Longboat Key, FL rental listings

130 rentals

Sort:

Recommended

ABOUT THIS HOME
Longboat Key, FL Rental Listings
Your Dream Vacation Starts Here! 🏖️✨ 💻 https://www.rvafl.com/vacation-rentals/lyons-lane Welcome to Lyons Lane – a stunning 4 bed, 2 bath canal-front home on the northern end of Longboat Key. Wi

$10,000/mo

4 beds2 baths1,718 sq ft

586 Lyons Ln, Longboat Key, FL 34228

Dogs welcome • Laundry in unit • A/C

ABOUT THIS HOME
Longboat Key, FL Rental Listings
2 Bd/2 Bath on Sarasota Bay Across from Gulf of Mexico Available now - December 13, 2025 and May 1, 2026 - December 12, 2026. Beautiful corner unit condo with an abundance of windows located betwee

$3,000/mo

2 beds2 baths1,330 sq ft

4340 Falmouth Dr, Longboat Key, FL 34228

Laundry in unit • A/C • Dishwasher

NEW 19 HRS AGO

ABOUT THIS HOME
Longboat Key, FL Rental Listings
Completely reimagined 1920s historic bungalow, originally the Longboat Key Post Office, located just two blocks from Whitney Beach and one block from Sarasota Bay and public boat ramp access. This cha

$14,400/mo

3 beds3 baths1,650 sq ft

701 Broadway St, Longboat Key, FL 34228

Parking • A/C • Car-dependent

ABOUT THIS HOME
Longboat Key, FL Rental Listings
Rent is $15,000 per month off season and $25,000 per month for the season ..beginning in December to the end of April. Possibility renting for one year.Best rental in Longboat Key.Lushly landcscaped l

$15,000/mo

3 beds3.5 baths4,322 sq ft

981 Longboat Club Rd, Longboat Key, FL 34228

Pets welcome • Laundry in unit • A/C

ABOUT THIS HOME
Longboat Key, FL Rental Listings
Picturesque Water view of Sarasota Bay . The Harbour Villa Club Complex consists of 38 condos in a 3-story plus pool, spa, community boatramp, kayak launch/storage, 3 tennis courts, covered parking an

$9,000/mo

2 beds2 baths1,514 sq ft

615 Dream Island Rd #201, Longboat Key, FL 34228

Available 01/08 • Laundry in unit • Parking

ABOUT THIS HOME
Longboat Key, FL Rental Listings
Experience the ultimate in coastal luxury with this exceptional residence on Longboat Key. Nestled along a canal with direct access to the Gulf, this expansive home is a dream for boating enthusiasts

$10,000/mo

6 beds5.5 baths4,676 sq ft

614 Norton St, Longboat Key, FL 34228

Pets welcome • Parking • A/C

Property at 690 Old Compass Rd, Longboat Key, FL, 34228, 3 beds, 3 baths, [object Object]

$25,000/mo

3 beds3 baths3,230 sq ft

690 Old Compass Rd, Longboat Key, FL 34228

Property at 537 Halyard Ln, Longboat Key, FL, 34228, 3 beds, 2 baths, [object Object]

$4,900/mo

3 beds2 baths1,600 sq ft

537 Halyard Ln, Longboat Key, FL 34228

Property at 573 Spanish Dr N, Longboat Key, FL, 34228, 2 beds, 2 baths, [object Object]

$3,500/mo

2 beds2 baths1,380 sq ft

573 Spanish Dr N, Longboat Key, FL 34228

Property at 957 Spanish Dr N, Longboat Key, FL, 34228, 2 beds, 2 baths, [object Object]

$5,500/mo

2 beds2 baths1,399 sq ft

957 Spanish Dr N, Longboat Key, FL 34228

Property at 5611 Gulf of Mexico Dr #1, Longboat Key, FL, 34228, 3 beds, 2 baths, [object Object]

$14,000/mo

3 beds2 baths1,675 sq ft

5611 Gulf of Mexico Dr #1, Longboat Key, FL 34228

Property at 1485 Gulf of Mexico Dr #109, Longboat Key, FL, 34228, 2 beds, 2 baths, [object Object]

$10,000/mo

2 beds2 baths1,839 sq ft

1485 Gulf of Mexico Dr #109, Longboat Key, FL 34228

Property at 830 Tarawitt Dr, Longboat Key, FL, 34228, 4 beds, 3 baths, [object Object]

$17,000/mo

4 beds3 baths2,447 sq ft

830 Tarawitt Dr, Longboat Key, FL 34228

Property at 5621 Gulf of Mexico Dr #102, Longboat Key, FL, 34228, 2 beds, 2 baths, [object Object]

$9,500/mo

2 beds2 baths1,346 sq ft

5621 Gulf of Mexico Dr #102, Longboat Key, FL 34228

Property at 5621 Gulf of Mexico Dr #103, Longboat Key, FL, 34228, 3 beds, 2 baths, [object Object]

$9,000/mo

3 beds2 baths1,731 sq ft

5621 Gulf of Mexico Dr #103, Longboat Key, FL 34228

Property at 4401 Gulf of Mexico Dr #703, Longboat Key, FL, 34228, 1 bed, 1.5 baths, [object Object]

$4,500/mo

1 bed1.5 baths725 sq ft

4401 Gulf of Mexico Dr #703, Longboat Key, FL 34228

Property at 825 Tarawitt Dr, Longboat Key, FL, 34228, 3 beds, 2.5 baths, [object Object]

$10,000/mo

3 beds2.5 baths1,882 sq ft

825 Tarawitt Dr, Longboat Key, FL 34228

Property at 5611 Gulf of Mexico Dr #5, Longboat Key, FL, 34228, 3 beds, 3 baths, [object Object]

$7,750/mo

3 beds3 baths1,672 sq ft

5611 Gulf of Mexico Dr #5, Longboat Key, FL 34228

Property at The Shore - 5757 Gulf of Mexico Dr, Longboat Key, FL, 34228, 2 beds, 2 baths, [object Object]

$5,500+/mo

2 beds2 baths1,561 sq ft

The Shore

| 5757 Gulf of Mexico Dr, Longboat Key, FL 34228

Property at 1065 Gulf of Mexico Dr #601, Longboat Key, FL, 34228, 2 beds, 2 baths, [object Object]

$12,000/mo

2 beds2 baths1,172 sq ft

1065 Gulf of Mexico Dr #601, Longboat Key, FL 34228

Property at 535 Forest Way, Longboat Key, FL, 34228, 2 beds, 2.5 baths, [object Object]

$6,900/mo

2 beds2.5 baths1,440 sq ft

535 Forest Way, Longboat Key, FL 34228

Property at 5135 Gulf of Mexico Dr #103, Longboat Key, FL, 34228, 3 beds, 2 baths, [object Object]

$5,950/mo

3 beds2 baths1,586 sq ft

5135 Gulf of Mexico Dr #103, Longboat Key, FL 34228

Property at 1445 Gulf of Mexico Dr #305, Longboat Key, FL, 34228, 2 beds, 2.5 baths, [object Object]

$10,000/mo

2 beds2.5 baths1,957 sq ft

1445 Gulf of Mexico Dr #305, Longboat Key, FL 34228

Property at 5801 Gulf of Mexico Dr, Longboat Key, FL, 34228, 4 beds, 4 baths, [object Object]

$19,975/mo

4 beds4 baths4,236 sq ft

5801 Gulf of Mexico Dr, Longboat Key, FL 34228

Property at 4420 Exeter Dr #208, Longboat Key, FL, 34228, 2 beds, 2 baths, [object Object]

$6,000/mo

2 beds2 baths1,168 sq ft

4420 Exeter Dr #208, Longboat Key, FL 34228

Property at 4540 Gulf of Mexico Dr #2, Longboat Key, FL, 34228, 2 beds, 2 baths, [object Object]

$7,500/mo

2 beds2 baths1,312 sq ft

4540 Gulf of Mexico Dr #2, Longboat Key, FL 34228

Property at 4780 Gulf of Mexico Dr Unit 5, Longboat Key, FL, 34228, 2 beds, 2 baths, [object Object]

$6,500/mo

2 beds2 baths1,256 sq ft

4780 Gulf of Mexico Dr Unit 5, Longboat Key, FL 34228

Property at 4360 Chatham Dr #108, Longboat Key, FL, 34228, 2 beds, 2 baths, [object Object]

$6,000/mo

2 beds2 baths1,316 sq ft

4360 Chatham Dr #108, Longboat Key, FL 34228

Property at 600 Sutton Pl #201, Longboat Key, FL, 34228, 1 bed, 1 bath, [object Object]

$3,200/mo

1 bed1 bath836 sq ft

600 Sutton Pl #201, Longboat Key, FL 34228

Property at 554 Sutton Pl, Longboat Key, FL, 34228, 2 beds, 2 baths, [object Object]

$3,000/mo

2 beds2 baths1,248 sq ft

554 Sutton Pl, Longboat Key, FL 34228

Property at 3440 Gulf of Mexico Dr #9, Longboat Key, FL, 34228, 2 beds, 2 baths, [object Object]

$5,500/mo

2 beds2 baths1,612 sq ft

3440 Gulf of Mexico Dr #9, Longboat Key, FL 34228

Property at 4825 Gulf of Mexico Dr #202, Longboat Key, FL, 34228, 2 beds, 2 baths, [object Object]

$7,000/mo

2 beds2 baths1,393 sq ft

4825 Gulf of Mexico Dr #202, Longboat Key, FL 34228

Property at 4825 Gulf of Mexico Dr #203, Longboat Key, FL, 34228, 2 beds, 2 baths, [object Object]

$6,500/mo

2 beds2 baths1,393 sq ft

4825 Gulf of Mexico Dr #203, Longboat Key, FL 34228

Property at 4825 Gulf of Mexico Dr #201, Longboat Key, FL, 34228, 2 beds, 2 baths, [object Object]

$7,800/mo

2 beds2 baths1,393 sq ft

4825 Gulf of Mexico Dr #201, Longboat Key, FL 34228

Property at 3240 Gulf of Mexico Dr Unit B404, Longboat Key, FL, 34228, 2 beds, 2 baths, [object Object]

$3,900/mo

2 beds2 baths1,260 sq ft

3240 Gulf of Mexico Dr Unit B404, Longboat Key, FL 34228

Property at Tiffany Plaza - 4325 Gulf of Mexico Dr, Longboat Key, FL, 34228, 2-3 beds, 2-2.5 baths, [object Object]

$5,000+/mo

2-3 beds2-2.5 baths1,336-1,411 sq ft

Tiffany Plaza

| 4325 Gulf of Mexico Dr, Longboat Key, FL 34228

Property at 1155 Bogey Ln, Longboat Key, FL, 34228, 3 beds, 3 baths, [object Object]

$16,000/mo

3 beds3 baths2,045 sq ft

1155 Bogey Ln, Longboat Key, FL 34228

Property at 6979 Longboat Dr S, Longboat Key, FL, 34228, 3 beds, 2 baths, [object Object]

$10,000/mo

3 beds2 baths1,454 sq ft

6979 Longboat Dr S, Longboat Key, FL 34228

Property at 640 Broadway St, Longboat Key, FL, 34228, 3 beds, 2 baths, [object Object]

$9,800/mo

3 beds2 baths1,500 sq ft

640 Broadway St, Longboat Key, FL 34228

Property at 534 Sutton Pl, Longboat Key, FL, 34228, 2 beds, 2 baths, [object Object]

$3,000/mo

2 beds2 baths1,278 sq ft

534 Sutton Pl, Longboat Key, FL 34228

Property at 4485 Gulf of Mexico Dr #2, Longboat Key, FL, 34228, 3 beds, 2 baths, [object Object]

$10,500/mo

3 beds2 baths1,576 sq ft

4485 Gulf of Mexico Dr #2, Longboat Key, FL 34228

Viewing page 1 of 4

Based on information submitted to the MLS GRID as of Tue Dec 02 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.

More to explore in Longboat Key, FL

Property Types
Bedrooms
Amenities
Price

Popular rental markets in Florida

Rentals
Apartments

Related searches in Longboat 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

Why Redfin?

Community Impact

Diversity & Inclusion

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.

Longboat Key, FL rental listings

More to explore in Longboat Key, FL

Rentals near Longboat Key, FL

Cities

Apartments for rent near Longboat Key, FL

Cities

Popular rental markets in Florida

Related searches in Longboat Key, FL