Explore Longboat Key Beaches Wedding-Friendly Rentals

     

House

Beach and Boaters Paradise! Heated pool, Fish off the dock, walk to the beach!

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

10.0

Exceptional

(38 Reviews)

4 Bedrooms 3 Baths 8 Guests 2500 ft²

• 
  Private Pool
• 
  Parking
• 
  Pool
• 
  Ocean View

US $474/Night 7 Nights - US $3,318

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Apartment

Seaside Escape!

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

10.0

Exceptional

(4 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

(1006 Reviews)

1 Bath

• 
  Hot Tub
• 
  Breakfast
• 
  Pool
• 
  Balcony/Terrace

US $417/Night 7 Nights - US $2,917

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      Frequently Viewed

Condo

Fall sale ready for a luxury 5-floor penthouse 60 ft from water,

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

10.0

Exceptional

(219 Reviews)

1 Bedroom 1 Bath 6 Guests 800 ft²

• 
  Oceanfront
• 
  Hot Tub
• 
  Parking
• 
  Pool

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

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Apartment

Direct Oceanview Open October 26th - 29th!

• 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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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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Condo

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

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

10.0

Exceptional

(139 Reviews)

1 Bedroom 1 Bath 6 Guests 800 ft²

• 
  Oceanfront
• 
  Parking
• 
  Pool
• 
  Ocean View

US $422/Night 7 Nights - US $2,954

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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

Longboat Key Private Beach Access Condo

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

2 Bedrooms 2 Baths 6 Guests

• 
  Air Conditioner
• 
  Internet
• 
  Laundry
• 
  Bedding/Linens

US $266/Night 7 Nights - US $1,864

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      Highly Rated

Condo

Direct Oceanview: Open October 26th - 29th!

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

10.0

Exceptional

(137 Reviews)

1 Bedroom 1 Bath 4 Guests 330 ft²

• 
  Oceanfront
• 
  Parking
• 
  Pool
• 
  Ocean View

US $422/Night 7 Nights - US $2,951

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Apartment

LaPlaya 206C

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

10.0

Exceptional

(1 Review)

3 Bedrooms 2 Baths 6 Guests

• 
  Pool
• 
  View
• 
  Air Conditioner
• 
  Child Friendly

US $517/Night 7 Nights - US $3,619

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      Price Dropped

Villa

1 of a kind home 13 steps to sand Fall easily best time of year

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

10.0

Exceptional

(122 Reviews)

2 Bedrooms 2 Baths 8 Guests 2000 ft²

• 
  Oceanfront
• 
  Hot Tub
• 
  Parking
• 
  Pool

US $819/Night 7 Nights - US $5,730

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Apartment

LaPlaya 204D

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

10.0

Exceptional

(1 Review)

3 Bedrooms 2 Baths 6 Guests

• 
  Pool
• 
  View
• 
  Air Conditioner
• 
  Child Friendly

US $957/Night 7 Nights - US $6,699

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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

(100 Reviews)

1 Bedroom 1 Bath 4 Guests 330 ft²

• 
  Oceanfront
• 
  Parking
• 
  Pool
• 
  Ocean View

US $451/Night 7 Nights - US $3,158

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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

• 
  Oceanfront
• 
  Hot Tub
• 
  Parking
• 
  Pool

US $606/Night 7 Nights - US $4,239

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Condo

Unit #210 Sand Cay Beach Resort Pool View

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

10.0

Exceptional

(37 Reviews)

2 Bedrooms 2 Baths 6 Guests

• 
  Parking
• 
  Pool
• 
  Ocean View
• 
  Balcony/Terrace

US $490/Night 7 Nights - US $3,430

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Condo

Exquisite Beachfront Condo with both Sunrise & Sunset Views

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

10.0

Exceptional

(26 Reviews)

2 Bedrooms 2 Baths 6 Guests 1400 ft²

• 
  Private Pool
• 
  Oceanfront
• 
  Parking
• 
  Pool

US $301/Night 7 Nights - US $2,108

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Condo

Unit #110 Sand Cay Beach Pool View

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

10.0

Exceptional

(24 Reviews)

2 Bedrooms 2 Baths 6 Guests

• 
  Parking
• 
  Pool
• 
  Balcony/Terrace
• 
  Kitchen

US $428/Night 7 Nights - US $2,997

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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

• 
  Oceanfront
• 
  Parking
• 
  Pool
• 
  Ocean View

US $498/Night 7 Nights - US $3,483

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Condo

Beachcomber unit 205

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

10.0

Exceptional

(16 Reviews)

1 Bedroom 1 Bath 4 Guests

• 
  Oceanfront
• 
  Parking
• 
  Pool
• 
  Ocean View

US $322/Night 7 Nights - US $2,257

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Condo

Seaside Escape!

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

10.0

Exceptional

(14 Reviews)

1 Bedroom 1 Bath 4 Guests

• 
  Parking
• 
  Pool
• 
  Ocean View
• 
  Balcony/Terrace

US $463/Night 7 Nights - US $3,238

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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

• 
  Oceanfront
• 
  Parking
• 
  Pool
• 
  Ocean View

US $705/Night 7 Nights - US $4,936

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Condo

Relaxing Beachside Retreat on Longboat Key

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

10.0

Exceptional

(12 Reviews)

2 Bedrooms 2 Baths 5 Guests

• 
  Oceanfront
• 
  Hot Tub
• 
  Parking
• 
  Pool

US $508/Night 7 Nights - US $3,558

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Condo

Bird's Eye View - Beachfront Penthouse - Gulf + Bay Views - 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 $450/Night 7 Nights - US $3,152

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