Anna Maria Island vacation rentals

14Results

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

Newest
New Listing
5400 Gulf Drive Bradenton Beach FL 34217

$3,600/month

Bradenton Beach, FL

5400 Gulf Drive, Unit 32

  • 2 Beds
  • 2 Baths
  • 1,188 SqFt
  • 22 Days on Market
MLS#: A4695275
New Listing

$3,000/month

Bradenton Beach, FL

2100 Avenue A

  • 3 Beds
  • 2 Baths
  • 2,077 SqFt
  • 22 Days on Market
MLS#: A4695264
New Listing

$16,000/month

Holmes Beach, FL

727 Key Royale Drive

  • 5 Beds
  • 6 Baths
  • 3,640 SqFt
  • 26 Days on Market
MLS#: TB8512567

$6,000/month

Anna Maria, FL

101 Palm Avenue, Unit 1

  • 1 Bed
  • 2 Baths
  • 800 SqFt
  • 34 Days on Market
MLS#: A4693385

$2,495/month

Holmes Beach, FL

3607 E Bay Drive, Unit 206

  • 2 Beds
  • 2 Baths
  • 980 SqFt
  • 38 Days on Market
MLS#: A4693831

$500/month

Holmes Beach, FL

8303 Marina Drive, Unit 12

  • 47 Days on Market
MLS#: A4693059

$12,000/month

Holmes Beach, FL

605 Concord Lane

  • 4 Beds
  • 3 Baths
  • 1,625 SqFt
  • 65 Days on Market
MLS#: A4690364

$6,000/month

Bradenton Beach, FL

2319 Avenue C, Unit 200

  • 3 Beds
  • 2 Baths
  • 1,698 SqFt
  • 96 Days on Market
MLS#: A4687025

$4,400/month

Holmes Beach, FL

403 63RD Street

  • 2 Beds
  • 2 Baths
  • 1,150 SqFt
  • 96 Days on Market
MLS#: A4687024

$3,900/month

Holmes Beach, FL

6400 Flotilla Drive, Unit 78

  • 2 Beds
  • 2 Baths
  • 1,377 SqFt
  • 111 Days on Market
MLS#: A4684747

$3,800/month

Holmes Beach, FL

305 57TH Street, Unit B

  • 2 Beds
  • 1 Bath
  • 750 SqFt
  • 131 Days on Market
MLS#: A4682533

$6,500/month

Bradenton Beach, FL

2511 Avenue C, Unit West

  • 2 Beds
  • 2 Baths
  • 1,511 SqFt
  • 134 Days on Market
MLS#: TB8472022

Listings courtesy of StellarMLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of June 24, 2026 7:05 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.