Holiday Homes in Osprey

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Our top choices for Osprey holiday homes

Charming Osprey Home

Charming Osprey Home
2.0 star property
Bay Acres
10.0 out of 10, Exceptional, (1 review)
"Upon entering the property, we felt it was clean, bright and very welcoming. We loved the decor and the nice spaces in this two bedroom, two bath home. We thought the location was perfect, right across the main street is Walmart for quick grocery items, and we liked the amenities including a kettle for hot tea, a coffeemaker and a fully equipped kitchen! We would have liked to have more than two beach towels, but we made do with two. The laundry room was convenient for washing clothes and did...
United States
Van-Ha N.
Charming Osprey Home

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, (1 review)
"The remodeling of this older building is amazing! Very comfortable with everything you need. We couldn't get the coffeemaker to work but no problem, we travel with our coffeemaker. Restful and relaxing atmosphere. We would choose this cottage again."
United States
HaroldnMarla J.
The price is €263
includes taxes & fees
15 Jan - 16 Jan
Charming 2-bedroom house in Englewood with WiFi and AC

The Balboa - Modern Luxury Getaway

The Balboa - Modern Luxury Getaway
2.0 star property
North Port
10.0 out of 10, Exceptional, (4 reviews)
"Place was great, host was friendly and checked in during stay. "
United States
Bill A.
The price is €323
includes taxes & fees
15 Jan - 16 Jan
The Balboa - Modern Luxury Getaway

PLACE TO BE. we have everything you need

PLACE TO BE. we have everything you need
Warm Mineral Springs
9.6 out of 10, Exceptional, (8 reviews)
"We thoroughly enjoyed our stay! The property was impeccably clean, boasted a prime location, and featured a well-equipped kitchen. It had everything we needed for a wonderful stay."
United States
Alex M.
The price is €274
includes taxes & fees
15 Jan - 16 Jan
PLACE TO BE. we have everything you need

Siesta Heron Suites & Villas

Siesta Heron Suites & Villas
3.5 star property
Siesta Key
8.6 out of 10, Excellent, (38 reviews)
"Clean pool great apartment could use more seating in living room. Beach chairs was cool patio was awesome parking good water pressure great bed clean and comfy "
United States
jason
The price is €304
includes taxes & fees
15 Jan - 16 Jan
Siesta Heron Suites & Villas

Myakka River

Myakka River
Venice
9.8 out of 10, Exceptional, (18 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 €401
includes taxes & fees
15 Jan - 16 Jan
Myakka River

Venice Dove Shell

Venice Dove Shell
2.0 star property
Venice East
10.0 out of 10, Exceptional, (2 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.
The price is €330
includes taxes & fees
21 Jan - 22 Jan
Venice Dove Shell

The Mermaid at Tiny House Siesta

The Mermaid at Tiny House Siesta
2.0 star property
Sarasota
10.0 out of 10, Exceptional, (2 reviews)
"It was exactly as listed on here. No problems with the check in it was very smooth as well as the check out process. Location was AMAZING, we were able to walk just 10 minutes to a longhorn to eat dinner and right next to it there was a bar near the beach and we were able to go back to the property just by walking. Really calm the area and the tiny house is very comfortable."
United States
Jackeline R.
The price is €184
includes taxes & fees
15 Jan - 16 Jan
The Mermaid at Tiny House Siesta

Charming 2-bedroom house in lovely Sarasota with yard.

Charming 2-bedroom house in lovely Sarasota with yard.
Kensington Park
10.0 out of 10, Exceptional, (6 reviews)
"Easy to check in, clean and comfortable "
United States
Hugo J.
The price is €191
includes taxes & fees
2 Feb - 3 Feb
Charming 2-bedroom house in lovely Sarasota with yard.

Mimosa Memories

Mimosa Memories
South Venice
9.4 out of 10, Exceptional, (30 reviews)
"Nice quiet home , very clean. "
United States
David M.
Mimosa Memories

HAPPY FUN BLUE HOUSE for 8 people kids, pets friendly, 3 miles from the beach🏖️

HAPPY FUN BLUE HOUSE for 8 people kids, pets friendly, 3 miles from the beach🏖️
South Venice
9.8 out of 10, Exceptional, (48 reviews)
"Great place to stay especially if you have dogs "
United States
Erica R.
HAPPY FUN BLUE HOUSE for 8 people kids, pets friendly, 3 miles from the beach🏖️

Perfect Getaway with the pool

Perfect Getaway with the pool
North Port
10.0 out of 10, Exceptional, (26 reviews)
"We enjoyed our stay very much. Will stay again"
United States
Christi K.
The price is €357
includes taxes & fees
15 Jan - 16 Jan
Perfect Getaway with the pool

Old Floridian cottage in Historic Gulf Village

Old Floridian cottage in Historic Gulf Village
Olde Englewood Village
9.8 out of 10, Exceptional, (60 reviews)
"Very good, great location 👍👍"
United States
James M.
The price is €278
includes taxes & fees
12 Feb - 13 Feb
Old Floridian cottage in Historic Gulf Village

Enjoy Coastal Townhome w/ sunset views! Near The Gulf’s most popular beaches!

Enjoy Coastal Townhome w/ sunset views! Near The Gulf’s most popular beaches!
2.0 star property
Sabal Harbour
10.0 out of 10, Exceptional, (22 reviews)
"Everything was great!"
United States
Lisa and Colin M.
The price is €293
includes taxes & fees
15 Jan - 16 Jan
Enjoy Coastal Townhome w/ sunset views! Near The Gulf’s most popular beaches!

Comfortable 3-bedroom home with WiFi and AC in Englewood, 3.5 mil. to beache

Comfortable 3-bedroom home with WiFi and AC in Englewood, 3.5 mil. to beache
2.0 star property
Englewood Central
9.8 out of 10, Exceptional, (7 reviews)
"The owner was very nice and responded right away if we had any questions. Nice clean place. Enjoyed our stay and location was great!"
United States
Barbara K.
The price is €401
includes taxes & fees
17 Jan - 18 Jan
Comfortable 3-bedroom home with WiFi and AC in Englewood, 3.5 mil. to beache

Small But Cute 1/1 In A Tropical Oasis, Close To Siesta Beach

Small But Cute 1/1 In A Tropical Oasis, Close To Siesta Beach
Sarasota
9.4 out of 10, Exceptional, (17 reviews)
"Great location! Clean, easy to find and perfect amount of room. "
United States
Maribeliz G.
The price is €211
includes taxes & fees
2 Feb - 3 Feb
Small But Cute 1/1 In A Tropical Oasis, Close To Siesta Beach

Beachy Sarasota Duplex

Beachy Sarasota Duplex
Sarasota
10.0 out of 10, Exceptional, (3 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 €361
includes taxes & fees
15 Jan - 16 Jan
Beachy Sarasota Duplex

Majestic Summer Sunsets just 50 steps to uncrowded beach & 2 King beds

Majestic Summer Sunsets just 50 steps to uncrowded beach & 2 King beds
Manasota Key
10.0 out of 10, Exceptional, (43 reviews)
"Very good location and very nice beach home"
United States
Kourtney B.
Majestic Summer Sunsets just 50 steps to uncrowded beach & 2 King beds

Waterfront! PET, Our Kayaks or your boat. JACUZZI, patios! EZ to shops and Beach

Waterfront! PET, Our Kayaks or your boat. JACUZZI, patios! EZ to shops and Beach
Englewood South
8.6 out of 10, Excellent, (10 reviews)
"Great place to stay right on the water! "
United States
Richard W.
The price is €338
includes taxes & fees
15 Jan - 16 Jan
Waterfront! PET, Our Kayaks or your boat. JACUZZI, patios! EZ to shops and Beach

Location! 10 minutes drive to Siesta Beach

Location! 10 minutes drive to Siesta Beach
Sarasota
9.4 out of 10, Exceptional, (9 reviews)
"Great place"
United States
Jose
The price is €326
includes taxes & fees
18 Jan - 19 Jan
Location! 10 minutes drive to Siesta 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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Top Osprey Hotel Reviews

Find out more about Osprey

Osprey Holiday Homes information

Number of reviews
344
Accommodation
3924 Holiday Homes
Lowest Price
€184
Highest Price
€401