Holmes Beach Vacation Rentals

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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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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
4.9IconIconIconIconIcon
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 - $522 / 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 - $502 / 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
$127 - $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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St Pete Beachside Condo
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St Pete Beachside Condo

1 Bedroom
1 Bathroom
4 Guides
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3 reviews
$155 / night (excl. fees & taxes)
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Your favorite beach getaway (4)
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Your favorite beach getaway (4)

1 Bedroom
1 Bathroom
4 Guides
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3 reviews
$155 / night (excl. fees & taxes)
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Private condo steps to beach (3)
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Private condo steps to beach (3)

1 Bedroom
1 Bathroom
4 Guides
$155 / 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)
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St Pete Beach Condo (2)
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St Pete Beach Condo

1 Bedroom
1½ Bathrooms
4 Guides
$150 / night (excl. fees & taxes)
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St Pete Beach Condo (1)
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In the Heart of St Pete Beach!

1 Bedroom
1½ Bathrooms
4 Guides
$150 - $199 / night (excl. fees & taxes)
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The Boca Cabana - w/ private beach & heated pools
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The Boca Cabana - w/ private beach & heated pools

3 Bedrooms
2 Bathrooms
4 Guides
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7 reviews
$165 / night (excl. fees & taxes)
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Bermuda Bay Beach and Racquet Club Condo. 2bdrm/2b
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Jan & April 2025 $4300/mo. May - Oct 2025 $2500/mo Nov - Dec 2025 $3000/mo Jan - April 2026 $4500/mo 1 month minimum applies.

2 Bedrooms
2 Bathrooms
4 Guides
4.67IconIconIconIconIcon
12 reviews
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Condo in Beachfront Resort with Heated Pool
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St. Pete Beach Condo w HEATED POOL in beachfront resort

1 Bedroom
1 Bathroom
4 Guides
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29 reviews
$199 - $445 / 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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Funshine Sunset Beach
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Steps from the beach! Heated Pool

1 Bedroom
1 Bathroom
4 Guides
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115 reviews
$125 - $300 / 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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Palm View at Siesta Dunes
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Updated 2/2 condo Wifi Pool~Private beach access!

2 Bedrooms
2 Bathrooms
4 Guides
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8 reviews
$263 - $500 / night (excl. fees & taxes)
    41 – 60 Rentals