Compare Osprey Cottage Rentals

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Featured Osprey Cottages

The Inn On Siesta Key

The Inn On Siesta Key

3.5 out of 5
515 Beach Road Siesta Key FL
$285 nightly
The price is $323 total per night
$323 total
Jan 29 - Jan 30
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 picnic area.
Pool
Kitchen
Best Location on Manasota Key, Cottage Sleeps 3, Kayaks and Wi-Fi

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

Englewood FL
At this cottage, guests have access to laundry facilities, local meal delivery service, and a garden.
Kitchen
Washer
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
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

Sarasota FL
$484 nightly
The price is $541 total per night
$541 total
Feb 17 - Feb 18
Total with taxes and fees
At this cottage, guests have access to features like laundry facilities.
Kitchen
Washer
Villa Margarita Sparkles

Villa Margarita Sparkles

Englewood FL
Guests staying at this cottage have access to local meal delivery service, barbecue grills, and a garden.
Pool
Kitchen
Direct Beachfront Cottage-Casey Key/Nokomis Beach-1 Bedroom

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

Nokomis FL
$491 nightly
The price is $548 total per night
$548 total
Feb 1 - Feb 2
Total with taxes and fees
Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.
Kitchen
Washer
Charming 1-bedroom cottage in peaceful RV Resort only 7 Miles from beaches

Charming 1-bedroom cottage in peaceful RV Resort only 7 Miles from beaches

2 out of 5
Bradenton FL
This cottage features a gym and laundry facilities.
Pool
Washer
New Pool! - Tropical Waterfront Cottage -Dock & Optional Boat

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

Nokomis FL
Guests staying at this cottage enjoy features like an outdoor pool.
Pool
Pet friendly
Charming Beach Bungalow with Private Pool and steps away from the Beach!

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

2 out of 5
Sarasota FL
At this cottage, guests have access to features like laundry facilities. This smoke-free cottage also has barbecue grills.
Pool
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
    $140 nightly
    The price is $159 total per night from Jan 26 to Jan 27
    $159 total
    Jan 26 - Jan 27
    Total with taxes and fees
    8.6/10 Excellent! (1,135 reviews)
    Golden Host Resort - Sarasota

    Golden Host Resort - Sarasota

    4675 N Tamiami Trl Sarasota FL
    $77 nightly
    The price is $87 total per night from Jan 27 to Jan 28
    $87 total
    Jan 27 - Jan 28
    Total with taxes and fees
    8.4/10 Very Good! (2,223 reviews)
    Kompose Boutique Hotel

    Kompose Boutique Hotel

    965 University Pkwy Sarasota FL
    $149 nightly
    The price is $168 total per night from Jan 28 to Jan 29
    $168 total
    Jan 28 - Jan 29
    Total with taxes and fees
    9/10 Wonderful! (4,937 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
$87
Highest Price
$548
Popular accommodation
The Inn On Siesta Key, Best Location on Manasota Key, Cottage Sleeps 3, Kayaks and Wi-Fi, Country Cottage Home, Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village, Villa Margarita Sparkles, Direct Beachfront Cottage-Casey Key/Nokomis Beach-1 Bedroom, Charming 1-bedroom cottage in peaceful RV Resort only 7 Miles from beaches, New Pool! - Tropical Waterfront Cottage -Dock & Optional Boat, Charming Beach Bungalow with Private Pool and steps away from the Beach!