Osprey Village Vacation Rentals

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Vacation Rentals in Osprey Village

Tropical Beach Resorts

3.5 star property
South Village
9.4 out of 10, Exceptional, (5140)
"Wonderful trip! Great location! Great staff!"
United States
Kevin
$155 nightly
The price is $175
Dec 9 - Dec 10
Total with taxes and fees
Tropical Beach Resorts

Captiva Beach Resort

3.0 star property
South Village
9.0 out of 10, Wonderful, (1171)
"Clean room, snd friendly staff. Great location "
United States
Stephanie
$167 nightly
The price is $187
Dec 9 - Dec 10
Total with taxes and fees
Captiva Beach Resort

Kon Tiki Inn

2.5 star property
Venice Island
10.0 out of 10, Exceptional, (246)
"Staff was great, room was clean and comfortable. It was a short stay but we enjoyed our time there. We will be back!"
United States
Joan
$140 nightly
The price is $159
Dec 15 - Dec 16
Total with taxes and fees
Kon Tiki Inn

Relax in Hot Tub, Walk to Springs: North Port Home

3.0 star property
North Port
$201 nightly
The price is $224
Dec 14 - Dec 15
Total with taxes and fees
Relax in Hot Tub, Walk to Springs: North Port Home

A Beach Retreat

2.5 star property
Casey Key
9.2 out of 10, Wonderful, (576)
"Location, very clean and comfortable. Nice efficiency."
United States
Chuck
$184 nightly
The price is $208
Dec 9 - Dec 10
Total with taxes and fees
A Beach Retreat

The Residences at Siesta Key Beach by Hyatt Vacation Club

3.5 star property
South Village
9.6 out of 10, Exceptional, (299)
"Loved our stay! "
United States
Michelle
$454 nightly
The price is $513
Dec 16 - Dec 17
Total with taxes and fees
The Residences at Siesta Key Beach by Hyatt Vacation Club

Tiny House Siesta

2.0 star property
Sarasota
8.4 out of 10, Very Good, (345)
"Enjoyable stay. "
United States
Lori
$215 nightly
The price is $242
Dec 9 - Dec 10
Total with taxes and fees
Tiny House Siesta

Casey Key Resort - Gulf Shores

3.0 star property
Casey Key
8.4 out of 10, Very Good, (264)
"Amazing place"
United States
Ricardo
$185 nightly
The price is $209
Dec 16 - Dec 17
Total with taxes and fees
Casey Key Resort - Gulf Shores

The Ringling Beach House

3.5 star property
Siesta Key
9.0 out of 10, Wonderful, (343)
"great location, very clean, quiet"
United States
Joaquin
$163 nightly
The price is $185
Dec 9 - Dec 10
Total with taxes and fees
The Ringling Beach House

Hibiscus Suites - Gateway to Siesta Key

2.5 star property
Sarasota
8.6 out of 10, Excellent, (2206)
"This place is a gem!! I only stayed one night but wish it was more. The room was very clean and the staff was fantastic. The area is beautiful and at an excellent price. I highly recommend you stay here if you are in Siesta Keys!!"
United States
Ryan
$150 nightly
The price is $170
Dec 9 - Dec 10
Total with taxes and fees
Hibiscus Suites - Gateway to Siesta Key

Siesta Key Island Rentals

3.0 star property
Siesta Key
9.6 out of 10, Exceptional, (52)
"Very nice place, we loved it. Great location. "
United States
Derrick
$261 nightly
The price is $295
Dec 18 - Dec 19
Total with taxes and fees
Siesta Key Island Rentals

The Inn On Siesta Key

3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (190)
"Great place to stay! "
United States
Carlos
$266 nightly
The price is $301
Dec 10 - Dec 11
Total with taxes and fees
The Inn On Siesta Key

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
$288 nightly
The price is $326
Dec 9 - Dec 10
Total with taxes and fees
Siesta Heron Suites & Villas

SeaSpray Resort

4.0 star property
Siesta Key
9.4 out of 10, Exceptional, (74)
"Clean room, incredibly helpful staff. Will be staying here again"
United States
Caleb
$249 nightly
The price is $281
Dec 9 - Dec 10
Total with taxes and fees
SeaSpray Resort

Siesta Sands Beach Resort 4th Floor With Elevator

3.5 star property
South Village
$615 nightly
The price is $693
Dec 24 - Dec 25
Total with taxes and fees
Siesta Sands Beach Resort 4th Floor With Elevator

4BR Spacious Paradise

2.0 star property
Siesta Key Village
$748 nightly
The price is $845
Dec 9 - Dec 10
Total with taxes and fees
4BR Spacious Paradise

Minorga on the Gulf

3.0 star property
Siesta Key Village
$448 nightly
The price is $505
Dec 21 - Dec 22
Total with taxes and fees
Minorga on the Gulf

House of The Sun Siesta Key Crescent Beach

4.0 star property
South Village
8.0 out of 10, Very Good, (2)
"The area is beautiful. The condo was very nice. Has everything in it. You can cook if you prefer. The Gulf of Mexico was right behind the condo walk out on to the beach. It also has a pool. I have no complains I would def go back again . "
United States
Margaret Theresa
$903 nightly
The price is $1,016
Dec 28 - Dec 29
Total with taxes and fees
House of The Sun Siesta Key Crescent Beach

Lulu's Key House Leatherback 2/2 Downstairs

4.0 star property
Siesta Key Village
$851 nightly
The price is $957
Dec 27 - Dec 28
Total with taxes and fees
Lulu's Key House Leatherback 2/2 Downstairs
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

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 $159 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 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 3 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.