Apartments in Osprey for Rent

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Find vacation rentals that suit your style

Check prices for these dates

Our top choices for Osprey apartments

1. Casey Key Resort

Casey Key Resort
3.0 star property
Casey Key
8.4 out of 10, Very good, (287 reviews)
"My boyfriend and I had a wonderful time. Easy late check in. Nice clean room. Property beautiful. Private beach beautiful. We definitely plan to come back and have family join."
United States
Jamie
$215 nightly
The price is $240
Dec 2 - Dec 3
Total with taxes and fees
Casey Key Resort

2. 2 Bedroom/2 Bath Villa (Second Level) - Unit 14/D

2 Bedroom/2 Bath Villa (Second Level) - Unit 14/D
Casey Key
10.0 out of 10, Exceptional, (1 review)
"Mark assisted us with all our needs and went beyond. Thanks"
United States
Matthew W.
$302 nightly
The price is $339
Nov 30 - Dec 1
Total with taxes and fees
2 Bedroom/2 Bath Villa (Second Level) - Unit 14/D

3. 2 Miles to Siesta Key

2 Miles to Siesta Key
Gulf Gate Estates
10.0 out of 10, Exceptional, (29 reviews)
"Had a great stay! "
United States
Keith K.
$157 nightly
The price is $176
Nov 11 - Nov 12
Total with taxes and fees
2 Miles to Siesta Key

4. Bright & Beachy–Beach Club Siesta Key 100A by RVA

Bright & Beachy–Beach Club Siesta Key 100A by RVA
South Village
9.0 out of 10, Wonderful, (119 reviews)
"The pool and proximity to the beach are great "
United States
Evan C.
$284 nightly
The price is $319
Dec 4 - Dec 5
Total with taxes and fees
Bright & Beachy–Beach Club Siesta Key 100A by RVA

5. Tiny House Calypso with 1st floor sleeping

Tiny House Calypso with 1st floor sleeping
Sarasota
9.0 out of 10, Wonderful, (11 reviews)
"Third time here and best visit will book again in future "
United States
Desirae
$151 nightly
The price is $170
Nov 10 - Nov 11
Total with taxes and fees
Tiny House Calypso with 1st floor sleeping

6. Tiny House Seashell - tiny living at the beach

Tiny House Seashell - tiny living at the beach
Sarasota
8.6 out of 10, Excellent, (10 reviews)
"Tons of fun"
United States
Michael
$140 nightly
The price is $157
Nov 10 - Nov 11
Total with taxes and fees
Tiny House Seashell - tiny living at the beach

7. Siesta Key, Sea Horse Villa, Pool. Daily rentals

Siesta Key, Sea Horse Villa, Pool. Daily rentals
South Village
9.4 out of 10, Exceptional, (55 reviews)
"Perfect weekend getaway stay for my husband and I! The cottage had everything we needed, was thoroughly cleaned and location was perfect for restaurant hopping and beach going. Would definitely stay again!"
United States
Allie A.
$246 nightly
The price is $276
Nov 10 - Nov 11
Total with taxes and fees
Siesta Key, Sea Horse Villa, Pool. Daily rentals

8. Sand Dollar Studio, King bed, Pool. Daily Rentals, Walk to Beach.

Sand Dollar Studio, King bed, Pool. Daily Rentals, Walk to Beach.
South Village
9.8 out of 10, Exceptional, (34 reviews)
"Great stay."
United States
James J.
$191 nightly
The price is $214
Nov 10 - Nov 11
Total with taxes and fees
Sand Dollar Studio, King bed, Pool. Daily Rentals, Walk to Beach.

9. VILLA 4, Siesta Key, Walk to Beach. Pool. Daily Rentals

VILLA 4, Siesta Key, Walk to Beach. Pool. Daily Rentals
Sarasota
9.4 out of 10, Exceptional, (50 reviews)
"We had one minor issue with TV when we checked in and David immediately fixed the issue. Villa was amazing and pool was nice/clean!!!!"
United States
Chris M.
$257 nightly
The price is $289
Nov 10 - Nov 11
Total with taxes and fees
VILLA 4, Siesta Key, Walk to Beach. Pool. Daily Rentals

10. [Sunny in Siesta] king bed + walk to beach

[Sunny in Siesta] king bed + walk to beach
South Village
9.6 out of 10, Exceptional, (15 reviews)
"Great location and accommodation. "
United States
ESTELEN
$286 nightly
The price is $293
Nov 12 - Nov 13
Total with taxes and fees
[Sunny in Siesta] king bed + walk to beach

11. Tiny House Yellow Lifeguard Stand- pet friendly

Tiny House Yellow Lifeguard Stand- pet friendly
Sarasota
9.4 out of 10, Exceptional, (51 reviews)
"Cute place!!"
United States
Lisa S.
$153 nightly
The price is $172
Nov 10 - Nov 11
Total with taxes and fees
Tiny House Yellow Lifeguard Stand- pet friendly

12. Tiny House Green Lifeguard Stand - sleeps 5

Tiny House Green Lifeguard Stand - sleeps 5
Sarasota
9.4 out of 10, Exceptional, (33 reviews)
"Very clean & tidy! The house stayed cool & comfortable the whole night! My husband & I enjoyed this unique place & would definitely book again!"
United States
Jennifer S.
$160 nightly
The price is $180
Nov 10 - Nov 11
Total with taxes and fees
Tiny House Green Lifeguard Stand - sleeps 5

13. VILLA 3 · Pool view. Walk to beach. Daily rentals

VILLA 3 · Pool view. Walk to beach. Daily rentals
Sarasota
9.6 out of 10, Exceptional, (47 reviews)
"Location is perfect!"
United States
Tevin H.
$257 nightly
The price is $289
Nov 10 - Nov 11
Total with taxes and fees
VILLA 3 · Pool view. Walk to beach. Daily rentals

14. Beachside Bliss- 1 mi to the beach w/ heated pool

Beachside Bliss- 1 mi to the beach w/ heated pool
Sarasota
9.0 out of 10, Wonderful, (7 reviews)
"The apartment is far from the Hotel, We have to walk a long way, I paid a certain amount price to be right near the Beach"
United States
Yalile
$235 nightly
The price is $264
Nov 10 - Nov 11
Total with taxes and fees
Beachside Bliss- 1 mi to the beach w/ heated pool

15. Red Lifeguard Stand - pet freindly

Red Lifeguard Stand - pet freindly
Sarasota
9.4 out of 10, Exceptional, (26 reviews)
"Easy to access, close to beach, and easy stay."
United States
Maribel R.
$158 nightly
The price is $177
Nov 10 - Nov 11
Total with taxes and fees
Red Lifeguard Stand - pet freindly

16. Tiny House Margarita - Sleeps 6

Tiny House Margarita - Sleeps 6
Sarasota
8.4 out of 10, Very good, (11 reviews)
"The setup was great, the location was better. Very close to beaches and nightlife loved it"
United States
Mark
$151 nightly
The price is $170
Nov 10 - Nov 11
Total with taxes and fees
Tiny House Margarita - Sleeps 6

17. [Beach Retreat] modern condo +5 min. walk to beach

[Beach Retreat] modern condo +5 min. walk to beach
South Village
9.4 out of 10, Exceptional, (6 reviews)
"Clean condo in great location. Would definitely stay again."
United States
Cyrus F.
$260 nightly
The price is $265
Nov 10 - Nov 11
Total with taxes and fees
[Beach Retreat] modern condo +5 min. walk to beach

18. Private Studio · Near Siesta Key · Pet-Friendly

Private Studio · Near Siesta Key · Pet-Friendly
South Gate Ridge
9.0 out of 10, Wonderful, (17 reviews)
"This was a beautiful unit. Just like the pictures"
United States
AhzLor B.
$148 nightly
The price is $166
Nov 17 - Nov 18
Total with taxes and fees
Private Studio · Near Siesta Key · Pet-Friendly

19. Literally 3 mins from Siesta with its number 1 beaches!!!! Location! Location!

Literally 3 mins from Siesta with its number 1 beaches!!!! Location! Location!
Sarasota
10.0 out of 10, Exceptional, (5 reviews)
"Wonderful place to stay, clean, exactly as described, and hosted by someone who’s easy to communicate with."
United States
Anonymous traveler
$519 nightly
The price is $580
Nov 10 - Nov 11
Total with taxes and fees
Literally 3 mins from Siesta with its number 1 beaches!!!! Location! Location!

20. Spacious 2BR/2BA Garden Condo w/ Heated Pool

Spacious 2BR/2BA Garden Condo w/ Heated Pool
Sarasota
9.2 out of 10, Wonderful, (17 reviews)
"Very clean and attractive. Kitchen needs more spoons. "
United States
Diana H.
$313 nightly
The price is $352
Nov 10 - Nov 11
Total with taxes and fees
Spacious 2BR/2BA Garden Condo w/ Heated Pool
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.

Learn more about Osprey

Paddle through Oscar Scherer State Park's serene waterways where you might spot eagles, turtles, and alligators along the way. Nearby Sarasota's white-sand beaches and Myakka River State Park offer perfect day trips from this peaceful Gulf Coast community.

A nest on a wooden platform by a lake at sunset with birds flying around.

Frequently Asked Questions

What's it like to stay at an apartment in Osprey?

There are plenty of places to stay in Osprey with 58 hotels and other lodging accommodations. Though there aren't many apartments, we can help you search for accommodations that are similar. When you search on Expedia, you can filter by amenities you might find in an apartment like a kitchen. Even filter by similar properties such as vacation homes, condos, or guest houses. You can relish the top-notch restaurants and lively bars during your visit. Take time to visit some favorite sights in the larger region like Siesta Key Beach and Lido Beach.

How do you know if an apartment is the right choice for your stay?

Often offering more space than a traditional hotel room, an apartment comes equipped with a kitchen, so you can cook some of your meals. Apartments are ideal for families who want the conveniences of home but also for couples who want to stay in a quieter area.

What's a favorite apartment for my stay in Osprey?

Here are some of the favorite apartments in the area to choose from: The Ringling Beach House: Located in Siesta Key, 6.6 mi/10.7 km from the heart of Osprey. Includes free WiFi, private patios, and separate dining areas. Free parking and an outdoor pool are on site. Sea Club I Beach Resort: Located 16.3 mi/26.2 km away in Longboat Key. Amenities include free WiFi. Free parking and onsite laundry facilities are on site. Beautiful,Cozy 3Bed/2 Siesta Key home on Ocean blvd, close to village, beaches,: Located in Siesta Key, 7.7 mi/12.3 km away. Includes free WiFi, separate dining areas, and Smart TVs. Access to onsite laundry facilities is available on site. Casey Key Resort : Located 4.8 mi/7.8 km away in Nokomis. Free WiFi and separate dining areas are included. Free parking and onsite laundry facilities are on site. Steps to Siesta Key BEACH! Pool, Tennis Court, Shuffle Board, Pickle Ball!: Located in Siesta Key, 5.5 mi/8.9 km from Osprey. Includes free WiFi, sofa beds, and premium mattresses. Onsite laundry facilities and an outdoor pool are on site.

How many apartments can I expect to find in Osprey?

Expedia has 5 apartments to book in Osprey.

What will the weather be like when I travel to Osprey?

Though weather is just one factor, it can really affect your travel plans, especially if you are planning a longer stay in Osprey. The hottest months are usually August and July with an average temp of 82°F, while the coldest months are January and February with an average of 66°F. Average annual precipitation for Osprey is 44 inches.

What should I see and do in Osprey?

People visiting Osprey come for its restaurants and beaches. Turtle Beach and Nokomis Beach are a couple of scenic spots to enjoy the outdoors, whereas Historic Spanish Point is one of the cultural attractions. Siesta Key Beach and Lido Beach are other popular places to visit in the area.

What's the best way to get to and around Osprey?

Knowing a bit about the transportation options can make your trip smoother when you get to your destination. Fly into Sarasota-Bradenton Intl. Airport (SRQ), which is located 13.8 mi (22.2 km) from the city center. If you'd like to venture out around the area, you may want to rent a car for your trip.

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