Search and Rent Osprey Condos

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Condo Rentals in Osprey

Property grounds
Chadwick Cove Resort & Marina

Chadwick Cove Resort & Marina

4.0 star property
Manasota Key
10.0 out of 10, Exceptional, (14)
"I don't care about tiki bars and pools, so this was great for me. beach access is a short walk, the unit was modern and clean. "
United States
Billie
$502 nightly
The price is $538
Nov 17 - Nov 18
Total with taxes and fees
Chadwick Cove Resort & Marina
Beach nearby
New! Renovated Coastal 2/2, 6 mins to IMG

New! Renovated Coastal 2/2, 6 mins to IMG

South Bradenton
9.8 out of 10, Exceptional, (17)
"Super close to IMG, 25 minutes from downtown Sarasota. Nice pool area, and condo was clean. Not brand new, but nice and comfortable."
United States
Deidre L.
$334 nightly
The price is $368
Nov 16 - Nov 17
Total with taxes and fees
New! Renovated Coastal 2/2, 6 mins to IMG
Sun loungers, beach towels
Cozy beach house! Just steps away from the world-class Manasota beach

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

3.5 star property
Manasota
9.8 out of 10, Exceptional, (6)
"Great place. "
United States
Chris M.
$412 nightly
The price is $459
Nov 15 - Nov 16
Total with taxes and fees
Cozy beach house! Just steps away from the world-class Manasota beach
Beach
Lavish Waterfront Condo! Heated Pools~Lanai~WiFi. By IMG~Beaches~AMI~Restaurants

Lavish Waterfront Condo! Heated Pools~Lanai~WiFi. By IMG~Beaches~AMI~Restaurants

Bradenton
10.0 out of 10, Exceptional, (117)
"The condo was beautiful and very spacious. Nice area and very close to the places we wanted to go."
United States
Brenda S.
$289 nightly
The price is $322
Nov 15 - Nov 16
Total with taxes and fees
Lavish Waterfront Condo! Heated Pools~Lanai~WiFi. By IMG~Beaches~AMI~Restaurants
Beach nearby
*Charming 2bed 2 bath 6 mins from IMG*

*Charming 2bed 2 bath 6 mins from IMG*

South Bradenton
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!"
United States
Cassandra
$329 nightly
The price is $362
Nov 16 - Nov 17
Total with taxes and fees
*Charming 2bed 2 bath 6 mins from IMG*
Sun loungers, beach towels
Beautifully furnished condo

Beautifully furnished condo

Bradenton
9.8 out of 10, Exceptional, (145)
"The condo was great and very clean. "
United States
Allison G.
$218 nightly
The price is $244
Dec 8 - Dec 9
Total with taxes and fees
Beautifully furnished condo
On the beach, sun loungers, beach towels
3 Bedroom-Beachfront Condo with Most Amazing Sunset Views of the Gulf

3 Bedroom-Beachfront Condo with Most Amazing Sunset Views of the Gulf

Manasota Key
9.6 out of 10, Exceptional, (58)
"Roomy condo with everything you need 2 rainy days but still enjoyed"
United States
Janet M.
$428 nightly
The price is $473
Nov 17 - Nov 18
Total with taxes and fees
3 Bedroom-Beachfront Condo with Most Amazing Sunset Views of the Gulf
Exterior
Fantastic Shorewalk Vacation 2 bed/2 bath condo/Lake view/close to IMG, beaches

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

Bradenton
9.8 out of 10, Exceptional, (59)
"clean, close to IMGcomfortable bedding- highly recommend"
United States
anjeanette b.
$342 nightly
The price is $382
Nov 15 - Nov 16
Total with taxes and fees
Fantastic Shorewalk Vacation 2 bed/2 bath condo/Lake view/close to IMG, beaches
Marina
Bayfront Condo Walkable to Everything. Unit 3

Bayfront Condo Walkable to Everything. Unit 3

Manasota Key
9.6 out of 10, Exceptional, (21)
"Stayed here many times. After major hurricane damage Erin is taking the opportunity to completely renovate the entire property.The condos are done and beautiful inside.Very well equipped and nicely decorated.Jim the manager is there for any issues and great to work with.When the property is completed this will be one of the nicest places to stay on the key"
United States
kim s.
$363 nightly
The price is $402
Nov 15 - Nov 16
Total with taxes and fees
Bayfront Condo Walkable to Everything. Unit 3
Beach
*Farmhouse 2/2 Renovated Condo 6 mins from IMG*

*Farmhouse 2/2 Renovated Condo 6 mins from IMG*

South Bradenton
9.8 out of 10, Exceptional, (26)
"Nice place! Clean, adequate, and even though they are constructing a new building, the workers were kind and accommodating and did not interfere with the Condo. They pool is new and BEAUTIFUL!!"
United States
Joan G.
$329 nightly
The price is $362
Nov 16 - Nov 17
Total with taxes and fees
*Farmhouse 2/2 Renovated Condo 6 mins from IMG*
Beach
Superb Waterfront Condo! Heated Pools~Lanai~WiFi. By IMG~Beaches~AMI~Restaurants

Superb Waterfront Condo! Heated Pools~Lanai~WiFi. By IMG~Beaches~AMI~Restaurants

Bradenton
9.8 out of 10, Exceptional, (113)
"I stayed 1 night with 2 of my friends and honestlyEverything was amazing, place was super clean, the host was super quick to answer my questions and I would for sure booked again."
United States
Jenifer M.
$289 nightly
The price is $322
Nov 15 - Nov 16
Total with taxes and fees
Superb Waterfront Condo! Heated Pools~Lanai~WiFi. By IMG~Beaches~AMI~Restaurants
Front of property - evening/night
Captiva Beach Resort

Captiva Beach Resort

3.0 star property
South Village
9.0 out of 10, Wonderful, (1156)
"Very good stay, clean, safe, and steps from the beach"
United States
Brandon
$153 nightly
The price is $170
Nov 16 - Nov 17
Total with taxes and fees
Captiva Beach Resort
Sun loungers
Charming Longboat Key Bungalow with beach access minutes away…

Charming Longboat Key Bungalow with beach access minutes away…

2.0 star property
Longboat Key
9.4 out of 10, Exceptional, (12)
"Property was very nice and conveniently located "
United States
Ryan C.
$343 nightly
The price is $383
Nov 15 - Nov 16
Total with taxes and fees
Charming Longboat Key Bungalow with beach access minutes away…
Beach
Beautiful 2BR Condo! Heated Pools~WiFi. By IMG Academy~Beaches~AMI~Restaurants.

Beautiful 2BR Condo! Heated Pools~WiFi. By IMG Academy~Beaches~AMI~Restaurants.

Bradenton
9.8 out of 10, Exceptional, (147)
"The location is great with stores very close, very close to IMG academy and for beaches.It had everything we needed for a short stay. There could be some improvements made but for the length of time we stayed it was okay. "
United States
Salisha H.
$289 nightly
The price is $322
Nov 15 - Nov 16
Total with taxes and fees
Beautiful 2BR Condo! Heated Pools~WiFi. By IMG Academy~Beaches~AMI~Restaurants.
On the beach, white sand
A Beach Retreat

A Beach Retreat

2.5 star property
Casey Key
9.2 out of 10, Wonderful, (571)
"Location, very clean and comfortable. Nice efficiency."
United States
Chuck
$184 nightly
The price is $208
Nov 16 - Nov 17
Total with taxes and fees
A Beach Retreat
Terrace/patio
Sapphire Shores Arcadia 1Bed/1Bath - Walk to Bay!

Sapphire Shores Arcadia 1Bed/1Bath - Walk to Bay!

Indian Beach Sapphire Shores
9.8 out of 10, Exceptional, (55)
"The place was very clean, the hosts very helpful. The apt where we stayed feels private, even though it is connected to the house in front. We felt safe there and it is close to all the places we needed to go to."
United States
victor k.
Sapphire Shores Arcadia 1Bed/1Bath - Walk to Bay!
Fridge, microwave, coffee/tea maker, toaster
Walk to beach Heated POOL King bed DAILY WEEKLY Villa 4 SPECIALS

Walk to beach Heated POOL King bed DAILY WEEKLY Villa 4 SPECIALS

Sarasota
9.4 out of 10, Exceptional, (46)
"Cute, clean little place. Had everything we needed and was a quick walk to the beach!"
United States
Robin P.
$253 nightly
The price is $283
Dec 4 - Dec 5
Total with taxes and fees
Walk to beach Heated POOL King bed DAILY WEEKLY Villa 4 SPECIALS
Beach nearby
In the heart of Siesta Key Village | Walk to Beach | Dog Friendly | Fully renovated & remodeled

In the heart of Siesta Key Village | Walk to Beach | Dog Friendly | Fully renovated & remodeled

Siesta Key Village
9.2 out of 10, Wonderful, (19)
"Nice property off of the beach, nice clubhouse, nice pools, good exercise facility, easy access, friendly staff and a good value off season. It's about 10 minutes from shops and restaurants in Vero Beach. The demographic of the area is strongly slanted toward 70+ age range, nice if you seek tranquility, but it will be too quiet for some. Hiram's is a fun restaurant but a bit of a drive, and the Ocean Grill is a good one for date night."
United States
Dean K.
In the heart of Siesta Key Village | Walk to Beach | Dog Friendly | Fully renovated & remodeled
Property grounds
Updated unit with easy beach access on Siesta Key

Updated unit with easy beach access on Siesta Key

Siesta Key
9.2 out of 10, Wonderful, (85)
"The beach condo was super clean and had everything that was needed for our five day/four night stay. Just a short walk to beach access. There is a trolley that drives the main road to take you right into town for shopping and restaurants. The locals are very friendly. It was perfect to celebrate my son's 15th birthday!"
United States
Stephanie P.
$390 nightly
The price is $435
Nov 15 - Nov 16
Total with taxes and fees
Updated unit with easy beach access on Siesta Key
On the beach
Drift & Dune – Longboat Beachfront #101 RVA

Drift & Dune – Longboat Beachfront #101 RVA

Longboat Key
8.6 out of 10, Excellent, (71)
"The location of the condo was perfect. The beach was amazing. Everything was clean and made our stay easy and enjoyable."
United States
Jillian H.
$314 nightly
The price is $349
Dec 11 - Dec 12
Total with taxes and fees
Drift & Dune – Longboat Beachfront #101 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.
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Top Osprey Hotel Reviews

The Westin Sarasota

The Westin Sarasota

10/10 Excellent
"Fantastic Stay! I had a wonderful experience at this hotel. The staff were friendly and welcoming, the room was spotless and comfortable, and every detail made the stay enjoyable. The location was convenient, and the amenities exceeded my expectations. I’d definitely stay here again and recommend it to anyone looking for a relaxing, high-quality stay!"
Robert 2-night trip
Posted 2 days ago
The Westin Sarasota

Find out more about Osprey

Osprey Condo Rentals information

Number of reviews
2,586
Accommodation
3725 Condo Rentals
Lowest Price
$170
Highest Price
$538

Frequently asked questions

How much do condos in Osprey cost?
Condos in Osprey range from $170 to $538 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 3725 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 $170 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 7 miles 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 5 miles 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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