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Compare 25 Guest Houses in Osprey with updated reviews, rates, and availability.

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

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

9.0 out of 10, Wonderful, (16)
"Like access to the restaurant and pool. Been 2 years in a row. Very clean, and staff was great! Both years parade people took over the pool. Unfortunately, rules were not followed in the pool area. "
The price is SAR 372
SAR 707 total
includes taxes & fees
5 Jan - 6 Jan
All-New, First Floor, Huge Pool, 70" TV, Tiki Bar!
Quick and Easy Walk Downtown - Tons of Amenities
Welcome to the Carriage House. Your base camp for exploring Sarasota.

Quick and Easy Walk Downtown - Tons of Amenities

9.8 out of 10, Exceptional, (97)
"The location was perfect for downtown access. We walked to the entire Bay Park, downtown, and surrounding neighborhoods—excellent shops and restaurants. Sarasota has a friendly, warm atmosphere with a plethora of events. This is the place to stay if you want to experience what downtown offers. The space was more than comfortable for two people, and the king-size bed was a haven of relaxation. We stayed for 5 nights and enjoyed every minute. Thank you, Stephanie! Your commitment to hosting and...
The price is SAR 746
SAR 1,121 total
includes taxes & fees
22 Jan - 23 Jan
Quick and Easy Walk Downtown - Tons of Amenities
The Cottages at Siesta Key
BBQ/picnic area

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
Close to Siesta Key beach with a hot tub and a large garden
Only about 2 miles from Siesta Key

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

10.0 out of 10, Exceptional, (87)
"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 SAR 496
SAR 1,034 total
includes taxes & fees
5 Jan - 6 Jan
Close to Siesta Key beach with a hot tub and a large garden
Adorable 1920s Cottage in a Tropical Wooded Setting!
Property grounds

Adorable 1920s Cottage in a Tropical Wooded Setting!

10.0 out of 10, Exceptional, (49)
"Thank you for a great experience "
Adorable 1920s Cottage in a Tropical Wooded Setting!
Amazing Location West of the Trail
Terrace/patio

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
Outdoor dining

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

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!
Siesta key Guest House 5 star on the water Private
Bedroom overlooking the fountain

Siesta key Guest House 5 star on the water Private

9.0 out of 10, Wonderful, (17)
"Pictures were a little misleading but over all a nice place to just get away. Very clean. Just needs a little TLC outside. Would not recommend for children."
The price is SAR 939
SAR 1,760 total
includes taxes & fees
1 Feb - 2 Feb
Siesta key Guest House 5 star on the water Private
All-New, Private, 70" TV, Heated Pool, Tiki Bar & Grill
Room

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 SAR 372
SAR 707 total
includes taxes & fees
5 Jan - 6 Jan
All-New, Private, 70" TV, Heated Pool, Tiki Bar & Grill
All-New, Ground-Floor, Huge Pool, Tiki Bar & Grill
Room

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 SAR 372
SAR 703 total
includes taxes & fees
7 Jan - 8 Jan
All-New, Ground-Floor, Huge Pool, Tiki Bar & Grill
NEW!! Gated 2/2 Single-family Guest House! 13 mins to Englewood Beach!
Guest House

NEW!! Gated 2/2 Single-family Guest House! 13 mins to Englewood Beach!

10.0 out of 10, Exceptional, (2)
"This gem is located in the center of multiple horse farms! Centrally located to everything you’ll want to see or do, including beaches, Dearborn Street, beachside dining, etc… Owners home is in front of cottage but not so close it feels on top of you. We met them and they are very nice and have a beautiful family. We loved petting one of their horses (you’re free to just wander the area around the cottage) and being a farm girl myself, I loved the roaming chickens and fresh eggs the owners...
NEW!! Gated 2/2 Single-family Guest House! 13 mins to Englewood Beach!
Lido Beach Walk! One block to beach!
Aerial view

Lido Beach Walk! One block to beach!

10.0 out of 10, Exceptional, (104)
"We booked this apartment because we had never been to Lido Key before and wanted to explore a new place. Shortly after booking we received a call from the owner. She was concerned that because of the two recent hurricanes we might be disappointed with the area. After a very honest and informative chat with the owner we were so impressed with her honesty we decided to book it anyway. Upon arriving Laveda, the owner, offered to pick us up at the airport. The hospitality continued throughout our...
Lido Beach Walk! One block to beach!
Bayfront Beauty
View from property

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

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 SAR 372
SAR 753 total
includes taxes & fees
5 Jan - 6 Jan
Heated Pool, King Bed, Bunk Bed, Huge TV, Marina, Tiki Bar & Grill
Private guesthouse near the beach
Exterior

Private guesthouse near the beach

9.6 out of 10, Exceptional, (17)
"Great stay, thank you for accommodating us."
Private guesthouse near the beach
Peaceful Riverfront Oasis with Private Island
RIVERFRONT VIEWS! BRING YOUR KAYAKS AND CANOES!

Peaceful Riverfront Oasis with Private Island

10.0 out of 10, Exceptional, (20)
"The property is amazing! Everything was excellent!"
Peaceful Riverfront Oasis with Private Island
Magical Guesthouse 1 mi from SRQ airport

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 SAR 590
SAR 1,048 total
includes taxes & fees
14 Jan - 15 Jan
Magical Guesthouse 1 mi from SRQ airport
Lido Beach Corner of Beach and St. Armand Circle B
Outdoor dining

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
Travelers Nook close to Venice Beach!
Open concept living area

Travelers Nook close to Venice Beach!

2.0 star property
Travelers Nook close to Venice 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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Other property types in Osprey

Tropical Beach Resorts
Outdoor pool

Tropical Beach Resorts

3.5 star property
9.4 out of 10, Exceptional, (4537)
"The stay at the hotel was good. Issue was if you didn’t purchase their chair and umbrella then you were forced to sit at the end where the beach area is not kept nice. You’re spending the same money as everyone else to stay at resort. Should have the same right to sit where you want on the beach. "
The price is SAR 674
SAR 846 total
includes taxes & fees
20 Jan - 21 Jan
Tropical Beach Resorts
The Residences at Siesta Key Beach by Hyatt Vacation Club
Exterior

The Residences at Siesta Key Beach by Hyatt Vacation Club

3.5 star property
9.8 out of 10, Exceptional, (220)
"Very lovely (and large!) accommodation. Extremely clean. Front desk staff kind of rude/pretentious.Great location right on the beach at Siesta Key. Heated pool with good poolside bar. Also had a hot tub, which was nice as the weather was a bit cool when we were there. Feel like I was misled a bit based on room description--thought we were booking a room with beach view, but instead got "city view"--which essentially looked into a back alley and at a 7-eleven. For the price/my personal budget,...
The price is SAR 1,836
SAR 2,266 total
includes taxes & fees
16 Jan - 17 Jan
The Residences at Siesta Key Beach by Hyatt Vacation Club
Hibiscus Suites - Gateway to Siesta Key
Outdoor pool

Hibiscus Suites - Gateway to Siesta Key

2.5 star property
8.6 out of 10, Excellent, (2081)
"Just over the bridge from the Key, stores with in walking distance. Room had a full size refrigerator! Two burner stove pots and pans and local super market not far, no need to eat out every night. The building has been upkept suprisingly very nice , and the staff was very helpful if anything came up. The area is a little older but overall you cant beat the value here. Oh yeah the pool was nice and hey have a grill you can use. "
The price is SAR 559
SAR 632 total
includes taxes & fees
6 Jan - 7 Jan
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.