![Property at 5100 Jessie Harbor Dr #504, Osprey, FL, 34229, 3 beds, 2 baths, [object Object]](https://ssl.cdn-redfin.com/photo/rent/c9da63b0-7684-46c9-89b2-ba936b24e0cc/islphoto/genIsl.0_1.webp)
5100 Jessie Harbor Dr #504, Osprey, FL, 34229
![Property at 5100 Jessie Harbor Dr #602, Osprey, FL, 34229, 2 beds, 2 baths, [object Object]](https://ssl.cdn-redfin.com/photo/rent/022f7114-bf66-4ce4-8341-f5d06c4113ec/islphoto/genIsl.0_2.webp)
5100 Jessie Harbor Dr #602, Osprey, FL, 34229![Property at 2313 Jessie Harbor Dr #2302, Osprey, FL, 34229, 2 beds, 2 baths, [object Object]](https://ssl.cdn-redfin.com/photo/rent/e7956948-b70d-466f-a584-9df46108a187/islphoto/genIsl.0_1.webp)
2313 Jessie Harbor Dr #2302, Osprey, FL, 34229![Property at 236 Woodland Dr, Osprey, FL, 34229, 2 beds, 2 baths, [object Object]](https://ssl.cdn-redfin.com/photo/rent/90ca9db2-7e5d-4502-be0d-9dc1e485c627/islphoto/genIsl.0_2.webp)
236 Woodland Dr, Osprey, FL, 34229![Property at 140 Sea Anchor Dr, Osprey, FL, 34229, 3 beds, 3 baths, [object Object]](https://ssl.cdn-redfin.com/photo/rent/7b478891-5eac-4879-8c8b-71ca0a5988ab/islphoto/genIsl.0_1.webp)
140 Sea Anchor Dr, Osprey, FL, 34229![Property at 101 Woodland Pl, Osprey, FL, 34229, 3 beds, 2.5 baths, [object Object]](https://ssl.cdn-redfin.com/photo/rent/e9ab9861-ba34-4847-9bb2-1c73ece47ad9/islphoto/genIsl.0_2.webp)
101 Woodland Pl, Osprey, FL, 34229![Property at 451 N Shore Dr, Osprey, FL, 34229, 3 beds, 3 baths, [object Object]](https://ssl.cdn-redfin.com/photo/rent/885cac94-125a-48ce-8efd-a16bdfa955c9/islphoto/genIsl.0_1.webp)
451 N Shore Dr, Osprey, FL, 34229![Property at 1817 Highland Rd, Osprey, FL, 34229, 2 beds, 2 baths, [object Object]](https://ssl.cdn-redfin.com/photo/rent/6afc87c8-5d5c-4900-8ef2-a4435aa977f0/islphoto/genIsl.0_1.webp)
1817 Highland Rd, Osprey, FL, 34229![Property at 184 Explorer Dr, Osprey, FL, 34229, 2 beds, 2 baths, [object Object]](https://ssl.cdn-redfin.com/photo/rent/050add1d-3bc2-4627-9dd8-bc35d0c9146f/islphoto/genIsl.0_1.webp)
184 Explorer Dr, Osprey, FL, 34229![Property at 304 Pine Run Dr #304, Osprey, FL, 34229, 2 beds, 2 baths, [object Object]](https://ssl.cdn-redfin.com/photo/rent/f8a466e2-0cc8-44f2-8a3d-cbcce656fc9d/islphoto/genIsl.0_1.webp)
304 Pine Run Dr #304, Osprey, FL, 34229![Property at 5420 Cicerone St #101, Sarasota, FL, 34238, 2 beds, 2 baths, [object Object]](https://ssl.cdn-redfin.com/photo/rent/b5a97a49-c593-4334-97b3-969adf78166b/islphoto/genIsl.0_2.webp)
5420 Cicerone St #101, Sarasota, FL, 34238![Property at 5305 Bartolomeo St, Sarasota, FL, 34238, 2 beds, 2 baths, [object Object]](https://ssl.cdn-redfin.com/photo/rent/bbd1c8fd-680c-4c52-b7c9-c6954aad23b5/islphoto/genIsl.0_2.webp)
5305 Bartolomeo St, Sarasota, FL, 34238![Property at 4256 Expedition Way Unit 107, Osprey, FL, 34229, 3 beds, 2 baths, [object Object]](https://ssl.cdn-redfin.com/photo/rent/99411255-2ec6-49fb-8c95-eb399c68557d/islphoto/genIsl.0_1.webp)
4256 Expedition Way Unit 107, Osprey, FL, 34229![Property at 12413 Osorio Ct #101, Sarasota, FL, 34238, 2 beds, 2 baths, [object Object]](https://ssl.cdn-redfin.com/photo/rent/1853a3ea-c189-4cfb-89e1-37737ac08aa4/islphoto/genIsl.0_1.webp)
12413 Osorio Ct #101, Sarasota, FL, 34238
Based on information submitted to the MLS GRID as of Sat Sep 27 2025. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.
More to explore in Rivendell, FL
Rentals near Rivendell, FL
Cities
- Neighborhoods
- Zip Codes
Apartments for rent near Rivendell, FL
- Cities
- Rental Buildings
- Neighborhoods
- Zip Codes
Popular rental markets in Florida
- Rentals
- Apartments
About us
Find us
Subsidiaries
United States
CanadaCopyright: © 2025 Redfin. All rights reserved.
Updated January 2023: By searching, you agree to the Terms of Use, and Privacy Policy.
Do not sell or share my personal information.
REDFIN and all REDFIN variants, TITLE FORWARD, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.
California DRE #01521930
Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures
New Mexico Real Estate Licenses
TREC: Info About Brokerage Services, Consumer Protection Notice
All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.
Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.
If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.
REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.