Search Guest Houses in Osprey

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Oct 10 - Oct 12
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Oct 31 - Nov 2
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Nov 28 - Nov 30

Guest Houses in Osprey

Close to Siesta Key beach with a hot tub and a large garden
Beach nearby, sun loungers, beach towels

Close to Siesta Key beach with a hot tub and a large garden

9.8 out of 10, Exceptional, (107)
"We really enjoyed staying at this guest house. The location is perfect for wanting to travel to different beaches in the area as well as great food and shopping options. It was very clean and set up really nicely. The washer and dryer was a huge plus also. The hosts were really nice and quick to respond to messages. Overall we had a great stay and would highly recommend it! "
$236 nightly
The price is $262
Oct 2 - Oct 3
Total with taxes and fees
Close to Siesta Key beach with a hot tub and a large garden
Lido Beach Walk! One block to beach!
Fridge, microwave, stovetop, dishwasher

Lido Beach Walk! One block to beach!

10.0 out of 10, Exceptional, (116)
"We had a wonderful stay at this property. The house was absolutely beautiful, extremely clean, very well stocked with supplies, and just a short block to Lido Beach. We would definitely stay there again when visiting Sarasota."
Lido Beach Walk! One block to beach!
Quick and Easy Walk Downtown - Tons of Amenities
Beach

Quick and Easy Walk Downtown - Tons of Amenities

9.8 out of 10, Exceptional, (115)
"Great little place to stay! "
$164 nightly
The price is $183
Oct 21 - Oct 22
Total with taxes and fees
Quick and Easy Walk Downtown - Tons of Amenities
Adorable 1 Bedroom, 1 Bath guesthouse < 1block to Lido Beach
Beach nearby, sun loungers, beach towels

Adorable 1 Bedroom, 1 Bath guesthouse < 1block to Lido Beach

10.0 out of 10, Exceptional, (20)
"Everything we needed for a grdat"
Adorable 1 Bedroom, 1 Bath guesthouse < 1block to Lido Beach
Modern, cozy family get-a-way: Bottomless Mimosa
Sun loungers, beach towels

Modern, cozy family get-a-way: Bottomless Mimosa

8.0 out of 10, Very Good, (2)
"Very relaxing and quite, just what we needed."
Modern, cozy family get-a-way: Bottomless Mimosa
Amazing Location West of the Trail
Outdoor pool

Amazing Location West of the Trail

9.6 out of 10, Exceptional, (20)
"Perfect for a getaway."
Amazing Location West of the Trail
Adorable 1920s Cottage in a Tropical Wooded Setting!
Outdoor dining

Adorable 1920s Cottage in a Tropical Wooded Setting!

9.8 out of 10, Exceptional, (61)
"This is my second stay at the cottage and it was just as pleasant as the first. It's extremely private, quiet and surrounded by a lovely garden. The host is wonderful and check in was seamless. I'm looking forward to further stays "
Adorable 1920s Cottage in a Tropical Wooded Setting!
Travelers Nook close to Venice Beach!
Beach nearby

Travelers Nook close to Venice Beach!

2.0 star property
9.4 out of 10, Exceptional, (3)
"Good place"
Travelers Nook close to Venice Beach!
Private guesthouse near the beach
Beach nearby, sun loungers, beach towels

Private guesthouse near the beach

9.4 out of 10, Exceptional, (20)
"Great stay, thank you for accommodating us."
Private guesthouse near the beach
Luxury Pool Retreat near Siesta Key
Classic Room | Private kitchen | Fridge, microwave, oven, stovetop

Luxury Pool Retreat near Siesta Key

2.0 star property
8.8 out of 10, Excellent, (3)
"Great property. Definitely worth the price "
Luxury Pool Retreat near Siesta Key
Downtown Sarasota 2BR Cottage
Exterior

Downtown Sarasota 2BR Cottage

2.0 star property
10.0 out of 10, Exceptional, (4)
"Great place. Comfortable,safe and convenient!!"
Downtown Sarasota 2BR Cottage
Magical Guesthouse 1 mi from SRQ airport
Beach

Magical Guesthouse 1 mi from SRQ airport

10.0 out of 10, Exceptional, (3)
"This house was absolutely charming! I caught myself In complete awe of every detail - from the fun decor, to the thoughtful inclusion of all kitchen supplies to make a full meal, to the soft shower towels and the incredibly comfortable bed, bedding and pillows! Fantastic stay."
$245 nightly
The price is $245
Oct 2 - Oct 3
Total with taxes and fees
Magical Guesthouse 1 mi from SRQ airport
Bayfront Beauty
Spa

Bayfront Beauty

2.5 star property
4.0 out of 10, (2)
"This is absolutely NOT anything as it is listed. This is a garage turned into an efficiency in someone’s private home. There are NO windows, NO A/C, NO access to the beach. I suppose there may be a pool, however you need to go down the road to find it. Also, the homeowners live in the house above you and you can hear their children and dog running around and barking. "
Bayfront Beauty
Luxe 3BR Siesta Key Home Pool
Outdoor pool

Luxe 3BR Siesta Key Home Pool

3.0 star property
Luxe 3BR Siesta Key Home Pool
Coastal Comfort Studio
Exterior

Coastal Comfort Studio

Coastal Comfort Studio
Siesta Key Dream Inn
Beach nearby, white sand, free beach shuttle, beach umbrellas

Siesta Key Dream Inn

3.5 star property
Siesta Key Dream Inn
Close to Siesta Key
Property grounds

Close to Siesta Key

2.0 star property
Close to Siesta Key
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

Tropical Breeze Resort

Tropical Breeze Resort

10/10 Excellent
"Good"
Darismel 2-night trip
Posted 2 days ago
Tropical Breeze Resort

Find out more about Osprey

Find out more about Osprey

Osprey Guest Houses information

Number of reviews
464
Accommodation
17 Guest Houses
Lowest Price
$183
Highest Price
$262

Frequently asked questions

What is the nightly rate for a guest house in Osprey?
Rates for Osprey guest houses vary, but travelers can find great-value prices from $183 with Expedia. A range of factors can affect nightly rates, such as the location, the breakfast offering, and the range of amenities. Travelers looking for a good deal should consider looking for a midweek stay, as weekend rates at Osprey guest houses tend to be higher. Remember to also use our filters to sort prices from low to high.
What's the difference between a Osprey guest house and a B&B?
A guest house in Osprey is typically a larger establishment with more rooms, offering a more hotel-like experience, and may provide additional amenities including luxury bedding. In contrast, a B&B is usually a smaller property that focuses primarily on providing a room and breakfast. A B&B is often more personal, and breakfast is typically included as part of the stay, but other services might be more limited compared to a guest house.

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