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Condo Rentals in Osprey Village

Captiva Beach Resort

3.0 star property
South Village
9.0 out of 10, Wonderful, (1171)
"Clean room, snd friendly staff. Great location "
United States
Stephanie
$167 nightly
The price is $187
Dec 9 - Dec 10
Total with taxes and fees
Captiva Beach Resort

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

South Bradenton
9.8 out of 10, Exceptional, (27)
"Great place. My family had a great time."
United States
AZAAM R.
$337 nightly
The price is $371
Dec 9 - Dec 10
Total with taxes and fees
*Modern 2/2 condo w/pool 6 mins to IMG*

Upscale 2/2 Key West style condo 6 mins from IMG

South Bradenton
10.0 out of 10, Exceptional, (22)
"Great location, attentive host, great stay"
United States
JUDY T.
$336 nightly
The price is $370
Dec 9 - Dec 10
Total with taxes and fees
Upscale 2/2 Key West style condo 6 mins from IMG

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

South Bradenton
9.8 out of 10, Exceptional, (17)
"Accommodating for family group, quick drive to the beach."
United States
Ginger B.
$336 nightly
The price is $370
Dec 9 - Dec 10
Total with taxes and fees
New! Renovated Coastal 2/2, 6 mins to IMG

*Charming 2bed 2 bath 6 mins from IMG*

South Bradenton
9.6 out of 10, Exceptional, (21)
"Cool place. Everything just as mentioned. Kids had a blast at pool and place was super clean"
United States
Jason G.
$330 nightly
The price is $363
Dec 9 - Dec 10
Total with taxes and fees
*Charming 2bed 2 bath 6 mins from IMG*

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

Sarasota
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."
United States
Mel S.
$235 nightly
The price is $262
Dec 11 - Dec 12
Total with taxes and fees
POOL VIEW Walk to beach King bed Heated pool DAILY WEEKLY SPECIALS villa 3

Lakefront Property on Siesta Key Among Tropical Landscape W/ Heated Pool

Siesta Key
9.0 out of 10, Wonderful, (21)
"Great stay. Great place."
United States
Jennifer h.
$296 nightly
The price is $330
Dec 11 - Dec 12
Total with taxes and fees
Lakefront Property on Siesta Key Among Tropical Landscape W/ Heated Pool

Riverside Oasis 1Bed/1Bath

Bayou Oaks
9.2 out of 10, Wonderful, (39)
"Excellent place to stay"
United States
garry s.
$130 nightly
The price is $144
Dec 22 - Dec 23
Total with taxes and fees
Riverside Oasis 1Bed/1Bath

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

Whitfield Estates
9.2 out of 10, Wonderful, (49)
"Great place and great location! We really enjoyed our stay!"
United States
Meghan I.
$197 nightly
The price is $218
Dec 9 - Dec 10
Total with taxes and fees
Waterfront Unit, Heated Pool, 70" TV, Tiki Bar & Grill, On The Marina!

Charming Longboat Key Bungalow with beach access minutes away…

2.0 star property
Longboat Key
9.4 out of 10, Exceptional, (12)
"Enjoyed our stay in this quiet little place with close access to restaurants and just a few minutes from Bradenton. Would come back!"
United States
Todd B.
$374 nightly
The price is $417
Dec 9 - Dec 10
Total with taxes and fees
Charming Longboat Key Bungalow with beach access minutes away…

The Sapphire Suite 1Bed/1Bath

Indian Beach Sapphire Shores
9.8 out of 10, Exceptional, (85)
"We loved our stay here, it was a perfect location with lots to do within even walking distance! "
United States
Austin S.
$130 nightly
The price is $144
Dec 14 - Dec 15
Total with taxes and fees
The Sapphire Suite 1Bed/1Bath

Escape the Cold: Enjoy 20% Off Your Beach Getaway!

Sarasota
9.4 out of 10, Exceptional, (27)
"The condo itself had everything we needed the covered out door balcony was perfect for relaxing with a drink before dinner with out having to be concerned with the sun or rain "
Canada
Joseph D C.
$565 nightly
The price is $630
Jan 3 - Jan 4, 2026
Total with taxes and fees
Escape the Cold: Enjoy 20% Off Your Beach Getaway!

A Beach Retreat

2.5 star property
Casey Key
9.2 out of 10, Wonderful, (576)
"Location, very clean and comfortable. Nice efficiency."
United States
Chuck
$184 nightly
The price is $208
Dec 9 - Dec 10
Total with taxes and fees
A Beach Retreat

Gulf Front Escape – Silver Sands #252 by RVA

Longboat Key
9.0 out of 10, Wonderful, (100)
"Perfect for our family "
United States
Alan B.
$317 nightly
The price is $354
Dec 9 - Dec 10
Total with taxes and fees
Gulf Front Escape – Silver Sands #252 by RVA

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

3.5 star property
Manasota
9.8 out of 10, Exceptional, (6)
"Nice place to stay, close to the beach, hunting for fossilized shark teeth was fun."
United States
Vance E.
$414 nightly
The price is $461
Dec 19 - Dec 20
Total with taxes and fees
Cozy beach house! Just steps away from the world-class Manasota beach

POOL VIEW King bed Walk to beach Covered porch overlooks pool DAILY RATES

South Village
9.6 out of 10, Exceptional, (41)
"Loved the pool and view!"
United States
Victoria P.
$257 nightly
The price is $287
Dec 14 - Dec 15
Total with taxes and fees
POOL VIEW King bed Walk to beach Covered porch overlooks pool DAILY RATES

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

Siesta Key
9.8 out of 10, Exceptional, (101)
"Great location and the private beach was so nice! "
United States
Ashley N.
$355 nightly
The price is $397
Jan 4 - Jan 5, 2026
Total with taxes and fees
Clean, modern and newly RENOVATED condo on US #1 Private Siesta Key Beach

Beachfront Studio – Cabana #5B by RVA

Longboat Key
8.2 out of 10, Very Good, (73)
"Wonderful spot. Highly recommend. "
United States
Regina T.
$184 nightly
The price is $205
Dec 20 - Dec 21
Total with taxes and fees
Beachfront Studio – Cabana #5B by RVA

Drift & Dune – Longboat Beachfront #101 RVA

Longboat Key
8.6 out of 10, Excellent, (74)
"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Condo is well appointed and spacious. Amenities galore! This unit can sleep five but we were only two so we had plenty of space. Comfortable bed and plenty of beach towels. Had some trouble working the tv’s but eventually got it sorted."
United States
Jim &.
$295 nightly
The price is $329
Dec 9 - Dec 10
Total with taxes and fees
Drift & Dune – Longboat Beachfront #101 RVA

🏝Beachfront Condo Overlooking Gulf of Mexico🏝

Casey Key
10.0 out of 10, Exceptional, (22)
"Great place to stay. Nice and clean and literally on the beach. Love this place. "
United States
Jason R.
$358 nightly
The price is $399
Dec 9 - Dec 10
Total with taxes and fees
🏝Beachfront Condo Overlooking Gulf of Mexico🏝
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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Osprey Village Condo Rentals information

Number of reviews
2,314
Accommodation
3449 Condo Rentals
Lowest Price
$144
Highest Price
$630

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