A marina with docked boats, a wooden bridge, and a building with a red roof.

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
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Jul 17 - Jul 19
In two months
Aug 28 - Aug 30
In three months
Sep 25 - Sep 27
In four months
Oct 23 - Oct 25

Our top choices for Osprey Village vacation rentals

Dining

Lakeview Bradenton Rental Near Beaches & IMG

Lakeview Bradenton Rental Near Beaches & IMG
South Bradenton
10.0 out of 10, Exceptional, (2 reviews)
The price is ￥22,614
￥47,091 total
includes taxes & fees
Jul 14 - Jul 15
Lakeview Bradenton Rental Near Beaches & IMG
Fridge, microwave, oven, stovetop

Path to Paradise.

Path to Paradise.
Olde Englewood Village
9.4 out of 10, Exceptional, (3 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 ￥14,411
￥45,811 total
includes taxes & fees
Jul 12 - Jul 13
Path to Paradise.
Interior

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.
Mimosa Memories
Fridge, microwave, oven, stovetop

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, (77 reviews)
"Her stay was outstanding everything was so professionally ready for us we felt at home comfortable the Privacy was impeccable"
United States
James W.
The price is ￥16,031
￥45,360 total
includes taxes & fees
Jul 25 - Jul 26
Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.
Interior

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 ￥7,287
￥22,452 total
includes taxes & fees
Jul 1 - Jul 2
Charming cottage for 2 across warm mineral springs park
Microwave, oven, stovetop

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 ￥14,120
￥33,812 total
includes taxes & fees
Jul 3 - Jul 4
Charming 2-bedroom house in lovely Sarasota with yard.
Beach nearby, sun loungers, beach towels

HAPPY FUN BLUE HOUSE for 8 people kids, pets friendly, 3 miles from the beach🏖️

HAPPY FUN BLUE HOUSE for 8 people kids, pets friendly, 3 miles from the beach🏖️
South Venice
9.8 out of 10, Exceptional, (56 reviews)
"The backyard was large and well kept , the grandchildren loved being able to use the swing and above ground pool."
United States
gale o.
The price is ￥22,589
￥66,989 total
includes taxes & fees
Jul 1 - Jul 2
HAPPY FUN BLUE HOUSE for 8 people kids, pets friendly, 3 miles from the beach🏖️
Fridge, microwave, oven, stovetop

[lounge like locals] walk to siesta beach +bikes

[lounge like locals] walk to siesta beach +bikes
Siesta Key
9.8 out of 10, Exceptional, (35 reviews)
"Only 10 mins walking from the Village, so easy to check in, great communication, super clean. "
United States
John
The price is ￥16,512
￥52,049 total
includes taxes & fees
Jul 1 - Jul 2
[lounge like locals] walk to siesta beach +bikes
On the beach, beach umbrellas

1BR Beach Getaway – Silver Sands #254 by RVA

1BR Beach Getaway – Silver Sands #254 by RVA
Longboat Key
9.2 out of 10, Wonderful, (96 reviews)
"Great view, clean, beautiful!"
United States
Bethany
The price is ￥37,406
￥70,713 total
includes taxes & fees
Jul 12 - Jul 13
1BR Beach Getaway – Silver Sands #254 by RVA
5365 Calle Florida, Siesta Key, FL W/Pool | Private kitchen

Siesta Key Island Rentals

Siesta Key Island Rentals
3.0 star property
Siesta Key
9.6 out of 10, Exceptional, (69 reviews)
"Excellent location , minute walk to local bars and supermarket. Right across from beautiful siesta key beach."
United States
Alessandra
The price is ￥29,505
￥67,944 total
includes taxes & fees
Jul 1 - Jul 2
Siesta Key Island Rentals
Beach nearby, sun loungers, beach towels

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 ￥21,861
￥88,568 total
includes taxes & fees
Jul 2 - Jul 3
IMG Lake & Beach Home with Pool White Sand Beaches MAY 16-10, Oct, Nov SPECIALS!
On the beach, beach umbrellas

Relax at Gulf – Silver Sands Resort #232, Longboat

Relax at Gulf – Silver Sands Resort #232, Longboat
Longboat Key
9.2 out of 10, Wonderful, (80 reviews)
"Very happy with my stay. Room was very clean, beautifully decorated and very comfortable. Perfect efficiency! Highly recommend"
United States
Gloria
The price is ￥27,366
￥57,231 total
includes taxes & fees
Jul 12 - Jul 13
Relax at Gulf – Silver Sands Resort #232, Longboat
Interior

Charming 2 bedroom 2 bathroom home with pool in Sarasota with central location.

Charming 2 bedroom 2 bathroom home with pool in Sarasota with central location.
Kensington Park
9.4 out of 10, Exceptional, (36 reviews)
"Nice place to stay "
United States
Kari O.
The price is ￥14,411
￥48,876 total
includes taxes & fees
Jul 8 - Jul 9
Charming 2 bedroom 2 bathroom home with pool in Sarasota with central location.
Terrace/patio

Kon Tiki Inn

Kon Tiki Inn
2.5 star property
Venice Island
10.0 out of 10, Exceptional, (288 reviews)
"Great place to stay!!!"
United States
Tara
The price is ￥22,537
￥25,467 total
includes taxes & fees
Jul 13 - Jul 14
Kon Tiki Inn
Beach nearby, sun loungers, beach towels

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 ￥24,047
￥61,974 total
includes taxes & fees
Jul 1 - Jul 2
Siesta Key Village-Suite #3: A Block to the Beach!
On the beach

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 ￥26,880
￥56,487 total
includes taxes & fees
Jul 12 - Jul 13
Oceanfront Bliss–Longboat Key Beach 106 by RVA
Beach nearby, sun loungers, beach towels

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 ￥20,962
￥55,099 total
includes taxes & fees
Jul 8 - Jul 9
BAREFOOT BUNGALOW- 1O MINUTES TO SIESTA BEACH AND AMENITIES! PET FRIENDLY!
1 bedroom, desk, free WiFi, bed sheets

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, (42 reviews)
"It was a lovely quiet place to stay! Clean and homey, everything I needed was there! Highly recommended "
United States
Joyce H.
The price is ￥12,131
￥27,909 total
includes taxes & fees
Jul 8 - Jul 9
Near to the Beach, UTC mall, SCF, IMG, Airport, Ringling Museum and much more
Beach nearby, white sand, beach umbrellas, beach towels

The Inn On Siesta Key

The Inn On Siesta Key
3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (199 reviews)
"This property was everything we wanted...although not on the beach, it was a short walk to the beach and chairs, umbrellas, coolers and wagons were provided to the beach. The pool area was very comfortable and clean. We like that there were only 6 units...each was unique and very clean. We stayed in "The Nook" which was perfect for our getaway."
United States
Michele
The price is ￥57,265
￥73,675 total
includes taxes & fees
Jul 12 - Jul 13
The Inn On Siesta Key
On the beach, sun loungers, beach towels

THE BEACH CONDO #107 BEACHFRONT FULL VIEW

THE BEACH CONDO #107 BEACHFRONT FULL VIEW
Longboat Key
10.0 out of 10, Exceptional, (92 reviews)
"Host was wondeful!Location and condo fabulous!"
United States
Linda D.
The price is ￥42,102
￥75,314 total
includes taxes & fees
Jul 1 - Jul 2
THE BEACH CONDO #107 BEACHFRONT FULL VIEW
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Osprey Village Hotel Reviews

Carlisle Inn

Carlisle Inn

10/10 Excellent
"This hotel exceeded all of my expectations. It was excellent in every way. The rooms and all common areas were spotless. In fact, it was the cleanest and most organized hotel I have ever stayed in. The staff was friendly, professional, and always willing to help. Everything was well maintained, making the stay very comfortable and enjoyable. I would definitely stay here again and highly recommend it to anyone looking for an exceptional place to stay."
Danildo 2-night trip
Posted 11 hours ago
Carlisle Inn

Find out more about Osprey Village

Search for holiday rentals in Osprey Village on Expedia! You can easily find your home rentals, villas, holiday apartments in Osprey Village using one of the methods below:

  • View our selection of featured holiday rentals in Osprey Village
  • Use the map to find apartments and other holiday homes in the Osprey Village neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Osprey Village while they last

Look no further and take a look at our great range of rental properties in Osprey Village!

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. Turtle 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.