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Bicycles available
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202 beach rentals

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A Pearl of a Beach Home - now with luxury Saltwater heated pool and hot tub

Holmes Beach house

3 bedrooms
3 bathrooms

sleeps 6

“Perfect Luxury” Our 5-week stay at this vacation rental was absolutely perfect. The house was everything you could ask for and more. We have stayed in many vacation rentals in the last 20 or so years that we have been coming to anna Maria Island and I have to say this one was right at the top of the list. The kitchen was outfitted with everything you could want. The beds were very comfortable. The neighborhood was nice and quiet. Short walk to the beach. The owners were very nice to deal with and always responded quickly and were very warm and helpful. Definitely can recommend this vacation rental.

Match: Bicycles available Children's pool

All filters match

Price per night from

$474

Venice Immaculate RemodeledHome-2 Bdr/2 Bath-Pool-WIFl&CABLE-2 Miles to Beach

South Venice house

2 bedrooms
2 bathrooms

sleeps 6

Match: Bicycles available Children's pool

All filters match

Price per night from

$172

Townhouse in Resort Community of Gran Paradiso

Venice apartment

3 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Bicycles available, Children's pool

1 of 2 filters match

Price per night from

$237

Anna Maria Islands best location Heated pool Best prices!

Anna Maria Island house

2 bedrooms
2 bathrooms

sleeps 8

1 of 2 match: Bicycles available, Children's pool

1 of 2 filters match

Price per night from

$856

Siesta Key Beach Cottages on Crescent

Siesta Key cottage

2 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Bicycles available, Children's pool

1 of 2 filters match

Price per night from

$223

Newly Remodeled Spacious Loft in Sarasota!

Sarasota apartment

2 bedrooms
2 bathrooms

sleeps 4

1 of 2 match: Children's pool, Bicycles available

1 of 2 filters match

Price per night from

$294

🏝Paradise on the Sarasota Bay, Close to Gulf Beaches🏝 (Sarasota)

Sarasota apartment

1 bedroom
1 bathroom

sleeps 3

1 of 2 match: Children's pool, Bicycles available

1 of 2 filters match

Price per night from

$193

Pineapple at The Wildflower

Siesta Key apartment

1 bedroom
1 bathroom

sleeps 4

1 of 2 match: Children's pool, Bicycles available

1 of 2 filters match

Price per night from

$488

Bromeliad at The Wildflower

Siesta Key apartment

1 bedroom
1 bathroom

sleeps 4

1 of 2 match: Children's pool, Bicycles available

1 of 2 filters match

Price per night from

$488

Hibiscus at The Wildflower

Siesta Key apartment

1 bedroom
1 bathroom

sleeps 4

1 of 2 match: Children's pool, Bicycles available

1 of 2 filters match

Price per night from

$488

NEW LISTING Downtown Beach-town Pet-Friendly 10 Acre Park 1 BD/1BA Apartment-621

Sarasota apartment

1 bedroom
1 bathroom

sleeps 3

1 of 2 match: Children's pool, Bicycles available

1 of 2 filters match

Price per night from

$137

Sarasota Rambler | Downtown MidMod Stay

Sarasota house

3 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Children's pool, Bicycles available

1 of 2 filters match

Price per night from

$314

Downtown Sarasota Historic Burns Court Adorable Bungalow

Sarasota house

2 bedrooms
1 bathroom

sleeps 4

1 of 2 match: Children's pool, Bicycles available

1 of 2 filters match

Price per night from

$294

SAPPHIRE - HARBOR ISLE

Bradenton Beach townhouse

3 bedrooms
3 bathrooms

sleeps 6

1 of 2 match: Children's pool, Bicycles available

1 of 2 filters match

Price per night from

$286

Beach-town Downtown Family and Pet-Friendly Home at 10 Acre Park in Sarasota-629

Sarasota house

3 bedrooms
4 bathrooms

sleeps 9

1 of 2 match: Children's pool, Bicycles available

1 of 2 filters match

Price per night from

$294

Luxury Sunshine Getaway with Pool!

Rotonda West house

3 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Children's pool, Bicycles available

1 of 2 filters match

Price per night from

$206

Orchid at The Wildflower

Siesta Key apartment

1 bedroom
1 bathroom

sleeps 4

1 of 2 match: Children's pool, Bicycles available

1 of 2 filters match

Price per night from

$488

Coconut at The Wildflower

Siesta Key apartment

1 bedroom
1 bathroom

sleeps 4

1 of 2 match: Children's pool, Bicycles available

1 of 2 filters match

Price per night from

$488

Split Leaf at The Wildflower

Siesta Key apartment

1 bedroom
1 bathroom

sleeps 4

1 of 2 match: Children's pool, Bicycles available

1 of 2 filters match

Price per night from

$488

Sunny Haven Retreat

Englewood house

3 bedrooms
2 bathrooms

sleeps 9

1 of 2 match: Children's pool, Bicycles available

1 of 2 filters match

Price per night from

$286

Parrot Paradise Sarasota ~Low cleaning fee~ near Dtwn, beach, airport, pinecraft

Sarasota house

2 bedrooms
2 bathrooms

sleeps 4

1 of 2 match: Children's pool, Bicycles available

1 of 2 filters match

Price per night from

$108

Stay near the beach and downtown

Sarasota house

1 bedroom
1 bathroom

sleeps 2

1 of 2 match: Children's pool, Bicycles available

1 of 2 filters match

Price per night from

$69

Great Location and Best Price in Sarasota

Sarasota apartment

1 bedroom
1 bathroom

sleeps 3

Responds fast! avg. 1 hour 57 minutes

1 of 2 match: Children's pool, Bicycles available

1 of 2 filters match

Price per night from

$92

Sarasota Apartment in Downtown !!!

Lido Key apartment

2 bedrooms
1 bathroom

sleeps 6

Responds fast! avg. 1 hour 57 minutes

1 of 2 match: Children's pool, Bicycles available

1 of 2 filters match

Price per night from

$189

Mid-Century Charm | Walk to Beach | Work Ready

Venice house

2 bedrooms
1 bathroom

sleeps 6

1 of 2 match: Children's pool, Bicycles available

1 of 2 filters match

Price per night from

$305

Heated pool house

Rotonda West house

3 bedrooms
2 bathrooms

sleeps 7

1 of 2 match: Children's pool, Bicycles available

1 of 2 filters match

Price per night from

$229

Beautiful Location On Bay Side, Water View, Pool

Sarasota villa

2 bedrooms
3 bathrooms

sleeps 4

1 of 2 match: Children's pool, Bicycles available

1 of 2 filters match

Price per night from

$229

Costal Surfside 298: By Beachside Management

Siesta Key townhouse

3 bedrooms
3 bathrooms

sleeps 6

1 of 2 match: Children's pool, Bicycles available

1 of 2 filters match

Price per night from

$456

Crescent Arms; by Beachside Management

Siesta Key condo

2 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Children's pool, Bicycles available

1 of 2 filters match

Price per night from

$410

Banana Cabana: By Beachside Management

Siesta Key apartment

2 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Children's pool, Bicycles available

1 of 2 filters match

Price per night from

$239

Direct Beachfront Delight: By Beachside Management

Siesta Key apartment

2 bedrooms
2 bathrooms

sleeps 4

1 of 2 match: Children's pool, Bicycles available

1 of 2 filters match

Price per night from

$239

Casa Mar - Unit 56: By Beachside Management

Siesta Key condo

1 bedroom
1 bathroom

sleeps 4

1 of 2 match: Children's pool, Bicycles available

1 of 2 filters match

Price per night from

$262

Super Cute Cottage--Private--Walk/Bike to Beach

Siesta Key house

2 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Children's pool, Bicycles available

1 of 2 filters match

Price per night from

$257

Longboat Key Cedars Beach House-Pet Friendly-2 Minute To The Beach

Longboat Key condo

2 bedrooms
2 bathrooms

sleeps 6

Responds fast! avg. 3 hours 20 minutes

1 of 2 match: Children's pool, Bicycles available

1 of 2 filters match

Price per night from

$191

Anna Maria Island Sunshine Kiss Villa

Holmes Beach studio

Studio
2 bathrooms

sleeps 6

Responds fast! avg. 3 hours 20 minutes

1 of 2 match: Children's pool, Bicycles available

1 of 2 filters match

Price per night from

$151

Siesta Beach House; by Beachside Management

Siesta Key villa

3 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Children's pool, Bicycles available

1 of 2 filters match

Price per night from

$320

Hidden Paradise - Bungalow 2; by Beachside Management

Siesta Key condo

2 bedrooms
1 bathroom

sleeps 6

1 of 2 match: Children's pool, Bicycles available

1 of 2 filters match

Price per night from

$286

Palm Bay Club - G46: By Beachside Management

Siesta Key condo

1 bedroom
1 bathroom

sleeps 6

1 of 2 match: Children's pool, Bicycles available

1 of 2 filters match

Price per night from

$286

Viewing 38 of 202
rentals in Siesta Key

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Vacation Rentals & Beach Rentals in Siesta Key

Per night

202 beach rentals

Viewing 38 of 202rentals in Siesta Key

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Viewing 38 of 202
rentals in Siesta Key