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 travelling 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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Featured Cottages in Osprey and around

Outdoor pool, a heated pool, open 8:00 AM to 8:00 PM, pool umbrellas

"Great place to stay! "

On the beach, sun-loungers, beach towels

"We enjoyed our stay so much! Just right for us with short walks to the Beach and Bay, peaceful back porch and comfy beds. It is a beautiful and clean house in the trees. Evan is a helpful host with great communication. We hope to go back again. "

"We loved this little cottage and will absolutely go back in the future. Thank you so much for a wonderful retreat. "

includes taxes & fees

13 Sept - 14 Sept

"We have stayed at this cottage before- just love this beach."

"We have stayed at this cottage before, and it’s always been obvious how much love the owners put into the cottage, and how much effort they put into making your stay an enjoyable one. Knowing how much work they had to do to get it rehabbed after last year’s hurricanes makes you appreciate it even more. The cottage is very clean and has everything you need for your stay. You are right on the beach with a spectacular view of the sunset. Communication with the hosts is a breeze and they are quick...

"Its right next to everything we needed"

"Perfect place for short stay. Great little cottage in a private quiet setting. Nothing super fancy but everything you need and exceptionally clean. "

"Beautiful area and unit. We will be back."

"We greatly enjoyed our stay. The yard is very secluded and quite large, which was ideal for us. The house was exceptionally clean, and is well laid out. Powerful a/c system, super welcome for hot florida days. It also has a very large screened in lanai, which is perfect for relaxing. "

"Perfect place to stay. 1 mile to the village and beach access. We loved making our own meals in the grill and swimming in the pool. "

"Wonderful quiet neighborhood property with very attentive property owners. Flamingo Cottage is ideally located for easy access to the beach as well as Shopping within walking distance. We look forward to our return next year!"

Beach nearby, sun-loungers, beach towels

"Very cute beach cottage! Great location,very clean ,no complaints,if ever in Siesta Key again would definitely stay here "

"Cottages for my daughter and I were adjacent. Having a pool was nice. The free washer and dryer was a plus. "

"Our family of four had a fantastic stay at this condo. It was incredibly clean and had wonderful amenities. We loved the kayaks and bikes. The location was perfect and the beach access was close by. We look forward to booking here again! "

"We had an awesome vacation! The house beach and pool were outstanding. Hope to return next year!!"

"my friends and I traveled from across the country to meet for our annual “girls” trip. Location is amazing. You can walk to the beach, you can rent cabanas and there are lounge chairs for your use. The pool is sparkling and the trolley stop is right outside the property entrance. I just love Siesta key and this is a wonderful place to get away from it all, but have easy access to all of the fun and shopping. "

"Owner easy to work with. Short walk to the beach and to restaurants in town."

"Wonderful location for a peaceful getaway "

"Clean & close to the convention center"

"I would highly recommend staying here."

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Top Osprey Hotel Reviews

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Osprey Cottages information

Number of reviews	384
Accommodation	319 Cottages
Lowest Price	€422
Highest Price	€422

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Frequently asked questions

How much do cottages in Osprey cost?

Cottages in Osprey range between €422 and €422 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 9.9. 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 319 cottages in Osprey. Whether you're holidaying with the kids or organising a weekend break with close friends, Expedia can help you find the right space to get in touch with nature.

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Search Cottages in Osprey

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Featured Cottages in Osprey and around

The Inn On Siesta Key

Private Gulf Beach-4 BRs- Luxury Cottage, Pet Friendly-Kayaks & SUPs-Grill

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

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

Best Location on Manasota Key, Cottage Sleeps 3, Kayaks and Wi-Fi

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

Country Cottage Home

Island Life! King Bed Studio-Steps to beach

1-bedroom cottage just 10 minutes from Siesta Key Beach

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

2Bd+2 Ba beach cottage w/private front/back yard, screened porch, firepit, grill

Across The Street From #1 Beach

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

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

Big Roomy Beach Cottage: 4 bd/3 ba -2,000 sq ft; 100 ft to beach path; priv pool

Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

Kozy Kottage on private road. 2 minute walk to private beach. Pet friendly!

Cozy Beach Cottage

12 Mi to Beach: Home w/ Patio & Yard in Bradenton

1 Bedroom Duplex On Intracoastal W/ Beach Access