Longboat Key Vacation Rentals

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Poolside paradise
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Poolside paradise Your family oasis

5 Bedrooms
4 Bathrooms
4 Guides
4.81IconIconIconIconIcon
21 reviews
$599 / night (excl. fees & taxes)
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Anna Maria Island - Azure Bliss Vacation Home
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Anna Maria Island - 3Bed 2Bath Home - Private Heated Pool - Walk to Beach

3 Bedrooms
2 Bathrooms
4 Guides
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49 reviews
$450 / night (excl. fees & taxes)
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Coconuts included!+Family Friendly!+Close to Beach
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Coconuts included!+Family Friendly!+Close to Beach

2 Bedrooms
2 Bathrooms
4 Guides
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1 review
$190 - $450 / night (excl. fees & taxes)
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Loggerhead - AMI Oasis w/ Private Pool
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Loggerhead - AMI Oasis w/ Private Pool

2 Bedrooms
2 Bathrooms
4 Guides
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13 reviews
$199 - $550 / night (excl. fees & taxes)
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Craig House with Heated Pool
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Craig House with Heated Pool

2 Bedrooms
2 Bathrooms
4 Guides
4.8IconIconIconIconIcon
107 reviews
$148 - $190 / night (excl. fees & taxes)
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Gorgeous Beach Home with heated pool
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Gorgeous Beach Home with heated pool

3 Bedrooms
3 Bathrooms
4 Guides
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2 reviews
$300 - $450 / night (excl. fees & taxes)
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Art Deco Masterpiece High Season Multi-Month
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Art Deco/Mid-Century Modern Masterpiece in the Heart of Downtown--Across from the Marina! Multi-Month High Season Only

2 Bedrooms
2 Bathrooms
4 Guides
$259 / night (excl. fees & taxes)
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Gulf Coast Paradise Hideaway
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Gulf Coast Paradise Hideaway

1 Bedroom
1 Bathroom
4 Guides
$95 / night (excl. fees & taxes)
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Sarasota Downtown Pet-Friendly 1BD/1BA-Lido Beach | Opera | The Arts
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Beach Downtown Pet-friendly 1 Bedroom Apartment at 10 acre Gillespie Park with tennis, pickle ball & basketball courts, playground, and two dog parks.

1 Bedroom
1 Bathroom
4 Guides
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20 reviews
$128 - $378 / night (excl. fees & taxes)
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Spacious Downtown |Pet Friendly | 2-Car Garage| Lido Beach | St. Armands Circle | Opera House
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Beach-town Pet-Friendly Downtown Sarasota Home @ 10 acre Gillespie Park with tennis, pickle ball & basketball courts, playground & two dog parks.

3 Bedrooms
3 Bathrooms
4 Guides
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43 reviews
$198 - $545 / night (excl. fees & taxes)
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Sarasota Pet Friendly Vaca Home | Balcony + Garage | The Arts & Opera |Beach | St. Armands Circle
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Beach Downtown Sarasota Pet-friendly Home @ 10 acre Gillespie Park with tennis, pickle ball & basketball courts, playground & two dog parks.

3 Bedrooms
3 Bathrooms
4 Guides
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28 reviews
$198 - $524 / night (excl. fees & taxes)
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Downtown Sarasota | 1 Bd 1 Ba | Beach | + Pets | Symphony |Opera | The Arts
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Beach Downtown Pet-friendly 1 Bedroom Apartment at 10 acre Gillespie Park with tennis, pickle ball & basketball courts, playground, and two dog parks.

1 Bedroom
1 Bathroom
4 Guides
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7 reviews
$128 - $378 / night (excl. fees & taxes)
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Downtown Compound |Pet Friendly | Families |Groups
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Downtown Compound |Pet Friendly | Families |Groups

8 Bedrooms
9 Bathrooms
4 Guides
$941 - $2970 / night (excl. fees & taxes)
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Golf Course Condo
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Breath taking view of the Golf Course and water with nature sounds...

2 Bedrooms
2 Bathrooms
4 Guides
$116 / night (excl. fees & taxes)
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The River House
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Relaxing Riverhouse - free parking pass in Pass A Grille beach- 30 min. drive

4 Bedrooms
3 Bathrooms
4 Guides
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3 reviews
$500 / night (excl. fees & taxes)
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Palm Paradise
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Palm Paradise

3 Bedrooms
2 Bathrooms
4 Guides
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3 reviews
$220 / night (excl. fees & taxes)
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#1 Siesta Key Beach, Pool GlassHouse
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(3) E-Z Payments, beach supply & more

2 Bedrooms
2 Bathrooms
4 Guides
4.57IconIconIconIconIcon
49 reviews
$225 / night (excl. fees & taxes)
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The Funky Fish House
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Tropical Oasis Heated Pool Hot Tub Near Siesta Key

2 Bedrooms
2 Bathrooms
4 Guides
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90 reviews
$200 - $580 / night (excl. fees & taxes)
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2 Bedroom/2 Bath, One Floor condominium
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Come enjoy all of Sarasota and Siesta Key amenities without the congestion and just minutes to Siesta Key Beach.

2 Bedrooms
2 Bathrooms
4 Guides
$100 / night (excl. fees & taxes)
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Golf Course and Private Pool Views
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For the Ultimate Vacation Come Stay at Rosedale Golf & Country Club!!

2 Bedrooms
2 Bathrooms
4 Guides
$225 / night (excl. fees & taxes)
    21 – 40 Rentals