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 €339
includes taxes & fees
16 Apr - 17 Apr
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 €347
includes taxes & fees
27 Apr - 28 Apr
Sunny Coastal Escape

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 €246
includes taxes & fees
29 Apr - 30 Apr
Charming 2-bedroom house in Englewood with WiFi and AC

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, (18 reviews)
"Great place to stay. "
United States
Scott
The price is €327
includes taxes & fees
16 Apr - 17 Apr
Coastal Quadruplex with private beach access & deck - dog-friendly

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 €191
includes taxes & fees
16 Apr - 17 Apr
Nestled in North Port. Updated 2 Bed / 1 Bath.

Relaxing 2 BED home near 🏖️Manasota Beach.

Relaxing 2 BED home near 🏖️Manasota Beach.
South Venice
9.4 out of 10, Exceptional, (29 reviews)
"The house is very well appointed and the location was very handy for the beach and historic Venice. The hosts were nice people and super helpful. "
United Kingdom
Chris C.
The price is €303
includes taxes & fees
16 Apr - 17 Apr
Relaxing 2 BED home near 🏖️Manasota Beach.

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 €220
includes taxes & fees
16 Apr - 17 Apr
Sunshine Hideaway 6 mins to 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 €281
includes taxes & fees
19 Apr - 20 Apr
Mimosa Memories

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 €286
includes taxes & fees
29 Apr - 30 Apr
Old Floridian cottage in Historic Gulf Village

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, (22 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 €387
includes taxes & fees
21 Apr - 22 Apr
New Two story Cozy House Near Warm Mineral Springs

Path to Paradise.

Path to Paradise.
Olde Englewood Village
The price is €327
includes taxes & fees
29 Apr - 30 Apr
Path to Paradise.

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, (39 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 €393
includes taxes & fees
4 May - 5 May
Relaxing Poolside- a Private Oasis -heated pool- 7min to beach-2 King beds

Centrally Located, Sarasota Home Close To Amish Community

Centrally Located, Sarasota Home Close To Amish Community
Sarasota Springs
10.0 out of 10, Exceptional, (173 reviews)
"This home was amazing! Honestly felt at home the moment I walked in. Everything you could need for your stay was provided. Very clean, great host. I'll be back!"
United States
Maudi B.
The price is €330
includes taxes & fees
16 Apr - 17 Apr
Centrally Located, Sarasota Home Close To Amish Community

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 €225
includes taxes & fees
19 Apr - 20 Apr
Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.

Paradise Retreat with HEATED POOL-- Need We Say More

Paradise Retreat with HEATED POOL-- Need We Say More
South Bradenton
10.0 out of 10, Exceptional, (182 reviews)
"Maggie ,the hostess, was great. Responsive and very accommodating for our needs. "
United States
David S.
The price is €312
includes taxes & fees
16 Apr - 17 Apr
Paradise Retreat with HEATED POOL-- Need We Say More

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
Home in quiet Bird Sanctuary Neighborhood, close to Beach

8 min to Beach ★ 5TV★Ice Hockey★ BBQ★ Bikes★Baby Gear ★Table Tennis ★Beach Gear

8 min to Beach ★ 5TV★Ice Hockey★ BBQ★ Bikes★Baby Gear ★Table Tennis ★Beach Gear
South Venice
10.0 out of 10, Exceptional, (43 reviews)
"Great Area! Clean home and friendly host! "
United States
Rhiannon S.
8 min to Beach ★ 5TV★Ice Hockey★ BBQ★ Bikes★Baby Gear ★Table Tennis ★Beach Gear

Venice Dove Shell

Venice Dove Shell
Venice East
9.8 out of 10, Exceptional, (6 reviews)
"The host was very welcoming, with timely communication and clear guidelines. The house was spacious, easily accommodating six guests. Also very orderly and clean. I'd recommend this property to friends."
United States
Angela B.
Venice Dove Shell

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 €429
includes taxes & fees
23 Apr - 24 Apr
Beachy Sarasota Duplex

Near beach• Hot tub• Heated pool• Fenced yard •Carport• Pet friendly•Private

Near beach• Hot tub• Heated pool• Fenced yard •Carport• Pet friendly•Private
South Venice
9.2 out of 10, Wonderful, (19 reviews)
"Great property and easy to contact host when needed. Grandkids loved the pool."
United States
Patty P.
Near beach• Hot tub• Heated pool• Fenced yard •Carport• Pet friendly•Private
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

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Osprey Holiday Homes information

Number of reviews
726
Accommodation
3724 Holiday Homes
Lowest Price
€191
Highest Price
€429