COVID-19 Update

The impact of COVID-19 on travel is unprecedented. Like you, we’re monitoring the situation. Rest assured, we’re here to help with questions about your plans. Learn more here: About the coronavirus outbreak (COVID-19)

Osprey Rentals

Updating...

age 0-16
1267 Results

Relevance

Price: low to high

Price: high to low

Number of reviews

1,267 Houses

Dunmore

Osprey house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$192

Sunny Oasis w/ New Appliances & Furnishings - Near Coast, Dining

Osprey house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$120

LUX VILLAs close to sparkling Siesta Key Beach.

Osprey villa

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$139

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

Osprey houseboat

1 bedroom / 1 bathroom / sleeps 7

Responds fast! avg. 1 hour 22 minutes

Price per night from

$289

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

$79

2Bedroom Beach Cottage - 3 Miles to Siesta Key

Osprey cottage

2 bedrooms / 1 bathroom / sleeps 2

Responds fast! avg. 2 hours 57 minutes

Price per night from

$93

CKBH (Casey Key Beach House)

Osprey house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$583

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

Osprey house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 53 minutes

Price per night from

$172

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

Osprey house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$191

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

Osprey condo

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$153

Tranquil Sarasota Home < 1 Mile to Boat Launch!

Osprey house

3 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 33 minutes

Price per night from

$93

Responds fast! avg. 4 minutes

Price per night from

$206

Great rentals within 20 miles that match your search

Welcome to Zen!

Venice house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$341

Bayshore Gardens Studio Apartment

Bradenton studio

Studio / 1 bathroom / sleeps 2

Price per night from

$72

Beautiful 2 bedroom 2 bath in Palm Aire Country Club near fabulous beaches

Sarasota condo

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$114

GROUND FLOOR CONDO IN GATED COMMUNITY

North Port condo

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 1 minutes

Price per night from

$122

Price per night from

$226

Park Model with lanai, large deck, block from pool

Venice house

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$138

GULF FRONT 2 BR 2 BATHROOM CONDO

Longboat Key condo

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$219

#7 Loft Apartment in Historic District Downtown Sarasota

Sarasota apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 17 minutes

Price per night from

$141

Woodstork Pond Cottage

Englewood house

2 bedrooms / 2 bathrooms / sleeps 7

Price per night from

$197

Close to the Bradenton beaches, shopping, dining

Bradenton condo

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$175

Gateway to Siesta Key 1/2 mile Walk to the Beach Adorable 2 Bedroom Condo

Gulf Gate Branch condo

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$144

Tropical retreat with pool and gardens in the heart of Sarasota

Sarasota house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$240

Palm Bay Club - 100 Yards From The Beach

Siesta Key condo

2 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$274

Downtown Sarasota #11

Sarasota condo

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$104

Charming Private Studio in Historic Downtown Area

Sarasota studio

Studio / 1 bathroom / sleeps 3

Responds fast! avg. 17 minutes

Price per night from

$130

Amazing Gulf Beech Rental with Fantastic FREE Amenities!!!

Longboat Key condo

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$380

Addy's Villas: 2BR

Nokomis villa

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$222

2 bedroom Condo Bay Oaks Siesta Key

Sarasota condo

2 bedrooms / 1 bathroom / sleeps 3

Price per night from

$655

One Bedroom in Historic Burns Square District downtown

Sarasota apartment

1 bedroom / 1 bathroom / sleeps 3

Responds fast! avg. 17 minutes

Price per night from

$150

Castel del Mare, Luxury Condo, Near Siesta Key

Sarasota condo

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$112

March 21-28, 2020 Springbreak 3bdr on the beach Longboat key

Longboat Key cottage

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$786

Secluded Cottage on 6 Acres IN TOWN 10min to Beach

Sarasota house

2 bedrooms / 1 bathroom / sleeps 5

Responds fast! avg. 1 hour 46 minutes

Price per night from

$164

Newly Remodeled Spacious Loft in Sarasota!

Sarasota apartment

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$337

It's Not Too Late! 2B/2B Condo available for season at the Plantation G & CC

Venice condo

2 bedrooms / 2 bathrooms / sleeps 3

Price per night from

$131

Piece of Paradise

Sarasota condo

2 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 2 hours 21 minutes

Price per night from

$109

Downtown Apartment in Historic Burns Square downtown Sarasota

Sarasota apartment

1 bedroom / 1 bathroom / sleeps 3

Responds fast! avg. 17 minutes

Price per night from

$150

Viewing 38 of 1,267
rentals in Osprey

×

Also consider