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
$368 nightly
The price is $416 total per night
$416 total
Apr 9 - Apr 10
Total with taxes and fees
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
$485 nightly
The price is $542 total per night
$542 total
Apr 19 - Apr 20
Total with taxes and fees
Guests staying at this cottage have access to laundry facilities, a garden, and barbecue grills.
Kitchen
Washer
#3 Small house walking distance to Warm Mineral Spring

#3 Small house walking distance to Warm Mineral Spring

North Port FL
At this cottage, guests have access to features like laundry facilities.
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 a garden. This smoke-free cottage also has barbecue grills.
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

Sarasota FL
$520 nightly
The price is $581 total per night
$581 total
Apr 12 - Apr 13
Total with taxes and fees
At this cottage, guests have access to features like laundry facilities.
Direct Beachfront 2BR Cottage on Casey Key!

Direct Beachfront 2BR Cottage on Casey Key!

Nokomis FL
$539 nightly
The price is $601 total per night
$601 total
Apr 9 - Apr 10
Total with taxes and fees
Guests staying at this cottage have access to laundry facilities, a garden, and barbecue grills.
Charming cottage for 2 across warm mineral springs park

Charming cottage for 2 across warm mineral springs park

North Port FL
$135 nightly
The price is $150 total per night
$150 total
Apr 12 - Apr 13
Total with taxes and fees
At this cottage, guests have access to features like laundry facilities.
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
Venetian Vacation! Close To Beaches, Restaurants & Shopping!

Venetian Vacation! Close To Beaches, Restaurants & Shopping!

Venice FL
At this cottage, guests have access to features like laundry facilities. This smoke-free cottage also has barbecue grills.
Kitchen
Washer
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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
    $145 nightly
    The price is $164 total per night from Apr 14 to Apr 15
    $164 total
    Apr 14 - Apr 15
    Total with taxes and fees
    8.8/10 Excellent! (1,130 reviews)
    Golden Host Resort - Sarasota

    Golden Host Resort - Sarasota

    4675 N Tamiami Trl Sarasota FL
    $75 nightly
    The price is $85 total per night from May 3 to May 4
    $85 total
    May 3 - May 4
    Total with taxes and fees
    8.4/10 Very Good! (2,384 reviews)
    Kompose Boutique Hotel

    Kompose Boutique Hotel

    965 University Pkwy Sarasota FL
    $128 nightly
    The price is $144 total per night from Apr 9 to Apr 10
    $144 total
    Apr 9 - Apr 10
    Total with taxes and fees
    9.2/10 Wonderful! (5,213 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
325 Cottages
Lowest Price
$85
Highest Price
$601
Popular accommodation
The Inn On Siesta Key, Casey Key Beachfront Escape: Charming 1BR Cottage, #3 Small house walking distance to Warm Mineral Spring, 5 Min walk to Beach & Village, Private Pool,On the Canal, Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village, Direct Beachfront 2BR Cottage on Casey Key!, Charming cottage for 2 across warm mineral springs park, Country Cottage Home, Venetian Vacation! Close To Beaches, Restaurants & Shopping!