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Compare 26 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, (18)
"Great location, central to a lot of things to do. Great resturant and bar on site. Room clean and nicely decorated. Toilet runs if not careful when flushing. Had to unplug fridge to use micro. Despite a few quires like that i would stay again. few"
The price is AED 547
AED 906 total
includes taxes & fees
2 Mar - 3 Mar
All-New, First Floor, Huge Pool, 70" TV, Tiki Bar!

Quick and Easy Walk Downtown - Tons of Amenities

9.8 out of 10, Exceptional, (101)
"This was such a perfect place to rent! Excellent location, the room was perfect for the two of us. Stephanie was a great host and helped us with all our questions and needs. She had bikes and kayaks and an amazing notebook with information about the area and all the appliances in the rental. Hoping to come to this are again. "
The price is AED 845
AED 1,208 total
includes taxes & fees
10 Mar - 11 Mar
Quick and Easy Walk Downtown - Tons of Amenities

The Cottages at Siesta Key

2.5 star property
9.2 out of 10, Wonderful, (232)
"Clean ,Beautiful and a caring person "
The Cottages at Siesta Key

Amazing Location West of the Trail

9.8 out of 10, Exceptional, (17)
"We had a fabulous day at Steven’s property. The photographs really don’t do the property justice. Everything was immaculately clean and the property had everything we needed for a stay near the beach. The property is in a very safe area with lots of amenities in close proximity. Steven was super helpful when my account with Vrbo wasn’t working and incredibly patient. Looking forward to visiting sunny Sarasota soon :) "
Amazing Location West of the Trail

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

8.0 out of 10, Very Good, (2)
"Close to beach. Very comfortable. Pool and patio very nice. Garage a plus for all our fishing stuff. Thankyou"
Modern, cozy family get-a-way: Bottomless Mimosa

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

9.8 out of 10, Exceptional, (92)
"We really enjoyed staying at this property- well appointed and convenient to everything!"
The price is AED 437
AED 924 total
includes taxes & fees
23 Feb - 24 Feb
Close to Siesta Key beach with a hot tub and a large garden

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

7.6 out of 10, Good, (5)
"Property was fine. There were hangers but no rod to hang them on. Also, no real place to hang wet towels. The shower doors do not really keep the water from leaking out and soaking the floor around the toilet. Other than these couple small things, the room was good. WiFi was pretty bad but not anything the owners can do about that."
The price is AED 474
AED 820 total
includes taxes & fees
18 Feb - 19 Feb
All-New, Ground-Floor, Huge Pool, Tiki Bar & Grill

Private guesthouse near the beach

9.6 out of 10, Exceptional, (17)
"Great stay, thank you for accommodating us."
Private guesthouse near the beach

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

7.4 out of 10, Good, (3)
"The property is within Ramada hotel and it is pretty run down. It was on the second floor no view. We had to keep curtains closed all day for privacy. "
The price is AED 474
AED 820 total
includes taxes & fees
18 Feb - 19 Feb
All-New, Private, 70" TV, Heated Pool, Tiki Bar & Grill

Bright, Light, Modern & Cozy Guesthouse. Minutes from the beach & downtown.

10.0 out of 10, Exceptional, (3)
"This small space was set up perfectly to maximize the stay. It was about a 15 minute drive to the beach or downtown Sarasota. They have everything needed in the space to make the stay enjoyable"
The price is AED 514
AED 869 total
includes taxes & fees
4 Mar - 5 Mar
Bright, Light, Modern & Cozy Guesthouse. Minutes from the beach & downtown.

Adorable 1920s Cottage in a Tropical Wooded Setting!

10.0 out of 10, Exceptional, (52)
"Perfect home base at the end of a long beach day, being gated felt like we were in our own little bubble. Nigel has super helpful with quick resolution when I had trouble with the key. All in all, good stay."
Adorable 1920s Cottage in a Tropical Wooded Setting!

Travelers Nook close to Venice Beach!

2.0 star property
9.0 out of 10, Wonderful, (2)
"Good place"
Travelers Nook close to Venice Beach!

Lido Beach Walk! One block to beach!

10.0 out of 10, Exceptional, (104)
"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!

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 639
AED 1,106 total
includes taxes & fees
11 Mar - 12 Mar
Magical Guesthouse 1 mi from SRQ airport

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 547
AED 959 total
includes taxes & fees
16 Mar - 17 Mar
Heated Pool, King Bed, Bunk Bed, Huge TV, Marina, Tiki Bar & Grill

Lido Beach Corner of Beach and St. Armand Circle B

9.4 out of 10, Exceptional, (84)
"Location, location, location!!!! Walk to anything and everything. Venue needs a little TLC.would book again."
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)
"This room was comfortable for myself and my two children 9 and 7. The beds were comfortable and new. The sheets didn’t stay on the mattresses very well though. The dresser and nightstand had more than adequate storage space for clothes for a week. Mugs, cups and silverware were available and a large refrigerator. The location was easy to access beaches and stores nearby. The tiki bar is delicious and we tried several food items and they were great. The service was fairly slow whether it was busy...
All-New, Bunk Bed, Huge Pool, 70" TV, Tiki Bar & Grill!

Warm Springs Nook near Boca Grande Beach

Warm Springs Nook near Boca Grande Beach

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

Tropical Beach Resorts

3.5 star property
9.4 out of 10, Exceptional, (4556)
"Loved the ambiance and close proximity to beach and dining."
The price is AED 940
AED 1,145 total
includes taxes & fees
9 Mar - 10 Mar
Tropical Beach Resorts

Tiny House Siesta

2.0 star property
8.4 out of 10, Very Good, (213)
"Very cute and great idea for a place to stay!! Clean and everything was very smooth as far as contact to get in and instructions, definitely would stay again"
The price is AED 448
AED 714 total
includes taxes & fees
26 Feb - 27 Feb
Tiny House Siesta

The Ringling Beach House

3.5 star property
9.0 out of 10, Wonderful, (290)
"Could be more clean and updated. Great location!"
The price is AED 951
AED 1,449 total
includes taxes & fees
24 Feb - 25 Feb
The Ringling Beach House
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.