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Monthly Rentals in Osprey

Discover long-term rentals that feel like home for stays of a month or longer.

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Nearby monthly rentals

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Guest suite in Sarasota

4.91 out of 5 average rating, 272 reviews

Private Suite, 10 minutes to Siesta Key!

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Guesthouse in Nokomis

5 out of 5 average rating, 29 reviews

Coastal Heaven

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Guesthouse in Osprey

4.99 out of 5 average rating, 301 reviews

Cozy Cottage by the Bay

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Home in Osprey

4.98 out of 5 average rating, 42 reviews

Bayview House - Osprey - 1 block to Bay!

Explore all

The comforts of home and great monthly rates

Fully furnished rentals

From peaceful mountain cabins to convenient urban apartments these furnished rentals have all the amenities of home.

Digital nomads & traveling professionals

Comfortable accommodations for nomadic and remote working professionals with wifi and dedicated work spaces.

Delight included

Sometimes the destination is the accommodation. From cliffside cabins to tranquil houseboats, these rentals are full of unique features.

Pets welcome

Discover places to stay that accommodate pets, so you can bring your four-legged friend along.

Amenities and perks for longer stays

Furnished rentals

Fully furnished rentals include a kitchen and the amenities you need to live comfortably for a month or longer. It’s the perfect alternative to a sublet.

Flexibility you need

Choose your exact move-in and move-out dates and easily book online, without any additional commitment or paperwork.*

Simple monthly prices

Special rates for long-term vacation rentals and a single monthly payment without additional charges.*

Book with confidence

Reviewed by our trusted community of guests and 24/7 support during your extended stay.

Work-friendly spaces for digital nomads

Traveling professional? Find a long-term stay with high-speed wifi and dedicated working spaces.

Looking for corporate housing?

Airbnb has fully furnished apartment homes ideal for staffing, corporate housing, and relocation needs.

Popular amenities for monthly rentals

Kitchen
Wifi
Pet friendly
Laptop-friendly workspace
Free parking on premises
Corporate Housing

Stay near Osprey's top sights

Historic Spanish Point73 locals recommend
Casey Key Fish House66 locals recommend
Ophelia's on the Bay64 locals recommend
Stoneybrook Golf & Country Club8 locals recommend
Turtles Restaurant23 locals recommend
Turtle Beach Grill Restaurant18 locals recommend

Destinations to explore

*Some exclusions may apply in certain geographies and for some properties.
  1. Airbnb
  2. United States
  3. Florida
  4. Sarasota County
  5. Osprey
  6. Monthly Rentals