Osprey Rentals

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799 Houses

Dunmore

Osprey house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Children under 5

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Price per night from

$218

LUX VILLAs close to sparkling Siesta Key Beach.

Osprey villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Children under 5

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Price per night from

$161

CKBH (Casey Key Beach House)

Osprey house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$654

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

Osprey condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$161

Great rentals within 20 miles that match your search

Beautiful Crescent Beach on Siesta Key One of the

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$300

10- minute walk to downtown Sarasota

Sarasota house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$98

A Comfortable getaway!

Sarasota house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$115

Just a mile to downtown Sarasota!

Sarasota house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Children under 5

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Price per night from

$98

Stay near the beach and downtown

Sarasota house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$69

Walk to the beach and downtown

Sarasota house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Match: Children under 5

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Price per night from

$69

Come join us for your Winter Migration!!!!!!!!!!

Bradenton Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Children under 5

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Price per night from

$103

Park Model with lanai, large deck, block from pool

Venice house

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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Price per night from

$121

Lovely Brandnew Pool Villa w/ Private Beach, WiFi

Venice house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Children under 5

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Price per night from

$212

Venice Florida Condo

Venice condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Children under 5

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Price per night from

$126

Amazing Beachfront Condo, Siesta Key,

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Children under 5

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Price per night from

$344

Stay near the heart of Sarasota

Sarasota house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Children under 5

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Price per night from

$115

FANTASTIC VACATION! STEPS FROM THE POOL AND BEACH, VERY CLEAN CONDO!

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$271

New 6 Bedroom, Luxury Home in Gated Community

Siesta Key house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14

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Price per night from

$999

Monthly Rental, 2 bed, 2 bath, Ocean view.

Sarasota condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$115

Vacation Home on Coral Sands Ct. Spring Special !

Venice house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

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Price per night from

$155

Shorewalk Condo ED near the Beaches Anna Maria Island, Longboat Key, IMG, Shops

Bradenton apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$401

3BR/4BA TOWNHOUSE - POOL VIEW PARADISE - PRIVATE BEACH ACCESS

Siesta Key townhouse

  • 2 bedrooms
  • 4 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 38 minutes

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Price per night from

$430

Cumberland Road Paradise

Venice apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 1

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Price per night from

$103

Little Palms Villa. A lakeside home with style.

Bradenton villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Excellent” Our stay at 4638 Runabout way was amazing. We loved that the house was very nice, spacious, and clean for my family and I. We loved swimming in the pool everyday. The service was excellent all around. We would definitely stay there again.

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Price per night from

$195

Reserve now! Beautiful Siesta key Beach

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$344

Beachfront Condo Siesta Key

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Great place” We couldn't have a better time. The condo had everything you could possibly need for cooking, or going to the pool and beach. The condo is a 3 minute walk to the beach, and the weather was perfect. Village is a 5 minute drive and the restaurants were perfect for a family. Definitely coming back!

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Price per night from

$453

Excellent Location - Gulf/Beach View - Siesta Key

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 1 hour 38 minutes

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Price per night from

$344

Super clean vacation Villa with Pool

North Port house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 1 minutes

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Price per night from

$138

2 MINUTE WALK TO SIESTA BEACH!! (really) 1 MINUTE TO POOL. GREAT VALUE!!!

Siesta Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

“Happy Customer” We had an amazing time. The owners were so nice & made us feel so welcomed. I couldnt have been happier with our stay & we look forward to staying there again soon when life slows back down. Highly recommend this home♡

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Price per night from

$310

Siesta Key 2 Bedroom 1 Bath Modern/Contemporary Decor Apartment

Siesta Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

“Amazing!” I stayed here with my husband and we had a great time! We were in Orlando visiting family and we decided to arrange some us time. The condo was excellent and very clean! Kathy and her husband were very informative, respond quickly,and available when we needed them. What was great was that we had all beach items available to us and were very useful. We were in close proximity to everything and the beach and restaurants were great! Everyone in the area was very friendly and my husband and I want to definitely come back!

Responds fast! avg. 1 hour 14 minutes

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Price per night from

$224

Siesta Key- Beach Chic Retreat, Siesta Key 3 Bedroom 2 Bath Apartment

Siesta Key apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

“This was the definition of home away from home” great value for your money...very cozy, with lots of new upgrades. Easy access to the beach and restaurants.

Responds fast! avg. 1 hour 14 minutes

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Price per night from

$315

Sunset Point Siesta Key FL AWESOME RENTAL !!

Siesta Key villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Beautiful inside and out. Perfect location” My family and I stayed in this beautiful rental during February 2015. We could not have asked for a more perfect spot. The rental is just steps away from the beach and has a wonderful view of the beautiful sunsets. Siesta Key Village is an easy walk away and has great restaurants and shops. We are hoping to go back as soon as we can!

Responds fast! avg. 3 hours 50 minutes

Match: Children under 5

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Price per night from

$802

Luxury Venice, Florida Gulf Coast Condo

Venice apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$138

Venice Island on BEACH 8th flr near Siesta Key

Venice apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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Price per night from

$241

Luxurious 2 BR Condo-Short Walk to Siesta Beach/1 Small Dog (25 lbs Max) Allowed

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“a fine 2 weeks in Siesta” charming property, that was comfortable for four. The unit was very clean and fresh upon arrival. The neighbours were friendly and the overall property well kept. Siesta Key is a quiet community with usual shopping amenities over the causeway. This property was a brief 10 minute walk to the beach. Would we stay again, yes.

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Price per night from

$165

Vacation Home on Alligator Drive . Winter 2025 Special !

Venice house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

Match: Children under 5

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Price per night from

$149

“Charming studio in lovely quiet neighborhood with fenced in private outside area.” This studio has everything you'll need. It's located in a beautiful neighborhood, great for walking. There's a small park just down the road a couple of blocks where you can sit and watch the amazing sun sets or just enjoy watching the boats ride by. The owners are very nice and have a few fur babies of their own, so they may allow you to bring your doggie,too! Sue/Dawn......thank you!!!! I hope to return & stay again.

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Price per night from

$229

Sandy Toes Town Home

Siesta Key townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

“Time in Paradise” We recently had the luck to spend two months in paradise. This condo was comfortably appointed, well stock to meet all our needs, and most importantly in the perfect location. The beach was a short walk to the left and stores and restaurants were just a short walk to the right. We had a great time and enjoyed everything Sarasota, Siesta Key, and this Sandy Toes Condo had to offer. Thanks Mark!

Match: Children under 5

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Price per night from

$272

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