Florida Keys Realty Home Seasonal Rental

Browse all of our listings below or click here to search for properties
that meet your specific needs.

TRADEWINDS EAST (Available Weekly) - 2 / 2 , Sleeps 4, Rates: low $1,200.00/wk - high $1,700.00/wk - Dock - Pool - Open water with excellent boating, bright and airy legal weekly rental, gated community with pool, ramp, marina and store

ISLAND ESCAPE (Available Weekly) - 3 / 2 , Sleeps 6, Rates: low $1,200.00/wk - high $1,800.00/wk - Dock - Quiet and private, Old Key's flavor, lots of foliage and excellent boating access, newly renovated

 

LAID BACK & AFFORDABLE - 2 / 2 , Sleeps 4, Rates: low $2,000.00/28 days - high $2,700.00/28 days - Dock - Very convenient, good boating, quiet area

 

ISLAND ESCAPE (Available Weekly) - 3 / 2 , Sleeps 6, Rates: low $1,200.00/wk - high $1,800.00/wk - Dock - Quiet and private, Old Key's flavor, lots of foliage and excellent boating access, newly renovated

 

HONEYMOON RETREAT - 3 / 4 , Sleeps 8, Rates: low $2,500.00/28 days - high $4,000.00/28 days -


 

TRANQUIL DISCOVERY - 3 / 2 , Sleeps 6, Rates: low $2,500.00/28 days - high $3,700.00/28 days - Dock - Canal front home with a large dock/sun deck plus a boat ramp in a quiet neighborhood

 

WATERFRONT ESCAPE - 3 / 2 , Sleeps 6, Rates: low $3,000.00/28 days - high $4,700.00/28 days - Great sunrise, directly on open water and good boating! Quiet area with boat ramp adjacent

 

SUGARLOAF BREEZE - 3 / 2 , Sleeps 6, Rates: low $3,000.00/28 days - high $4,000.00/28 days - Dock - Private, loads of room, good boating access and close to Key West

 

SUNSATIONAL! - 3 / 3 , Sleeps 6, Rates: low $5,000.00/28 days - high $8,500.00/28 days - Very quiet area, loads of room, great views and close to everything

 

SOUTHERN COMFORTS - 4 / 2 , Sleeps 8, Rates: low $5,000.00/28 days - high $7,000.00/28 days - Large ground level open water home with spectacular views and pool


 

TRADEWINDS EAST (Available Weekly) - 2 / 2 , Sleeps 4, Rates: low $1,200.00/wk - high $1,700.00/wk - Dock - Pool - Open water with excellent boating, bright and airy legal weekly rental, gated community with pool, ramp, marina and store

 

WATERFRONT TREASURE - 2 / 2 , Sleeps 4, Rates: low $2,000.00/28 days - high $3,500.00/28 days - Dock - sunrise open water views, good boating, newly furnished

 

ISLAND COLORS - 2 / 2 , Sleeps 4, Rates: low $2,200.00/28 days - high $3,200.00/28 days - Quiet area, close to everything, good boating access

 

BOATERS PARADISE - 2 / 2 , Sleeps 4, Rates: low $2,500.00/28 days - high $3,500.00/28 days - New custom home, great area, great boating, close to everything

 

TROPICAL TRANQUILITY - 2 / 2 , Sleeps 4, Rates: low $2,500.00/28 days - high $3,500.00/28 days - Quiet area, loads of vegetation and convenient to everything

 

CHOICE BOATING - 2 / 2 , Sleeps 4, Rates: low $2,800.00/28 days - high $4,000.00/28 days - Great boating, loads of sun and trade breezes, close to everything

 

TROPICAL ESCAPE - 2 / 2 , Sleeps 6, Rates: low $2,500.00/28 days - high $3,300.00/28 days - Dock - Quiet area, beautifully decorated, everything you need and close to everything.

 

LAZY DAYS - 3 / 2 , Sleeps 6, Rates: low $2,000.00/28 days - high $3,500.00/28 days - Wide deep canal with boat ramp for kayaks and small boats, close to conveniences, quiet area

 

DOLPHINS IN THE BAY - 3 / 2 , Sleeps 6, Rates: low $2,500.00/28 days - high $3,500.00/28 days - Great views, great boating and very close to everything

 

SHILOH - 3 / 3 , Sleeps 6, Rates: low $2,500.00/28 days - high $4,000.00/28 days - Large home, good boating, close to everything

 

CUDJOE BAY OVERLOOK - 3 / 2 , Sleeps 6, Rates: low $2,500.00/28 days - high $3,700.00/28 days - Quiet area, good boating, close to amenities

 

BLUE HEAVEN - 3 / 2 , Sleeps 6, Rates: low $2,700.00/28 days - high $3,700.00/28 days - Great boating, ground level, convenient to everything

 

NAUTICAL LANDING - 3 / 3 , Sleeps 6, Rates: low $3,000.00/28 days - high $4,000.00/28 days - Large home, great views, quiet area

 

SPORTSMAN'S PARADISE - 3 / 2 , Sleeps 6, Rates: low $3,000.00/28 days - high $4,700.00/28 days - Dock - Elegant, spacious and airy canal front home with quick ocean and gulf access

 

BUTTONWOOD SECLUSION - 3 / 2 , Sleeps 6, Rates: low $3,000.00/28 days - high $4,200.00/28 days - Dock - Pool - Secluded, private, quiet area with loads of mature tropical trees and close to everything

 

OCEANFRONT GRANDEUR - 3 / 2 , Sleeps 6, Rates: low $3,000.00/28 days - high $4,500.00/28 days - Dock - Escape to oceanfront luxury in this 2 story home that offers fantastic openwater and sunrise views and water for kayaking, canoeing or sailboarding

 

SUNSET VILLA - 3 / 2 , Sleeps 6, Rates: low $3,500.00/28 days - high $4,500.00/28 days - Nice area, deep clean canals, excellent boating and close to everything

 

LOCATION OCEAN - 3 / 2 , Sleeps 6, Rates: low $3,500.00/28 days - high $5,500.00/28 days - Dock - Enjoy spectacular openwater views from this beautiful airy and spacious ocean front home with quick access to ocean and gulf

 

ALWAYS SATURDAY - 3 / 2 , Sleeps 6, Rates: low $3,500.00/28 days - high $5,200.00/28 days - Great area, deep draft boating, swim spa, close to everything

 

SUNSET VIEWS - 3 / 2 , Sleeps 6, Rates: low $4,000.00/28 days - high $4,700.00/28 days - Dock - Rustic openwater cypress home offers fabulous sunset views with protected canal front docking

 

SPECTACULAR SUNSETS - 3 / 2 , Sleeps 6, Rates: low $4,500.00/28 days - high $6,500.00/28 days - Dock - Great open water view, airy and light, excellent boating access

 

SEA SIDE PARADISE - 3 / 2 , Sleeps 6, Rates: low $4,500.00/28 days - high $7,000.00/28 days - Pool - Beautiful view, privacy, 250 feet water frontage, new pool

 

OCEANFRONT SECLUSION - 3 / 2 , Sleeps 6, Rates: low $5,000.00/28 days - high $8,500.00/28 days - Very private, quiet area, beautiful open water views, close to everything

 

OASIS - 3 / 2 , Sleeps 6, Rates: low $5,000.00/28 days - high $6,500.00/28 days - Dock - Pool - Open water views, private pool, quiet area, close to everything

 

ISLAND VILLA - 4 / 3 , Sleeps 8, Rates: low $6,500.00/28 days - high $7,500.00/28 days - Dock - Pool - Spacious and beautiful, great location with outstanding boating, custom pool, huge open great room


 

SUMMERLAND DREAM - 3 / 3 , Sleeps 6, Rates: low $2,500.00/28 days - high $3,500.00/28 days - Neat , real Keys style home with great boating, close to everything

 

CARIBBEAN SUNSHINE - 3 / 3 , Sleeps 6, Rates: low $3,000.00/28 days - high $3,800.00/28 days - Great deep daft boating, beautifully decorated

 

OCEAN MIST - 3 / 2 , Sleeps 6, Rates: low $3,000.00/28 days - high $4,500.00/28 days - Spectacular view and excellent boating, close to everything

 

CARIBBEAN BREEZE - 3 / 2.5 , Sleeps 6, Rates: low $3,000.00/28 days - high $4,500.00/28 days - Dock - Cool and breezy, excellent boating, close to everything

 

MARY'S TROPICAL DREAM - 3 / 2 , Sleeps 6, Rates: low $3,500.00/28 days - high $3,700.00/28 days - Deep canal, close to everything, quiet area

 

SUMMER ISLE SOJOURN - 3 / 2 , Sleeps 6, Rates: low $4,000.00/28 days - high $6,000.00/28 days - Dock - Pool - Lagoon sunrise, deep water boating, tradewinds, close to everything

 

TROPICAL SECLUSION - 3 / 2.5 , Sleeps 6, Rates: low $4,500.00/28 days - high $7,000.00/28 days - Dock - Pool - Hot Tub - Beautiful, spacious, private with lagoon pool and spa. Full office with DSL and everything else!

 

OCEAN SPLENDOR - 3 / 3 , Sleeps 6, Rates: low $6,000.00/28 days - high $9,000.00/28 days - Dock - Pool - Hot Tub - Splendor may be an understatement for this

 

PARADISE VIEWS - 3 / 3 , Sleeps 6, Rates: low $8,000.00/28 days - high $10,000.00/28 days - Incredible open water views! Just renovated, furnished Caribbean and Tommy Bahama style, great kitchen, excellent boating and private!

 

CHANGES IN LATITUDES . . . - 4 / 2.5 , Sleeps 7, Rates: low $4,500.00/28 days - high $7,500.00/28 days - Dock - This comfortable, bright and airy, 2 story boater's paradise offers a pool, openwater views and plenty of dock space with quick and deep access to both ocean and gulf.

 

SUNSET DREAM - 4 / 2.5 , Sleeps 8, Rates: low $3,500.00/28 days - high $4,700.00/28 days - Sunset view, fantastic boating, quiet area and close to everything

 

CORAL ISLE ESCAPE - 4 / 2 , Sleeps 8, Rates: low $3,500.00/28 days - high $4,700.00/28 days - Dock - Hot Tub - New, light and airy, prestigious area, excellent boating, close to everything

 

OCEAN HORIZONS - 4 / 3.5 , Sleeps 8, Rates: low $6,500.00/28 days - high $9,000.00/28 days - Incredible ocean view, excellent deep draft boating and close to everything!

 

OCEAN INTERLUDE - 4 / 4 , Sleeps 8, Rates: low $6,500.00/28 days - high $9,000.00/28 days - Dock - Pool - Hot Tub - Spectacular views, screened in pool/hot tub,three levels with master BR at top, close to everything

 

OCEANFRONT HEAVEN - 4 / 4 , Sleeps 8, Rates: low $6,500.00/28 days - high $8,500.00/28 days - Dock - Pool - Hot Tub - Great views, privacy, excellent boating, lots of sun! New pool!


 

BREEZESWEPT BEACH - 2 / 2 , Sleeps 4, Rates: low $2,500.00/28 days - high $4,000.00/28 days - Pool and Great shallow water sunrise views, close to everything

 

MYSTICAL PALMS - 4 / 2 , Sleeps 8, Rates: low $4,000.00/28 days - high $7,000.00/28 days - Quiet, private, large pool and very close to everything


 

CARIBBEAN COMFORT - 4 / 3 , Sleeps 8, Rates: low $3,500.00/28 days - high $5,000.00/28 days - Spacious, close to everything, excellent deep draft boating, Caribbean flair


 


Florida Keys Realty, Inc.
P.O. Box 421177 Summerland Key, FL 33042
Mile Marker 21.5 Cudjoe Key
Office: (305) 745-3717 Toll Free: (800) 277-7756
EMAIL: info@floridakeysrealty.com