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Compare 27 Guest Houses in Osprey with updated reviews, rates, and availability.

All-New, First Floor, Huge Pool, 70" TV, Tiki Bar!

9.0 out of 10, Wonderful, (26)
"Great "
The price is AED 437
AED 771 total
includes taxes & fees
19 Apr - 20 Apr
All-New, First Floor, Huge Pool, 70" TV, Tiki Bar!

Quick and Easy Walk Downtown - Tons of Amenities

9.8 out of 10, Exceptional, (107)
"The property was well taken care of and easy to access. There was almost every amenity you could need and we wished we had been able to stay longer to utilize them. Everything was clean and well kept and the instructions clear and simple. All in all, it was a fabulous place and experience. "
The price is AED 536
AED 841 total
includes taxes & fees
29 Apr - 30 Apr
Quick and Easy Walk Downtown - Tons of Amenities

All-New, Ground-Floor, Huge Pool, Tiki Bar & Grill

7.6 out of 10, Good, (5)
"We enjoyed our stay"
The price is AED 437
AED 771 total
includes taxes & fees
19 Apr - 20 Apr
All-New, Ground-Floor, Huge Pool, Tiki Bar & Grill

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

9.8 out of 10, Exceptional, (96)
"We had a wonderful time, the guest house was perfect! Great location, easy to get around. I would recommend this place and if I could give 10 stars I would. We look forward to going back again. "
The price is AED 492
AED 982 total
includes taxes & fees
24 Apr - 25 Apr
Close to Siesta Key beach with a hot tub and a large garden

Lido Beach Walk! One block to beach!

10.0 out of 10, Exceptional, (106)
"The host is actually wonderful and goes above and beyond. The property is exactly as described. The location is rigjt across from the beach and free trolley access that takes you to st armands circle and downtown sarasota. So easy access to great food without the need of driving. No complaints "
Lido Beach Walk! One block to beach!

Downtown Sarasota 2BR Cottage

2.0 star property
10.0 out of 10, Exceptional, (2)
"My husband and I rented this house and were inspired by its close proximity to downtown Sarasota. The house was a haven of cleanliness and comfort, equipped with everything we needed, including beach furniture that enhanced our experience. We look forward to returning to this special place again."
Downtown Sarasota 2BR Cottage

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

Private guesthouse near the beach

9.4 out of 10, Exceptional, (20)
"Great stay, thank you for accommodating us."
Private guesthouse near the beach

Heated Pool, King Bed, Bunk Bed, Huge TV, Marina, Tiki Bar & Grill

7.4 out of 10, Good, (3)
"Great little stay. Kids loved the pool and the food at the restaurant."
The price is AED 437
AED 812 total
includes taxes & fees
20 Apr - 21 Apr
Heated Pool, King Bed, Bunk Bed, Huge TV, Marina, Tiki Bar & Grill

All-New, Private, 70" TV, Heated Pool, Tiki Bar & Grill

7.2 out of 10, Good, (5)
"Great location, close to the airport"
The price is AED 437
AED 771 total
includes taxes & fees
19 Apr - 20 Apr
All-New, Private, 70" TV, Heated Pool, Tiki Bar & Grill

Luxury Pool Retreat near Siesta Key

2.0 star property
10.0 out of 10, Exceptional, (1)
"Conveniently located. This is a beautiful and spacious home. The staff were super responsive and kind. The traffic is a little loud due to its central location, but not horrible. Ice/water dispenser didn’t work but they ordered the part while we were there."
Luxury Pool Retreat near Siesta Key

Amazing Location West of the Trail

9.8 out of 10, Exceptional, (18)
"Perfect for a getaway."
Amazing Location West of the Trail

Adorable 1920s Cottage in a Tropical Wooded Setting!

9.8 out of 10, Exceptional, (57)
"Great place. Owners were very kind and lovely place. Very clean!"
Adorable 1920s Cottage in a Tropical Wooded Setting!

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!

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."
The price is AED 459
AED 863 total
includes taxes & fees
28 Apr - 29 Apr
Magical Guesthouse 1 mi from SRQ airport

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

10.0 out of 10, Exceptional, (18)
"I had a great time at the guesthouse. It was clean, nice and in great conditions. It is close to St Armand's Circle and to the beach. Recommend this place to anyone and will definitely come back."
Adorable 1 Bedroom, 1 Bath guesthouse < 1block to Lido Beach

Lido Beach Corner of Beach and St. Armand Circle B

9.4 out of 10, Exceptional, (84)
"Wonderful stay"
Lido Beach Corner of Beach and St. Armand Circle B

Bayfront Beauty

2.5 star property
4.0 out of 10, (2)
"This was a basement room with an add-on kitchen. Nothing like pictured. Not very clean. Not really any waterfront view or access. Your grandma might like it. "
Bayfront Beauty

All-New, Bunk Bed, Huge Pool, 70" TV, Tiki Bar & Grill!

9.2 out of 10, Wonderful, (14)
"Good hotel"
All-New, Bunk Bed, Huge Pool, 70" TV, Tiki Bar & Grill!

Luxe 3BR Siesta Key Home Pool

3.0 star property
Luxe 3BR Siesta Key Home Pool
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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Other property types in Osprey

Huge Pool, Close to Beaches, Restaurants, Shopping & More!

9.6 out of 10, Exceptional, (22)
"What a wonderful place to relax! Will definitely recommend to family and friends and even come back to stay!"
Huge Pool, Close to Beaches, Restaurants, Shopping & More!

Tropical Beach Resorts

3.5 star property
9.4 out of 10, Exceptional, (4627)
"Wonderful stay. I enjoy that the resort is so close to the beautiful beach and also local dining and shopping."
The price is AED 590
AED 750 total
includes taxes & fees
20 Apr - 21 Apr
Tropical Beach Resorts

Hibiscus Suites - Gateway to Siesta Key

2.5 star property
8.6 out of 10, Excellent, (2113)
"Friendly staff, clean and roomy"
The price is AED 606
AED 684 total
includes taxes & fees
1 May - 2 May
Hibiscus Suites - Gateway 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.