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

Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,575 reviews)
"perfect stay and location for a family!"
United States
Jessica
The price is CA $263
CA $366 total
includes taxes & fees
Jun 28 - Jun 29
Tropical Beach Resorts

Nestled in North Port. Updated 2 Bed / 1 Bath.

Nestled in North Port. Updated 2 Bed / 1 Bath.
North Port
10.0 out of 10, Exceptional, (25 reviews)
"Great place loved how clean and put together everything was would definitely stay here again"
United States
Jacob
The price is CA $120
CA $312 total
includes taxes & fees
Jun 19 - Jun 20
Nestled in North Port. Updated 2 Bed / 1 Bath.

Path to Paradise.

Path to Paradise.
Olde Englewood Village
9.0 out of 10, Wonderful, (2 reviews)
"The house was very clean and well accommodating. There was room for our boat in the driveway. Will definitely stay again if in the area."
United States
Jeremy
The price is CA $99
CA $368 total
includes taxes & fees
Jun 30 - Jul 1
Path to Paradise.

Mimosa Memories

Mimosa Memories
South Venice
9.6 out of 10, Exceptional, (38 reviews)
"We had a very comfortable stay and had all the amenities that we needed."
United States
Susan H.
The price is CA $157
CA $468 total
includes taxes & fees
Jun 24 - Jun 25
Mimosa Memories

Charming cottage for 2 across warm mineral springs park

Charming cottage for 2 across warm mineral springs park
Warm Mineral Springs
9.2 out of 10, Wonderful, (24 reviews)
"Easy check in, clean and cozy."
United States
Robert J.
The price is CA $63
CA $194 total
includes taxes & fees
Jun 24 - Jun 25
Charming cottage for 2 across warm mineral springs park

Kon Tiki Inn

Kon Tiki Inn
2.5 star property
Venice Island
10.0 out of 10, Exceptional, (287 reviews)
"Great place to stay!!!"
United States
Tara
The price is CA $159
CA $180 total
includes taxes & fees
Jun 22 - Jun 23
Kon Tiki Inn

Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.

Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.
Southgate
10.0 out of 10, Exceptional, (76 reviews)
"Wonderful Stay"
United States
Christopher R.
The price is CA $99
CA $346 total
includes taxes & fees
Jun 24 - Jun 25
Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.

Charming 2-bedroom house in lovely Sarasota with yard.

Charming 2-bedroom house in lovely Sarasota with yard.
Kensington Park
9.0 out of 10, Wonderful, (28 reviews)
"Easy check in . Clear communication.Beautiful home .Quiet neighborhood ! No surprises. Highly recommend."
United States
Paula
The price is CA $120
CA $292 total
includes taxes & fees
Jun 21 - Jun 22
Charming 2-bedroom house in lovely Sarasota with yard.

Beautiful University Pines Studio in Sarasota

Beautiful University Pines Studio in Sarasota
Sarasota
9.8 out of 10, Exceptional, (41 reviews)
"Perfect area, close to all the stores and restaurants"
United States
Maria B.
The price is CA $103
CA $279 total
includes taxes & fees
Jul 13 - Jul 14
Beautiful University Pines Studio in Sarasota

Two Miles to Siesta Key

Two Miles to Siesta Key
Gulf Gate Estates
10.0 out of 10, Exceptional, (55 reviews)
"Great place to stay! Very close to Siesta Key and anything you need, easy check in and out. Would stay here again! "
United States
Brian K.
The price is CA $111
CA $199 total
includes taxes & fees
Jul 6 - Jul 7
Two Miles to Siesta Key

Siesta Key Village-Suite #1: A block to the Beach!

Siesta Key Village-Suite #1: A block to the Beach!
Siesta Key Village
9.8 out of 10, Exceptional, (47 reviews)
"The apartment is clean and comfortable! Location is amazing! The beach, restaurants, and bars are all very close. The beach is great and easily accessible. 100% would stay here again! "
United States
Alex
The price is CA $229
CA $570 total
includes taxes & fees
Jun 21 - Jun 22
Siesta Key Village-Suite #1: A block to the Beach!

Siesta Key Village-Suite #3: A Block to the Beach!

Siesta Key Village-Suite #3: A Block to the Beach!
Siesta Key Village
9.2 out of 10, Wonderful, (76 reviews)
"Perfect location, super clean.comfortable"
United States
matthew w.
The price is CA $229
CA $570 total
includes taxes & fees
Jun 21 - Jun 22
Siesta Key Village-Suite #3: A Block to the Beach!

IMG Lake & Beach Home with Pool White Sand Beaches MAY 16-10, Oct, Nov SPECIALS!

IMG Lake & Beach Home with Pool White Sand Beaches MAY 16-10, Oct, Nov SPECIALS!
South Bradenton
9.8 out of 10, Exceptional, (140 reviews)
"Beautiful pool, nice kitchen, and close to Anna Marie Island."
United States
Gary B.
The price is CA $190
CA $780 total
includes taxes & fees
Jun 30 - Jul 1
IMG Lake & Beach Home with Pool White Sand Beaches MAY 16-10, Oct, Nov SPECIALS!

Step from the Beach.Renovated ground Floor unit 63

Step from the Beach.Renovated ground Floor unit 63
Longboat Key
9.4 out of 10, Exceptional, (71 reviews)
"Our stay was excellent. Nice and clean and plenty of room however it doesn’t have a beach view, but the beach is a very short, easy walk. Staff was extra nice, especially Margaret."
United States
Faye
Step from the Beach.Renovated ground Floor unit 63

Siesta Key Island Rentals

Siesta Key Island Rentals
3.0 star property
Siesta Key
9.6 out of 10, Exceptional, (68 reviews)
"Excellent location , minute walk to local bars and supermarket. Right across from beautiful siesta key beach."
United States
Alessandra
The price is CA $237
CA $568 total
includes taxes & fees
Jun 19 - Jun 20
Siesta Key Island Rentals

Oceanfront Bliss–Longboat Key Beach 106 by RVA

Oceanfront Bliss–Longboat Key Beach 106 by RVA
Longboat Key
8.8 out of 10, Excellent, (102 reviews)
"Beautiful sunset view. "
United States
Rhonda V.
The price is CA $189
CA $432 total
includes taxes & fees
Jun 21 - Jun 22
Oceanfront Bliss–Longboat Key Beach 106 by RVA

BAREFOOT BUNGALOW- 1O MINUTES TO SIESTA BEACH AND AMENITIES! PET FRIENDLY!

BAREFOOT BUNGALOW- 1O MINUTES TO SIESTA BEACH AND AMENITIES! PET FRIENDLY!
Ridge Wood Heights
10.0 out of 10, Exceptional, (17 reviews)
"Great place. Clean with everything you need"
United States
Thomas Lee
The price is CA $175
CA $468 total
includes taxes & fees
Jun 24 - Jun 25
BAREFOOT BUNGALOW- 1O MINUTES TO SIESTA BEACH AND AMENITIES! PET FRIENDLY!

Beach Rd, 300ft to Beach Access & 500ft to Siesta Key Village, Studio

Beach Rd, 300ft to Beach Access & 500ft to Siesta Key Village, Studio
Siesta Key Village
9.8 out of 10, Exceptional, (11 reviews)
"Repeat guests! Great location and exactly what we needed for amenities! Property was clean and host made everything from check in to check out very easy! "
United States
Christine H.
The price is CA $352
CA $449 total
includes taxes & fees
Jul 7 - Jul 8
Beach Rd, 300ft to Beach Access & 500ft to Siesta Key Village, Studio

Near to the Beach, UTC mall, SCF, IMG, Airport, Ringling Museum and much more

Near to the Beach, UTC mall, SCF, IMG, Airport, Ringling Museum and much more
Bayshore Gardens
9.2 out of 10, Wonderful, (41 reviews)
"The host was excellent and the place was clean and just as expected."
United States
Jim M.
The price is CA $105
CA $241 total
includes taxes & fees
Jun 24 - Jun 25
Near to the Beach, UTC mall, SCF, IMG, Airport, Ringling Museum and much more

Affordable Beach Studio – Silver Sands #257A by RVA

Affordable Beach Studio – Silver Sands #257A by RVA
Longboat Key
9.6 out of 10, Exceptional, (79 reviews)
"Right on beach-perfect for a short stay"
United States
Sean P.
The price is CA $206
CA $456 total
includes taxes & fees
Jun 24 - Jun 25
Affordable Beach Studio – Silver Sands #257A by RVA
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 Venice Beach are other popular places to visit in the 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.