Osprey vacation rentals

26Results

View Osprey vacation rentals. Search all Osprey FL rentals including homes and condos for rent. Michael Saunders & Company® the expert on monthly, winter, vacation and seasonal rentals in Osprey, Florida.

Newest
New Listing
124 Turquoise Lane Osprey FL 34229

$4,500/month

Osprey, FL

124 Turquoise Lane

  • 3 Beds
  • 2 Baths
  • 2,306 SqFt
  • 1 Day on Market
MLS#: A4707451
New Listing

$2,250/month

Osprey, FL

4271 Expedition Way, Unit 103

  • 2 Beds
  • 2 Baths
  • 1,135 SqFt
  • 6 Days on Market
MLS#: A4706001
New Listing

$4,000/month

Osprey, FL

1279 Thornapple Drive

  • 3 Beds
  • 2 Baths
  • 2,261 SqFt
  • 17 Days on Market
MLS#: A4705379
New Listing

$2,195/month

Osprey, FL

4248 Expedition Way

  • 3 Beds
  • 2 Baths
  • 1,430 SqFt
  • 26 Days on Market
MLS#: A4704095

$6,000/month

Osprey, FL

14041 Bellagio Way, Unit 214

  • 3 Beds
  • 2 Baths
  • 1,799 SqFt
  • 66 Days on Market
MLS#: A4700702

$3,295/month

Osprey, FL

4401 Conchfish Lane

  • 4 Beds
  • 3 Baths
  • 2,370 SqFt
  • 69 Days on Market
MLS#: A4700255

$3,750/month

Osprey, FL

534 Oak Bay Drive

  • 4 Beds
  • 3 Baths
  • 2,077 SqFt
  • 80 Days on Market
MLS#: A4699469

$4,995/month

Osprey, FL

6100 Jessie Harbor Drive, Unit 202

  • 3 Beds
  • 4 Baths
  • 3,771 SqFt
  • 87 Days on Market
MLS#: A4698732

$1,600/month

Osprey, FL

51 Mac Ewen Drive, Unit 8

  • 1 Bed
  • 1 Bath
  • 595 SqFt
  • 114 Days on Market
MLS#: A4695928

$4,395/month

Osprey, FL

260 Hidden Bay Drive, Unit 401

  • 3 Beds
  • 3 Baths
  • 2,168 SqFt
  • 138 Days on Market
MLS#: A4693277

$2,000/month

Osprey, FL

4219 Frontier Way, Unit 105

  • 2 Beds
  • 2 Baths
  • 1,244 SqFt
  • 139 Days on Market
MLS#: N6144275

$2,250/month

Osprey, FL

51 Macewen Drive, Unit 12

  • 1 Bed
  • 1 Bath
  • 623 SqFt
  • 197 Days on Market
MLS#: A4686127

Listings courtesy of StellarMLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of September 26, 2026 10:33 AM EDT. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. IDX information is provided exclusively for consumers’ personal noncommercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed by MLS GRID. The use of the MLS GRID Data may be subject to an end user license agreement.