Search Condos Rentals in Osprey from CA $139

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Browse Select Osprey Condo Rentals

Chadwick Cove Resort & Marina

4.0 star property
10.0 out of 10, Exceptional, (11)
"Nic place to stay and enjoy the area"
The price is CA $113
CA $748 total
includes taxes & fees
Aug 24 - Aug 25
Chadwick Cove Resort & Marina

Captiva Beach Resort

2.0 star property
9.0 out of 10, Wonderful, (1123)
"Everything was great and a walking distance to the beach❤️❤️❤️❤️❤️. Everyone was very friendly and kind, thank you so much."
The price is CA $202
CA $276 total
includes taxes & fees
Aug 21 - Aug 22
Captiva Beach Resort

Steps to Water! Sea Glass - Beach to Bay, Heated Pool and Dock

9.8 out of 10, Exceptional, (35)
"The property was very nice and convenient. We really enjoyed our stay and would come again. "
Steps to Water! Sea Glass - Beach to Bay, Heated Pool and Dock

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 CA $282
CA $550 total
includes taxes & fees
Aug 21 - Aug 22
2nd Floor Retreat Overlooking the Pool & Gulf Silver Sands #251 Resort by RVA

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 CA $161
CA $601 total
includes taxes & fees
Aug 21 - Aug 22
Cozy beach house! Just steps away from the world-class Manasota beach

Casa Azul 2Bed/1Bath

9.4 out of 10, Exceptional, (63)
"Very comfortable and perfect location to the airport! "
The price is CA $124
CA $269 total
includes taxes & fees
Aug 21 - Aug 22
Casa Azul 2Bed/1Bath

Hidden Paradise on Lakefront Property Among Tropical Landscape on Siesta Key

9.0 out of 10, Wonderful, (40)
"Perfect location for a winter getaway. Can walk or bike to Turtle Beach or Crescent Beach. The place was clean and modern with excellent wifi and all the beach items we needed (chairs, towels, umbrella). "
The price is CA $224
CA $480 total
includes taxes & fees
Aug 21 - Aug 22
Hidden Paradise on Lakefront Property Among Tropical Landscape on Siesta Key

Charming Longboat Key Bungalow with beach access minutes away…

2.0 star property
9.4 out of 10, Exceptional, (12)
"Very cute place. It was in a great spot for easy access to the beach and restaurants. "
The price is CA $160
CA $513 total
includes taxes & fees
Aug 25 - Aug 26
Charming Longboat Key Bungalow with beach access minutes away…

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

8.8 out of 10, Excellent, (84)
"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 CA $196
CA $440 total
includes taxes & fees
Aug 21 - Aug 22
Oceanfront Bliss - The Beach on Longboat Key #106 Resort by RVA

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

9.8 out of 10, Exceptional, (95)
"Lovely unit and the perfect location. Short walk to the beach and easy to get to the shopping/eating areas. "
The price is CA $217
CA $566 total
includes taxes & fees
Aug 22 - Aug 23
Clean, modern and newly RENOVATED condo on US #1 Private Siesta Key Beach

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

10.0 out of 10, Exceptional, (113)
"Great place to stay. Accomodations were very good."
The price is CA $139
CA $423 total
includes taxes & fees
Aug 21 - Aug 22
Lavish Waterfront Condo! Heated Pools~Lanai~WiFi. By IMG~Beaches~AMI~Restaurants

*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 CA $159
CA $485 total
includes taxes & fees
Aug 21 - Aug 22
*Charming 2bed 2 bath 6 mins from IMG*

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 CA $159
CA $483 total
includes taxes & fees
Aug 21 - Aug 22
Modern Coastal 2/2 condo w/pool 6 mins to IMG

The Sapphire Suite 1Bed/1Bath

9.8 out of 10, Exceptional, (82)
"We loved our stay here, it was a perfect location with lots to do within even walking distance! "
The price is CA $104
CA $199 total
includes taxes & fees
Aug 25 - Aug 26
The Sapphire Suite 1Bed/1Bath

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

9.8 out of 10, Exceptional, (59)
"Perfect accommodation "
The price is CA $185
CA $529 total
includes taxes & fees
Aug 23 - Aug 24
Fantastic Shorewalk Vacation 2 bed/2 bath condo/Lake view/close to IMG, beaches

Waterfront Unit, Heated Pool, 70" TV, Tiki Bar & Grill, On The Marina!

9.2 out of 10, Wonderful, (49)
"We liked the room. It was clean and very reasonable for the price. The live music was done by 10pm and great view of the water. Definitely a nice little getaway. "
The price is CA $159
CA $299 total
includes taxes & fees
Aug 21 - Aug 22
Waterfront Unit, Heated Pool, 70" TV, Tiki Bar & Grill, On The Marina!

Riverside Oasis 1Bed/1Bath

9.4 out of 10, Exceptional, (34)
"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 CA $70
CA $162 total
includes taxes & fees
Sep 1 - Sep 2
Riverside Oasis 1Bed/1Bath

Spacious Renovated 1 Bedroom Siesta Key Beachside Vacation Rental Getaway

9.4 out of 10, Exceptional, (130)
"Loved how close it is to siesta key beach"
The price is CA $170
CA $505 total
includes taxes & fees
Sep 11 - Sep 12
Spacious Renovated 1 Bedroom Siesta Key Beachside Vacation Rental Getaway

POOL VIEW Walk to beach King bed Heated pool DAILY WEEKLY SPECIALS villa 3

9.6 out of 10, Exceptional, (44)
"The location of the property could not have been better. A very short walk to the quietest beach on Siesta Key. The manager was very attentive when we called with a minor issue and had it resolved quickly. The property could use a pretty thorough cleaning of the baseboards and other nooks and crannies but overall it was pretty clean. We would stay again."
The price is CA $137
CA $342 total
includes taxes & fees
Aug 21 - Aug 22
POOL VIEW Walk to beach King bed Heated pool DAILY WEEKLY SPECIALS villa 3

Sun, Sand & Serenity – Beach Castle #17 by RVA

9.2 out of 10, Wonderful, (63)
"We LOVE this place"
Sun, Sand & Serenity – Beach Castle #17 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.
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