Updating...

More filters (1)

Wireless Internet
Air conditioning
Swimming pool
Private pool

Heated pool
Private indoor pool
Balcony or terrace
Washing machine
Garden
Internet access
DVD player
Grill
Cot available
Sauna
Sea view
Safe
Dishwasher
Children's pool
Pool or snooker table
Table tennis
Games room
Clothes dryer
Shared outdoor pool (heated)
Private outdoor pool (unheated)
Private outdoor pool (heated)
Shared indoor pool
Shared outdoor pool (unheated)
Cribs
Ceiling Fans
Fax machine
Climbing frame
Video player
Freezer
Kettle
Toaster
Iron
Hair dryer
Stove
Fridge
Microwave
Boat available
Linen provided
Towels provided
Bicycles available
Swing set or jungle gym
Trampoline
Private fishing lake or river
Staffed property
Housekeeping Included

See all

Less

Pets allowed
Parking
Car not required
Children under 5

Smoking allowed
Non-Smoking property
Smoking - Ask
Elevator access
Wheelchair adapted
Wheelchair accessible

See all

Less

City breaks
Skiing – property near ski resort
Walking trips
Tennis in town

Nightlife
Water sports
Fishing
Waterfront
Golf within 30mins drive
Lakefront

See all

Less

193 houses

Sort by:

Chinaberry 924 at Midnight Cove Siesta Key, FL.

Sarasota house

2 bedrooms
2 bathrooms

sleeps 6

Match: Rental types Staffed property

All filters match

Price per night from

$171

Firethorn 830 at Midnight Cove Siesta Key

Sarasota house

2 bedrooms
1 bathroom

sleeps 4

Match: Rental types Staffed property

All filters match

Price per night from

$142

Doveplum 221 at Midnight Cove Siesta Key, FL.

Sarasota house

2 bedrooms
2 bathrooms

sleeps 6

Match: Rental types Staffed property

All filters match

Price per night from

$256

Oceanfront home

Gulf Gate Estates house

3 bedrooms
2 bathrooms

sleeps 10

Match: Rental types Staffed property

All filters match

Price per night from

$685

The Suite Retreat Room at The Breathing Space Wellness House

Sarasota house

1 bedroom
1 bathroom

sleeps 2

Match: Rental types Staffed property

All filters match

Price per night from

$344

120 Steps to the Beach with beach gear included!

Siesta Key condo

2 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Rental types, Staffed property

1 of 2 filters match

Price per night from

$423

Tiny House Siesta - Sand Dollar – A private master loft and open living space

Siesta Key hotel apartment

2 bedrooms
1 bathroom

sleeps 6

1 of 2 match: Rental types, Staffed property

1 of 2 filters match

Price per night from

$447

Buttonwood 442

Gulf Gate Estates condo

3 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Rental types, Staffed property

1 of 2 filters match

Price per night from

$290

Amazing views, 11th flr, On the beach

Siesta Key apartment

2 bedrooms
2 bathrooms

sleeps 4

1 of 2 match: Rental types, Staffed property

1 of 2 filters match

Price per night from

$409

Palm Bay Club - 343: By Beachside Management

Siesta Key condo

2 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Rental types, Staffed property

1 of 2 filters match

Price per night from

$286

Private Beach Access - Home away from Home - 2 BR 2 BA - Furnished Condo

Siesta Key condo

2 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Rental types, Staffed property

1 of 2 filters match

Price per night from

$178

Ten35 Seaside - North Water View: Residence 606

Siesta Key condo

3 bedrooms
3 bathrooms

sleeps 6

1 of 2 match: Rental types, Staffed property

1 of 2 filters match

Price per night from

$776

Ten35 Seaside - Island View: Residence 406

Siesta Key condo

3 bedrooms
3 bathrooms

sleeps 6

1 of 2 match: Rental types, Staffed property

1 of 2 filters match

Price per night from

$559

Ten35 Seaside - Direct Gulf View: Residence 301

Siesta Key condo

3 bedrooms
3 bathrooms

sleeps 6

1 of 2 match: Rental types, Staffed property

1 of 2 filters match

Price per night from

$856

Ten35 Seaside - Island View: Residence 408

Siesta Key condo

2 bedrooms
3 bathrooms

sleeps 4

1 of 2 match: Rental types, Staffed property

1 of 2 filters match

Price per night from

$548

Ten35 Seaside - North Water View: Residence 506

Siesta Key condo

4 bedrooms
3 bathrooms

sleeps 8

1 of 2 match: Rental types, Staffed property

1 of 2 filters match

Price per night from

$776

Ten35 Seaside - Island View: Residence 404

Siesta Key condo

2 bedrooms
3 bathrooms

sleeps 4

1 of 2 match: Rental types, Staffed property

1 of 2 filters match

Price per night from

$548

Ten35 Seaside - South Water View: Residence 302

Siesta Key condo

3 bedrooms
3 bathrooms

sleeps 6

1 of 2 match: Rental types, Staffed property

1 of 2 filters match

Price per night from

$605

Ten35 Seaside - North Water View: Residence 310

Siesta Key condo

3 bedrooms
3 bathrooms

sleeps 6

1 of 2 match: Rental types, Staffed property

1 of 2 filters match

Price per night from

$628

Ten35 Seaside - Direct Gulf View: Residence 303

Siesta Key condo

3 bedrooms
3 bathrooms

sleeps 6

1 of 2 match: Rental types, Staffed property

1 of 2 filters match

Price per night from

$856

Ten35 Seaside - North Water View: Residence 410

Siesta Key condo

3 bedrooms
3 bathrooms

sleeps 6

1 of 2 match: Rental types, Staffed property

1 of 2 filters match

Price per night from

$628

Ten35 Seaside - Direct Gulf View: Residence 405

Siesta Key condo

3 bedrooms
4 bathrooms

sleeps 6

1 of 2 match: Rental types, Staffed property

1 of 2 filters match

Price per night from

$856

Ten35 Seaside - South Water View: Residence 602

Siesta Key condo

3 bedrooms
3 bathrooms

sleeps 6

1 of 2 match: Rental types, Staffed property

1 of 2 filters match

Price per night from

$685

Ten35 Seaside - South Water View: Residence 502

Siesta Key condo

4 bedrooms
3 bathrooms

sleeps 8

1 of 2 match: Rental types, Staffed property

1 of 2 filters match

Price per night from

$753

Ten35 Seaside - Island View: Residence 308

Siesta Key condo

2 bedrooms
3 bathrooms

sleeps 6

1 of 2 match: Rental types, Staffed property

1 of 2 filters match

Price per night from

$548

Ten35 Seaside - Direct Gulf View: Residence 307

Siesta Key condo

3 bedrooms
3 bathrooms

sleeps 6

1 of 2 match: Rental types, Staffed property

1 of 2 filters match

Price per night from

$856

Ten35 Seaside - Direct Gulf View: Residence 403

Siesta Key condo

3 bedrooms
3 bathrooms

sleeps 6

1 of 2 match: Rental types, Staffed property

1 of 2 filters match

Price per night from

$856

Ten35 Seaside - Island View: Residence 604

Siesta Key condo

3 bedrooms
3 bathrooms

sleeps 6

1 of 2 match: Rental types, Staffed property

1 of 2 filters match

Price per night from

$559

Ten35 Seaside - Direct Gulf View: Residence 501

Siesta Key condo

3 bedrooms
3 bathrooms

sleeps 6

1 of 2 match: Rental types, Staffed property

1 of 2 filters match

Price per night from

$947

Chinaberry 911 at Midnight Cove Siesta Key, FL.

Siesta Key apartment

2 bedrooms
2 bathrooms

sleeps 4

1 of 2 match: Rental types, Staffed property

1 of 2 filters match

Price per night from

$171

Chinaberry 435 at Midnight Cove Siesta Key, FL.

Siesta Key apartment

2 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Rental types, Staffed property

1 of 2 filters match

Price per night from

$264

Buttonwood 432 at Midnight Cove Siesta Key, FL.

Siesta Key apartment

3 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Rental types, Staffed property

1 of 2 filters match

Price per night from

$290

Chinaberry 424 at Midnight Cove Siesta Key

Siesta Key apartment

2 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Rental types, Staffed property

1 of 2 filters match

Price per night from

$264

Buttonwood 417 at Midnight Cove Siesta Key, FL.

Siesta Key apartment

3 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Rental types, Staffed property

1 of 2 filters match

Price per night from

$290

Firethorn 323 at Midnight Cove Siesta Key

Siesta Key apartment

2 bedrooms
2 bathrooms

sleeps 4

1 of 2 match: Rental types, Staffed property

1 of 2 filters match

Price per night from

$249

Firethorn 321 at Midnight Cove Siesta Key, FL.

Siesta Key apartment

2 bedrooms
2 bathrooms

sleeps 4

1 of 2 match: Rental types, Staffed property

1 of 2 filters match

Price per night from

$249

Chinaberry 443 at Midnight Cove Siesta Key, FL.

Siesta Key apartment

2 bedrooms
2 bathrooms

sleeps 4

1 of 2 match: Rental types, Staffed property

1 of 2 filters match

Price per night from

$264

Firethorn 712 at Midnight Cove Siesta Key, FL.

Siesta Key apartment

2 bedrooms
1 bathroom

sleeps 6

1 of 2 match: Rental types, Staffed property

1 of 2 filters match

Price per night from

$142

Viewing 38 of 193
rentals in Osprey

Also consider

Florida Panhandle 2,875 properties
Siesta Key 405 properties
Brevard County 370 properties
Indian Shores 169 properties
Tampa 141 properties
Fort Pierce 96 properties
Daytona Beach Shores 69 properties
Ormond Beach 46 properties
Jacksonville Beach 45 properties
Largo 30 properties
Lakewood Ranch 24 properties
Vero Beach 24 properties
Key Biscayne 18 properties
Temple Terrace 18 properties
Seminole 14 properties
Bal Harbour 14 properties
Pelican Bay 13 properties
Brandon 13 properties
Port Orange 12 properties
Pinellas Park 12 properties
Holly Hill 11 properties
Steinhatchee 9 properties
Palmetto 8 properties
Biggar 9 properties
Old Town 7 properties
Ponce Inlet 7 properties
Apollo Beach 6 properties
Palm Beach 6 properties
Homosassa Springs 6 properties
Redington Shores 6 properties
Ormond-by-the-Sea 5 properties
Bokeelia 5 properties

Houses Osprey

Per night

193 houses

Viewing 38 of 193rentals in Osprey

Also consider

Viewing 38 of 193
rentals in Osprey