A marina with docked boats, a wooden bridge, and a building with a red roof.

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Check prices for these dates

In two weeks
Aug 14 - Aug 16
In two months
Sep 25 - Sep 27
In three months
Oct 23 - Oct 25
In four months
Nov 20 - Nov 22

Our top choices for Osprey cottages

Exterior

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

Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
South Village
9.6 out of 10, Exceptional, (89 reviews)
"Would definitely stay here again. Great location and great house! Owner was quick and helpful with communication."
United States
Clarissa S.
The price is CA $140
CA $427 total
includes taxes & fees
Aug 2 - Aug 3
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
Exterior

Yellow Palm Cottage steps from the beach

Yellow Palm Cottage steps from the beach
Siesta Key Village
10.0 out of 10, Exceptional, (1 review)
"This place was so cute and quaint! It was just a short walk to the village and to the beach. The grounds were beautiful! A little oasis in the backyard. . Would stay here again!!!"
United States
Tami B.
The price is CA $210
CA $914 total
includes taxes & fees
Aug 3 - Aug 4
Yellow Palm Cottage steps from the beach
On the beach, sun loungers, beach towels

Casey Key Beachfront Escape: Charming 1BR Cottage

Casey Key Beachfront Escape: Charming 1BR Cottage
Casey Key
9.4 out of 10, Exceptional, (128 reviews)
"We loved the cottage on the beach. The view was wonderful. Very peaceful location. The cottage was clean and had everything we needed. Highly recommend!"
United States
Virginia W.
The price is CA $350
CA $769 total
includes taxes & fees
Aug 14 - Aug 15
Casey Key Beachfront Escape: Charming 1BR Cottage
Outdoor dining

Cozy Lido Key Studio Steps to Beach & Kayaking

Cozy Lido Key Studio Steps to Beach & Kayaking
Lido Key
The price is CA $124
CA $472 total
includes taxes & fees
Jul 31 - Aug 1
Cozy Lido Key Studio Steps to Beach & Kayaking
Exterior

Blue Dolphin Cottage steps from the beach

Blue Dolphin Cottage steps from the beach
Siesta Key Village
The price is CA $201
CA $901 total
includes taxes & fees
Jul 30 - Jul 31
Blue Dolphin Cottage steps from the beach
Property grounds

Pink Mango Cottage steps from the beach

Pink Mango Cottage steps from the beach
Siesta Key Village
The price is CA $210
CA $914 total
includes taxes & fees
Aug 3 - Aug 4
Pink Mango Cottage steps from the beach
Hair dryer, towels, soap, shampoo

Sunny Lido Studio - Modern Touches

Sunny Lido Studio - Modern Touches
Lido Key
The price is CA $140
CA $490 total
includes taxes & fees
Aug 2 - Aug 3
Sunny Lido Studio - Modern Touches
Interior

Siesta Heron 6 / Sunset

Siesta Heron 6 / Sunset
3.0 star property
Siesta Key
The price is CA $685
CA $1,147 total
includes taxes & fees
Aug 25 - Aug 26
Siesta Heron 6 / Sunset
Exterior

Charming cottage for 2 across warm mineral springs park

Charming cottage for 2 across warm mineral springs park
Warm Mineral Springs
9.2 out of 10, Wonderful, (26 reviews)
"We were enjoying our stay."
United States
Inna K.
The price is CA $56
CA $187 total
includes taxes & fees
Jul 31 - Aug 1
Charming cottage for 2 across warm mineral springs park
1 bedroom, iron/ironing board, WiFi, bed sheets

Cozy Lido Key Bungalow by Pool & Beach

Cozy Lido Key Bungalow by Pool & Beach
Lido Key
The price is CA $124
CA $473 total
includes taxes & fees
Aug 28 - Aug 29
Cozy Lido Key Bungalow by Pool & Beach
Exterior

Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
Sarasota
9.2 out of 10, Wonderful, (187 reviews)
"Right across the beach Less then 5 minutes Good space - rooms nice ad clean "
United States
ASHISH
The price is CA $383
CA $696 total
includes taxes & fees
Aug 15 - Aug 16
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
House (3 Bedrooms) | Interior

Unwind Poolside + Walk to Beach! Sarasota Retreat

Unwind Poolside + Walk to Beach! Sarasota Retreat
3.0 star property
South Village
8.0 out of 10, Very good, (1 review)
"The location of the property was excellent. The home was clean and had everything we needed to prepare breakfast in the morning. The 3 bedrooms and 3 bathrooms made it easy for the six of us wash up and get ready for dinner after a fun fill day at the walkable beach. Beach was great. Having a pool at the property was great for the 2 youngsters. We also made use of the wagon that was available to carry items to the beach., The property is nothing fancy but a great value for the money. "
United States
Eleuterio
The price is CA $470
CA $961 total
includes taxes & fees
Aug 5 - Aug 6
Unwind Poolside + Walk to Beach! Sarasota Retreat
Terrace/patio

Direct Beachfront 2BR Cottage on Casey Key!

Direct Beachfront 2BR Cottage on Casey Key!
Casey Key
9.4 out of 10, Exceptional, (80 reviews)
"This is a great spot, this was our 2nd time staying and we will definitely be back. "
United States
Jason W.
The price is CA $350
CA $805 total
includes taxes & fees
Aug 9 - Aug 10
Direct Beachfront 2BR Cottage on Casey Key!
1 bedroom, iron/ironing board, WiFi, bed sheets

Lido Bungalow Walk to Beach & St. Armand's Circle

Lido Bungalow Walk to Beach & St. Armand's Circle
Lido Key
The price is CA $124
CA $471 total
includes taxes & fees
Aug 2 - Aug 3
Lido Bungalow Walk to Beach & St. Armand's Circle
Exterior

2 bedroom, walk to beach-bikes-kayaks-grill-picnic-hot outdoor shower-beach gear

2 bedroom, walk to beach-bikes-kayaks-grill-picnic-hot outdoor shower-beach gear
Manasota Key
9.6 out of 10, Exceptional, (4 reviews)
"Beautiful decor, perfect location to the beach (5min walking). very thoughtful touches throughout the rental. The kitchen is well- equipped with all you need. Bedroom with excellent mattress. The patio with BBQ, kayaks, free parking, beach chair /loungers available, the property was immaculate.10/10. I would recommend""
United States
Anabel P.
The price is CA $204
CA $612 total
includes taxes & fees
Aug 26 - Aug 27
2 bedroom, walk to beach-bikes-kayaks-grill-picnic-hot outdoor shower-beach gear
Outdoor dining

Miles of Private Gulf Beach-Luxury 4 BR-Pets Okay-Kayaks & SUPs-Best Shark Teeth

Miles of Private Gulf Beach-Luxury 4 BR-Pets Okay-Kayaks & SUPs-Best Shark Teeth
Englewood
9.8 out of 10, Exceptional, (42 reviews)
"Wow....this is one of the best VRBOs we've stayed in. Evan was a great host, very welcoming, helpful and quick to respond to questions. Location is so convenient to either Lemon Bay or the beach."
United States
Marla W.
The price is CA $777
CA $1,428 total
includes taxes & fees
Jul 31 - Aug 1
Miles of Private Gulf Beach-Luxury 4 BR-Pets Okay-Kayaks & SUPs-Best Shark Teeth
Outdoor dining

Siesta Heron 7

Siesta Heron 7
3.0 star property
Siesta Key
The price is CA $967
CA $1,613 total
includes taxes & fees
Aug 3 - Aug 4
Siesta Heron 7
House (4 Bedrooms) | Interior

Home < 1-mi Walk to Warm Mineral Springs Park!

Home < 1-mi Walk to Warm Mineral Springs Park!
3.0 star property
North Port
The price is CA $211
CA $629 total
includes taxes & fees
Aug 1 - Aug 2
Home < 1-mi Walk to Warm Mineral Springs Park!
Interior

Beach Road

Beach Road
2.0 star property
Siesta Key
The price is CA $1,076
CA $1,453 total
includes taxes & fees
Aug 15 - Aug 16
Beach Road
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

Inn at the Beach

Inn at the Beach

10/10 Excellent
"The staff couldn’t have been more helpful with annswers and support. This is a very welcoming environment and a great location for beach and town."
Lynn 5-night trip
Posted 1 hour ago
Inn at the Beach

Find out more about Osprey

Osprey Cottages information

Number of reviews
350
Accommodation
378 Cottages
Lowest Price
CA $187
Highest Price
CA $1,613

Frequently asked questions

How much do cottages in Osprey cost?
Cottages in Osprey range between CA $187 and CA $1,613 per night. These stays offer a chance to soak in nature's beauty — at a price you can afford. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
What are the best cottages in Osprey?
Osprey has multiple cottages with a total average guest review rating of 9.3. The Inn On Siesta Key is a terrific option if you're into nature and an easy-breezy pace. Guests of this 3.5-star stay will have access to a swimming pool and a garden. Flip Flop Cottages is another popular choice. This 3-star cottage features a swimming pool and a barbecue grill.
How many cottages are there in Osprey?
Take your pick of 378 cottages in Osprey. Whether you're vacationing with the kids or organizing a weekend break with close friends, Expedia can help you find the right space to get in touch with nature.
Are there any family-friendly cottages in Osprey?
Many travellers searching for a family-friendly cottage in Osprey choose The Inn On Siesta Key. With a 3.5-star rating and amenities including a nearby beach and a barbecue grill, you're sure to feel right at home here. Another superb option for travelling families is Flip Flop Cottages. A barbecue grill and a picnic area help make this 3-star cottage a comfortable base for your Osprey getaway. Osprey has tons of family-friendly attractions to check out that'll keep the kids entertained. Siesta Key Beach and Venice Beach promise a fun day out for both young and old.
Why book your cottage in Osprey with Expedia?
We think that traveling should be simple, so if you're after cottages in Osprey at a competitive rate, Expedia has you covered. Keep the budget in check and stay in an economical option far away from the city rush, or book a 5-star cottage to spoil the ones you love most.
How can I find cheap cottages in Osprey?
The quickest way to track down cheap cottages in Osprey is with Expedia's useful filter tool. Refine your search by budget, amenities and star rating to grab unbeatable deals in just a few keystrokes.
What is there to do in Osprey near my cottage?
The most useful travel accessory is a well-planned itinerary. Oscar Scherer State Park is a good spot to begin your sightseeing in Osprey.

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