Longboat Key Beaches Vacation Rentals & Ski-in/Ski-out Homes

      Highly Rated

Condo

End-of-summer sale ready for a luxury 5-floor penthouse 60 ft from water,

• Sarasota
• ·
• Longboat Key
• 1.08 mi to center

10.0

Exceptional

(216 Reviews)

1 Bedroom 1 Bath 6 Guests 800 ft²

• 
  Oceanfront
• 
  Hot Tub
• 
  Parking
• 
  Pool

US $605/Night 7 Nights - US $4,237

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Apartment

LaPlaya 202E Catch the gentle Gulf breezes on your private balcony beneath the swaying palms

• Sarasota
• ·
• Longboat Key
• 1.36 mi to center

10.0

Exceptional

(6 Reviews)

2 Bedrooms 1 Bath 4 Guests 1259.38 ft²

• 
  Private Pool
• 
  Private Beach
• 
  Oceanfront
• 
  Parking

US $283/Night 7 Nights - US $1,981

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      Highly Rated

Apartment

Sea Club I Beach Resort

• Sarasota
• ·
• Longboat Key
• 1.01 mi to center

9.2

Exceptional

(351 Reviews)

1 Bedroom 1 Bath 2 Guests

• 
  Parking
• 
  Pool
• 
  Ocean View
• 
  Balcony/Terrace

US $202/Night 7 Nights - US $1,414

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      Price Dropped

Condo

Stunning -late summer sale 50 ft from sand, Private Island 125 +review

• Sarasota
• ·
• Longboat Key
• 1.07 mi to center

10.0

Exceptional

(137 Reviews)

1 Bedroom 1 Bath 6 Guests 800 ft²

• 
  Oceanfront
• 
  Parking
• 
  Pool
• 
  Ocean View

US $581/Night 7 Nights - US $4,065

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Apartment

The Sea Is Calling August Dates Open!

• Sarasota
• ·
• Longboat Key
• 0.05 mi to center

10.0

Exceptional

(3 Reviews)

1 Bedroom 1 Bath 4 Guests 409.03 ft²

• 
  Private Beach
• 
  Oceanfront
• 
  Parking
• 
  Pool

US $343/Night 7 Nights - US $2,403

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      Highly Rated

Resort

Zota Beach Resort

• Sarasota
• ·
• Longboat Key
• 1.77 mi to center

9.2

Exceptional

(1034 Reviews)

1 Bath

• 
  Hot Tub
• 
  Breakfast
• 
  Pool
• 
  Ocean View

US $304/Night 7 Nights - US $2,126

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      Price Dropped

Condo

Island Time: Discounted August & September!

• Sarasota
• ·
• Longboat Key
• 0.05 mi to center

10.0

Exceptional

(132 Reviews)

1 Bedroom 1 Bath 4 Guests 330 ft²

• 
  Parking
• 
  Pool
• 
  Ocean View
• 
  Balcony/Terrace

US $393/Night 7 Nights - US $2,751

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Apartment

Beach Bliss August and September Low Rates!

• Sarasota
• ·
• Longboat Key
• 0.05 mi to center

10.0

Exceptional

(2 Reviews)

1 Bedroom 1 Bath 4 Guests 322.92 ft²

• 
  Private Beach
• 
  Oceanfront
• 
  Parking
• 
  Pool

US $254/Night 7 Nights - US $1,779

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Apartment

Sunset and beach view from your balcony Unit 501

• Sarasota
• ·
• Longboat Key
• 1.08 mi to center

1 Bedroom 1 Bath 4 Guests 700 ft²

• 
  Oceanfront
• 
  Parking
• 
  Pool
• 
  Ocean View

US $426/Night 7 Nights - US $2,980

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      Highly Rated

Apartment

THE BEACH CONDO #107 BEACHFRONT FULL VIEW

• Sarasota
• ·
• Longboat Key
• 0.24 mi to center

10.0

Exceptional

(97 Reviews)

1 Bedroom 1 Bath 4 Guests 330 ft²

• 
  Parking
• 
  Pool
• 
  Ocean View
• 
  Balcony/Terrace

US $425/Night 7 Nights - US $2,972

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Apartment

Island Time Open Sun, July 19th!

• Sarasota
• ·
• Longboat Key
• 0.05 mi to center

10.0

Exceptional

(2 Reviews)

1 Bedroom 1 Bath 4 Guests 333.68 ft²

• 
  Private Beach
• 
  Oceanfront
• 
  Parking
• 
  Pool

US $437/Night 7 Nights - US $3,057

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      Highly Rated

Condo

Beautiful, renovated Gulf Front at Sand Cay with private beach on Longboat

• Sarasota
• ·
• Longboat Key
• 1.84 mi to center

10.0

Exceptional

(96 Reviews)

2 Bedrooms 2 Baths 6 Guests 1100 ft²

• 
  Hot Tub
• 
  Parking
• 
  Pool
• 
  Ocean View

US $527/Night 7 Nights - US $3,688

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Apartment

Top Floor Sunset Paradise Gulf View Unit 501

• Sarasota
• ·
• Longboat Key
• 1.08 mi to center

10.0

Exceptional

(2 Reviews)

1 Bedroom 1 Bath 6 Guests 699.65 ft²

• 
  Private Beach
• 
  Oceanfront
• 
  Parking
• 
  Pool

US $418/Night 7 Nights - US $2,926

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Condo

Upscale Beachplace Condo.availability starting in May 2026.please inquire

• Sarasota
• ·
• Longboat Key
• 2.69 mi to center

10.0

Exceptional

(38 Reviews)

2 Bedrooms 2 Baths 4 Guests 1503 ft²

• 
  Private Pool
• 
  Hot Tub
• 
  Parking
• 
  Pool

US $251/Night 7 Nights - US $1,757

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Condo

Unit #210 Sand Cay Beach Resort Pool View

• Sarasota
• ·
• Longboat Key
• 1.85 mi to center

10.0

Exceptional

(36 Reviews)

2 Bedrooms 2 Baths 6 Guests

• 
  Oceanfront
• 
  Parking
• 
  Pool
• 
  Ocean View

US $459/Night 7 Nights - US $3,210

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      Top 10% in Longboat Key

Condo

Beachcomber unit 204

• Sarasota
• ·
• Longboat Key
• 0.88 mi to center

10.0

Exceptional

(23 Reviews)

2 Bedrooms 2 Baths 4 Guests

• 
  Parking
• 
  Pool
• 
  Ocean View
• 
  Balcony/Terrace

US $493/Night 7 Nights - US $3,450

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      Top 20% in Longboat Key

Condo

LaPlaya 102B-Directly on the beach with the warm Gulf waters waiting!

• Sarasota
• ·
• Longboat Key
• 1.36 mi to center

10.0

Exceptional

(12 Reviews)

2 Bedrooms 2 Baths 4 Guests 1200 ft²

• 
  Parking
• 
  Pool
• 
  Ocean View
• 
  Balcony/Terrace

US $699/Night 7 Nights - US $4,892

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Condo

Sun, Salt, Sand: Open Monday, $225/nt + Fees!

• Sarasota
• ·
• Longboat Key
• 0.05 mi to center

10.0

Exceptional

(12 Reviews)

1 Bedroom 1 Bath 4 Guests

• 
  Parking
• 
  Pool
• 
  Ocean View
• 
  Balcony/Terrace

US $548/Night 7 Nights - US $3,835

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Condo

PENTHOUSE DOUBLE BALCONY FULL GULF & BAY VIEWS FROM EVERY ROOM Beachplace 5-602

• Sarasota
• ·
• Longboat Key
• 2.75 mi to center

10.0

Exceptional

(12 Reviews)

2 Bedrooms 2 Baths 4 Guests 1400 ft²

• 
  Private Pool
• 
  Oceanfront
• 
  Hot Tub
• 
  Parking

US $375/Night 7 Nights - US $2,626

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      Top 10% in Longboat Key

Condo

LaPlaya 108B-Dream views of the Gulf.

• Sarasota
• ·
• Longboat Key
• 1.36 mi to center

10.0

Exceptional

(11 Reviews)

2 Bedrooms 2 Baths 4 Guests 1260 ft²

• 
  Private Pool
• 
  Oceanfront
• 
  Parking
• 
  Pool

US $684/Night 7 Nights - US $4,788

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      Price Dropped

Condo

Perfect FL Longboat Key Getaway, steps from the Gulf! Sleeps 4

• Sarasota
• ·
• Longboat Key
• 0.74 mi to center

10.0

Exceptional

(11 Reviews)

1 Bedroom 1 Bath 4 Guests 657 ft²

• 
  Parking
• 
  Balcony/Terrace
• 
  Kitchen
• 
  Air Conditioner

US $134/Night 7 Nights - US $937

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Condo

Beachcomber unit 305

• Sarasota
• ·
• Longboat Key
• 0.88 mi to center

10.0

Exceptional

(10 Reviews)

1 Bedroom 1 Bath 4 Guests

• 
  Parking
• 
  Pool
• 
  Ocean View
• 
  Balcony/Terrace

US $318/Night 7 Nights - US $2,227

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Condo

Unit #202 Sand Cay Beach Resort Gulf Front

• Sarasota
• ·
• Longboat Key
• 1.85 mi to center

10.0

Exceptional

(8 Reviews)

2 Bedrooms 2 Baths 6 Guests

• 
  Pool
• 
  Ocean View
• 
  Balcony/Terrace
• 
  View

US $577/Night 7 Nights - US $4,039

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Condo

Beachcomber unit 302

• Sarasota
• ·
• Longboat Key
• 0.88 mi to center

10.0

Exceptional

(7 Reviews)

2 Bedrooms 2 Baths 6 Guests

• 
  Pool
• 
  Ocean View
• 
  Balcony/Terrace
• 
  View

US $494/Night 7 Nights - US $3,461

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