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Compare 294 Cottages in Osprey with updated reviews, rates, and availability.

The Inn On Siesta Key

3.5 star property
10.0 out of 10, Exceptional, (173)
"Great place to stay! "
The price is SAR 1,120
SAR 1,406 total
includes taxes & fees
23 Apr - 24 Apr
The Inn On Siesta Key

Direct Beachfront Cottage-Casey Key/Nokomis Beach-2 bedrooms

9.2 out of 10, Wonderful, (52)
"Really enjoyed our stay. Location is excellent."
The price is SAR 1,869
SAR 3,164 total
includes taxes & fees
26 Apr - 27 Apr
Direct Beachfront Cottage-Casey Key/Nokomis Beach-2 bedrooms

Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

9.0 out of 10, Wonderful, (172)
"It was a quiet place we ended up not going very many places."
The price is SAR 559
SAR 1,859 total
includes taxes & fees
27 Apr - 28 Apr
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

Villa Margarita Sparkles

9.8 out of 10, Exceptional, (138)
"Everything was perfect. Location was great, and had a good time."
Villa Margarita Sparkles

Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.

9.6 out of 10, Exceptional, (73)
"Its right next to everything we needed"
The price is SAR 413
SAR 1,161 total
includes taxes & fees
19 May - 20 May
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.

Direct Beachfront Cottage-Casey Key/Nokomis Beach-1 Bedroom

9.2 out of 10, Wonderful, (84)
"We have known and loved this part of Florida, visiting in the Winter time for 35-plus years. We feel this is the best way for us to get away from northern snows and relax in an true Old Florida atmosphere. No glitz or glamour, just a gorgeous sunny beach, wildlife, starry skies at night, great seafood in numerous local restaurants, and many conveniences nearby. This was a perfect cottage for the two of us to relax in, and the proximity to the beach is what makes it worth every penny. We hope...
The price is SAR 1,681
SAR 2,871 total
includes taxes & fees
21 Apr - 22 Apr
Direct Beachfront Cottage-Casey Key/Nokomis Beach-1 Bedroom

ONLY 2 WKS LEFT IN MAY 5 Min walk to Beach & Village, Private Pool,On the Canal

9.8 out of 10, Exceptional, (16)
"We had an amazing time at Sophie’s Cottage. We lucked out and got a renovated home due to the Hurricanes. The proximity to the beach and town are great. Short bike ride to both. Jim, the owner, helped us immediately with any issues. Our kids caught snappers, catfish, jacks, sting rays and needle fish off of the dock of the home. Great time, great home, great location!!! "
ONLY 2 WKS LEFT IN MAY 5 Min walk to Beach & Village, Private Pool,On the Canal

Across The Street From #1 Beach

10.0 out of 10, Exceptional, (321)
"Great accommodations, great location."
Across The Street From #1 Beach

This cottage is a 2 bedroom(s), 2 bathrooms, located in Englewood, FL.

9.4 out of 10, Exceptional, (184)
"We were actually at a property in Venice Beach, a house with private pool. It was very nicely decorated and so comfortable. Close to everything. We had a blast."
This cottage is a 2 bedroom(s), 2 bathrooms, located in Englewood, FL.

Palm Shade Cottage | Charming 1-Bedroom in SK, Access to Pool, Walk to Beach!

10.0 out of 10, Exceptional, (1)
"The property was very nice and clean. It's also in a great location - very close to the beach and the Village. I will definitely stay here again."
Palm Shade Cottage | Charming 1-Bedroom in SK, Access to Pool, Walk to Beach!

Mermaid Cottage

10.0 out of 10, Exceptional, (11)
"Loved the decor and separate spaces. Liked that there was everything needed to prepare meals there. Nice stay."
Mermaid Cottage

Charming cottage for 2 across warm mineral springs park

8.8 out of 10, Excellent, (6)
"I stayed for 3 days to visit my aunt; this was a perfect space for me. Close to her but also to restaurants, shopping and everything I needed. Alik is great, and I'll be making sure to check in here first when I come back for more visits. Super clean, comfy and perfect for 1-2 people. Can't go wrong!! "
Charming cottage for 2 across warm mineral springs park

Island Life! King Bed Studio-Steps to beach

9.6 out of 10, Exceptional, (154)
"Great location, great price - close to beach and restaurants"
Island Life! King Bed Studio-Steps to beach

New Pool! - Tropical Waterfront Cottage -Dock & Optional Boat

10.0 out of 10, Exceptional, (14)
"We loved our stay in the cottage home celebrating out 1 year anniversary! Clean and fantastic communication with the owner..."
New Pool! - Tropical Waterfront Cottage -Dock & Optional Boat

Lovely ❤ Cottage - VERY close to Siesta Beach, Downtown, Shopping and More!!!

9.2 out of 10, Wonderful, (35)
"Perfect location!"
Lovely ❤ Cottage - VERY close to Siesta Beach, Downtown, Shopping and More!!!

The Coastal Oasis. 8 Mins from Englewood Beach!

10.0 out of 10, Exceptional, (14)
"This was one of the nicest, cutest little cottages we've ever stayed in. Bryan and his wife thought of everything. The place was spotless, bed was comfortable and really had everything that we needed. They left no stone unturned. Plenty of extras were provided including toilet paper, paper towels, trash bags, dish soap and hand soap including a stool in the shower perfect for us ladies to shave our legs. We enjoyed being able to walk to Dearborn St. and going to the farmers market on Thursdays....
The Coastal Oasis. 8 Mins from Englewood Beach!

Oystercatcher at Shorebirds, Bikes and Kayaks 3 minutes walk to beach!

10.0 out of 10, Exceptional, (65)
"Our family had a great time staying at this location. Super nice and clean, close to the beach and all the needed amenities. Highly recommend and we will book again in the future."
Oystercatcher at Shorebirds, Bikes and Kayaks 3 minutes walk to beach!

Light filled walk to bay 1 King BR,1 BA private cottage by the Ringling Museum

9.8 out of 10, Exceptional, (30)
"Fun stay, great location"
The price is SAR 563
SAR 923 total
includes taxes & fees
21 Apr - 22 Apr
Light filled walk to bay 1 King BR,1 BA private cottage by the Ringling Museum

Sarasota Home in Historic District w/ Patio!

9.8 out of 10, Exceptional, (11)
"This place was great. They were very accommodating of our changing schedule. Thank you"
Sarasota Home in Historic District w/ Patio!

#3 Small house walking distance to Warm Mineral Spring

8.6 out of 10, Excellent, (4)
"We really enjoyed our stay! Cozy little spot in a quiet area right by the park. Had everything we needed!"
#3 Small house walking distance to Warm Mineral Spring
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, (4628)
"Wonderful stay. I enjoy that the resort is so close to the beautiful beach and also local dining and shopping."
The price is SAR 522
SAR 674 total
includes taxes & fees
21 Apr - 22 Apr
Tropical Beach Resorts

Hibiscus Suites - Gateway to Siesta Key

2.5 star property
8.6 out of 10, Excellent, (2113)
"Spacious, clean, affordable and good location for a first trip to Sarasota. "
The price is SAR 619
SAR 699 total
includes taxes & fees
4 May - 5 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.