Siesta Key, FL rental listings

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Recommended

$2,250/mo

1 bed1 bath500 sq ft

319 Beach Rd #1, Sarasota, FL 34242

Somewhat walkable

ABOUT THIS HOME
Siesta Key, FL Rental Listings
Step into island living with this updated 2-bedroom, 2-bath condo just steps from Siesta Key Village and the #1 beach in the U.S. This move-in ready second-floor unit features an open, bright layout,

$7,900/mo

2 beds2 baths1,200 sq ft

4660 Ocean Blvd Unit Q2, Sarasota, FL 34242

Available 01/15 • Pets welcome • Parking

ABOUT THIS HOME
Siesta Key, FL Rental Listings
SIESTA KEY WATERFRONT UNIT AVAILABLE now until 12/20/25 and again starting April 1, 2026. Close proximity to beach. Sea Village offers million dollar views and is situated on 5 acres overlooking the G

$3,800/mo

3 beds2 baths1,645 sq ft

4660 Ocean Blvd Unit B2, Sarasota, FL 34242

Dogs welcome • Laundry in unit • Parking

NEW 29 HRS AGO

ABOUT THIS HOME
Siesta Key, FL Rental Listings
The stunning vistas of The Jamaica Royale Penthouse welcome you to your dream condo located on the 8th floor, overlooking the magnificent Siesta Key Beach. This fully remodeled and elegantly furnished

$5,850/mo

2 beds2 baths1,285 sq ft

5830 Midnight Pass Rd #802, Sarasota, FL 34242

Available 11/01 • Pets welcome • Laundry in unit

ABOUT THIS HOME
Siesta Key, FL Rental Listings
Welcome to your perfect beach getaway with this 1 Bedroom 1 Bath Condo in Sandy Cove II, located in beautiful Sarasota, FL. This cozy condo offers a serene escape with a partial ocean view, private be

$2,500/mo

1 bed1 bath656 sq ft

111 Pass Key Rd #111, Sarasota, FL 34242

A/C • Dishwasher • Car-dependent

ABOUT THIS HOME
Siesta Key, FL Rental Listings
Sandy Cove - 2-Bedroom Vacation Rental! Available Nov 1 and beyond! Private Beach!The owner is offering unbelievable seasonal rates!Located in the sought-after Sandy Cove Community, just steps from Si

$3,900/mo

2 beds1.5 baths1,122 sq ft

11 Sandy Cove Rd Unit 8F, Sarasota, FL 34242

Available 11/01 • Parking • A/C

Property at 4900 Ocean Blvd #501, Sarasota, FL, 34242, 3 beds, 3 baths, [object Object]

$4,700/mo

3 beds3 baths1,867 sq ft

4900 Ocean Blvd #501, Sarasota, FL 34242

Property at 5830 Midnight Pass Rd #54, Sarasota, FL, 34242, 1 bed, 1 bath, [object Object]

$7,500/mo

1 bed1 bath728 sq ft

5830 Midnight Pass Rd #54, Sarasota, FL 34242

Property at 4822 Ocean Blvd Unit 3D, Sarasota, FL, 34242, 2 beds, 2 baths, [object Object]

$4,750/mo

2 beds2 baths1,435 sq ft

4822 Ocean Blvd Unit 3D, Sarasota, FL 34242

Property at 4822 Ocean Blvd Unit 2F, Sarasota, FL, 34242, 2 beds, 2 baths, [object Object]

$9,000/mo

2 beds2 baths1,435 sq ft

4822 Ocean Blvd Unit 2F, Sarasota, FL 34242

Property at 20 Whispering Sands Dr #903, Sarasota, FL, 34242, 2 beds, 2 baths, [object Object]

$12,000/mo

2 beds2 baths1,282 sq ft

20 Whispering Sands Dr #903, Sarasota, FL 34242

Property at 460 Beach Rd Unit A1, Sarasota, FL, 34242, 2 beds, 2 baths, [object Object]

$7,500/mo

2 beds2 baths1,363 sq ft

460 Beach Rd Unit A1, Sarasota, FL 34242

Property at 4852 Featherbed Ln, Sarasota, FL, 34242, 4 beds, 3 baths, [object Object]

$7,000/mo

4 beds3 baths2,439 sq ft

4852 Featherbed Ln, Sarasota, FL 34242

Property at 412 Treasure Boat Way, Sarasota, FL, 34242, 4 beds, 3 baths, [object Object]

$14,000/mo

4 beds3 baths2,341 sq ft

412 Treasure Boat Way, Sarasota, FL 34242

Property at 137 Avenida Messina #2, Sarasota, FL, 34242, 2 beds, 2 baths, [object Object]

$4,500/mo

2 beds2 baths900 sq ft

137 Avenida Messina #2, Sarasota, FL 34242

Property at 5400 Ocean Blvd Unit 1-5, Sarasota, FL, 34242, 1 bed, 1 bath, [object Object]

$4,900/mo

1 bed1 bath698 sq ft

5400 Ocean Blvd Unit 1-5, Sarasota, FL 34242

Property at 4946 Commonwealth Dr, Sarasota, FL, 34242, 3 beds, 2.5 baths, [object Object]

$5,000/mo

3 beds2.5 baths2,080 sq ft

4946 Commonwealth Dr, Sarasota, FL 34242

Property at 339 Avenida de Paradisio, Sarasota, FL, 34242, 3 beds, 2 baths, [object Object]

$15,000/mo

3 beds2 baths1,716 sq ft

339 Avenida de Paradisio, Sarasota, FL 34242

Property at 345 Avenida Leona, Sarasota, FL, 34242, 3 beds, 2 baths, [object Object]

$18,000/mo

3 beds2 baths1,617 sq ft

345 Avenida Leona, Sarasota, FL 34242

Property at 1300 N Portofino Dr #205, Sarasota, FL, 34242, 1 bed, 2 baths, [object Object]

$2,000/mo

1 bed2 baths780 sq ft

1300 N Portofino Dr #205, Sarasota, FL 34242

Property at 726 Birdsong Ln, Sarasota, FL, 34242, 3 beds, 2 baths, [object Object]

$5,250/mo

3 beds2 baths1,822 sq ft

726 Birdsong Ln, Sarasota, FL 34242

Property at 735 Birdsong Ln, Sarasota, FL, 34242, 3 beds, 2 baths, [object Object]

$5,000/mo

3 beds2 baths1,840 sq ft

735 Birdsong Ln, Sarasota, FL 34242

Property at 5178 Oakmont Pl, Sarasota, FL, 34242, 3 beds, 3 baths, [object Object]

$15,000/mo

3 beds3 baths2,898 sq ft

5178 Oakmont Pl, Sarasota, FL 34242

Property at 5855 Midnight Pass Rd #404, Sarasota, FL, 34242, 2 beds, 2 baths, [object Object]

$5,000/mo

2 beds2 baths1,152 sq ft

5855 Midnight Pass Rd #404, Sarasota, FL 34242

Property at 5153 Sandy Cove Ave, Sarasota, FL, 34242, 4 beds, 3 baths, [object Object]

$7,400/mo

4 beds3 baths2,248 sq ft

5153 Sandy Cove Ave, Sarasota, FL 34242

Property at 327 Avenida Milano, Sarasota, FL, 34242, 3 beds, 2 baths, [object Object]

$16,000/mo

3 beds2 baths1,704 sq ft

327 Avenida Milano, Sarasota, FL 34242

Property at 5310 Hidden Harbor Rd, Sarasota, FL, 34242, 4 beds, 2 baths, [object Object]

$7,400/mo

4 beds2 baths2,295 sq ft

5310 Hidden Harbor Rd, Sarasota, FL 34242

Property at 5880 Midnight Pass Rd #204, Sarasota, FL, 34242, 2 beds, 2 baths, [object Object]

$11,000/mo

2 beds2 baths1,600 sq ft

5880 Midnight Pass Rd #204, Sarasota, FL 34242

Property at 5518 Shadow Lawn Dr, Sarasota, FL, 34242, 2 beds, 2 baths, [object Object]

$4,500/mo

2 beds2 baths1,790 sq ft

5518 Shadow Lawn Dr, Sarasota, FL 34242

Property at 5334 Calle Florida, Sarasota, FL, 34242, 4 beds, 3 baths, [object Object]

$15,000/mo

4 beds3 baths2,838 sq ft

5334 Calle Florida, Sarasota, FL 34242

Property at 306 Island Cir, Sarasota, FL, 34242, 4 beds, 3 baths, [object Object]

$7,500/mo

4 beds3 baths2,392 sq ft

306 Island Cir, Sarasota, FL 34242

Property at 4439 Ocean Blvd Unit 2A, Siesta Key, FL, 34242, 3 beds, 2 baths, [object Object]

$2,490/mo

3 beds2 baths1,300 sq ft

4439 Ocean Blvd Unit 2A, Siesta Key, FL 34242

Property at 211 Island Cir, Sarasota, FL, 34242, 3 beds, 2 baths, [object Object]

$14,000/mo

3 beds2 baths1,452 sq ft

211 Island Cir, Sarasota, FL 34242

Property at 5216 Calle de Costa Rica, Sarasota, FL, 34242, 3 beds, 2 baths, [object Object]

$8,500/mo

3 beds2 baths1,290 sq ft

5216 Calle de Costa Rica, Sarasota, FL 34242

Property at 5519 Azure Way, Sarasota, FL, 34242, 4 beds, 3 baths, [object Object]

$12,000/mo

4 beds3 baths2,460 sq ft

5519 Azure Way, Sarasota, FL 34242

Property at 6327 Midnight Pass Rd Unit 999, Sarasota, FL, 34242, 2 beds, 1 bath, [object Object]

$2,000/mo

2 beds1 bath900 sq ft

6327 Midnight Pass Rd Unit 999, Sarasota, FL 34242

Property at 446 Canal Rd #5, Sarasota, FL, 34242, 2 beds, 1 bath, [object Object]

$2,450/mo

2 beds1 bath680 sq ft

446 Canal Rd #5, Sarasota, FL 34242

Property at 5516 Avenida del Mare, Sarasota, FL, 34242, 3 beds, 2 baths, [object Object]

$15,000/mo

3 beds2 baths2,259 sq ft

5516 Avenida del Mare, Sarasota, FL 34242

Property at 5577 Contento Dr, Sarasota, FL, 34242, 2 beds, 2 baths, [object Object]

$5,000/mo

2 beds2 baths1,424 sq ft

5577 Contento Dr, Sarasota, FL 34242

Property at 5911 Midnight Pass Rd #601, Sarasota, FL, 34242, 3 beds, 2.5 baths, [object Object]

$6,300/mo

3 beds2.5 baths2,260 sq ft

5911 Midnight Pass Rd #601, Sarasota, FL 34242

Property at 1256 Riegels Landing Dr, Sarasota, FL, 34242, 3 beds, 4 baths, [object Object]

$8,500/mo

3 beds4 baths2,168 sq ft

1256 Riegels Landing Dr, Sarasota, FL 34242

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Based on information submitted to the MLS GRID as of Thu Oct 23 2025. 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.

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