Homes for Sale - Whitney Boland

716 BAYPORT WAY #716, Longboat Key, FL 34228

$13,500

Active

Condo

3 Beds 2 Baths 2,134 SqFt

716 BAYPORT WAY #716, Longboat Key, FL 34228

GORGEOUS INSIDE! This beautifully remodeled ground floor, corner unit, features 3 bedrooms, 2 bathrooms with an open ...

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522 BAYPORT WAY #522, Longboat Key, FL 34228

56

$10,000

Active

Condo

2 Beds 2 Baths 1,260 SqFt

522 BAYPORT WAY #522, Longboat Key, FL 34228

GORGEOUS LONG TERM RENTAL!! Bayport Beach & Tennis CLub is an amenity-rich community at sea's edge and is situated in th...

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519 BAYPORT WAY #519, Longboat Key, FL 34228

57

$9,500

Active

Condo

2 Beds 2 Baths 1,456 SqFt

519 BAYPORT WAY #519, Longboat Key, FL 34228

Seasonal rental in Bayport Beach and Tennis Club which is a beautiful, established, award-winning, amenity-rich communit...

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706 BAYPORT WAY #706, Longboat Key, FL 34228

56

$6,000

Active

Condo

2 Beds 2 Baths 1,601 SqFt

706 BAYPORT WAY #706, Longboat Key, FL 34228

This beautiful 2 bedroom/2 bath split and open floor plan condo is spacious and bright. The kitchen featuring a built-in...

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2109 GULF OF MEXICO DR #1203, Longboat Key, FL 34228

63

$10,000

Active

Condo

2 Beds 2 Baths 1,463 SqFt

2109 GULF OF MEXICO DR #1203, Longboat Key, FL 34228

***NEW VACATION RENTAL LISTING** * Booked Dec1st-March 31st 2026. Welcome to your amazing beachfront Longboat Key at Su...

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6680 GULF OF MEXICO DR, Longboat Key, FL 34228

77

$14,750,000

Active

Single Family Home

6 Beds 7 Baths 6,408 SqFt

6680 GULF OF MEXICO DR, Longboat Key, FL 34228

Expansive, gated, waterfront family estate featuring custom designed main home along with a separate three bedroom guest...

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4325 GULF OF MEXICO DR #208, Longboat Key, FL 34228

40

$5,500

Active

Condo

3 Beds 2 Baths 1,411 SqFt

4325 GULF OF MEXICO DR #208, Longboat Key, FL 34228

Longboat Key vacation rental, rarely available Tiffany Plaza direct Gulf Front condo with amazing views! As you enter yo...

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720 BAYPORT WAY #720, Longboat Key, FL 34228

68

$10,000

Active

Condo

2 Beds 2 Baths 1,260 SqFt

720 BAYPORT WAY #720, Longboat Key, FL 34228

Bright and Spacious! This lovely 2 bedroom, 2 bathroom furnished condominium is nestled comfortably in a lush tropical s...

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3240 GULF OF MEXICO DR #603, Longboat Key, FL 34228

47

$4,800

Active

Condo

2 Beds 2 Baths 1,260 SqFt

3240 GULF OF MEXICO DR #603, Longboat Key, FL 34228

VACATION RENTAL!!! AVAILABLE JAN - MARCH 2026! Spacious 6th floor condo awaits your arrival! This lovely 2 Bedroom, 2 Ba...

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2369 HARBOUR OAKS DR, Longboat Key, FL 34228

100

$8,000

Active

Single Family Home

3 Beds 3 Baths 2,424 SqFt

2369 HARBOUR OAKS DR, Longboat Key, FL 34228

LIVE THE LIFE ON LONGBOAT KEY...in this three bedroom, two-and-a-half bathroom villa in the BAY ISLES gated community. O...

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1050 LONGBOAT CLUB RD #804, Longboat Key, FL 34228

31

$5,000

Active

Condo

2 Beds 2 Baths 1,409 SqFt

1050 LONGBOAT CLUB RD #804, Longboat Key, FL 34228

AVAILABLE OFF SEASON RENTAL JULY 1, 2025 THROUGH NOVEMBER 30, 2025 AT $5000 A MONTH AND SEASONAL JANUARY 2026 THROUGH AP...

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1050 LONGBOAT CLUB RD #502, Longboat Key, FL 34228

24

$5,000

Active

Condo

2 Beds 2 Baths 1,290 SqFt

1050 LONGBOAT CLUB RD #502, Longboat Key, FL 34228

Available 07/15/2025 through 12/30/2025. LEASED SEASON JAN, 2026 THROUGH MARCH, 2026. This residence is gulf and bay vie...

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1925 GULF OF MEXICO DR #309, Longboat Key, FL 34228

42

$12,000

Active

Condo

3 Beds 3 Baths 2,698 SqFt

1925 GULF OF MEXICO DR #309, Longboat Key, FL 34228

LONGBOAT KEY'S SEAPLACE Enjoy the tropical sea breezes and the magical Water Views from this custom designed THREE BEDRO...

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75

$11,550

Active

Single Family Home

2 Beds 2 Baths 1,657 SqFt

500 SCHOONER LN, Longboat Key, FL 34228

Booked May 1st- June 16th, July13th-July 27th, Nov 14th-rest of 2025. Booked January, May, October, and Dec 2026 through...

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2425 GULF OF MEXICO DR #14B, Longboat Key, FL 34228

55

$11,900

Active

Condo

2 Beds 2 Baths 1,470 SqFt

2425 GULF OF MEXICO DR #14B, Longboat Key, FL 34228

Escape to the beauty of Southern Longboat Key with this stunning direct Gulf front vacation rental. From the moment you ...

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3804 GULF OF MEXICO DR #B307, Longboat Key, FL 34228

55

$7,000

Active

Condo

2 Beds 2 Baths 1,133 SqFt

3804 GULF OF MEXICO DR #B307, Longboat Key, FL 34228

Welcome to Sunset On The Gulf! This gorgeous 2-bedroom, 2-bathroom, third-floor, corner condo offers the perfect locatio...

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6925 LONGBOAT DR S, Longboat Key, FL 34228

39

$30,000

Active

Single Family Home

3 Beds 4 Baths 2,230 SqFt

6925 LONGBOAT DR S, Longboat Key, FL 34228

Available May-December with a 90 Day minimum at $15,550 per month plus taxes and fees booked for 2024 season. <br> <br>...

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744 BAYPORT WAY #744, Longboat Key, FL 34228

60

$9,500

Active

Condo

2 Beds 2 Baths 1,456 SqFt

744 BAYPORT WAY #744, Longboat Key, FL 34228

Delightfully appealing seasonal/short term rental at Bayport Beach and Tennis Club on Longboat Key. This spacious 2/2 re...

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1050 LONGBOAT CLUB RD #1006, Longboat Key, FL 34228

41

$6,000

Active

Condo

2 Beds 2 Baths 1,409 SqFt

1050 LONGBOAT CLUB RD #1006, Longboat Key, FL 34228

Available 07/01/2025 THROUGH 12/30/2025 RENTED SEASON JAN, 2026 THROUGH APRIL, 2026(POSSIBLE ANNUAL)Privateer North PH ...

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1485 GULF OF MEXICO DR #109, Longboat Key, FL 34228

72

$10,000

Active

Condo

2 Beds 2 Baths 1,839 SqFt

1485 GULF OF MEXICO DR #109, Longboat Key, FL 34228

LOCATION, LOCATION, LOCATION!!!!! Gorgeous beach front condo in the sought after Longboat Key community of the Players C...

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2425 GULF OF MEXICO DRIVE #7B, Longboat Key, FL 34228

30

$12,000

Active

Condo

2 Beds 2 Baths 1,470 SqFt

2425 GULF OF MEXICO DRIVE #7B, Longboat Key, FL 34228

..."' short stories. ....on the island of longboat key You are on the beach included is swimming pool...and a world ...

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4325 GULF OF MEXICO DR #102, Longboat Key, FL 34228

37

$5,500

Active

Condo

2 Beds 2 Baths 1,336 SqFt

4325 GULF OF MEXICO DR #102, Longboat Key, FL 34228

Gorgeous Gulf front, turnkey furnished rental in Tiffany Plaza. Walk out to the beach from this lovely updated and exqui...

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750 BAYPORT WAY #750, Longboat Key, FL 34228

45

$5,000

Active

Condo

2 Beds 2 Baths 1,370 SqFt

750 BAYPORT WAY #750, Longboat Key, FL 34228

Seasonal Turnkey Furnished Rental at Bayport Beach and Tennis Club. You will fall in love with this wonderful Longboat ...

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4325 GULF OF MEXICO DR #507, Longboat Key, FL 34228

23

$9,587

Active

Condo

3 Beds 3 Baths 1,336 SqFt

4325 GULF OF MEXICO DR #507, Longboat Key, FL 34228

THIS WONDERFUL PROPERTY IS FOR RENT...NOT FOR SALE...short stories inc...be careful of 3rd party web sites. Stunning di...

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407 Properties Available In Longboat Key

716 BAYPORT WAY #716, Longboat Key, FL 34228

522 BAYPORT WAY #522, Longboat Key, FL 34228

519 BAYPORT WAY #519, Longboat Key, FL 34228

706 BAYPORT WAY #706, Longboat Key, FL 34228

2109 GULF OF MEXICO DR #1203, Longboat Key, FL 34228

6680 GULF OF MEXICO DR, Longboat Key, FL 34228

4325 GULF OF MEXICO DR #208, Longboat Key, FL 34228

720 BAYPORT WAY #720, Longboat Key, FL 34228

3240 GULF OF MEXICO DR #603, Longboat Key, FL 34228

2369 HARBOUR OAKS DR, Longboat Key, FL 34228

1050 LONGBOAT CLUB RD #804, Longboat Key, FL 34228

1050 LONGBOAT CLUB RD #502, Longboat Key, FL 34228

1925 GULF OF MEXICO DR #309, Longboat Key, FL 34228

500 SCHOONER LN, Longboat Key, FL 34228

2425 GULF OF MEXICO DR #14B, Longboat Key, FL 34228

3804 GULF OF MEXICO DR #B307, Longboat Key, FL 34228

6925 LONGBOAT DR S, Longboat Key, FL 34228

744 BAYPORT WAY #744, Longboat Key, FL 34228

1050 LONGBOAT CLUB RD #1006, Longboat Key, FL 34228

1485 GULF OF MEXICO DR #109, Longboat Key, FL 34228

2425 GULF OF MEXICO DRIVE #7B, Longboat Key, FL 34228

4325 GULF OF MEXICO DR #102, Longboat Key, FL 34228

750 BAYPORT WAY #750, Longboat Key, FL 34228

4325 GULF OF MEXICO DR #507, Longboat Key, FL 34228

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