Holiday Homes in Osprey

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Our top choices for Osprey holiday homes

Charming Osprey Home

Charming Osprey Home
Bay Acres
10.0 out of 10, Exceptional, (2 reviews)
"We had a positive experience staying at Linda’s duplex in Osprey. Linda was a lovely host and even furnished us with beach chairs and a cabana . The place was spotless & location was convenient for us as we explored most of the Sarasota, Venice & Naples area. Highly recommended staying at this lovely duplex. "
United States
Diane S.
The price is AU$573
includes taxes & fees
10 May - 11 May
Charming Osprey Home

Sunny Coastal Escape

Sunny Coastal Escape
Bay Acres
10.0 out of 10, Exceptional, (5 reviews)
"Great location for exploring north & south! House was very clean and comfy. We appreciated the excellent communication with our nice host, Lynn."
United States
Kaja F.
The price is AU$577
includes taxes & fees
10 May - 11 May
Sunny Coastal Escape

Coastal Quadruplex with private beach access & deck - dog-friendly

Coastal Quadruplex with private beach access & deck - dog-friendly
Manasota Key
8.2 out of 10, Very good, (17 reviews)
"Great place to stay. "
United States
Scott
The price is AU$537
includes taxes & fees
12 Apr - 13 Apr
Coastal Quadruplex with private beach access & deck - dog-friendly

Charming 2-bedroom house in Englewood with WiFi and AC

Charming 2-bedroom house in Englewood with WiFi and AC
Englewood South
10.0 out of 10, Exceptional, (3 reviews)
"Cute, clean, comfortable beds. Perfect for our needs."
United States
Sharon K.
The price is AU$411
includes taxes & fees
3 May - 4 May
Charming 2-bedroom house in Englewood with WiFi and AC

Dog-Friendly Quadruplex w/Snowbird Discounts and Private Beach Access

Dog-Friendly Quadruplex w/Snowbird Discounts and Private Beach Access
Manasota Key
9.0 out of 10, Wonderful, (11 reviews)
"Perfect getaway beach trip."
United States
jill s.
The price is AU$537
includes taxes & fees
12 Apr - 13 Apr
Dog-Friendly Quadruplex w/Snowbird Discounts and Private Beach Access

Nestled in North Port. Updated 2 Bed / 1 Bath.

Nestled in North Port. Updated 2 Bed / 1 Bath.
North Port
10.0 out of 10, Exceptional, (21 reviews)
"Great place loved how clean and put together everything was would definitely stay here again"
United States
Jacob
The price is AU$315
includes taxes & fees
12 Apr - 13 Apr
Nestled in North Port. Updated 2 Bed / 1 Bath.

PLACE TO BE we have everything you need

PLACE TO BE we have everything you need
Warm Mineral Springs
9.0 out of 10, Wonderful, (15 reviews)
"Perfect size for the three of us and my dog. We had a wonderful week."
United States
Ariel B.
The price is AU$448
includes taxes & fees
11 Apr - 12 Apr
PLACE TO BE we have everything you need

Myakka River

Myakka River
Venice
10.0 out of 10, Exceptional, (21 reviews)
"We loved everything about the property it’s nice and quiet. Nicely decorated and has a nice outdoor area and dock. The bed was a little firm for my taste but not terrible. 10/10 would stay here again "
United States
Ty
The price is AU$646
includes taxes & fees
10 Apr - 11 Apr
Myakka River

Old Floridian cottage in Historic Gulf Village

Old Floridian cottage in Historic Gulf Village
Olde Englewood Village
9.8 out of 10, Exceptional, (61 reviews)
"Very good, great location 👍👍"
United States
James M.
The price is AU$393
includes taxes & fees
1 May - 2 May
Old Floridian cottage in Historic Gulf Village

Waterfront Getaway, a Boating Paradise

Waterfront Getaway, a Boating Paradise
Englewood
10.0 out of 10, Exceptional, (52 reviews)
"Always an amazing stay"
United States
christine w.
The price is AU$495
includes taxes & fees
13 Apr - 14 Apr
Waterfront Getaway, a Boating Paradise

New Two story Cozy House Near Warm Mineral Springs

New Two story Cozy House Near Warm Mineral Springs
North Port
10.0 out of 10, Exceptional, (21 reviews)
"Great home to stay in with extended family, the three bathrooms were a must, the only downside is the home is on a busy road. "
United States
LaVar R.
The price is AU$642
includes taxes & fees
12 Apr - 13 Apr
New Two story Cozy House Near Warm Mineral Springs

Mimosa Memories

Mimosa Memories
South Venice
9.6 out of 10, Exceptional, (37 reviews)
"Me and my significant other took a little mini vacation wonderful house. It was very clean very beautiful inside, I like the beach vibes beautiful bedrooms. I recommend anybody to book this place. If I had to go back, I’ll book again. "
United States
Alexus
The price is AU$471
includes taxes & fees
12 Apr - 13 Apr
Mimosa Memories

Sunshine Hideaway 6 mins to Warm Mineral Springs

Sunshine Hideaway 6 mins to Warm Mineral Springs
North Port
10.0 out of 10, Exceptional, (7 reviews)
"Home was clean and inviting, and served us well during our stay. Loved the Christmas decorations! "
United States
Andrea and Dennis B.
The price is AU$372
includes taxes & fees
15 Apr - 16 Apr
Sunshine Hideaway 6 mins to Warm Mineral Springs

Relaxing Poolside- a Private Oasis -heated pool- 7min to beach-2 King beds

Relaxing Poolside- a Private Oasis -heated pool- 7min to beach-2 King beds
South Venice
10.0 out of 10, Exceptional, (38 reviews)
"The hosts Dorcia and Mac provide a quality vacation rental that feels like home. We enjoyed the pool and comfortable home. Any questions were quickly answered. The home has everything you could need during your vacation."
United States
R P.
The price is AU$657
includes taxes & fees
4 May - 5 May
Relaxing Poolside- a Private Oasis -heated pool- 7min to beach-2 King beds

Path to Paradise.

Path to Paradise.
Olde Englewood Village
The price is AU$435
includes taxes & fees
12 Apr - 13 Apr
Path to Paradise.

Home in quiet Bird Sanctuary Neighborhood, close to Beach

Home in quiet Bird Sanctuary Neighborhood, close to Beach
South Venice
9.6 out of 10, Exceptional, (19 reviews)
"Good location for us"
United States
EdgefieldFarm
The price is AU$608
includes taxes & fees
14 Apr - 15 Apr
Home in quiet Bird Sanctuary Neighborhood, close to Beach

Beachy Sarasota Duplex

Beachy Sarasota Duplex
Sarasota
10.0 out of 10, Exceptional, (4 reviews)
"Great experience. House was in a great location and having a Dunkin walking distance was a plus. Definitely would recommend. Thank you A"
United States
pete t.
The price is AU$646
includes taxes & fees
14 Apr - 15 Apr
Beachy Sarasota Duplex

Coastal 2-Bedroom Home Minutes to Beach

Coastal 2-Bedroom Home Minutes to Beach
3.0 star property
Englewood Central
10.0 out of 10, Exceptional, (3 reviews)
"Great space- had everything needed to enjoy a beach stay"
United States
Adriana
The price is AU$601
includes taxes & fees
10 Apr - 11 Apr
Coastal 2-Bedroom Home Minutes to Beach

Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.

Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.
Southgate
10.0 out of 10, Exceptional, (73 reviews)
"Wonderful Stay"
United States
Christopher R.
The price is AU$383
includes taxes & fees
13 Apr - 14 Apr
Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.

Peaceful And Private Unit, With Cover Parking

Peaceful And Private Unit, With Cover Parking
Ridge Wood Heights
9.6 out of 10, Exceptional, (22 reviews)
"Had everything you would need…great communication from the owner!"
United States
Marty B.
The price is AU$436
includes taxes & fees
14 Apr - 15 Apr
Peaceful And Private Unit, With Cover Parking
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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Top Osprey Hotel Reviews

Find out more about Osprey

Osprey Holiday Homes information

Number of reviews
398
Accommodation
3724 Holiday Homes
Lowest Price
AU$315
Highest Price
AU$657

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