Siesta Key vacation rentals

267Results

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

Newest
1080 Seagrove Lane Sarasota FL 34242

$29,750/month

Sarasota, FL

1080 Seagrove Lane, Unit CH2

  • 4 Beds
  • 6 Baths
  • 4,610 SqFt
  • 56 Days on Market
MLS#: A4705027
New Listing

$8,900/month

Sarasota, FL

19 Whispering Sands Drive, Unit 106

  • 2 Beds
  • 2 Baths
  • 1,282 SqFt
  • 2 Days on Market
MLS#: A4711053
New Listing

$4,695/month

Sarasota, FL

5354 Shadow Lawn Drive

  • 3 Beds
  • 2 Baths
  • 2,083 SqFt
  • 3 Days on Market
MLS#: A4710293
New Listing

$3,000/month

Sarasota, FL

6600 Peacock Road, Unit 203

  • 2 Beds
  • 2 Baths
  • 1,196 SqFt
  • 6 Days on Market
MLS#: A4710617
New Listing

$8,250/month

Sarasota, FL

1249 Dockside Place, Unit 110

  • 2 Beds
  • 2 Baths
  • 1,217 SqFt
  • 8 Days on Market
MLS#: A4710270
New Listing

$3,500/month

Sarasota, FL

9226 Midnight Pass Road, Unit 4A

  • 2 Beds
  • 2 Baths
  • 1,223 SqFt
  • 15 Days on Market
MLS#: A4708850
New Listing

$3,300/month

Sarasota, FL

11 Sandy Cove Road, Unit 8F

  • 2 Beds
  • 2 Baths
  • 1,122 SqFt
  • 22 Days on Market
MLS#: A4708826
New Listing

$10,000/week

Sarasota, FL

6480 Midnight Pass Road, Unit 311

  • 2 Beds
  • 2 Baths
  • 1,265 SqFt
  • 30 Days on Market
MLS#: A4707675
New Listing

$7,500/week

Sarasota, FL

5830 Midnight Pass Road, Unit 54

  • 1 Bed
  • 1 Bath
  • 728 SqFt
  • 30 Days on Market
MLS#: A4707681

$6,000/month

Sarasota, FL

5021 Midnight Pass Road

  • 3 Beds
  • 3 Baths
  • 2,298 SqFt
  • 31 Days on Market
MLS#: A4707682

$7,100/month

Sarasota, FL

  • 2 Beds
  • 2 Baths
  • 1,115 SqFt
  • 36 Days on Market
MLS#: A4705820

$16,750/month

Sarasota, FL

4879 Commonwealth Drive

  • 4 Beds
  • 3 Baths
  • 2,450 SqFt
  • 37 Days on Market
MLS#: A4706975

Listings courtesy of StellarMLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of October 29, 2026 5:34 PM 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.