Osprey, FL, USA Vacation Rentals

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United States Florida Siesta Key vacation rental compare prices direct by owner 19581234

Steps from the Beach with Outdoor Retreat - Inviting Coastal Haven

4.5 (205)

2 Bedrooms • 4 Guests

$247 avg/night

United States Florida Siesta Key vacation rental compare prices direct by owner 247131

Beach & Pool Open! Direct Beachfront Condo! Sunset

4.9 (163)

2 Bedrooms • 6 Guests

$355 avg/night

United States Florida Siesta Key vacation rental compare prices direct by owner 11593812

Beach & Pool Open! Beachfront View Every Room

4.9 (170)

2 Bedrooms • 6 Guests

$232 avg/night

United States Florida Siesta Key vacation rental compare prices direct by owner 157737

Beach & Pool Open! Beachfront View All Rooms. Chai

4.8 (222)

2 Bedrooms • 5 Guests

$326 avg/night

United States Florida Siesta Key vacation rental compare prices direct by owner 40716162

3 bed, 4 bath, private pool home, steps to beach

5.0 (11)

3 Bedrooms • 8 Guests

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United States Florida Siesta Key vacation rental compare prices direct by owner 40857291

Beachside Bliss Awaits - Aloha Kai #55

5.0 (1)

1 Bedroom • 4 Guests

$388 avg/night

United States Florida Siesta Key vacation rental compare prices direct by owner 40857437

Charming Studio with Pool and Beach Access - Delightful Coastal Getaway

5.0 (3)

1 Bedroom • 2 Guests

$182 avg/night

United States Florida Siesta Key vacation rental compare prices direct by owner 40857507

It Doesn't Get Any Better than This!-Aloha Kai #28

5.0 (1)

2 Bedrooms • 6 Guests

$356 avg/night

United States Florida Siesta Key vacation rental compare prices direct by owner 40857667

Beachfront Escape with Views – Aloha Kai #24N

5.0 (5)

1 Bedroom • 2 Guests

$475 avg/night

United States Florida Sarasota vacation rental compare prices direct by owner 40857670

A Great Day At The Beach! - Aloha Kai #6

5.0 (1)

2 Bedrooms • 4 Guests

$461 avg/night

United States Florida Siesta Key vacation rental compare prices direct by owner 40857678

Beachside Fun & Family Comfort – Aloha Kai #16

5.0 (2)

2 Bedrooms • 4 Guests

$441 avg/night

United States Florida Siesta Key vacation rental compare prices direct by owner 40874427

Beachside Bliss Retreat – Aloha Kai #63

5.0 (5)

1 Bedroom • 4 Guests

$338 avg/night

United States Florida Siesta Key vacation rental compare prices direct by owner 40857649

Beachfront Escape & Sun-Filled Fun – Aloha Kai #24

4.8 (6)

2 Bedrooms • 6 Guests

$649 avg/night

United States Florida Siesta Key vacation rental compare prices direct by owner 40705509

Siesta Key Cottage with Beach and Pool Access

4.8 (5)

2 Bedrooms • 6 Guests

$323 avg/night

United States Florida Siesta Key vacation rental compare prices direct by owner 19700640

Two Heated Pools and Tennis Courts - Charming Tropical Haven

4.8 (63)

3 Bedrooms • 7 Guests

$332 avg/night

United States Florida Siesta Key vacation rental compare prices direct by owner 40705514

Short walk to beach, access to heated pool

4.7 (97)

2 Bedrooms • 6 Guests

$314 avg/night

United States Florida Siesta Key vacation rental compare prices direct by owner 40715285

Updated Siesta Key Vacation Rental at Bay Oaks

4.7 (21)

2 Bedrooms • 5 Guests

$267 avg/night

United States Florida Siesta Key vacation rental compare prices direct by owner 40715286

Beachside Vacation Rental with Beach Access

4.7 (7)

1 Bedroom • 4 Guests

$236 avg/night

United States Florida Siesta Key vacation rental compare prices direct by owner 40705490

Updated unit with beach and pool access

4.7 (33)

1 Bedroom • 4 Guests

$263 avg/night

United States Florida Siesta Key vacation rental compare prices direct by owner 40705491

Walk to beaches and restaurants, updated unit

4.7 (104)

2 Bedrooms • 6 Guests

$301 avg/night

United States Florida Sarasota vacation rental compare prices direct by owner 40705492

Beachfront Condo w/ Heated Pool & WIFI

4.7 (3)

2 Bedrooms • 6 Guests

$253 avg/night

United States Florida Siesta Key vacation rental compare prices direct by owner 20324626

Walk to beach, updated unit, with pool access

4.6 (228)

1 Bedroom • 4 Guests

$241 avg/night

United States Florida Siesta Key vacation rental compare prices direct by owner 175008

Charming Outdoor Patio and Beach Access - Inviting Coastal Retreat

4.6 (195)

2 Bedrooms • 4 Guests

$253 avg/night

United States Florida Siesta Key vacation rental compare prices direct by owner 40705510

Close to beach, heated pool, lakeside, updated

4.6 (83)

1 Bedroom • 4 Guests

$263 avg/night

United States Florida Siesta Key vacation rental compare prices direct by owner 40705511

Private Patio and Heated Swimming Pool - Stunning Tropical Escape

4.6 (75)

1 Bedroom • 4 Guests

$215 avg/night

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