Vacation Rentals & Beach Rentals in Siesta Key

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75 beach rentals

Anna Maria Island/ IMG Academy/ Beach/ HotTub/ Bikes/ Kayaks/ Golf/ Fishing

Bradenton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Trampoline Golf course on site or within 15 min walk

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Price per night from

$287

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Serene Sarasota Getaway near shopping and golfing.

Fruitville villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Trampoline, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$127

3 bedrooms luxurious home,2 full bath, swimming pool, fully remodeled,pool table

Gulf Gate Estates house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Trampoline, Golf course on site or within 15 min walk

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Price per night from

$544

GUEST HOUSE

Fruitville guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 29 minutes

1 of 2 match: Trampoline, Golf course on site or within 15 min walk

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Price per night from

$107

Responds fast! avg. 0 minutes

1 of 2 match: Trampoline, Golf course on site or within 15 min walk

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Price per night from

$229

Venice Island Bellagio Home w/ 3BR & 3BA

Venice house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

“Great Vacation” Thanks for allowing us to stay in your beautiful home in Venice Florida. It was very comfortable and had all the convenience of home. Everything we needed was close by (restaurants and grocery store). We really liked the bike trails along the canal since we brought our bikes. We would rent your house again.

1 of 2 match: Trampoline, Golf course on site or within 15 min walk

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Price per night from

$103

Beautiful Home Near Many Golf Courses in LWR/Sarasota, FL.

Lakewood Ranch apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Trampoline, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$100

Stunning & Bright Sarasota Home

Sarasota house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Trampoline, Golf course on site or within 15 min walk

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Price per night from

$395

Endless Summer

Lakewood Ranch apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 3 hours 36 minutes

1 of 2 match: Trampoline, Golf course on site or within 15 min walk

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Price per night from

$252

Skyline Resort

Lakewood Ranch apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 3 hours 36 minutes

1 of 2 match: Trampoline, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$252

Eagles Nest

Lakewood Ranch apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 3 hours 36 minutes

1 of 2 match: Trampoline, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$252

Sarasota Stoneybrook Golf Condo, overlooking #3 Hole, near Siesta Key

Osprey condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Trampoline, Golf course on site or within 15 min walk

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Price per night from

$161

Mid Century Home With Private Heated Pool

Tallevast house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Trampoline, Golf course on site or within 15 min walk

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Price per night from

$182

1 of 2 match: Trampoline, Golf course on site or within 15 min walk

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Price per night from

$132

AMI Lighthouse Cottage-One Minute Walk To The Beach-Keyless Locks

Cortez cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 3 hours 20 minutes

1 of 2 match: Trampoline, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$157

Anna Maria Island Beach Watch

Bradenton Beach house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 3 hours 20 minutes

1 of 2 match: Trampoline, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$251

Anna Maria Island Beach Happy-Direct Beach Front-1BR-1BR

Bradenton Beach house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 3 hours 20 minutes

1 of 2 match: Trampoline, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$226

#7 Loft Apartment in Historic District Downtown Sarasota

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Trampoline, Golf course on site or within 15 min walk

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Price per night from

$305

Siesta Key Beach : 2 Bedroom, 3 Beds, 3 Bathroom Duplex & Heated Pool

Siesta Key apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Trampoline, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$182

Anna Maria Island Beach Sands 201

Bradenton Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 20 minutes

1 of 2 match: Trampoline, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$282

Anna Maria Island Beach Palms 5B

Bradenton Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 20 minutes

1 of 2 match: Trampoline, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$228

Grand accomdation on USA #1 Beach - Siesta Key Fl

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Trampoline, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$205

Anna Maria Island Beach Palms 6B

Bradenton Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 20 minutes

1 of 2 match: Trampoline, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$184

Anna Maria Island Beach Sands

Bradenton Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

“Paradise” We loved this place, felt right at home the minute we walked in the door. Had a view minor problems and the service to deal with them was awesome. Thanks Terry for a great experience, being our first time here on anna Maria Island. If we didn't need the extra bedroom, we would have booked for next yr. Location~~!! wow, close to great restaurants Love the view...can't say enough of the sunsets and of course the dolphins, got chills every time I seen them, almost daily...first class...thanks...

Responds fast! avg. 3 hours 20 minutes

1 of 2 match: Trampoline, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$313

Anna Maria Island Absolute Anna Maria-Private Beach Access-Heated Pool-Wi-Fi

Anna Maria Island apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

“A little gem” Lovely condo, great views and ideally situated for restaurants and shopping (all within walking distance). Would definitely come back again.

Responds fast! avg. 3 hours 20 minutes

1 of 2 match: Trampoline, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$244

Heritage Oaks

Heritage Oaks Golf and Country Club condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 3 hours 56 minutes

1 of 2 match: Trampoline, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$98

Anna Maria Island Beach Bay Breeze

Bradenton Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 20 minutes

1 of 2 match: Trampoline, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$185

Cozy & Bright+++Minutes to Anna Maria Island, IMG Academy and more

Bradenton apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 9 minutes

1 of 2 match: Trampoline, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$117

Arnold Palmer Design 36 Holes - Lakewood National Resort

Lakewood Ranch villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Trampoline, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$241

Anna Maria Island Beach Palms 2B

Bradenton Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 20 minutes

1 of 2 match: Trampoline, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$247

Anna Maria Island Beach View 207

Bradenton Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 20 minutes

1 of 2 match: Trampoline, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$179

Anna Maria Island Beach Sands 203

Bradenton Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 3 hours 20 minutes

1 of 2 match: Trampoline, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$211

Anna Maria Island Beach Palms 2A

Bradenton Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 20 minutes

1 of 2 match: Trampoline, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$184

Anna Maria Island Beach Palace

Bradenton Beach house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 3 hours 20 minutes

1 of 2 match: Trampoline, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$559

Amazing Gulf Beech Rental with Fantastic FREE Amenities!!!

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Trampoline, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$435

Anna Maria Island Retreat

Bradenton Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 20 minutes

1 of 2 match: Trampoline, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$206

Just Minutes from the White Sandy Siesta Beach

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“It was very cozy and comfortable apartment!” We loved to spend our vacation at this place. Really close to the beach, to different restaurants, and all kind of stores.

1 of 2 match: Trampoline, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$115

LUX VILLAs close to sparkling Siesta Key Beach.

Osprey villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Trampoline, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$161

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