Compare Osprey Cottage Rentals

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Featured Cottages in Osprey

The Inn On Siesta Key

The Inn On Siesta Key

3.5 out of 5
515 Beach Road Siesta Key FL
Guests of The Inn On Siesta Key enjoy features like an outdoor pool, free WiFi in public areas, and free use of bicycles. If you decide to drive, there's free parking. Front-desk staff can help with concierge services, and provide local restaurant recommendations. Other amenities at this beach cottage include a terrace, laundry facilities, and a garden.
Pool
Kitchen
Casey Key Beachfront Escape: Charming 1BR Cottage

Casey Key Beachfront Escape: Charming 1BR Cottage

Nokomis FL
$486 nightly
The price is $542 total per night
$542 total
Sep 26 - Sep 27
Total with taxes and fees
Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.
Kitchen
Washer
Charming Beach Bungalow with Private Pool and steps away from the Beach!

Charming Beach Bungalow with Private Pool and steps away from the Beach!

Sarasota FL
At this cottage, guests have access to a gym, laundry facilities, and barbecue grills.
Pool
Kitchen
Across The Street From #1 Beach

Across The Street From #1 Beach

Siesta Key FL
At this cottage, guests have access to features like laundry facilities. This smoke-free cottage also has barbecue grills.
Kitchen
Washer
5 Min walk to Beach & Village, Private Pool,On the Canal

5 Min walk to Beach & Village, Private Pool,On the Canal

Siesta Key FL
At this cottage, guests have access to an outdoor pool, laundry facilities, and barbecue grills. This smoke-free cottage also has a garden.
Pool
Kitchen
Country Cottage Home

Country Cottage Home

Bradenton FL
Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.
Kitchen
Washer
Cottage Across The Street From #1 Beach

Cottage Across The Street From #1 Beach

Siesta Key FL
At this cottage, guests have access to barbecue grills.
Kitchen
Washer
Charming 2-bedroom cottage in Englewood minutes to the Gulf Beaches-Dog Friendly

Charming 2-bedroom cottage in Englewood minutes to the Gulf Beaches-Dog Friendly

Englewood FL
$215 nightly
The price is $240 total per night
$240 total
Oct 17 - Oct 18
Total with taxes and fees
At this cottage, guests have access to features like laundry facilities. This smoke-free cottage also has a garden.
Kitchen
Washer
Roomy Cottage: 4bd3 ba; 2,000 sq ft; 5min thru dune 2 bch; priv pool VR22-00058

Roomy Cottage: 4bd3 ba; 2,000 sq ft; 5min thru dune 2 bch; priv pool VR22-00058

Sarasota FL
At this cottage, guests have access to an outdoor pool, laundry facilities, and barbecue grills. This beach cottage also has a garden.
Pool
Kitchen
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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.

Hotel Options in Osprey

    Casey Key Resorts - Mainland

    Casey Key Resorts - Mainland

    1650 South Tamiami Trail Osprey FL
    $106 nightly
    The price is $119 total per night from Oct 5 to Oct 6
    $119 total
    Oct 5 - Oct 6
    Total with taxes and fees
    Kompose Boutique Hotel

    Kompose Boutique Hotel

    965 University Pkwy Sarasota FL
    $62 nightly
    The price is $71 total per night from Oct 6 to Oct 7
    $71 total
    Oct 6 - Oct 7
    Total with taxes and fees
    9.2/10 Wonderful! (6,036 reviews)
    Tropical Beach Resorts

    Tropical Beach Resorts

    6717 Sara Sea Circle Siesta Key FL
    $158 nightly
    The price is $179 total per night from Sep 27 to Sep 28
    $179 total
    Sep 27 - Sep 28
    Total with taxes and fees
    9.4/10 Exceptional! (5,916 reviews)

Cottages

Book a cottage in Osprey
Spend your next getaway treating yourself to a quieter, simpler way of life in a private cottage in Osprey. Cozy and charming, cottage rentals are the ideal spot when you want the comforts of home paired with a one-of-a-kind experience. They’re perfect for a single traveler looking for peace and quiet, or small groups who want to get to know Osprey better.

Cottage apartments in Osprey range from rustic to luxurious, with just about everything in between. Orbitz gives you the best deals on all of them.

Find the best cottages in Osprey
City cottages are great if you want a cozy, comfy place to stay without being far from the all the cool spots you want to check out. A cottage makes a great home base for a day filled with adventure in Osprey and the surrounding area. Not willing to give up all the comforts of a fine hotel? A luxury cottage turns up the charm while offering perks like room service, cable television, sunken spa tubs and housekeeping.

Stay in a Osprey cottage and swap busy days for peaceful evenings. Use the kitchenette or full kitchen to come up with a meal or reheat leftovers from your afternoon in Osprey. You may even be able to use a pool and laundry facilities. Whether you’re in the mood for quiet relaxation or a night on the town, a cottage puts you right where you want to be.

Osprey Cottages essential information

Accommodation
384 Cottages
Lowest Price
$71
Highest Price
$542
Popular accommodation
The Inn On Siesta Key, Casey Key Beachfront Escape: Charming 1BR Cottage, Charming Beach Bungalow with Private Pool and steps away from the Beach!, Across The Street From #1 Beach, 5 Min walk to Beach & Village, Private Pool,On the Canal, Country Cottage Home, Cottage Across The Street From #1 Beach, Charming 2-bedroom cottage in Englewood minutes to the Gulf Beaches-Dog Friendly, Roomy Cottage: 4bd3 ba; 2,000 sq ft; 5min thru dune 2 bch; priv pool VR22-00058