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Oct 17 - Oct 19
In two weeks
Oct 24 - Oct 26
In one month
Nov 7 - Nov 9
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Dec 5 - Dec 7

Condo Rentals in Osprey

Chadwick Cove Resort & Marina
Property grounds

Chadwick Cove Resort & Marina

4.0 star property
10.0 out of 10, Exceptional, (14)
"Great place and location "
The price is ￥19,246
￥89,871 total
includes taxes & fees
Oct 21 - Oct 22
Chadwick Cove Resort & Marina
2nd Floor Retreat Overlooking the Pool & Gulf Silver Sands #251 Resort by RVA
A heated pool

2nd Floor Retreat Overlooking the Pool & Gulf Silver Sands #251 Resort by RVA

8.6 out of 10, Excellent, (41)
"Beautiful place with a private beach and a really nice clean condo. Had everything we needed for a relaxing weekend. Will definitely come back! Thank you."
The price is ￥19,735
￥45,500 total
includes taxes & fees
Oct 9 - Oct 10
2nd Floor Retreat Overlooking the Pool & Gulf Silver Sands #251 Resort by RVA
The Sapphire Suite 1Bed/1Bath
1 bedroom, desk, iron/ironing board, WiFi

The Sapphire Suite 1Bed/1Bath

9.8 out of 10, Exceptional, (83)
"We loved our stay here, it was a perfect location with lots to do within even walking distance! "
The price is ￥11,386
￥21,906 total
includes taxes & fees
Oct 14 - Oct 15
The Sapphire Suite 1Bed/1Bath
Cozy beach house! Just steps away from the world-class Manasota beach
Sun loungers, beach towels

Cozy beach house! Just steps away from the world-class Manasota beach

3.5 star property
9.8 out of 10, Exceptional, (6)
"Great place. "
The price is ￥16,395
￥64,107 total
includes taxes & fees
Oct 9 - Oct 10
Cozy beach house! Just steps away from the world-class Manasota beach
Riverside Oasis 1Bed/1Bath
Terrace/patio

Riverside Oasis 1Bed/1Bath

9.4 out of 10, Exceptional, (37)
"Perfect little place for a couple days. Clean and conveniently located just a short drive away from everything you need. Host was responsive and accommodating. We would definitely stay here again. "
The price is ￥7,894
￥17,961 total
includes taxes & fees
Oct 26 - Oct 27
Riverside Oasis 1Bed/1Bath
Casa Azul 2Bed/1Bath
Interior

Casa Azul 2Bed/1Bath

9.4 out of 10, Exceptional, (66)
"The home was decorated beautiful! We enjoyed ourselves. Comfortable and kitchen were stocked nicely. Great location, 5-10 minutes from most places of interest. Nice communication and easy to check in and out. "
The price is ￥13,663
￥29,778 total
includes taxes & fees
Oct 13 - Oct 14
Casa Azul 2Bed/1Bath
Oceanfront Bliss - The Beach on Longboat Key #106 Resort by RVA
On the beach

Oceanfront Bliss - The Beach on Longboat Key #106 Resort by RVA

8.8 out of 10, Excellent, (85)
"Gorgeous location, the beach was exceptional and the area was quiet and felt secluded. The condo was a bit shabby but clean and had everything we needed. "
The price is ￥19,735
￥45,956 total
includes taxes & fees
Oct 9 - Oct 10
Oceanfront Bliss - The Beach on Longboat Key #106 Resort by RVA
Captiva Beach Resort
Front of property - evening/night

Captiva Beach Resort

3.0 star property
9.0 out of 10, Wonderful, (1141)
"2nd time and excellent as always..close to the beach and great surroundings "
Captiva Beach Resort
*Charming 2bed 2 bath 6 mins from IMG*
Beach nearby

*Charming 2bed 2 bath 6 mins from IMG*

9.6 out of 10, Exceptional, (21)
"Great place, spacious for 6 adults, clean, comfortable, organized with all the amenities one would need. Everything was simple from check in to check out. The queen-size air mattress fits seamlessly in the living room's common area and comes equipped with all necessary bedding to ensure a comfortable and restful experience.​ I would stay again!"
The price is ￥17,458
￥54,560 total
includes taxes & fees
Oct 9 - Oct 10
*Charming 2bed 2 bath 6 mins from IMG*
Spacious Renovated 1 Bedroom Siesta Key Beachside Vacation Rental Getaway
Property grounds

Spacious Renovated 1 Bedroom Siesta Key Beachside Vacation Rental Getaway

9.2 out of 10, Wonderful, (131)
"Loved how close it is to siesta key beach"
Spacious Renovated 1 Bedroom Siesta Key Beachside Vacation Rental Getaway
Fantastic Shorewalk Vacation 2 bed/2 bath condo/Lake view/close to IMG, beaches
Exterior

Fantastic Shorewalk Vacation 2 bed/2 bath condo/Lake view/close to IMG, beaches

9.8 out of 10, Exceptional, (59)
"It was clean, comfy and ideal locarion. Close to beaches AMI and the pool was great. "
The price is ￥20,358
￥58,848 total
includes taxes & fees
Oct 12 - Oct 13
Fantastic Shorewalk Vacation 2 bed/2 bath condo/Lake view/close to IMG, beaches
Walk to the Beach and More from this Fully Renovated Unit W/ Heated Pool
Fridge, microwave, oven, stovetop

Walk to the Beach and More from this Fully Renovated Unit W/ Heated Pool

9.4 out of 10, Exceptional, (95)
"A very pleasant and comfortable experience in a beautiful location."
The price is ￥24,637
￥53,479 total
includes taxes & fees
Oct 9 - Oct 10
Walk to the Beach and More from this Fully Renovated Unit W/ Heated Pool
Modern Coastal 2/2 condo w/pool 6 mins to IMG
Beach nearby

Modern Coastal 2/2 condo w/pool 6 mins to IMG

10.0 out of 10, Exceptional, (25)
"Had a great time and the pool are was super fun!"
The price is ￥17,458
￥54,355 total
includes taxes & fees
Oct 9 - Oct 10
Modern Coastal 2/2 condo w/pool 6 mins to IMG
Beautifully furnished condo
Sun loungers, beach towels

Beautifully furnished condo

9.8 out of 10, Exceptional, (140)
"Perfect for our weekend football tournament. Had everything we needed. "
The price is ￥13,056
￥37,874 total
includes taxes & fees
Oct 28 - Oct 29
Beautifully furnished condo
Resort w Private Beach Access/Pool-The Beach Club at Siesta Key #100B by RVA
Beach nearby, beach umbrellas

Resort w Private Beach Access/Pool-The Beach Club at Siesta Key #100B by RVA

8.8 out of 10, Excellent, (80)
"The place was tastefully decorated and clean. I loved the deck area. The location was close to the beach and walking distance to restaurants. There was a mildew smell that we didn't care for, but we after being in there we didn't notice it as much."
The price is ￥20,494
￥46,258 total
includes taxes & fees
Oct 9 - Oct 10
Resort w Private Beach Access/Pool-The Beach Club at Siesta Key #100B by RVA
Large Studio on Gulf! Cabana Beach Club #5B Longboat Key-Steps to Sand by RVA
Dining

Large Studio on Gulf! Cabana Beach Club #5B Longboat Key-Steps to Sand by RVA

8.2 out of 10, Very Good, (71)
"Wonderful spot. Highly recommend. "
The price is ￥18,976
￥42,018 total
includes taxes & fees
Oct 9 - Oct 10
Large Studio on Gulf! Cabana Beach Club #5B Longboat Key-Steps to Sand by RVA
Right on the beach.Renovated ground Floor unit 63.
Beach nearby

Right on the beach.Renovated ground Floor unit 63.

9.4 out of 10, Exceptional, (54)
"We thoroughly enjoyed our stay-perfect location, great accommodations, and wonderful staff!"
The price is ￥21,253
￥50,583 total
includes taxes & fees
Oct 21 - Oct 22
Right on the beach.Renovated ground Floor unit 63.
Beautiful 2BR Condo! Pools~Free WiFi. Near IMG Academy~Beaches~AMI~Restaurants.
Beach

Beautiful 2BR Condo! Pools~Free WiFi. Near IMG Academy~Beaches~AMI~Restaurants.

9.8 out of 10, Exceptional, (143)
"Great location, clean, everything we needed for a low key beach vacation!"
The price is ￥14,422
￥46,332 total
includes taxes & fees
Oct 12 - Oct 13
Beautiful 2BR Condo! Pools~Free WiFi. Near IMG Academy~Beaches~AMI~Restaurants.
Small and Quiet Lakefront Resort on Siesta Key W/ Heated Pool and Kayaks
Fridge, microwave

Small and Quiet Lakefront Resort on Siesta Key W/ Heated Pool and Kayaks

9.0 out of 10, Wonderful, (42)
"The property was clean and comfortable. Having two bathrooms was very convenient. The only downside was that the pool was not well kept and could use a deep clean."
The price is ￥26,939
￥66,435 total
includes taxes & fees
Oct 21 - Oct 22
Small and Quiet Lakefront Resort on Siesta Key W/ Heated Pool and Kayaks
Clean, modern and newly RENOVATED condo on US #1 Private Siesta Key Beach
Smart TV, books

Clean, modern and newly RENOVATED condo on US #1 Private Siesta Key Beach

9.8 out of 10, Exceptional, (97)
"The Oystercatcher cottage was an A+! It has great amenities. The screened porch with the fans was very comfortable. We enjoyed the games in the evenings after dinner. The beach cart was very functional and hauled all the provided beach supplies easily. Today we are going to try the kayaks! "
The price is ￥25,276
￥63,395 total
includes taxes & fees
Oct 17 - Oct 18
Clean, modern and newly RENOVATED condo on US #1 Private Siesta Key Beach
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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Top Osprey Hotel Reviews

Spark by Hilton Sarasota Siesta Key Gateway

Spark by Hilton Sarasota Siesta Key Gateway

10/10 Excellent
"Staff was friendly and professional. It was quiet and clean. Very acommodating."
Mary 2-night trip
Posted 1 day ago
Spark by Hilton Sarasota Siesta Key Gateway

Find out more about Osprey

Find out more about Osprey

Osprey Condo Rentals information

Number of reviews
2,110
Accommodation
3739 Condo Rentals
Lowest Price
￥17,961
Highest Price
￥89,871

Frequently asked questions

How much do condos in Osprey cost?
Condos in Osprey range from ￥17,961 to ￥89,871 per night. These stays provide loads of space for your whole crew at a price that's friendly on the pocket. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
What are the best condos in Osprey?
Choose from multiple condos in Osprey with a total average guest review rating of 9.4. Venice Beach Villas comes highly recommended if you're traveling with the whole crew or just want to stretch out. This 3-star condo also features therapeutic mineral springs and a barbecue grill. Walk To The Beach From Modern Condo Or Hop On A Bike To Siesta Village is another guest fave. It has a 3-star rating and amenities such as a deck and a lanai.
How many condos are there in Osprey?
Work out your vacation dates and then pick from 3739 condos in Osprey. For an official business trip, a couples' getaway or anything in between, Expedia will help you find the perfect place in a few quick clicks.
What are the best cheap condos in Osprey?
With condos starting from ￥17,961 per night, you may be tempted to stay a little longer in Osprey! One property that's easy on the pocket is Captiva Beach Resort. It comes with the layout you're looking for as well as pillow top mattresses and a swimming pool. Another cost-effective pick is Bs 1350 - #1 Siesta And Crescent Beach Are Walking Distance Away, which offers a lake view and a sauna. If you prefer to save your hard-earned cash and still experience the best of Osprey, add a couple of fun and free attractions to your must-do list. Siesta Key Beach and Venice Beach will keep you on the go. This price was available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
Are there any family-friendly condos in Osprey?
Get comfortable at Venice Beach Villas, a 3-star option just a quick drive from downtown. Amenities here include a barbecue grill and a swimming pool. Another family-friendly condo is Walk To The Beach From Modern Condo Or Hop On A Bike To Siesta Village. A deck and a lanai help make this 3-star property a favorite among guests. Once you've checked in and unpacked, there's a host of family-friendly attractions to visit around Osprey. Siesta Key Beach and Venice Beach are two of our top suggestions.
Are there any 5-star condos in Osprey?
Although there are no 5-star condos in Osprey, there are 4-star accommodations that have what you're looking for. Located about 11 kilometers from the downtown area, Gulf Holiday By Beachside Management comes with concierge services and a swimming pool. Another upscale retreat is Excelsior Beach To Bay - Bayside. It's roughly 8 kilometers from the center of Osprey and has amenities like a swimming pool and a deck.
Why book your condo in Osprey with Expedia?
With Expedia, it's a cinch to find your ideal condo in Osprey. After someplace luxurious? Make the most of our filters to search for properties that have a 5-star rating. If you have a set budget, select how much you're willing to spend and then browse our amazing options. We'll help you find the perfect fit whatever your escape looks like.
How can I find cheap condos in Osprey?
With Expedia's user-friendly filter tool, comparing cheap condos in Osprey is a snap. To discover properties that'll make your wallet happy, refine your search by amenities, budget and star rating.
What is there to do in Osprey near my condo?
If you'd like to make the most of your time in Osprey, be sure to stop by Oscar Scherer State Park. It's a hit with locals and travelers alike.

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