Osprey Rentals

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653 Houses

Dunmore

Osprey house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$218

LUX VILLAs close to sparkling Siesta Key Beach.

Osprey villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$161

Coral Reef Cutie 2Bedroom Bungalow - 4 Miles to Siesta Key

Osprey cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 2 hours 14 minutes

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$132

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

Osprey condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$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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$302

Park Model with lanai, large deck, block from pool

Venice house

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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$121

Venice Florida Condo

Venice condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$127

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

$1,003

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

Sarasota condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$115

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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$403

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

$432

Manasota Beach Vacation Rental

Englewood house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$271

ZILLI VILLA

Longboat Key villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 10

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$489

Beach front condo in Longboat Key

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$432

Quiet pool home with lake view, close to beaches

Venice house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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$230

Tara Golf & Country Club Condo

Bradenton condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Wonderful, peaceful location and beautiful condo.” This condo is wonderful and has everything anyone would want or need for a wonderful stay. We loved the property and the owners. It is located in a private championship golf course community and is just across the street from all the amenities. The amenities include tennis, pool, workout room, and of course golf at its best. There is a wonderful grill room and beautiful dining room facing the driving range. Very close to a hugh shopping area and enclosed mall. Very convenient to travel anywhere from here. Very nice rental in a wonderful area.

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$144

Brand new villa with heated pool for swimmers

Venice house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$190

“Clean comfortable Siesta Key Condo with all the comforts of home...Perfect!” The condo is walking distance to shops, restaurants and quaint local tiki bar! The beach is a short walk across the street and through the beach-front section of the complex with lounge chairs and umbrellas available, very nice! I didn't mention the 2 pools (one beachside) and nice gym facilities also just downstairs of the unit. The covered parking space was an added plus! The condo was clean and very comfortable with all of the amenities of home which is greatly appreciated! You can even enjoy the view of the bayside inlet and beautiful landscaping from the kitchen through the entire wall of glass doors in the living/dining room! We had a wonderful week! The property owner Vic supplied more than enough information on the condo, local businesses and area maps! He was such a pleasure to work with! Thanks again Vic! We are already planning our next trip to Siesta Key in May!!

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Price per night from

$144

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$144

Serene Sarasota Getaway near shopping and golfing.

Fruitville villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$128

Piece of Paradise

Sarasota condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 3 minutes

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$96

Ideal Retreat next to USA's #1 Beach—Siesta Key

Sarasota condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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$161

Quiet and Comfortable Condo Near Turtle Beach

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

“Siesta sweet spot” Great value for location. Nice pool, visits with the manitees. Close to everything. This time of year ocean water was amazing

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$127

Luxury Sarasota Golf Home

Sarasota house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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$369

Light and Airy and Private, Great Location

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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Price per night from

$230

Siesta Vacation Home - 3 miles to beach

Venice house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$212

Lido Sunshine M

Lido Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$183

Jamaica Royale #104! Completely renovated, Gulf side, beautiful 2b/2b Condo!

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$338

Ground Level 2 Bedroom Beach Themed Condo

Venice condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$230

~ Cozy Apartment Close to Siesta Key with own washer and dryer ~

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 1 hour 56 minutes

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Price per night from

$68

Newly Remodeled Spacious Loft in Sarasota!

Sarasota apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$296

Siesta Key - 2bdrm on the beach - amazing views!!

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

“Escape from reality” We had an amazing vacation. Accommodations were great and very comfortable. Breakfast on the lanai and sunset fishing on the beach were 2 of our families favorite things to do. You also have the bay right behind you where you can kayak or paddle board. The community was quiet which was prefect for our getaway. We will definitely be staying here again.

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$604

Heritage Oaks

Heritage Oaks Golf and Country Club condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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Price per night from

$97

Stunning 2,550 Sq.ft House, FL

Bradenton house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$287

Port Charlotte 3 bedroom, 2 bathroom heated pool villa

Port Charlotte villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$99

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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$196

Luxury Beach Cotttage

Sarasota cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

“Beautiful little cottage” We stayed at this lovely little cottage on Siesta Key mid-April. The cottage is very nice, with all the amenities, even a washer/dryer for extended stays. It's cozy, with high ceilings, a nice bathroom and kitchen/living room. The bed seemed a little small (only a double), but it was very comfortable. The wireless internet was not working when we were there, which was a little frustrating. There is a beautiful pool and nice garden areas. The private beach was also very nice. All of the staff and the owner were extremely pleasant and welcoming. We enjoyed our time there.

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$534

Reserve now! Beautiful Siesta key Beach

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$345

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