Siesta Key Vacation Rentals

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Poolside paradise
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Poolside paradise Your family oasis

5 Bedrooms
4 Bathrooms
4.81IconIconIconIconIcon
21 reviews
$599 / night (excl. fees & taxes)
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Cozy Outdoor Living+Private Yard+AMI in Mins!
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Prime location+Private HTD Saltwater Pool+Spacious Master Suite w/private pool access. New Furniture, Appliances, Quartz Countertops, Travertine Patio

4 Bedrooms
2 Bathrooms
4.98IconIconIconIconIcon
54 reviews
$279 - $844 / 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
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3 reviews
$500 / night (excl. fees & taxes)
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Gulf Coast Paradise Hideaway
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Gulf Coast Paradise Hideaway

1 Bedroom
1 Bathroom
$95 / night (excl. fees & taxes)
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Florida Pool Villa Happy Gator
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10 Minutes to the Beach! Heated Pool with ♥SUNSHELF♥SW exposure♥

3 Bedrooms
2 Bathrooms
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102 reviews
$185 - $270 / night (excl. fees & taxes)
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Coastal Palm Hideaway
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Spring Sale: Hot Tub, Anna Maria, Pool, EV Ready!

4 Bedrooms
2 Bathrooms
4.81IconIconIconIconIcon
16 reviews
$187 - $1246 / night (excl. fees & taxes)
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2 Neighboring Homes with Pools! Close to AMI/IMG!
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Rent 2 homes right next to each other! Perfect for multiple families and friends. Both homes are 3BR/2 bath with pools.

6 Bedrooms
4 Bathrooms
$798 / night (excl. fees & taxes)
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Palma Rosa
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Heated Pool-Game Room-Close to AMI Beaches/IMG!

3 Bedrooms
2 Bathrooms
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41 reviews
$251 - $926 / night (excl. fees & taxes)
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Palma Janoli
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NEW saltwater pool/spa! Amazing outdoor space!

3 Bedrooms
2 Bathrooms
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41 reviews
$262 - $927 / night (excl. fees & taxes)
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Gulf Coast Home w/Private Pool  Near AMI & Beaches
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Updated two stories home with private pool, pool table, ping pong table and games. Only 5 miles to Anna Maria Island and 23 miles to Siesta Key.

4 Bedrooms
3 Bathrooms
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22 reviews
$369 - $619 / night (excl. fees & taxes)
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356 Azure
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Creative Coastal Cottage - 5 min to beach

3 Bedrooms
2 Bathrooms
$70 - $250 / night (excl. fees & taxes)
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Unit 379
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2/2 Ground Unit 10 Min to beach on golf course

2 Bedrooms
2 Bathrooms
4.6IconIconIconIconIcon
30 reviews
$55 - $270 / night (excl. fees & taxes)
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Unit 485
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2/2 Vaulted Ceiling 10 Min to beach on golf course

2 Bedrooms
2 Bathrooms
4.67IconIconIconIconIcon
15 reviews
$65 - $270 / night (excl. fees & taxes)
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Unit 171
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Ground unit Pool 10 Min to beach on golf course

2 Bedrooms
2 Bathrooms
4.67IconIconIconIconIcon
9 reviews
$55 - $270 / night (excl. fees & taxes)
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Unit 270
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2/2 Vaulted Ceiling 10 Min to beach on golf course

2 Bedrooms
2 Bathrooms
$55 - $270 / night (excl. fees & taxes)
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Manasota Beach Vacation Villa
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Perfect for FAMILIES and SNOWBIRDS! PRIVATE and spacious 3 bedroom villa with HEATED POOL & SPA. WALKING distance to the BEACH!

3 Bedrooms
3 Bathrooms
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12 reviews
$207 - $285 / 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
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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
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1 review
$190 - $500 / 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
4.95IconIconIconIconIcon
20 reviews
$321 - $550 / 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
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2 reviews
$300 - $460 / night (excl. fees & taxes)
    41 – 60 Rentals