Holiday Homes in Osprey

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Featured Holiday Homes in Osprey

Siesta Key Island Rentals

3.0 star property
9.6 out of 10, Exceptional, (35)
"Great vacation stay "
The price is AU$689
includes taxes & fees
19 July - 20 July
Siesta Key Island Rentals

Tropical Villas of Venice Beach

3.5 star property
9.6 out of 10, Exceptional, (237)
"Great Location !!"
Tropical Villas of Venice Beach

Charming Beach Cottage

9.6 out of 10, Exceptional, (25)
"Perfect bnb by the beach"
Charming Beach Cottage

Newly Renovated 2-bedroom w/Pool, Garage and a just a bike ride to Siesta Key!

9.4 out of 10, Exceptional, (19)
"We stayed for just a few nights but this is easy to find and in a quiet neighborhood. We enjoyed our stay. Don't hesitate to book. "
Newly Renovated 2-bedroom w/Pool, Garage and a just a bike ride to Siesta Key!

Private Home Directly on Siesta Key Beach!

10.0 out of 10, Exceptional, (1)
"The home was beautiful and well equipped and management was quick to respond to any questions that we had. Direct access to a gorgeous beach was definitely the highlight!! "
Private Home Directly on Siesta Key Beach!

This house is a 3 bedroom(s), 2 bathrooms, located in Venice, FL.

9.8 out of 10, Exceptional, (176)
"Great spot to enjoy all Venice has to offer. Easy access to beach and downtown. Clean accommodations with good outdoor space."
This house is a 3 bedroom(s), 2 bathrooms, located in Venice, FL.

Gorgeous Pool house 5 min from the beach, shopping and restaurants I

9.2 out of 10, Wonderful, (54)
"Loved our stay! "
The price is AU$552
includes taxes & fees
22 July - 23 July
Gorgeous Pool house 5 min from the beach, shopping and restaurants I

Serene yard and pool, 1 mile to beach, pets OK, patio TV, Kayaks

10.0 out of 10, Exceptional, (29)
"Just 9 minutes to Siesta Key Beach and when you get back enjoy a late swim in the pool. Very nice home and neighborhood. Close to restaurants and shopping. We enjoyed our stay! "
Serene yard and pool, 1 mile to beach, pets OK, patio TV, Kayaks

Beachside Retreat with Pool and Beach Access

9.0 out of 10, Wonderful, (38)
"Great location for all our visitors to walk to many various restaurants and shops"
The price is AU$1,984
includes taxes & fees
7 Aug - 8 Aug
Beachside Retreat with Pool and Beach Access

Bungalow w/ Heated Pool by Downtown & Beaches

10.0 out of 10, Exceptional, (33)
"Wonderful family set up. The hosts are great and the house is well equipped. The pool is lovely and a beautiful setting, especially in the evening. The house is in an historical area and parks and groceries are in walking distance (under a mile). We would stay there again."
Bungalow w/ Heated Pool by Downtown & Beaches

AUG SEPT OCT DISCOUNTS! IMG AMIsland BEACHES KAYAKS FISHING ON LAKE KIDS PETS OK

9.8 out of 10, Exceptional, (128)
"We had a great time! The house was great and had everything we needed. The pool was amazing! Jackie was very communicative and was available should we need anything. Overall a great stay and would recommend!"
The price is AU$732
includes taxes & fees
22 July - 23 July
AUG SEPT OCT DISCOUNTS! IMG AMIsland BEACHES KAYAKS FISHING ON LAKE KIDS PETS OK

Comfy, clean, private home IN Venice, Florida; Heated Pool, Minutes to the Beach

10.0 out of 10, Exceptional, (155)
"The house was very clean and the owners were nice when we talked through email. The house is in a quiet neighborhood and it was stocked with towels and beach equipment in case we didn’t bring any. We enjoyed the pool and the lights out there at night. It was a great stay would definitely recommend."
Comfy, clean, private home IN Venice, Florida; Heated Pool, Minutes to the Beach

Beach Retreat - Completely Renovated!!Half Duplex, WIFI/TV,1mile to Beach.

9.8 out of 10, Exceptional, (26)
"We had a lovely stay for three weeks in this well appointed duplex. Location was convenient to beaches ,restaurants and shopping. Communication with Ken the host was great. "
Beach Retreat - Completely Renovated!!Half Duplex, WIFI/TV,1mile to Beach.

3-bedroom pool house in Bradenton/Sarasota with fenced area for pets and kids

10.0 out of 10, Exceptional, (4)
"This place is a gem! So much space, great location, and lots of thoughtful touches like family games and pool towels and floats!"
3-bedroom pool house in Bradenton/Sarasota with fenced area for pets and kids

6 Mi to Beach: Bradenton Home w/ Pool & Yard

8.6 out of 10, Excellent, (46)
"Bad odor. "
6 Mi to Beach: Bradenton Home w/ Pool & Yard

Tranquil Siesta Key Retreat ~ Walk to Beach ~ Pool

9.4 out of 10, Exceptional, (16)
"We had a great stay at this property! We had five adults and one infant with plenty of room to be comfortable. We enjoyed the short walk to the beach and that beach chairs were provided by the HOA (umbrellas are not but there was one at the property). The owners were wonderful, fast responses to any messages and made sure we had everything we needed to have a great time! Definitely recommend this property if you’re in Siesta Key and looking to be very close to the beach!"
Tranquil Siesta Key Retreat ~ Walk to Beach ~ Pool

2-Car Garage, Private Pool & Beach Access, BBQ grill & Pool/Beach Things

10.0 out of 10, Exceptional, (103)
"We had a great stay at this spacious, clean, conveniently located property"
2-Car Garage, Private Pool & Beach Access, BBQ grill & Pool/Beach Things

Cozy 3 bedr townhouse beach retreat, only 60 steps to Siesta Key Public Beach!

9.6 out of 10, Exceptional, (77)
"Accommodations were perfect for our family Thanksgiving get away. "
The price is AU$1,636
includes taxes & fees
20 July - 21 July
Cozy 3 bedr townhouse beach retreat, only 60 steps to Siesta Key Public Beach!

2 Bedrooms, Bay WaterViews, Beaches, shops, Marina, fishing, all near by

9.6 out of 10, Exceptional, (11)
"The property was exactly what we hoped it would be. It is in a quiet neighborhood not far from great beaches and restaurants. My friend and I loved every minute! The sunsets were beautiful!"
2 Bedrooms, Bay WaterViews, Beaches, shops, Marina, fishing, all near by

Suite w/ Shared Pool, Free WiFi, Central AC - Steps to the White Sand Beach

9.0 out of 10, Wonderful, (52)
"Some errors in listing. No laundry, pool not heated. Otherwise very good place."
Suite w/ Shared Pool, Free WiFi, Central AC - Steps to the White Sand Beach
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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