Siesta Key, FL rental listings

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ABOUT THIS HOME
Siesta Key, FL Rental Listings
Siesta Key Furnished Annual or Seasonal Rental (4 month minimum). You will love living in this quiet enclave of 6 homes, tucked away from all of the hustle and bustle but walkable to all of the many d

$6,000/mo

3 beds2.5 baths2,012 sq ft

357 Tierra Mar Ln #5, Sarasota, FL 34242

Parking • A/C • Somewhat walkable

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

2 bd: $6,000

3 bd: $3,800

Sea Village

| 4660 Ocean Blvd, Sarasota, FL 34242

2 units available

NEW 1 DAY AGO

ABOUT THIS HOME
Siesta Key, FL Rental Listings
**DON'T MISS THIS OPPORTUNITY TO LIVE ON WORLD-FAMOUS SIESTA KEY!**ALL UTILITIES & WIFI INCLUDED**Welcome to Midnight Cove II--an impeccably maintained community on Siesta Key, just moments from the p

$2,000/mo

2 beds1 bath1,100 sq ft

6327 Midnight Pass Rd Unit 999, Sarasota, FL 34242

Available 01/01 • Dishwasher • Fitness Center

ABOUT THIS HOME
Siesta Key, FL Rental Listings
Immaculate well maintained 2 beds 2 bath condo situated in the desirable Gulf & Bay Club on Siesta Key. This 4th floor unit is meticulously maintained and tastefully decorated. Amenities include three

$4,995/mo

2 beds2 baths1,337 sq ft

5770 Midnight Pass Rd #405, Sarasota, FL 34242

Parking • A/C • Car-dependent

ABOUT THIS HOME
Siesta Key, FL Rental Listings
Experience coastal living at its finest in this 3-bedroom, 2-bathroom second-floor lakefront condo located in the desirable Gulf and Bay Club Bayside community in Siesta Key. With breathtaking views o

$8,900/mo

3 beds2 baths1,495 sq ft

1206 Siesta Bayside Dr Unit 1206B, Sarasota, FL 34242

Parking • A/C • Car-dependent

ABOUT THIS HOME
Siesta Key, FL Rental Listings
Newly remodeled and furnished "Bougie beach bungalow" on Siesta Key Island. This Condo will "wow" you from the first moment you enter. Just say Alexa turn lights on and your command will be answered.

$8,500/mo

2 beds2 baths1,012 sq ft

5623 Midnight Pass Rd #615, Sarasota, FL 34242

Available 01/01 • Pets welcome • Parking

Property at Harbor Towers Yacht & Racquet Club - 5855 Midnight Pass Rd, Sarasota, FL, 34242, 1-2 bed, 1-2 bath, [object Object]

$2,800+/mo

1-2 bed1-2 bath751-1,256 sq ft

Harbor Towers Yacht & Racquet Club

| 5855 Midnight Pass Rd, 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 5830 Midnight Pass Rd #802, Sarasota, FL, 34242, 2 beds, 2 baths, [object Object]

$5,850/mo

2 beds2 baths1,285 sq ft

5830 Midnight Pass Rd #802, Sarasota, FL 34242

Property at 5600 Beach Way Dr #113, Sarasota, FL, 34242, 2 beds, 2 baths, [object Object]

$6,900/mo

2 beds2 baths1,182 sq ft

5600 Beach Way Dr #113, 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 1195 Coquille St #309, Sarasota, FL, 34242, 2 beds, 2 baths, [object Object]

$8,500/mo

2 beds2 baths1,455 sq ft

1195 Coquille St #309, Sarasota, FL 34242

Property at 6157 Midnight Pass Rd Unit D32, Sarasota, FL, 34242, 2 beds, 2.5 baths, [object Object]

$5,000/mo

2 beds2.5 baths1,332 sq ft

6157 Midnight Pass Rd Unit D32, Sarasota, FL 34242

Property at 143 Whispering Sands Dr Unit N/A, Siesta Key, FL, 34242, 2 beds, 2 baths, [object Object]

$6,500/mo

2 beds2 baths1,264 sq ft

143 Whispering Sands Dr Unit N/A, Siesta Key, FL 34242

Property at 1137 N Moonmist Ct Unit L7, Sarasota, FL, 34242, 2 beds, 2 baths, [object Object]

$7,500/mo

2 beds2 baths896 sq ft

1137 N Moonmist Ct Unit L7, Sarasota, FL 34242

Property at 5640 Cape Leyte Dr, Sarasota, FL, 34242, 3 beds, 2 baths, [object Object]

$8,000/mo

3 beds2 baths2,002 sq ft

5640 Cape Leyte Dr, Sarasota, FL 34242

Property at Siesta Harbor - 1250 N Portofino Dr, Sarasota, FL, 34242, 2 beds, 2 baths, [object Object]

$3,150+/mo

2 beds2 baths929 sq ft

Siesta Harbor

| 1250 N Portofino Dr, Sarasota, FL 34242

Property at 4879 Commonwealth Dr, Sarasota, FL, 34242, 4 beds, 3 baths, [object Object]

$12,000/mo

4 beds3 baths2,450 sq ft

4879 Commonwealth Dr, 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 5760 Midnight Pass Rd Unit 208D, Siesta Key, FL, 34242, 2 beds, 2 baths, [object Object]

$5,000/mo

2 beds2 baths1,361 sq ft

5760 Midnight Pass Rd Unit 208D, Siesta Key, 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 1257 S Portofino Dr Unit 36, Sarasota, FL, 34242, 1 bed, 2 baths, [object Object]

$5,000/mo

1 bed2 baths780 sq ft

1257 S Portofino Dr Unit 36, Sarasota, FL 34242

Property at 1257 S Portofino Dr Unit 38ALBA, Sarasota, FL, 34242, 2 beds, 2 baths, [object Object]

$4,500/mo

2 beds2 baths929 sq ft

1257 S Portofino Dr Unit 38ALBA, Sarasota, FL 34242

Property at Siesta Towers - 4822 Ocean Blvd, Sarasota, FL, 34242, 2 beds, 2 baths, [object Object]

$5,950+/mo

2 beds2 baths1,435 sq ft

Siesta Towers

| 4822 Ocean Blvd, Sarasota, FL 34242

Property at 314 Avenida de Paradisio, Sarasota, FL, 34242, 3 beds, 3 baths, [object Object]

$5,850/mo

3 beds3 baths1,590 sq ft

314 Avenida de Paradisio, Sarasota, FL 34242

Property at 1250 N Portofino Dr Unit 102MAR, Siesta Key, FL, 34242, 2 beds, 2 baths, [object Object]

$6,500/mo

2 beds2 baths929 sq ft

1250 N Portofino Dr Unit 102MAR, Siesta Key, FL 34242

Property at 1350 N Portofino Dr Unit 108TAR, Siesta Key, FL, 34242, 2 beds, 2 baths, [object Object]

$6,500/mo

2 beds2 baths929 sq ft

1350 N Portofino Dr Unit 108TAR, Siesta Key, FL 34242

Property at 22 Sandy Cove Rd Apt 10-5, Sarasota, FL, 34242, 3 beds, 3 baths, [object Object]

$15,000/mo

3 beds3 baths1,898 sq ft

22 Sandy Cove Rd Apt 10-5, Sarasota, FL 34242

Property at 1215 S Portofino Dr Unit 1215-308, Siesta Key, FL, 34242, 2 beds, 2 baths, [object Object]

$3,500/mo

2 beds2 baths991 sq ft

1215 S Portofino Dr Unit 1215-308, Siesta Key, FL 34242

Property at 111 Pass Key Rd #111, Sarasota, FL, 34242, 1 bed, 1 bath, [object Object]

$2,500/mo

1 bed1 bath656 sq ft

111 Pass Key Rd #111, Sarasota, FL 34242

Property at 11 Sandy Cove Rd Unit 8F, Sarasota, FL, 34242, 2 beds, 1.5 baths, [object Object]

$3,500/mo

2 beds1.5 baths1,122 sq ft

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

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 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 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 759 Birdsong Ln, Sarasota, FL, 34242, 3 beds, 2 baths, [object Object]

$7,000/mo

3 beds2 baths1,867 sq ft

759 Birdsong Ln, 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 5310 Hidden Harbor Rd, Sarasota, FL, 34242, 4 beds, 2 baths, [object Object]

$6,900/mo

4 beds2 baths2,295 sq ft

5310 Hidden Harbor Rd, 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

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Based on information submitted to the MLS GRID as of Sat Dec 13 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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