Osprey Village Vacation Rentals

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Vacation Rentals in Osprey Village

Tropical Beach Resorts

3.5 star property
9.4 out of 10, Exceptional, (4935)
"Wonderful resort "
$159 nightly
The price is $180
Sep 3 - Sep 4
Total with taxes and fees
Tropical Beach Resorts

Hibiscus Suites - Gateway to Siesta Key

2.5 star property
8.6 out of 10, Excellent, (2168)
"Bed comfort , great location, friendly staff. "
$136 nightly
The price is $154
Sep 3 - Sep 4
Total with taxes and fees
Hibiscus Suites - Gateway to Siesta Key

SeaSpray Resort

4.0 star property
9.2 out of 10, Wonderful, (31)
"Renovated resort, a block away from the beach, very clean and friendly staff. Would stay there again. "
$229 nightly
The price is $259
Sep 3 - Sep 4
Total with taxes and fees
SeaSpray Resort

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

Luxury Beach Home! Pool, Rooftop Deck & Fun Amenities! - Shell-Abrate Good Times

9.8 out of 10, Exceptional, (24)
"The house was in great condition and near everything. "
Luxury Beach Home! Pool, Rooftop Deck & Fun Amenities! - Shell-Abrate Good Times

Captiva Beach Resort

2.0 star property
9.0 out of 10, Wonderful, (1127)
"2nd time and excellent as always..close to the beach and great surroundings "
$182 nightly
The price is $203
Sep 3 - Sep 4
Total with taxes and fees
Captiva Beach Resort

Tiny House Siesta

2.0 star property
8.4 out of 10, Very Good, (318)
"Super helpful staff."
$130 nightly
The price is $147
Sep 3 - Sep 4
Total with taxes and fees
Tiny House Siesta

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

Siesta Palms By the Beach

3.5 star property
9.2 out of 10, Wonderful, (127)
"An outstanding experience — a place that leaves you with a strong desire to return."
Siesta Palms By the Beach

Kon Tiki Inn

2.5 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"
Kon Tiki Inn

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

The Residences at Siesta Key Beach by Hyatt Vacation Club

3.5 star property
9.8 out of 10, Exceptional, (285)
"Great location. Everyone was very friendly and accommodating!"
$440 nightly
The price is $497
Sep 29 - Sep 30
Total with taxes and fees
The Residences at Siesta Key Beach by Hyatt Vacation Club

Private Home Directly on Siesta Key Beach!

10.0 out of 10, Exceptional, (4)
"Beautiful place to stay… direct walk to the beach from your back door. Amazing view! Clean with all the amenities you need. "
Private Home Directly on Siesta Key Beach!

Siesta Key Island Rentals

3.0 star property
9.6 out of 10, Exceptional, (47)
"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. "
$272 nightly
The price is $308
Sep 3 - Sep 4
Total with taxes and fees
Siesta Key Island Rentals

Venice Beach Villas

3.0 star property
9.4 out of 10, Exceptional, (433)
"Clean and welcoming property"
Venice Beach Villas

The Inn On Siesta Key

3.5 star property
10.0 out of 10, Exceptional, (183)
"Great place to stay! "
The Inn On Siesta Key

Tropical Villas of Venice Beach

3.5 star property
9.6 out of 10, Exceptional, (239)
"Great Location !!"
Tropical Villas of Venice Beach

Tranquil Siesta Key Retreat ~ Walk to Beach ~ Pool

9.6 out of 10, Exceptional, (20)
"Close to beach. Easy to get to locations with the Frog Hop! Plenty of space for 8 of us!"
Tranquil Siesta Key Retreat ~ Walk to Beach ~ Pool

Beachfront 3-Bedroom Condo on Siesta Key – Steps to the Sand & Gulf Views

9.4 out of 10, Exceptional, (64)
"This is our second time staying here. Absolutely love this rental. Very clean and walking distance to the village "
Beachfront 3-Bedroom Condo on Siesta Key – Steps to the Sand & Gulf Views

Stunning Home, Resort Pool Area w/ Waterslide and Spa, Gulf Views

10.0 out of 10, Exceptional, (40)
"This was the perfect place to stay for a large family with kids. The location to the beach and restaurants couldn't have been more convenient. Amazing vacation!"
Stunning Home, Resort Pool Area w/ Waterslide and Spa, Gulf Views
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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Find out more about Osprey Village

Find out more about Osprey Village

Everything you need to know about Osprey Village 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 Village 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 Village vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Osprey Village vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Osprey Village. 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 Village 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 $147 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 Village rentals

At Expedia, we put the best Osprey Village 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 Village 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 Village 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 Village. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find a vacation rental in Osprey Village?

Yes, we give you a choice of vacation rentals in Osprey Village close to Nancy's Consignments, or you can go with a more remote option if you're looking for extra privacy while you relax.

What's the top vacation rental that Osprey Village has to offer?

Siesta Key Island Rentals: This vacation home rental near Osprey Village 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 will I find in Osprey Village?

Expedia has 5 vacation 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 larger area.

What are vacation rentals like in Osprey Village?

Vacation rentals are privately owned accommodations you can book for a couple days or more in Osprey Village. Vacation rentals feature amenities such as patios, hot tubs, and fire pits so you'll be comfy for your stay. If you're concerned about a sanitized environment, vacation rentals can offer a sense of safety away from public hotel elevators and busy lobbies while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular option for a family getaway.