shores
Longboat Bay Club
Outdoor pool

Longboat Bay Club

3.5 star property
10.0 out of 10, Exceptional, (1)
"Great property with beach access across the street! 2 br unit was huge as were the balconies. Our unit 105 was quite dated but still nice."
Longboat Bay Club
Charming Florida Beach Home w King Bed Patio
House | 2 bedrooms, Internet

Charming Florida Beach Home w King Bed Patio

2.0 star property
10.0 out of 10, Exceptional, (2)
"The best place to stay! Super clean home and friendly service. I would stay here again. "
The price is 3.372.755 ₫
8.466.269 ₫ total
includes taxes & fees
27 Aug - 28 Aug
Charming Florida Beach Home w King Bed Patio
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

Kompose Boutique Hotel

Kompose Boutique Hotel

10/10 Excellent
"Exceptional boutique hotel experience with high class"
Shaun 5-night trip
Posted 1 day ago
Kompose Boutique Hotel

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.

How many holiday rentals will I find in Osprey Village?

Expedia has 5 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.