Monthly Rentals in Osprey

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

Nearby monthly rentals

Superhost
Home in Osprey
5 out of 5 average rating, 4 reviews

Mattie’s Cottage by the Bay.

JimRating, 5 stars1 month ago
This was my second time staying at Mattie’s cottage. I’m sure I’ll stay here again. The neighborhood is walkable and safe. The cottage is close to beaches, restaurants, shopping, and my favorite the bike trail. The hosts are friendly and welcoming.
Top guest favourite
Home in Osprey
5 out of 5 average rating, 36 reviews

Heated Pool | 3 Beds | Near Beaches and parks

MarkRating, 5 stars2 months ago
This was a never nice and comfortable place, clearly newly renovated and tastefully decorated. The kitchen was very well-equipped and the host quickly responded with a new toaster to replace one that was broken and to make a minor plumbing repair. Very nice and well-maintained swimming pool, which mainly served as a background decoration for us. We brought our bicycles and kept them in the garage. The washer and dryer functioned well and there were also drier racks, which is something my wife loves for air drying. We stayed here for the entire month and we'd gladly rent the place again. We very much like the area, both Osprey and greater Sarasota.
Superhost
Home in Osprey
5 out of 5 average rating, 6 reviews

Sunny Coastal Escape | By LussoStay

ChasityRating, 5 stars3 weeks ago
Good place, good location. Exactly what I was looking for. Ceiling fans didn’t work, they tried to fix the issue but were unsuccessful. Other than that the place was great.
Guest favourite
Flat in Nokomis
5 out of 5 average rating, 13 reviews

Noko Beach/CaseyKey. Best Location!

RamonaRating, 5 stars3 months ago
Janie’s place is terrific. Location was wonderful anything you need minutes away. Inside spotless, backyard sitting area so relaxing. Janie’s response time was only minutes before a response. Would definitely stay again.

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 holiday 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

Travelling 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.

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