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Vacation Rentals in Osprey, FL

Professionally managed typically means…
  • Dedicated on-site help
  • Experienced local staff
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Verified property owner typically means…
  • Enhanced property ownership verification in addition to verification of owner name and address via valid credit card
  • Established history of renting online
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
Property owner typically means…
  • Verification of owner name and address via valid credit card
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
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All 358 Rentals in the Osprey Area
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From
$143
Per Night
Osprey
3 Bedrooms, 3 Bathrooms, Sleeps 8
17 photos Details
Reviews (1) Make Inquiry
From
$700
Per Week
Osprey
2 Bedrooms, 2 Bathrooms, Sleeps 6
14 photos Details
Make Inquiry

The following rentals are within 10 miles of Osprey, Florida.

From
$450
Per Week
Venice
1 Bedroom, 1 Bathroom, Sleeps 2
17 photos Details
Reviews (2) Make Inquiry
Also consider
Emily's Bungalow: Nokomis, Florida Weekly / Monthly Rental! Stunning! Clean! Fun!!!
1 Bedroom, sleeps 5
$125 / night
Historic 1/1 cottage with Old Florida charm
1 Bedroom, sleeps 2
$100 / night
Luxurious 2 BR Condo - 150 Yards Walk to Siesta Key Beach, Florida
2 Bedrooms, sleeps 6
$79 - $150 / night
Siesta Key 2/2 Near Beach
2 Bedrooms, sleeps 5
$550 - $1,050 / week
From
$950
Per Week
Venice
4 Bedrooms, 3 Bathrooms, Sleeps 10
15 photos Details
Reviews (3) Make Inquiry
From
$1,400
Per Week
Venice
3 Bedrooms, 3 Bathrooms, Sleeps 6
21 photos Details
Reviews (1) Make Inquiry
From
$130
Per Night
Venice
Studio, 1 Bathroom, Sleeps 2
8 photos Details
Reviews (1) Make Inquiry
From
$199
Per Night
Venice
3 Bedrooms, 2 Bathrooms, Sleeps 8
48 photos Details
Reviews (18) Make Inquiry
From
$175
Per Night
Venice
2 Bedrooms, 1 Bathroom, Sleeps 4
36 photos Details
Reviews (5) Make Inquiry
Get the List
From
$97
Per Night
Venice
4 Bedrooms, 3 Bathrooms, Sleeps 8
12 photos Details
Reviews (1) Make Inquiry
From
$600
Per Week
Venice
2 Bedrooms, 2 Bathrooms, Sleeps 6
14 photos Details
Reviews (9) Make Inquiry
From
$107
Per Night
Venice
2 Bedrooms, 2 Bathrooms, Sleeps 6
12 photos Details
Reviews (2) Make Inquiry
From
$225
Per Night
Siesta Key
2 Bedrooms, 2 Bathrooms, Sleeps 6
15 photos Details
Reviews (3) Make Inquiry
From
$285
Per Night
Venice
3 Bedrooms, 2 Bathrooms, Sleeps 12
18 photos Details
Reviews (5) Make Inquiry
From
$117
Per Night
Venice
2 Bedrooms, 2 Bathrooms, Sleeps 6
17 photos Details
Reviews (2) Make Inquiry
From
$170
Per Night
Venice
3 Bedrooms, 3 Bathrooms, Sleeps 6
8 photos Details
Reviews (4) Make Inquiry
From
$121
Per Night
Siesta Key
2 Bedrooms, 3 Bathrooms, Sleeps 4
16 photos Details
Reviews (4) Make Inquiry
From
$875
Per Week
Venice
3 Bedrooms, 2 Bathrooms, Sleeps 6
44 photos Details
Reviews (1) Make Inquiry
From
$100
Per Night
Siesta Key
2 Bedrooms, 2 Bathrooms, Sleeps 4
13 photos Details
Reviews (3) Make Inquiry
From
$127
Per Night
Siesta Key
2 Bedrooms, 2 Bathrooms, Sleeps 4
9 photos Details
Reviews (4) Make Inquiry
From
$139
Per Night
Siesta Key
2 Bedrooms, 2 Bathrooms, Sleeps 6
11 photos Details
Reviews (1) Make Inquiry
From
$320
Per Night
Siesta Key
3 Bedrooms, 3 Bathrooms, Sleeps 8
23 photos Details
Reviews (1) Make Inquiry
From
$122
Per Night
Siesta Key
2 Bedrooms, 1 Bathroom, Sleeps 6
9 photos Details
Reviews (3) Make Inquiry
From
$66
Per Night
Siesta Key
2 Bedrooms, 1 Bathroom, Sleeps 7
25 photos Details
Reviews (2) Make Inquiry
From
$143
Per Night
Siesta Key
2 Bedrooms, 2 Bathrooms, Sleeps 7
15 photos Details
Reviews (23) Make Inquiry
From
$150
Per Night
Siesta Key
2 Bedrooms, 1 Bathroom, Sleeps 6
9 photos Details
Reviews (8) Make Inquiry
From
$115
Per Night
Siesta Key
2 Bedrooms, 2 Bathrooms, Sleeps 6
33 photos Details
Reviews (7) Make Inquiry
From
$217
Per Night
Siesta Key
3 Bedrooms, 3 Bathrooms, Sleeps 10
40 photos Details
Reviews (21) Make Inquiry
From
$650
Per Week
Venice
1 Bedroom, 1 Bathroom, Sleeps 6
-76 photos Details
Reviews (20) Make Inquiry
From
$500
Per Night
Siesta Key
5 Bedrooms, 4 Bathrooms, Sleeps 10
15 photos Details
Reviews (2) Make Inquiry
From
$134
Per Night
Siesta Key
1 Bedroom, 1 Bathroom, Sleeps 4
51 photos Details
Reviews (29) Make Inquiry
From
$166
Per Night
Siesta Key
2 Bedrooms, 2 Bathrooms, Sleeps 4
38 photos Details
Reviews (2) Make Inquiry
From
$180
Per Night
Venice
2 Bedrooms, 1 Bathroom, Sleeps 4
19 photos Details
Reviews (2) Make Inquiry
From
$125
Per Night
Siesta Key
2 Bedrooms, 2 Bathrooms, Sleeps 6
23 photos Details
Reviews (5) Make Inquiry
From
$400
Per Night
Siesta Key
3 Bedrooms, 3 Bathrooms, Sleeps 6
31 photos Details
Reviews (3) Make Inquiry
From
$120
Per Night
Venice
4 Bedrooms, 2 Bathrooms, Sleeps 9
11 photos Details
Reviews (3) Make Inquiry
From
$160
Per Night
Siesta Key
2 Bedrooms, 2 Bathrooms, Sleeps 6
14 photos Details
Reviews (2) Make Inquiry
From
$199
Per Night
Siesta Key
2 Bedrooms, 2 Bathrooms, Sleeps 6
15 photos Details
Reviews (8) Make Inquiry
From
$413
Per Night
Venice
4 Bedrooms, 2 Bathrooms, Sleeps 12
34 photos Details
Reviews (32) Make Inquiry
From
$293
Per Night
Siesta Key
4 Bedrooms, 4 Bathrooms, Sleeps 10
14 photos Details
Reviews (6) Make Inquiry
From
$220
Per Night
Siesta Key
2 Bedrooms, 2 Bathrooms, Sleeps 6
16 photos Details
Reviews (3) Make Inquiry
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Book Online(192)
Use filters to find the best results!

Suitability

  • Wheelchair access (62)
  • Elder access (173)
  • Suitable for children (218)
  • Pet friendly (74)
  • Smoking allowed (2)

Amenities

  • Air Conditioning (284)
  • Internet (281)
  • All pools (244)
  • Other outdoor space (243)
  • Parking (201)
  • View all amenities
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Book Online(192)

Suitability

  • Wheelchair access (62)
  • Elder access (173)
  • Suitable for children (218)
  • Pet friendly (74)
  • Smoking allowed (2)

Amenities

  • Air Conditioning (284)
  • Internet (281)
  • All pools (244)
  • Other outdoor space (243)
  • Parking (201)
  • View all amenities