Siesta Key, FL rental listings

48 rentals

Sort:

Recommended

ABOUT THIS HOME
Siesta Key, FL Rental Listings
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
Siesta Key, FL Rental Listings
SCHEDULE A SHOWING ONLINE AT: showmojo.com/lrt/57edb87074 ----

$2,100+/mo

1 bed2 baths780 sq ft

Siesta Harbor

| 1300 N Portofino Dr, Sarasota, FL 34242

2 units available

NEW 17 HRS AGO

ABOUT THIS HOME
Siesta Key, FL Rental Listings
Luxury beachside rental - Seagrove on Siesta - turn key furnished available for annual rental or 3-month minimum seasonal. Seagrove is a gated enclave of 12 private residences on America's number one...

$29,750/mo

4 beds5.5 baths4,610 sq ft

1080 Seagrove Ln Unit CH2, Sarasota, FL 34242

Laundry in unit • Parking • A/C

ABOUT THIS HOME
Siesta Key, FL Rental Listings
Discover your sunlit retreat in the desirable waterfront community of Sea Village on Siesta Key! This ground-floor, 2-bedroom, 2-bathroom condo offers a bright and spacious living environment. The...

$2,800/mo

2 beds2 baths1,200 sq ft

4660 Ocean Blvd Unit G1, Sarasota, FL 34242

Pets welcome • Laundry in unit • Parking

ABOUT THIS HOME
Siesta Key, FL Rental Listings
Embrace the perfect blend of vintage charm and modern luxury at this newly renovated mid-century modern bungalow. Located on a spacious, private lot on Siesta Key, this bright and airy 2-bedroom,...

$5,000/mo

2 beds1 bath959 sq ft

4626 Gleason Ave, Sarasota, FL 34242

Pets welcome • Laundry in unit • A/C

ABOUT THIS HOME
Siesta Key, FL Rental Listings
- UNFURNISHED - ANNUAL RENTAL ~ Rarely available in the exclusive Hamilton Club, this spacious 3-bedroom, 3.5-bath townhome offers over 4,000 square feet of space in one of Siesta Key's most...

$5,500/mo

3 beds3.5 baths2,798 sq ft

3954 Hamilton Club Cir #14, Sarasota, FL 34242

Pets welcome • Laundry in unit • Parking

Property at 216 Pass Key Rd #216, Sarasota, FL, 34242, 2 beds, 2 baths, [object Object]

$3,900/mo

2 beds2 baths998 sq ft

216 Pass Key Rd #216, Sarasota, FL 34242

Property at 19 Whispering Sands Dr #401, Sarasota, FL, 34242, 2 beds, 2 baths, [object Object]

$12,000/mo

2 beds2 baths1,282 sq ft

19 Whispering Sands Dr #401, 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 4830 Higel Ave, Sarasota, FL, 34242, 3 beds, 2 baths, [object Object]

$5,800/mo

3 beds2 baths1,724 sq ft

4830 Higel Ave, 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 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 5157 Sandy Beach Ave, Sarasota, FL, 34242, 4 beds, 2.5 baths, [object Object]

$5,800/mo

4 beds2.5 baths2,288 sq ft

5157 Sandy Beach Ave, 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 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 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 460 Beach Rd Unit A1, Sarasota, FL, 34242, 2 beds, 2 baths, [object Object]

$8,000/mo

2 beds2 baths1,363 sq ft

460 Beach Rd Unit A1, Sarasota, FL 34242

Property at 420 Beach Rd #706, Sarasota, FL, 34242, 3 beds, 2 baths, [object Object]

$6,000/mo

3 beds2 baths2,022 sq ft

420 Beach Rd #706, 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 5770 Midnight Pass Rd #605, Sarasota, FL, 34242, 2 beds, 2 baths, [object Object]

$6,000/mo

2 beds2 baths1,337 sq ft

5770 Midnight Pass Rd #605, Sarasota, FL 34242

Property at 5649 Midnight Pass Rd #803, Sarasota, FL, 34242, 2 beds, 2 baths, [object Object]

$2,395/mo

2 beds2 baths1,012 sq ft

5649 Midnight Pass Rd #803, Sarasota, FL 34242

Property at 1255 Dockside Pl #211, Sarasota, FL, 34242, 3 beds, 2 baths, [object Object]

$3,600/mo

3 beds2 baths1,737 sq ft

1255 Dockside Pl #211, Sarasota, FL 34242

Property at Provincial Gardens - 6005 Midnight Pass Rd, Sarasota, FL, 34242, 1-2 bed, 1-2 bath, [object Object]

$2,800+/mo

1-2 bed1-2 bath748-1,210 sq ft

Provincial Gardens

| 6005 Midnight Pass Rd, Sarasota, FL 34242

Property at 5855 Midnight Pass Rd #524, Sarasota, FL, 34242, 1 bed, 1 bath, [object Object]

$2,100/mo

1 bed1 bath751 sq ft

5855 Midnight Pass Rd #524, 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 6006 Midnight Pass Rd #16, Sarasota, FL, 34242, 1 bed, 1 bath, [object Object]

$5,000/mo

1 bed1 bath600 sq ft

6006 Midnight Pass Rd #16, Sarasota, 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 Dolphin Building - 1215 S Portofino Dr, Sarasota, FL, 34242, 2 beds, 2 baths, [object Object]

$4,000+/mo

2 beds2 baths929-991 sq ft

Dolphin Building

| 1215 S Portofino Dr, Sarasota, FL 34242

Property at 1355 S Portofino Dr #103, Sarasota, FL, 34242, 2 beds, 2 baths, [object Object]

$10,000/mo

2 beds2 baths1,389 sq ft

1355 S Portofino Dr #103, 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 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 Siesta Harbor - 1250 N Portofino Dr, Sarasota, FL, 34242, 2 beds, 2 baths, [object Object]

$3,150+/mo

2 beds2 baths929-991 sq ft

Siesta Harbor

| 1250 N Portofino Dr, Sarasota, FL 34242

Property at 6415 Midnight Pass Rd #602, Sarasota, FL, 34242, 2 beds, 2 baths, [object Object]

$9,500/mo

2 beds2 baths1,489 sq ft

6415 Midnight Pass Rd #602, Sarasota, FL 34242

Property at 1700 Cove II Pl #310, Sarasota, FL, 34242, 2 beds, 1.5 baths, [object Object]

$2,950/mo

2 beds1.5 baths860 sq ft

1700 Cove II Pl #310, Sarasota, FL 34242

Property at 5963 Midnight Pass Rd #332, Sarasota, FL, 34242, 2 beds, 2 baths, [object Object]

$10,500/mo

2 beds2 baths1,270 sq ft

5963 Midnight Pass Rd #332, Sarasota, FL 34242

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

$12,600/mo

2 beds2 baths1,144 sq ft

301 Avenida Madera Unit B, Siesta Key, FL 34242

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

$5,950/mo

2 beds2 baths1,435 sq ft

4822 Ocean Blvd, Siesta Key, 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 1250 N Portofino Dr Unit 102MAR, Siesta Key, FL, 34242, 2 beds, 2 baths, [object Object]

$4,500/mo

2 beds2 baths929 sq ft

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

Viewing page 1 of 2

Based on information submitted to the MLS GRID as of Sat Sep 05 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.

More to explore in Siesta Key, FL

Property Types
Bedrooms
Amenities
Price

Popular rental markets in Florida

Rentals
Apartments

Related searches in Siesta Key, FL

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Find us

Subsidiaries

Affiliated Business

Countries

United States

Canada

Updated September 2025: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.

Siesta Key, FL rental listings

More to explore in Siesta Key, FL

Rentals near Siesta Key, FL

Cities

Apartments for rent near Siesta Key, FL

Cities

Popular rental markets in Florida

Related searches in Siesta Key, FL