Osprey Rentals

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950 Houses

Dunmore

Osprey house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$218

LUX VILLAs close to sparkling Siesta Key Beach.

Osprey villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$160

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

Price per night from

$132

CKBH (Casey Key Beach House)

Osprey house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$653

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

Osprey condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$160

Great rentals within 20 miles that match your search

Convenient + Cozy + Quite + Comfortable :-)

Sarasota house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 1 hour 55 minutes

Price per night from

$315

Newly Remodeled Spacious Loft in Sarasota!

Sarasota apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$294

Price per night from

$332

2 bedroom Condo Bay Oaks Siesta Key

Sarasota condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3

Price per night from

$572

Beautiful Crescent Beach on Siesta Key One of the

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$300

Park Model with lanai, large deck, block from pool

Venice house

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Price per night from

$120

Lovely Brandnew Pool Villa w/ Private Beach, WiFi

Venice house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$212

Venice Florida Condo

Venice condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$126

Amazing Beachfront Condo, Siesta Key,

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$343

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

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$271

New 6 Bedroom, Luxury Home in Gated Community

Siesta Key house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14

Price per night from

$998

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

Sarasota condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$115

Vacation Home on Coral Sands Ct. Spring Special !

Venice house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

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

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

Price per night from

$429

Luxury Venice Florida 4 Bedroom home with Pool

Venice villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$286

Price per night from

$263

Casa Calm: King Room, Yoga, Spa

Sarasota private room

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$182

Charming Lido Key Beach House 5 min Walk to Beach!

Sarasota house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$409

~ 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. 1 hour 56 minutes

Price per night from

$194

Manasota Beach Vacation Rental

Englewood house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$269

ZILLI VILLA

Longboat Key villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 10

Price per night from

$486

Beach front condo in Longboat Key

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$429

Beachfront Getaway in Siesta Key

Siesta Key townhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“Very comfortable, nice amenities and well run.” Loved the beach and the nearby restaurants. The free trolly ride was easy to use and a great way to go into the village.

Price per night from

$223

Manasota Beachy Cottage

Manasota Key house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

“Our 2017 vacation” This was our first time ever renting a house. Peter was the best. This house had everything we need or wanted. It was super clean and beautiful. The screened porch was perfect to drink coffee in the morning. Didn't have to worry about the bugs or anything. Beach was a short walk around the corner over a bridge. The town was great and hardly no traffic. Safe for younger kids to play in the yard. Can't wait to rent again next year. Thank you!!

Price per night from

$155

Quiet pool home with lake view, close to beaches

Venice house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$229

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.

Price per night from

$143

Price per night from

$143

“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!!

Price per night from

$143

Price per night from

$284

Serene Sarasota Getaway near shopping and golfing.

Fruitville villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$127

Piece of Paradise

Sarasota condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 3 minutes

Price per night from

$95

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

Sarasota condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$160

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