Osprey Vacation Rentals

1-24 of 44 rentals
Waterfront home with pool dock accessible to Gulf with AC & WD

Waterfront home with pool dock accessible to Gulf with AC & WD

House in Osprey, FL

Persons
10Persons
Bedrooms
4Bedrooms
Bathrooms
2Bathrooms
$359/night
Nokomis Nirvana

Nokomis Nirvana

House in Nokomis, FL

Rating5.00
Persons
5Persons
Bedrooms
3Bedrooms
Bathrooms
2Bathrooms
$201/night
Parrot Beach Cottages Suite #1

Parrot Beach Cottages Suite #1

Studio in Siesta Key, FL

Rating4.52
Persons
2Persons
Bedrooms
0Bedrooms
Bathrooms
1Bathrooms
$243/night
Parrot Beach Cottages Suite #3

Parrot Beach Cottages Suite #3

Apartment in Siesta Key, FL

Rating4.29
Persons
4Persons
Bedrooms
1Bedrooms
Bathrooms
1Bathrooms
$277/night
Parrot Beach Cottages Suite #2

Parrot Beach Cottages Suite #2

Studio in Siesta Key, FL

Rating4.62
Persons
2Persons
Bedrooms
0Bedrooms
Bathrooms
1Bathrooms
$237/night
Sea- Esta' Winds 209

Sea- Esta' Winds 209

Condo in Siesta Key, FL

Rating4.80
Persons
4Persons
Bedrooms
1Bedrooms
Bathrooms
1Bathrooms
$288/night
Blue Fin Beach House

Blue Fin Beach House

House in Siesta Key, FL

Rating5.00
Persons
8Persons
Bedrooms
3Bedrooms
Bathrooms
2Bathrooms
$676/night
Peppertree Perfection

Peppertree Perfection

Condo in Siesta Key, FL

Rating4.33
Persons
4Persons
Bedrooms
2Bedrooms
Bathrooms
2Bathrooms
$284/night
Parrot Beach Cottages Suite #4

Parrot Beach Cottages Suite #4

Apartment in Siesta Key, FL

Rating4.37
Persons
4Persons
Bedrooms
1Bedrooms
Bathrooms
1Bathrooms
$278/night
Luxe 5BR Retreat Minutes to Beach - Golf Cart - Heated Plunge Pool

Luxe 5BR Retreat Minutes to Beach - Golf Cart - Heated Plunge Pool

House in Sarasota, FL

Persons
10Persons
Bedrooms
5Bedrooms
Bathrooms
7Bathrooms
$1,538/night
Family Fiesta

Family Fiesta

House in Sarasota, FL

Rating4.50
Persons
9Persons
Bedrooms
3Bedrooms
Bathrooms
2Bathrooms
$266/night
The Tropical Oasis

The Tropical Oasis

House in Sarasota, FL

Rating4.50
Persons
10Persons
Bedrooms
4Bedrooms
Bathrooms
3Bathrooms
$412/night
Peaceful Pinecone

Peaceful Pinecone

Condo in Sarasota, FL

Rating4.64
Persons
4Persons
Bedrooms
2Bedrooms
Bathrooms
2Bathrooms
$129/night
The Key Escape

The Key Escape

House in Sarasota, FL

Rating4.50
Persons
4Persons
Bedrooms
2Bedrooms
Bathrooms
2Bathrooms
$143/night
Alta Vista Respite

Alta Vista Respite

House in Sarasota, FL

Rating4.23
Persons
6Persons
Bedrooms
2Bedrooms
Bathrooms
2Bathrooms
$156/night
East Side Escape

East Side Escape

House in Sarasota, FL

Rating4.75
Persons
8Persons
Bedrooms
3Bedrooms
Bathrooms
2Bathrooms
$151/night
Anything Is Possible

Anything Is Possible

House in Sarasota, FL

Rating4.67
Persons
8Persons
Bedrooms
3Bedrooms
Bathrooms
3Bathrooms
$504/night
The Aquarium

The Aquarium

Condo in Sarasota, FL

Rating5.00
Persons
8Persons
Bedrooms
3Bedrooms
Bathrooms
3Bathrooms
$590/night
Salt & Sun Siesta

Salt & Sun Siesta

Condo in Sarasota, FL

Rating5.00
Persons
4Persons
Bedrooms
2Bedrooms
Bathrooms
2Bathrooms
$277/night
Organic Fun

Organic Fun

House in Sarasota, FL

Rating4.09
Persons
8Persons
Bedrooms
4Bedrooms
Bathrooms
2Bathrooms
$398/night
You Only Live Once

You Only Live Once

House in Sarasota, FL

Rating4.85
Persons
8Persons
Bedrooms
4Bedrooms
Bathrooms
4Bathrooms
$641/night
The Midnight Pearl

The Midnight Pearl

Condo in Sarasota, FL

Rating3.00
Persons
4Persons
Bedrooms
2Bedrooms
Bathrooms
2Bathrooms
$218/night
Lido Beach Respite

Lido Beach Respite

Condo in Sarasota, FL

Rating4.75
Persons
6Persons
Bedrooms
2Bedrooms
Bathrooms
2Bathrooms
$217/night
8 Pines - Sarasota Bay

8 Pines - Sarasota Bay

House in Sarasota, FL

Rating4.77
Persons
8Persons
Bedrooms
2Bedrooms
Bathrooms
3Bathrooms
$326/night
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