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Osprey Rentals

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Number of reviews

1,002 Houses

Dunmore

Osprey house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 56 minutes

Price per night from

$234

LUX VILLAs close to sparkling Siesta Key Beach.

Osprey villa

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$276

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

Osprey cottage

2 bedrooms / 1 bathroom / sleeps 2

Price per night from

$132

WATERFRONT SARASOTA COUNTY, CASEY KEY. 5 MILES TO SIESTA KEY BEACH. POOL HOT TUB

Osprey houseboat

3 bedrooms / 1 bathroom / sleeps 11

Price per night from

$435

PIRATE'S TREASURE WATERFRONT HOUSEBOAT/TINY HOUSE/FLOATING HOME

Osprey houseboat

1 bedroom / 1 bathroom / sleeps 7

Price per night from

$274

CKBH (Casey Key Beach House)

Osprey house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$630

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

Osprey condo

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$81

Responds fast! avg. 3 minutes

Price per night from

$261

Great rentals within 20 miles that match your search

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.

Responds fast! avg. 2 hours 16 minutes

Price per night from

$394

Sarasota Villa

Sarasota villa

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$116

The Great (Sunshine and Sea) Escape

Bradenton apartment

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 2 hours 47 minutes

Price per night from

$105

PALM'S HOUSE

Siesta Key house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 14 minutes

Price per night from

$179

Heritage Oaks

Heritage Oaks Golf and Country Club condo

2 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$85

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.

Responds fast! avg. 2 hours 18 minutes

Price per night from

$188

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.

Responds fast! avg. 3 hours 11 minutes

Price per night from

$386

Luxury Condominium at Siesta Dunes Beachside Pool Hot Tub Tennis Sun Deck

Sarasota apartment

2 bedrooms / 2 bathrooms / sleeps 4

“Very comfortable lodgings” Loads of extras in this unit. Well cared for, updated very nicely. Disappointed that the large deck was taken out of service, possibly for a year! It seems to me that usage could have been sustained by posting signs that caution all users to wear appropriate foot-ware on the deck at all times, and to avoid running or playing on the deck. Also the deck restoration could be tackled section by section so as to retain the use by all tenants and owners.

Responds fast! avg. 3 hours 25 minutes

Price per night from

$269

Reserve now! Beautiful Siesta key Beach

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 27 minutes

Price per night from

$342

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!

Responds fast! avg. 1 hour 25 minutes

Price per night from

$220

Luxury Romantic Oceanfront Siesta Beach Condo #304

Siesta Key apartment

1 bedroom / 1 bathroom / sleeps 4

“What a View!” This is a very nicely decorated 1 bedroom and bath on Siesta Key Beach. You have an unobstructed view of the beach the minute you look into the condo. There's a great view from the bedroom as well! Very easy walk fo the beach..chairs and umbrella provided as well as all the amenities of home. We'd stay here again!

Responds fast! avg. 2 hours 9 minutes

Price per night from

$188

Super clean vacation Villa with Pool

North Port house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 13 minutes

Price per night from

$133

Venice Island Bellagio Home w/ 3BR & 3BA

Venice house

3 bedrooms / 3 bathrooms / sleeps 6

“beautiful, relaxing vacation!” Beautiful home with all the amenities a family would need. Enjoyed the open kitchen, dining area. The two bedrooms were very comfortable each with their own baths. So close to the beaches, canal and lovely town of Venice.

Price per night from

$100

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♡

Responds fast! avg. 1 hour 34 minutes

Price per night from

$243

Lovely beachside villa

Sarasota villa

2 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$201

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!

Price per night from

$772

2 bdrm Condo Villa in Birds Bay venice, florida

Venice villa

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$138

Luxury Venice, Florida Gulf Coast Condo

Venice apartment

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 23 minutes

Price per night from

$89

Grand accomdation on USA #1 Beach - Siesta Key Fl

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$121

Venice Island on BEACH 8th flr near Siesta Key

Venice apartment

2 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$191

St.Armands Circle condo ( Kingston Arms )

Sarasota apartment

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 1 hour 51 minutes

Price per night from

$198

Amazing views, 11th flr, On the beach

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$315

Luxurious 2 BR Condo - Short Walk to Siesta Beach, #1 in The USA

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.

Price per night from

$150

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

Lakewood Ranch apartment

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$96

Sarasota 2BR 2BTH Condo Close to Siesta Key Beach

Sarasota apartment

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 1 hour 17 minutes

Price per night from

$10

Price per night from

$254

Casa Calm: King Room, Yoga, Spa

Sarasota private room

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$176

Charming Lido Key Beach House 5 min Walk to Beach!

Sarasota house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$394

Secluded Cottage on 6 Acres IN TOWN 10min to Beach

Sarasota house

2 bedrooms / 1 bathroom / sleeps 5

Responds fast! avg. 2 hours 1 minutes

Price per night from

$171

~ SUPER SPECIAL from $99/night ~ OCEAN FRONT DLX STUDIO

Longboat Key studio

Studio / 1 bathroom / sleeps 3

“Nice Beachfront Location” We stayed there in late June and found it very suitable for our needs. The beach was very accessible. View was awesome. The unit was clean and comfortable for 2 adults.

Responds fast! avg. 2 hours 25 minutes

Price per night from

$154

Viewing 38 of 1,002
rentals in Osprey

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