Osprey Rentals

Updating...

age 0-16
957 Results

Relevance

Price: low to high

Price: high to low

Reviews

957 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

$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

Price per night from

$132

CKBH (Casey Key Beach House)

Osprey house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$655

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

Osprey condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 11 minutes

Price per night from

$161

Great rentals within 20 miles that match your search

Responds fast! avg. 1 hour 3 minutes

Price per night from

$268

Three bedroom house directly on beach with gulf vi

Siesta Key house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 7

Price per night from

$402

Luxury accommodation in Venetia, 3 months stay

Venice house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Price per night from

$192

LEMON BAY COTTAGE

Englewood house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Perfect family cottage in Lemon Bay” Such a great little house and surprisingly bigger than pictures reveal. Perfect for a family with kids. 3rd toilet tucked away in laundry shed for easy access from pool. Great location as well, close to beaches, parks and many restaurants within walking distance. Definitely will rent there again. House was fresh, clean and inviting.

Responds fast! avg. 3 hours 18 minutes

Price per night from

$104

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

Lakewood Ranch apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$100

Sarasota 2BR 2BTH Condo Close to Siesta Key Beach

Sarasota apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$60

Luxury Venice Florida 4 Bedroom home with Pool

Venice villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$287

Price per night from

$264

Casa Calm: King Room, Yoga, Spa

Sarasota private room

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$183

Charming Lido Key Beach House 5 min Walk to Beach!

Sarasota house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$410

Secluded Cottage on 6 Acres IN TOWN 10min to Beach

Sarasota house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

Price per night from

$178

~ 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 5 minutes

Price per night from

$194

Manasota Beach Vacation Rental

Englewood house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$270

Beach front condo in Longboat Key

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$430

Charming 'Old Florida' One bed Suite, Close to Downtown Sarasota and Beaches

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$129

Quiet pool home with lake view, close to beaches

Venice house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$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.

Price per night from

$144

Price per night from

$144

Serene Sarasota Getaway near shopping and golfing.

Fruitville villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$128

Piece of Paradise

Sarasota condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$96

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

Sarasota condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Siesta Harbor” We stayed at Siesta Harbor for the month of February 2018 and had a great time. Beach is across the street and easy access. Don the owner was outstanding and met us on our first day and gave us a tour of Siesta Key. We have reserved for 2019 and look forward to another great time at Siesta Harbor.

Price per night from

$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

Price per night from

$127

All Inclusive Executive Rental

Sarasota apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Responds fast! avg. 1 hour 42 minutes

Price per night from

$167

Luxury Sarasota Golf Home

Sarasota house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Price per night from

$368

Light and Airy and Private, Great Location

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Responds fast! avg. 1 hour 32 minutes

Price per night from

$230

Siesta Vacation Home - 3 miles to beach

Venice house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$211

****Walk to Beach-5min! Waterfront Canal! Private Pool~spa~Kayaks, Bikes!

Siesta Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$454

Shorewalk waterfront Condo Bradenton

Bradenton condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Nice and affordable condo convenient to shopping and restaurants.” This unit has been updated and is a very comfortable place to stay. The owner responded promptly when we contacted him.

Responds fast! avg. 1 hour 51 minutes

Price per night from

$96

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

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$338

Ground Level 2 Bedroom Beach Themed Condo

Venice condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$230

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.

Price per night from

$195

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

$532

Reserve now! Beautiful Siesta key Beach

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$390

Viewing 38 of 957
rentals in Osprey

×

Also consider