Osprey Village Vacation Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Osprey Village vacation rentals

Kon Tiki Inn

Kon Tiki Inn
2.5 star property
Venice Island
10.0 out of 10, Exceptional, (266 reviews)
"Wonderful place! Super friendly host! Very clean, affordable! Great place!!"
United States
Carolyn
The price is CA $179
CA $202 total
includes taxes & fees
May 4 - May 5
Kon Tiki Inn

4 Mi to Siesta Key Beach: Condo w/ Private Patio

4 Mi to Siesta Key Beach: Condo w/ Private Patio
3.5 star property
Sarasota
The price is CA $153
CA $480 total
includes taxes & fees
Apr 19 - Apr 20
4 Mi to Siesta Key Beach: Condo w/ Private Patio

SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (105 reviews)
"Perfect location, nice amenities for the beach, pet friendly, would stay here again! Super convenient and clean "
United States
Jayline
The price is CA $430
CA $486 total
includes taxes & fees
May 3 - May 4
SeaSpray Resort

Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,223 reviews)
"Clean and very close to beach. "
United States
Daniel
The price is CA $308
CA $371 total
includes taxes & fees
Apr 12 - Apr 13
Captiva Beach Resort

Venice Beach Villas

Venice Beach Villas
3.0 star property
Venice Island
9.4 out of 10, Exceptional, (478 reviews)
"Exceptional location both to the beach and restaurants. The facility has everything you need to augment your stay: bikes, beach chairs and umbrellas, coolers and pool floats. The room is immaculate too."
United States
Kathy
The price is CA $176
CA $198 total
includes taxes & fees
Apr 27 - Apr 28
Venice Beach Villas

Siesta Heron 7

Siesta Heron 7
3.0 star property
Siesta Key
Siesta Heron 7

Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,397 reviews)
"Love the location, excellent service and place clean and quite "
United States
Dayami
The price is CA $283
CA $355 total
includes taxes & fees
Apr 12 - Apr 13
Tropical Beach Resorts

Tropical Villas of Venice Beach

Tropical Villas of Venice Beach
3.5 star property
Venice Island
9.6 out of 10, Exceptional, (245 reviews)
"Staff very accommodating."
United States
Genevieve
The price is CA $230
CA $291 total
includes taxes & fees
Apr 22 - Apr 23
Tropical Villas of Venice Beach

Siesta Key Pool House

Siesta Key Pool House
2.5 star property
Siesta Key
The price is CA $1,048
CA $1,642 total
includes taxes & fees
Apr 11 - Apr 12
Siesta Key Pool House

Sleeps 8 Pets Welcome Fenced In Backyard

Sleeps 8 Pets Welcome Fenced In Backyard
2.0 star property
Southgate
The price is CA $228
CA $505 total
includes taxes & fees
Apr 8 - Apr 9
Sleeps 8 Pets Welcome Fenced In Backyard

Lulu's Key House Loggerhead 2/2 Upstairs

Lulu's Key House Loggerhead 2/2 Upstairs
3.5 star property
Siesta Key Village
The price is CA $505
CA $1,006 total
includes taxes & fees
Apr 29 - Apr 30
Lulu's Key House Loggerhead 2/2 Upstairs

A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (618 reviews)
"Love this place"
United States
Marialis
The price is CA $250
CA $283 total
includes taxes & fees
May 3 - May 4
A Beach Retreat

Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.6 out of 10, Excellent, (2,275 reviews)
"Clean room, quiet and in a location convenient to Siesta Key. The pool is very nice, although located at the front of the property alongside a busy road. Would definitely recommend this hotel, especially if a kitchenette is desired."
United States
CAROLYN
The price is CA $230
CA $260 total
includes taxes & fees
May 3 - May 4
Hibiscus Suites - Gateway to Siesta Key

4BR Spacious Paradise

4BR Spacious Paradise
2.0 star property
Siesta Key Village
4BR Spacious Paradise

The Ringling Beach House

The Ringling Beach House
3.5 star property
Siesta Key
9.0 out of 10, Wonderful, (359 reviews)
"Property is a great location, very friendly and attentive staff. Some items need to be upgraded and little things like extra bath and beach towels would go a long way in making stays more enjoyable for guests. "
United States
Julie M
The Ringling Beach House

Stylish Retro Vibes Private BBQ & Beach Access

Stylish Retro Vibes Private BBQ & Beach Access
3.0 star property
Sarasota
The price is CA $100
CA $526 total
includes taxes & fees
Apr 13 - Apr 14
Stylish Retro Vibes Private BBQ & Beach Access

Lanai & Pond at Tranquil Bradenton Retreat!

Lanai & Pond at Tranquil Bradenton Retreat!
3.0 star property
Bradenton
10.0 out of 10, Exceptional, (2 reviews)
"I really enjoyed how easy it was to get to the location, and how clean and spacious it was. Although it was a short visit to help my daughter move out of college, it provided a great place to relax after the busy move. The environment was very peaceful and safe."
United States
Ching-Wei Tabitha
Lanai & Pond at Tranquil Bradenton Retreat!

Casey Key Resort - Gulf Shores

Casey Key Resort - Gulf Shores
3.0 star property
Casey Key
8.4 out of 10, Very good, (272 reviews)
"Great place"
United States
tony
The price is CA $257
CA $305 total
includes taxes & fees
May 3 - May 4
Casey Key Resort - Gulf Shores

The Inn On Siesta Key

The Inn On Siesta Key
3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (196 reviews)
"The room was clean and spacious with all the amenities. The location was perfect. I would highly recommend!"
United States
Amanda
The price is CA $473
CA $611 total
includes taxes & fees
Apr 9 - Apr 10
The Inn On Siesta Key

Waterfront Heated Pool House Kayaks Boat Dock

Waterfront Heated Pool House Kayaks Boat Dock
2.0 star property
Siesta Key
The price is CA $1,143
CA $1,622 total
includes taxes & fees
Apr 11 - Apr 12
Waterfront Heated Pool House Kayaks Boat Dock
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Osprey Village Hotel Reviews

Find out more about Osprey Village

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Osprey Village. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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 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 Jim Neville Marine Preserve 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.