Siesta Key vacation rentals

272Results

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
New Listing
420 Beach Road Sarasota FL 34242

$6,500/month

Sarasota, FL

420 Beach Road, Unit 502

  • 2 Beds
  • 2 Baths
  • 1,316 SqFt
  • 23 Days on Market
MLS#: A4696888

$8,000/month

Sarasota, FL

7372 Melaleuca Way

  • 4 Beds
  • 2 Baths
  • 2,600 SqFt
  • 85 Days on Market
MLS#: A4690292
New Listing

$5,500/month

Sarasota, FL

3954 Hamilton Club Circle, Unit 14

  • 3 Beds
  • 4 Baths
  • 2,798 SqFt
  • 1 Day on Market
MLS#: A4699460
New Listing

$5,800/month

Sarasota, FL

5585 Contento Drive

  • 4 Beds
  • 3 Baths
  • 1,798 SqFt
  • 9 Days on Market
MLS#: A4698865
New Listing

$6,195/month

Sarasota, FL

5456 Azure Way

  • 3 Beds
  • 3 Baths
  • 2,476 SqFt
  • 10 Days on Market
MLS#: A4698734
New Listing

$7,500/month

Sarasota, FL

734 Birdsong Lane

  • 3 Beds
  • 2 Baths
  • 1,890 SqFt
  • 12 Days on Market
MLS#: A4696907
New Listing

$10,000/month

Sarasota, FL

5159 Oakmont Place

  • 3 Beds
  • 2 Baths
  • 1,953 SqFt
  • 12 Days on Market
MLS#: A4698222
New Listing

$2,950/month

Sarasota, FL

1700 Cove II Place, Unit 310

  • 2 Beds
  • 2 Baths
  • 860 SqFt
  • 16 Days on Market
MLS#: A4697340
New Listing

$4,500/month

Sarasota, FL

5253 Avenida Del Mare

  • 3 Beds
  • 2 Baths
  • 1,438 SqFt
  • 22 Days on Market
MLS#: A4697624
New Listing

$2,995/month

Sarasota, FL

9393 Midnight Pass Road, Unit 806

  • 2 Beds
  • 2 Baths
  • 1,029 SqFt
  • 23 Days on Market
MLS#: A4695138
New Listing

$9,975/month

Sarasota, FL

1232 Northport Drive

  • 3 Beds
  • 2 Baths
  • 1,794 SqFt
  • 25 Days on Market
MLS#: TB8519681

$7,000/month

Sarasota, FL

1308 Old Stickney Point Road, Unit W32

  • 3 Beds
  • 3 Baths
  • 2,467 SqFt
  • 41 Days on Market
MLS#: A4695458

Listings courtesy of StellarMLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of July 10, 2026 11:33 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.