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Osprey Rentals

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1,040 Houses

Dunmore

Osprey house

3 bedrooms / 2 bathrooms / sleeps 6

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

$286

2Bedroom Beach Cottage - 4 Miles to Siesta Key

Osprey cottage

2 bedrooms / 1 bathroom / sleeps 2

Price per night from

$115

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

Osprey houseboat

3 bedrooms / 1 bathroom / sleeps 11

Responds fast! avg. 2 hours 28 minutes

Price per night from

$342

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

Osprey houseboat

1 bedroom / 1 bathroom / sleeps 7

Responds fast! avg. 2 hours 28 minutes

Price per night from

$285

CKBH (Casey Key Beach House)

Osprey house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$579

Responds fast! avg. 1 hour 47 minutes

Price per night from

$147

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

Osprey condo

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$152

Responds fast! avg. 1 hour 47 minutes

Price per night from

$186

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 50 minutes

Price per night from

$465

Sarasota Villa

Sarasota villa

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$119

The Great (Sunshine and Sea) Escape

Bradenton apartment

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 2 hours 57 minutes

Price per night from

$109

PALM'S HOUSE

Siesta Key house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 23 minutes

Price per night from

$214

Heritage Oaks

Heritage Oaks Golf and Country Club condo

2 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$95

Stunning 2,550 Sq.ft House, FL

Bradenton house

4 bedrooms / 2 bathrooms / sleeps 8

“Awesome stay” We had a great stay at this property. We were there for my wife graduation our family and us loved it and will rent this property again.

Price per night from

$271

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.

Price per night from

$530

Peaceful Haven on Siesta Key with Beach Access

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Tropical paradise! Perfect condo for family vacay!” Midnight Cove II is perfectly situated in the center of Siesta Key! The Village is just a short drive north and Turtle Beach is an equally short drive south. It is within walking distance of many restaurants, shops and attractions. Beach access is just a short walk across the street. The grounds are well-maintained and the staff is super friendly and helpful. Great pool area, too! I will definitely be back.

Price per night from

$128

TORTUGA BEACH CLUB, SIESTA KEY

Sarasota apartment

2 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$248

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 4 minutes

Price per night from

$277

Reserve now! Beautiful Siesta key Beach

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$303

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 22 minutes

Price per night from

$227

“Stunning views! Very Special!” A fantastic stay for our family with young children. Beach was clean and was only 49 steps from the front door. We caught lots of fish in the surf of the beach and found over 1000 sharks teeth. Very family friendly beach and area. Condo was very tastefully decorated. Thank-you for creating a wonderful haven for our family. Both owner and Realtor were easy to deal with. We will definitely return.

Price per night from

$343

Super clean vacation Villa with Pool

North Port house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 20 minutes

Price per night from

$137

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

$103

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 18 minutes

Price per night from

$251

Villa Grande - Minutes From Beaches - Spacious Fenced Yard! Free WiFi

Venice house

2 bedrooms / 2 bathrooms / sleeps 6

“Top experience” Our experience was outstanding. The house was lovely and very well-appointed. There were even starter spices, coffee and coffee filters in the cupboards. Nice amenities in the bathrooms and a very clean place. The yard was big and the dog loved it. Our rental agent was very responsive with any concern I voiced.

Price per night from

$129

“As advertised, great price, and the hidden bonus - read on ...” We like the Venice area however, have never stayed there until finding this gem. For the month my wife and I plus my sister and little dachshund were the occupants. Another couple visited us for 3 nights. The home is nicely furnished and equipped, the 2 bedrooms each size of the main room hence nicely separated, a nice back yard, deck adequate although a little small around the (small) barbecue. A lanai would have been great although I suspect another price bracket! Great location for riding my bicycle - 50km round trip along the heritage trail towards Sarasota, c. 30km to Manasota Key. Short distance to the ferry to the private beach. Handy for shopping (Walmart, Publix, etc.), Venice high street, and the great restaurant at Venice airport! Btw worth a visit if you like planes - and lots of different stuff occasionally there including, really, a B-29. The hidden bonus - the very best landlady Ruth Miller.

Price per night from

$114

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. 26 minutes

Price per night from

$200

Lovely beachside villa

Sarasota villa

2 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$208

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

$799

Las Hermanas/Starfish #3 Beach front Longboat Key

Longboat Key apartment

1 bedroom / 1 bathroom / sleeps 4

“Little Piece Of Paradise” Everything you could want in a vacation rental. We wanted to be right on the beach and this place offers that and more. Great kitchen,stocked with everything you need. Beach views from almost every room. We really enjoyed eating on the porch. We will be returning soon.

Responds fast! avg. 3 hours 24 minutes

Price per night from

$223

Luxury Venice, Florida Gulf Coast Condo

Venice apartment

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$92

Grand accomdation on USA #1 Beach - Siesta Key Fl

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$125

Venice Island on BEACH 8th flr near Siesta Key

Venice apartment

2 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$186

St.Armands Circle condo ( Kingston Arms )

Sarasota apartment

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 2 hours 57 minutes

Price per night from

$156

Crystal Sands Siesta Key

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$408

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

$148

Vacation Home with Private Beach !

Venice house

3 bedrooms / 2 bathrooms / sleeps 5

“Pleasantly surprised!” We stayed at this property in March, 2014 for five nights. The house was very well maintained and clean and appears to have been renovated recently. The furniture throughout the house and the appliances all looked new. The kitchen was very well equipped and the bathrooms were very neat and spotless. We enjoyed staying at this house and recommend it to everyone without any hesitation.

Responds fast! avg. 2 hours 26 minutes

Price per night from

$132

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