Longboat Key, FL rental listings

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ABOUT THIS HOME
Longboat Key, FL Rental Listings
Welcome to your elevated coastal retreat on Longboat Key, located behind the gate of the prestigious Longboat Key Club. Available annually at $9,000/month or seasonally from November through April at

$11,000/mo

2 beds2 baths1,409 sq ft

1000 Longboat Club Rd, Longboat Key, FL 34228

A/C • Fitness Center

ABOUT THIS HOME
Longboat Key, FL Rental Listings
Seasonal/short term rental on Longboat Key Beautifully renovated 3 bedroom 2 1/2 bathroom villa right on the golf course in prestigious, guard gated, Bay Isles. This spacious light filled delight has

$10,995/mo

3 beds2.5 baths2,396 sq ft

2339 Harbour Oaks Dr, Longboat Key, FL 34228

Parking • A/C • Dishwasher

ABOUT THIS HOME
Longboat Key, FL Rental Listings
LIVE THE LIFE ON LONGBOAT KEY...in this three bedroom, two-and-a-half bathroom villa in the BAY ISLES gated community. Open floor plan, with vaulted ceilings, hardwood floors throughout. Private scree

$8,000/mo

3 beds2.5 baths2,424 sq ft

2369 Harbour Oaks Dr, Longboat Key, FL 34228

Available 02/01 • Parking • A/C

ABOUT THIS HOME
Longboat Key, FL Rental Listings
AVAILABLE - APRIL 2026 - ANNUAL RENTAL - Welcome home! Enjoy the serenity of this 3 bed, 3 bath, 2 car garage residence, located in Harbour Oaks within the gated community of Bay Isles in the heart o

$8,000/mo

3 beds3 baths2,487 sq ft

2377 Harbour Oaks Dr, Longboat Key, FL 34228

Available 04/01 • Parking • A/C

ABOUT THIS HOME
Longboat Key, FL Rental Listings
Available for 2026 and 2027 Season!! Welcome to The Privateer, one of Longboat Key's most coveted beachfront communities. This 10th-floor residence offers a rare opportunity to experience refined coas

$12,000/mo

2 beds2 baths1,409 sq ft

1000 Longboat Club Rd #1001, Longboat Key, FL 34228

Parking • A/C • Dishwasher

ABOUT THIS HOME
Longboat Key, FL Rental Listings
SEASONAL: All three baths have been 100% renovated. Just gorgeous! Photos to come. Harbour Oaks is resort-style living positioned behind the guarded Harbourside gates of Bay Isles. This updated 3 bedr

$12,500/mo

3 beds2.5 baths2,532 sq ft

2319 Harbour Oaks Dr, Longboat Key, FL 34228

Parking • A/C • Car-dependent

Property at 2254 Harbour Court Dr, Longboat Key, FL, 34228, 3 beds, 3.5 baths, [object Object]

$11,500/mo

3 beds3.5 baths3,101 sq ft

2254 Harbour Court Dr, Longboat Key, FL 34228

Property at 1912 Harbourside Dr #603, Longboat Key, FL, 34228, 2 beds, 2.5 baths, [object Object]

$5,000/mo

2 beds2.5 baths1,590 sq ft

1912 Harbourside Dr #603, Longboat Key, FL 34228

Property at 615 Dream Island Rd #201, Longboat Key, FL, 34228, 2 beds, 2 baths, [object Object]

$9,000/mo

2 beds2 baths1,514 sq ft

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

Property at 1922 Harbourside Dr #1102, Longboat Key, FL, 34228, 2 beds, 2.5 baths, [object Object]

$5,000/mo

2 beds2.5 baths1,590 sq ft

1922 Harbourside Dr #1102, Longboat Key, FL 34228

Property at 1930 Harbourside Dr #134, Longboat Key, FL, 34228, 2 beds, 2 baths, [object Object]

$7,000/mo

2 beds2 baths1,192 sq ft

1930 Harbourside Dr #134, Longboat Key, FL 34228

Property at 2105 Gulf of Mexico Dr #3404, Longboat Key, FL, 34228, 2 beds, 2 baths, [object Object]

$8,721/mo

2 beds2 baths1,461 sq ft

2105 Gulf of Mexico Dr #3404, Longboat Key, FL 34228

Property at 744 Bayport Way, Longboat Key, FL, 34228, 2 beds, 2 baths, [object Object]

$6,000/mo

2 beds2 baths1,456 sq ft

744 Bayport Way, Longboat Key, FL 34228

Property at 2109 Gulf of Mexico Dr #1203, Longboat Key, FL, 34228, 2 beds, 2 baths, [object Object]

$10,000/mo

2 beds2 baths1,463 sq ft

2109 Gulf of Mexico Dr #1203, Longboat Key, FL 34228

Property at 1945 Gulf of Mexico Dr Unit M2-402, Longboat Key, FL, 34228, 2 beds, 2 baths, [object Object]

$3,000/mo

2 beds2 baths928 sq ft

1945 Gulf of Mexico Dr Unit M2-402, Longboat Key, FL 34228

Property at 1925 Gulf of Mexico Dr Unit G8-208, Longboat Key, FL, 34228, 3 beds, 2 baths, [object Object]

$8,000/mo

3 beds2 baths1,604 sq ft

1925 Gulf of Mexico Dr Unit G8-208, Longboat Key, FL 34228

Property at 737 Bayport Way Unit D, Longboat Key, FL, 34228, 3 beds, 2 baths, [object Object]

$7,000/mo

3 beds2 baths1,909 sq ft

737 Bayport Way Unit D, Longboat Key, FL 34228

Property at 1945 Gulf of Mexico Dr Unit M2-314, Longboat Key, FL, 34228, 2 beds, 1 bath, [object Object]

$5,000/mo

2 beds1 bath933 sq ft

1945 Gulf of Mexico Dr Unit M2-314, Longboat Key, FL 34228

Property at 1945 Gulf of Mexico Dr Unit M2-107, Longboat Key, FL, 34228, 2 beds, 2 baths, [object Object]

$2,500/mo

2 beds2 baths1,027 sq ft

1945 Gulf of Mexico Dr Unit M2-107, Longboat Key, FL 34228

Property at 1465 Gulf of Mexico Dr #504, Longboat Key, FL, 34228, 3 beds, 3 baths, [object Object]

$15,000/mo

3 beds3 baths1,710 sq ft

1465 Gulf of Mexico Dr #504, Longboat Key, FL 34228

Property at 100 Sands Point Rd #223, Longboat Key, FL, 34228, 2 beds, 2 baths, [object Object]

$9,000/mo

2 beds2 baths1,941 sq ft

100 Sands Point Rd #223, Longboat Key, FL 34228

Property at 531 Birdie Ln, Longboat Key, FL, 34228, 4 beds, 3.5 baths, [object Object]

$14,000/mo

4 beds3.5 baths3,268 sq ft

531 Birdie Ln, Longboat Key, FL 34228

Property at The Promenade - 1211 Gulf of Mexico Dr, Longboat Key, FL, 34228, 2 beds, 2-2.5 baths, [object Object]

$14,000+/mo

2 beds2-2.5 baths1,598-2,135 sq ft

The Promenade

| 1211 Gulf of Mexico Dr, Longboat Key, FL 34228

Property at 724 Bayport Way, Longboat Key, FL, 34228, 2 beds, 2 baths, [object Object]

$10,500/mo

2 beds2 baths1,531 sq ft

724 Bayport Way, Longboat Key, FL 34228

Property at 1045 Gulf of Mexico Dr #402, Longboat Key, FL, 34228, 2 beds, 2 baths, [object Object]

$11,250/mo

2 beds2 baths1,392 sq ft

1045 Gulf of Mexico Dr #402, Longboat Key, FL 34228

Property at 1125 Gulf of Mexico Dr #403, Longboat Key, FL, 34228, 2 beds, 2 baths, [object Object]

$11,000/mo

2 beds2 baths1,642 sq ft

1125 Gulf of Mexico Dr #403, Longboat Key, FL 34228

Property at 1135 Gulf of Mexico Dr #504, Longboat Key, FL, 34228, 2 beds, 2 baths, [object Object]

$11,400/mo

2 beds2 baths1,503 sq ft

1135 Gulf of Mexico Dr #504, Longboat Key, FL 34228

Property at 6701 Gulf of Mexico Dr #326, Longboat Key, FL, 34228, 1 bed, 1 bath, [object Object]

$6,500/mo

1 bed1 bath936 sq ft

6701 Gulf of Mexico Dr #326, Longboat Key, FL 34228

Property at 1050 Longboat Club Rd #702, Longboat Key, FL, 34228, 2 beds, 2 baths, [object Object]

$7,500/mo

2 beds2 baths1,290 sq ft

1050 Longboat Club Rd #702, Longboat Key, FL 34228

Property at 1050 Longboat Club Rd #804, Longboat Key, FL, 34228, 2 beds, 2 baths, [object Object]

$5,000/mo

2 beds2 baths1,409 sq ft

1050 Longboat Club Rd #804, Longboat Key, FL 34228

Property at 500 Schooner Ln, Longboat Key, FL, 34228, 2 beds, 2 baths, [object Object]

$11,550/mo

2 beds2 baths1,657 sq ft

500 Schooner Ln, Longboat Key, FL 34228

Property at 535 Sanctuary Dr Unit A102, Longboat Key, FL, 34228, 3 beds, 2.5 baths, [object Object]

$6,000/mo

3 beds2.5 baths2,580 sq ft

535 Sanctuary Dr Unit A102, Longboat Key, FL 34228

Property at 601 Longboat Club Rd Unit 404S, Longboat Key, FL, 34228, 2 beds, 2 baths, [object Object]

$15,500/mo

2 beds2 baths1,560 sq ft

601 Longboat Club Rd Unit 404S, Longboat Key, FL 34228

Property at 775 Longboat Club Rd #405, Longboat Key, FL, 34228, 2 beds, 2 baths, [object Object]

$9,000/mo

2 beds2 baths1,602 sq ft

775 Longboat Club Rd #405, Longboat Key, FL 34228

Property at 1050 Longboat Club Rd #1006, Longboat Key, FL, 34228, 2 beds, 2 baths, [object Object]

$6,000/mo

2 beds2 baths1,409 sq ft

1050 Longboat Club Rd #1006, Longboat Key, FL 34228

Property at 3040 Grand Bay Blvd, Longboat Key, FL, 34228, 3 beds, 3.5 baths, [object Object]

$8,000/mo

3 beds3.5 baths2,143 sq ft

3040 Grand Bay Blvd, Longboat Key, FL 34228

Property at 501 Channel Ln, Longboat Key, FL, 34228, 4 beds, 3 baths, [object Object]

$13,000/mo

4 beds3 baths2,349 sq ft

501 Channel Ln, Longboat Key, FL 34228

Property at The Pierre - 455 Longboat Club Rd, Longboat Key, FL, 34228, 3 beds, 3.5 baths, [object Object]

$8,000+/mo

3 beds3.5 baths2,780 sq ft

The Pierre

| 455 Longboat Club Rd, 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 380 Gulf of Mexico Dr #513, Longboat Key, FL, 34228, 3 beds, 2.5 baths, [object Object]

$7,500/mo

3 beds2.5 baths2,490 sq ft

380 Gulf of Mexico Dr #513, Longboat Key, FL 34228

Property at 3240 Gulf of Mexico Dr Apt 603, Longboat Key, FL, 34228, 2 beds, 2 baths, [object Object]

$4,800/mo

2 beds2 baths1,260 sq ft

3240 Gulf of Mexico Dr Apt 603, Longboat Key, FL 34228

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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.

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