Houses for Rent in Siesta Key, FL

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ABOUT THIS HOME
House for Rent in Siesta Key:
Only 1 booking allowed in a 30 day period. You will be close to everything when you stay at this centrally-located house. It's a 2 min drive to Siesta Key village restaurants and shops. A 5 min drive...

$7,500/mo

3 beds2 baths1,714 sq ft

4421 Ocean Blvd, Sarasota, FL 34242

Laundry in unit • A/C • Dishwasher

(610) 547-3872

ABOUT THIS HOME
House for Rent in Siesta Key:
Charming 3 bed/2 bath waterfront estate located on the coveted north end of Siesta Key. This parcel is one of the last of its kind, featuring 1.3 acres of prime waterfront property overlooking...

$5,995/mo

3 beds2 baths1,835 sq ft

4237 Higel Ave, Sarasota, FL 34242

Pets welcome • Parking • A/C

ABOUT THIS HOME
House for Rent in Siesta Key:
More pictures to come, waiting for the rest of the furniture to arrive. Florida charm at it's best in this turnkey furnished vacation home on Siesta Key. The home is a mid-century in the style of the...

$6,500/mo

2 beds2 baths1,724 sq ft

4830 Higel Ave, Sarasota, FL 34242

Pets welcome • Laundry in unit • Parking

ABOUT THIS HOME
House for Rent in Siesta Key:
Available as a monthly rental in May, August, September, October, November and December 2026 only!Discover your perfect slice of "Island Time" at Just Breathe, a serene 3 bedroom, 2.5 bathroom home...

$5,000/mo

3 beds2.5 baths2,080 sq ft

4946 Commonwealth Dr, Sarasota, FL 34242

Pets welcome • Laundry in unit • Parking

ABOUT THIS HOME
House for Rent in Siesta Key:
Welcome to your dream escape on Siesta Key--a completely reimagined coastal retreat designed to make every moment unforgettable.Tucked away on a quiet stretch of Avenida de Parasido, this stunning...

$12,000/mo

3 beds2 baths1,511 sq ft

307 Avenida de Paradisio, Sarasota, FL 34242

Laundry in unit • Parking • A/C

ABOUT THIS HOME
House for Rent in Siesta Key:
Listing reflects peak season rate. Welcome to Leona's Retreat, a beautifully renovated, ground-level bungalow perfectly poised on the intercoastal canal waterway. This charming home offers the...

$18,000/mo

3 beds2 baths1,617 sq ft

345 Avenida Leona, Sarasota, FL 34242

Laundry in unit • Parking • A/C

Property at 734 Birdsong Ln, Sarasota, FL, 34242, 3 beds, 2 baths, [object Object]

$7,500/mo

3 beds2 baths1,890 sq ft

734 Birdsong Ln, Sarasota, FL 34242

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

$5,525/mo

3 beds2 baths1,822 sq ft

726 Birdsong Ln, Sarasota, FL 34242

Property at 5157 Sandy Beach Ave, Sarasota, FL, 34242, 4 beds, 2.5 baths, [object Object]

$6,000/mo

4 beds2.5 baths2,288 sq ft

5157 Sandy Beach Ave, Sarasota, FL 34242

Property at 5151 Oakmont Pl, Sarasota, FL, 34242, 3 beds, 2 baths, [object Object]

$2,950/mo

3 beds2 baths1,953 sq ft

5151 Oakmont Pl, Sarasota, FL 34242

Property at 5159 Oakmont Pl, Sarasota, FL, 34242, 3 beds, 2 baths, [object Object]

$10,000/mo

3 beds2 baths1,953 sq ft

5159 Oakmont Pl, Sarasota, FL 34242

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

$9,000/mo

3 beds2 baths1,704 sq ft

327 Avenida Milano, Sarasota, FL 34242

Property at 431 Island Cir, Sarasota, FL, 34242, 4 beds, 2.5 baths, [object Object]

$8,000/mo

4 beds2.5 baths2,346 sq ft

431 Island Cir, Sarasota, FL 34242

Property at 5253 Avenida del Mare, Sarasota, FL, 34242, 3 beds, 2 baths, [object Object]

$4,500/mo

3 beds2 baths1,438 sq ft

5253 Avenida del Mare, Sarasota, 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 681 Avenida de Mayo, Sarasota, FL, 34242, 3 beds, 3 baths, [object Object]

$11,000/mo

3 beds3 baths3,324 sq ft

681 Avenida de Mayo, Sarasota, FL 34242

Property at 5456 Azure Way, Sarasota, FL, 34242, 3 beds, 3 baths, [object Object]

$6,195/mo

3 beds3 baths2,476 sq ft

5456 Azure Way, 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 5585 Contento Dr, Sarasota, FL, 34242, 4 beds, 3 baths, [object Object]

$5,800/mo

4 beds3 baths1,798 sq ft

5585 Contento Dr, 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 1232 Northport Dr, Sarasota, FL, 34242, 3 beds, 2 baths, [object Object]

$9,975/mo

3 beds2 baths1,794 sq ft

1232 Northport Dr, Sarasota, FL 34242

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

$6,500/mo

3 beds4 baths2,168 sq ft

1256 Riegels Landing Dr, Sarasota, FL 34242

Property at 5628 Cape Leyte Dr, Sarasota, FL, 34242, 3 beds, 3 baths, [object Object]

$10,000/mo

3 beds3 baths2,030 sq ft

5628 Cape Leyte Dr, 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 5624 Cape Leyte Dr, Sarasota, FL, 34242, 5 beds, 5 baths, [object Object]

$17,000/mo

5 beds5 baths3,126 sq ft

5624 Cape Leyte Dr, Sarasota, FL 34242

Property at 3919 Roberts Point Rd, Sarasota, FL, 34242, 4 beds, 2.5 baths, [object Object]

$7,995/mo

4 beds2.5 baths2,497 sq ft

3919 Roberts Point Rd, Sarasota, FL 34242

Property at 301 Avenida Madera Unit A, Siesta Key, FL, 34242, 2 beds, 2 baths, [object Object]

$12,600/mo

2 beds2 baths1,144 sq ft

301 Avenida Madera Unit A, Siesta Key, FL 34242

Property at 5740 Midnight Pass Rd Unit 303F, Siesta Key, FL, 34242, 2 beds, 2 baths, [object Object]

$6,500/mo

2 beds2 baths1,337 sq ft

5740 Midnight Pass Rd Unit 303F, Siesta Key, FL 34242

Property at 1250 N Portofino Dr Unit 203MARLIN, Siesta Key, FL, 34242, 2 beds, 2 baths, [object Object]

$3,900/mo

2 beds2 baths929 sq ft

1250 N Portofino Dr Unit 203MARLIN, Siesta Key, 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 111 Pass Key Rd, Siesta Key, FL, 34242, 1 bed, 1 bath, [object Object]

$2,500/mo

1 bed1 bath656 sq ft

111 Pass Key Rd, Siesta Key, FL 34242

Property at 212 Pass Key Rd, Siesta Key, FL, 34242, 1 bed, 1 bath, [object Object]

$2,200/mo

1 bed1 bath800 sq ft

212 Pass Key Rd, Siesta Key, FL 34242

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Based on information submitted to the MLS GRID as of Sun Jul 12 2026. 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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