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Osprey Rentals

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Price: high to low

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1,714 Houses

Sarasota Condo w/Deck - 1/2 mile to Turtle Beach!

Osprey apartment

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 5 minutes

Price per night from

$137

Dunmore

Osprey house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$163

Sunny 3BR Oasis w/ New Appliances & Furnishings—Near Coast, Dining

Osprey house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$125

Price per night from

$232

Fisherman's Cove -A207-Full Gulf front!

Osprey apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$165

LUX VILLAs close to sparkling Siesta Key Beach.

Osprey villa

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$138

2 BR / 2 BA Condo in Stoneybrook Golf & County Club - Sarasota & Siesta Key

Osprey condo

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$70

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

Osprey houseboat

1 bedroom / 1 bathroom / sleeps 7

Responds fast! avg. 1 hour 21 minutes

Price per night from

$229

South Sarasota Home 5.3 Miles From Siesta Key

Osprey house

2 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 4 minutes

Price per night from

$119

CKBH (Casey Key Beach House)

Osprey house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 3 hours 17 minutes

Price per night from

$587

BEACH NEAR, EXCLUSIVE VILLA, PRIVATE POOL, QUIET SEA VIEW

Osprey house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 21 minutes

Price per night from

$190

BEACH NEAR, EXCLUSIVE VILLA, PRIVATE POOL, QUIET SEA VIEW

Osprey house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 21 minutes

Price per night from

$174

NEW! Tranquil Sarasota Home 0.8 Mi to Boat Launch!

Osprey house

3 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 5 minutes

Price per night from

$83

Great rentals within 20 miles that match your search

Siesta Key, FL contemporary condo - 2 blocks to the beach!

Siesta Key condo

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$138

Piece of Paradise

Sarasota townhouse

2 bedrooms / 3 bathrooms / sleeps 7

Price per night from

$110

Longboat Key Bayfront condo in Bay Isles

Longboat Key condo

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$213

Welcome to Zen!

Venice house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$302

Remodeled DT home 10 min. drive from beach

Sarasota house

3 bedrooms / 2 bathrooms / sleeps 7

Responds fast! avg. 2 hours 57 minutes

Price per night from

$173

Walk to the Beach on MANASOTA KEY, private deck and Lemon Bay access!

Englewood condo

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 50 minutes

Price per night from

$114

Venice Pool Home Centrally Located, Just Waiting For You

Venice house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$175

Cutest little bungalow west of the trail.

Nokomis house

2 bedrooms / 1 bathroom / sleeps 5

Price per night from

$100

Spectacular Gulf Front Luxury Condo with Amazing Views!

Manasota Key condo

4 bedrooms / 6 bathrooms / sleeps 8

Price per night from

$427

Quite newer home minutes from shopping and beaches

North Port house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 20 minutes

Price per night from

$121

Tara 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

Venice Pool Home Near Beaches

South Venice house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$157

Sea Turtle Cottage

Sarasota cottage

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 3 minutes

Price per night from

$144

Lakewood National Golf 4 Star resort living 2 bedroom Veranda

Lakewood Ranch condo

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$116

Englewood Lighthouse Resort Cottage 5

Englewood cottage

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 2 hours 22 minutes

Price per night from

$127

WALK to Siesta Beach from this vacation paradise!!

Siesta Key house

3 bedrooms / 2 bathrooms / sleeps 7

Responds fast! avg. 2 hours 3 minutes

Price per night from

$225

Siesta Key Townhouse across from Pristine Sands of Siesta Key 2B/2B sleeps 6

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Fantastic week in Siesta Key” The townhouse was fantastic and fully equipped with everything we needed for a very comfortable week. The location was outstanding - right across from the beach and the free trolley to the Village stopped right outside. The garage had everything the family needed to take to the beach and we met some lovely people around the pool. Thank you Michelle for your hospitality - we hope to be back soon.

Responds fast! avg. 1 hour 29 minutes

Price per night from

$162

LEMON BAY COTTAGE

Englewood house

3 bedrooms / 2 bathrooms / sleeps 6

“Englewood” Nice home near downtown Englewood. Short walk to shops,stores, and restaurants. I would definitely stay again.

Price per night from

$104

Tortoise

Siesta Key hotel apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$207

Shorewalk Condo CF near the Beaches Anna Maria Island, Longboat Key, IMG, Shops

Bradenton apartment

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 1 hour 24 minutes

Price per night from

$114

Sea Shell Condo-Right On Crescent Beach-Siesta Key

Siesta Key condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 38 minutes

Price per night from

$279

Cosy 4 bedms/2.5 bathms with pool close to Siesta Key

Siesta Key house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$124

Heated saltwater pool home on Venice Island

Venice house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 26 minutes

Price per night from

$242

Manasota Key

Manasota Key condo

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$154

Condo on Private Golf Course - Close to Siesta Key

Sarasota apartment

2 bedrooms / 2 bathrooms / sleeps 6

“What a great surprise!!” This Condo was everything we asked for and more. It's located in a quiet area directly in front of a large pond, overlooking the golf course. Each morning we enjoyed our coffee in the fully screened in porch watching the golfers and nature go by. This large condo has new furniture throughout and the beds are extremely comfortable. The closest of the 5 pools was just across the street from our private garage and was it's own paradise. Every day we either walked the complex's trails or participated in one of the many Yoga or Pilate's classes available right in the club house/gym. If you are a golfer, the course is beautifully maintained with plenty of options for match play and tournaments. This was a gem of a find, we pinched ourselves every day to make sure we weren't dreaming!!

Price per night from

$173

Viewing 38 of 1,714
rentals in Osprey

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