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| Middle Keys Properties | ![]()
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| About Rates:The rates below reflect a range, from Low (Fall) to Peak (Holidays & Events). The actual High Season rates (Winter to Summer) vary widely, but are usually closer to the Peak rates than the Fall rates, so please do not assume the lowest rate applies to your dates. Please contact us for availability, and for the exact rates for your dates. |
| Key West & Lower Keys - Studios & One Bedroom |
| Property Name | BR/BA | Highest (Peak) Rate (Holidays/Events) |
Lowest (Fall) Rate (Aug 15 to Dec 15) Cottage # 729 Rear | Studio | $2,575 | $1,385
| Cottage # 729 Up | Studio | $2,435 | $1,175
| Southernmost Studios | Studio | $2,085 | $1,105
| Cottage # 512-5A | Studio | contact us | contact us
| Cottage # 516-4 | Studio | contact us | contact us
| Cottage # 706-1 | 1/1 | $2,785 | $1,385
| Cottage # 708-1 | 1/1 | $2,365 | $1,105
| Cottage # 714-2 | 1/1 | $2,715 | $1,315
| Margaritavillas | 1/1 | $1,800 | $1,000
| Townhome #921-4 | 1/1 | $2,435 | $1,245
| Townhome #921-8 | 1/1 | $2,435 | $1,245
| Cottage # 512-5 | 1/1 | contact us | contact us
| Cottage # 516-1 | 1/1 | contact us | contact us
| Cottage # 516-2 | 1/1 | contact us | contact us
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| Key West & Lower Keys - Two Bedrooms |
| Key West & Lower Keys - Three Bedrooms |
| Property Name | BR/BA | Highest (Peak) Rate (Holidays/Events) |
Lowest (Fall) Rate (Aug 15 to Dec 15) Sunset Harbor | 3/.25 | $4,750 | $3,000
| Conch Lane | 3/2 | $3,675 | $2,500
| Margaritavillas | 3/2 | $3,675 | $2,500
| Paradise Island Villas | 3/2 | $2,950 | $1,950
| Private Home # 729 | 3/2 | $4,255 | $2,855
| Private Home # 1400-A | 3/2 | $3,835 | $2,435
| Sand Cabana | 3/2 | $4,500 | $2,500
| Sunset Harbor | 3/2 | $4,750 | $3,000
| Beach Front Villa | 3/2.5 | $4,500 | $3,000
| Private Home # 535 | 3/2.5 | $5,165 | $3,065
| Private Home # 1011-3 | 3/2.5 | $4,250 | $2,850
| Conch Village | 3/3 | $3,000 | $1,500
| Harborfront Retreat | 3/3 | $3,835 | $2,435
| Private Home # 509-N | 3/3 | contact us | contact us
| Sunset Harbor | 3/3 | $4,750 | $3,000
| Private Home # 318 | 3/3.5 | $6,500 | $4,500
| Private Home # 314 | 3/4 | $6,500 | $4,500
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| Key West & Lower Keys - Four Bedrooms & Up |
| Property Name | BR/BA | Highest (Peak) Rate (Holidays/Events) |
Lowest (Fall) Rate (Aug 15 to Dec 15) Atlantic Breeze 4 BR | 4/2 | $5,500 | $2,650
| Townhome # 219 | 4/2 | $3,835 | $2,435
| Coral Palms | 4/3 | $6,000 | $3,000
| Private Home # 100-1 | 4/3 | $6,500 | $4,500
| Private Home # 500 | 4/3 | $5,500 | $3,500
| Private Home # 514 | 4/3 | $6,500 | $4,500
| Private Home # 102 | 4/3.5 | $4,750 | $3,000
| Sea Watch | 4/3.5 | $5,500 | $3,500
| Harborfront Retreat | 4/4 | $4,535 | $3,135
| Private Home # 118-A | 4/4 | $7,500 | $4,500
| Private Home # 316 | 4/4 | $7,500 | $5,500
| Private Home # 320 | 4/4 | $7,500 | $5,500
| Sand Castle | 5/3.5 | $8,000 | $4,500
| Private Home # 509-S | 5/4 | $5,000 | $8,500
| Summertime | 5/4 | $8,000 | $4,500
| Atlantic Breeze Estate | 6/4 | $7,500 | $3,750
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| Please contact us for rates on Monthly Rental properties. |
| Property Name |
BR/BA
| Island Bungalow | 1/1
| Ocean Gallery | 1/1
| Key West Charm | 1/1 and 2/2
| Dolphin Beach Retreat | 2/2
| Emerald Vista | 2/2
| Island House | 2/2
| Sunset Bay | 2/2
| Under the Sea | 2/2
| Private Home # 316W | 2+Den/2
| Captains Hideaway | 3/2
| Front Row Seats | 3/2
| Key Lime Pie | 3/2
| Private Haven | 3/2
| Sea View | 3/2
| Seaport Palms | 3/2
| Towering Palms | 3/2
| Truly Conch | 3/2
| Winter Haven | 3/2
| Ocean Blue | 3/3
| Conch Manor | 4/2
| Gulf Retreat | 4/2
| Victorian Secret | 4/2.5
| Paradise Key | 4/3
| Captain's Folly | 4/3.5
| Water's Edge | 4/4
| Bella Vista | 4/4.5
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| (Click here to see Middle Keys Properties in Alphabetical order.) |
| About Rates:The rates below reflect a range, from Low (Fall) to Peak (Holidays & Events). The actual High Season rates (Winter to Summer) vary widely, but are usually closer to the Peak rates than the Fall rates, so please do not assume the lowest rate applies to your dates. Please contact us for availability, and for the exact rates for your dates. |
| Upper Keys | Key West |
| Middle Keys - Studios & One Bedroom |
| Property Name | BR/BA | Highest (Peak) Rate (Holidays/Events) |
Lowest (Fall) Rate (Aug 15 to Dec 15) Admiral's Hideaway | 2/2 | $2,600 | $1,400
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| Middle Keys - Two Bedrooms |
| Property Name | BR/BA | Highest (Peak) Rate (Holidays/Events) |
Lowest (Fall) Rate (Aug 15 to Dec 15) Blue View | 2/2 | $3,350 | $1,200
| Tiki Terrace | 2/2 | $1,850 | $1,250
| Bay Breezes | 2/2.5 | $1,950 | $1,250
| Gulf Front | 2/2.5 | $2,150 | $1,450
| Gulf Getaway | 2/2.5 | $1,750 | $1,250
| Gulf Haven | 2/2.5 | $1,850 | $1,350
| Gulf Paradise One | 2/2.5 | $2,150 | $1,450
| Gulf Paradise Two | 2/2.5 | $2,150 | $1,450
| Gulf Perch | 2/2.5 | $1,900 | $1,400
| Margarita Villa | 2/2.5 | $1,800 | $1,300
| Palm View | 2/2.5 | $1,500 | $1,000
| Pool View | 2/2.5 | $1,500 | $1,000
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| Middle Keys - Three Bedrooms |
| Property Name | BR/BA | Highest (Peak) Rate (Holidays/Events) |
Lowest (Fall) Rate (Aug 15 to Dec 15) Beach Chalet | 3/2 | $4,000 | $2,400
| Beach Haven | 3/2 | $4,000 | $2,400
| Beach Sanctuary | 3/2 | $4,000 | $2,400
| Emerald Palms | 3/2 | $2,650 | $1,550
| Havana Daydreamin' | 3/2 | $4,000 | $2,400
| Island Colors | 3/2 | $3,150 | $2,150
| Palm Oasis | 3/2 | $3,350 | $1,800
| Southern Comfort | 3/2 | $2,950 | $1,950
| Emerald Isle | 3/2.5 | $2,150 | $1,450
| Heart of Paradise | 3/2.5 | $2,400 | $1,250
| Emerald Playground | 3/3 | $3,000 | $1,800
| Mariner's Hideaway | 3/3 | $2,800 | $1,600
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| Middle Keys - Four Bedrooms & Up |
| Property Name | BR/BA | Highest (Peak) Rate (Holidays/Events) |
Lowest (Fall) Rate (Aug 15 to Dec 15) Reflections | 4/2 | $6,000 | $3,000
| Gulf Watch | 4/3 | $5,500 | $3,250
| Private Home # 4-I | 4/3 | $5,000 | $3,500
| Sea Chalet | 4/3 | $5,000 | $3,500
| Sombrero Lane | 4/3 | $5,000 | $2,650
| Sombrero Splendor | 4/3 | $4,500 | $2,250
| On Green Dolphin Street | 4/4 | $6,000 | $2,500
| Admiral's Landing | 5/3 | $7,500 | $4,500
| The Blue Lagoon | 5/4 | $10,000 | $5,000
| Admiral's Playground | 6/5 | $6,500 | $4,500
| Grand Paradise | 6/5 | $12,000 | $6,000
| African Palms | 7/4 | $7,500 | $4,500
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![]() (Click here to see Upper Keys Properties in Alphabetical order.) |
| About Rates:The rates below reflect a range, from Low (Fall) to Peak (Holidays & Events). The actual High Season rates (Winter to Summer) vary widely, but are usually closer to the Peak rates than the Fall rates, so please do not assume the lowest rate applies to your dates. Please contact us for availability, and for the exact rates for your dates. |
| Middle Keys | Key West |
| Upper Keys - Studios & One Bedroom |
| Property Name | BR/BA | Highest (Peak) Rate (Holidays/Events) |
Lowest (Fall) Rate (Aug 15 to Dec 15) Oceanpointe | 1/1 | $1,815 | $835
| On The Bay | 1/1 | $2,100 | $1,050
| Sea Gulls | 1/1 | $1,600 | $1,000
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| Upper Keys - Two Bedrooms |
| Property Name | BR/BA | Highest (Peak) Rate (Holidays/Events) |
Lowest (Fall) Rate (Aug 15 to Dec 15) Sand Piper | 2/1.5 | $2,200 | $1,350
| Sun Flower | 2/1.5 | $2,200 | $1,350
| Sailfish Reef | 2/2 | $2,250 | $1,050
| Ocean Perch | 2/2 | $2,100 | $975
| Sea Gulls | 2/2 | $1,800 | $1,200
| The View | 2/2 | $1,650 | $1,050
| Oceanpointe | 2/2 | $2,100 | $900
| Flip-Flop Beach | 2/2 | $2,500 | $1,500
| On The Bay | 2/2 | $2,600 | $1,950
| Ocean Roost | 2/2 | $2,100 | $975
| Plantation Palms | 2/2 | $3,500 | $2,500
| Sea World | 2/2 | $1,850 | $1,250
| Beach Rest | 2/2 | $1,800 | $900
| Private Home # 95-4 | 2/2 | $4,500 | $3,000
| Private Home # 134-C | 2/2 | $2,100 | $1,600
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| Upper Keys - Three Bedrooms |
| Property Name | BR/BA | Highest (Peak) Rate (Holidays/Events) |
Lowest (Fall) Rate (Aug 15 to Dec 15) Beach Delight | 3/2 | $3,750 | $2,750
| Private Home # 74-0 | 3/2 | $5,000 | $3,850
| Treasure Chest | 3/2 | $3,500 | $1,800
| Ocean's Edge | 3/3 | $3,500 | $2,500
| Ocean Mural | 3/3 | $2,500 | $1,800
| Keys Safari | 3/3 | $3,750 | $2,500
| Mockingbird House | 3/3 | $2,250 | $1,350
| Private Home # 75-90 | 3/3 | $8,500 | $6,500
| Private Home # 402-G | 3/3 | $6,000 | $4,500
| Seaview Villa | 3/3 | $2,500 | $1,800
| Private Home # 121-N | 3/3 | $4,500 | $3,000
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| Upper Keys - Four Bedrooms & Up |
| Property Name | BR/BA | Highest (Peak) Rate (Holidays/Events) |
Lowest (Fall) Rate (Aug 15 to Dec 15) Flamingo Beach | 4/3 | $5,000 | $3,000
| Private Home # 85-2 | 4/3 | $4,200 | $3,200
| Reef Motif | 4/3 | $5,000 | $3,500
| Island Oasis | 4/3 | $5,500 | $3,500
| Finding Nemo | 4/3 | $5,000 | $3,000
| Private Home # 82-5 | 4/3 | $7,000 | $5,000
| Plantation Palms | 4/3.5 | $5,500 | $3,500
| Oceanfront Oasis | 4/4 | $20,000 | $4,200
| Ship Ahoy! | 4/4 | $5,500 | $4,000
| Private Home # 22-A | 4/4 | $10,000 | $6,000
| Private Home # 75-94 | 4/4 | $8,500 | $6,500
| Private Home # MB-1 | 4/4 | $7,000 | $5,500
| Private Home # 105-S | 5/3 | $6,000 | $4,500
| Private Home # 209-O | 5/4 | $5,000 | $3,500
| Seashells & Starfish | 7/6 | $8,500 | $5,000
| Casa Contenta | 8/5 | $9,000 | $5,500
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| Property Name | BR/BA | Highest (Peak) Rate (Holidays/Events) |
Lowest (Fall) Rate (Aug 15 to Dec 15) Cottage # 96-0 | 1/1 | $3,500 | $2,500
| Private Home # 34-S | 2/1 | $3,600 | $2,600
| Private Home # 24-C | 3/2 | $4,200 | $3,200
| Private Home # 57-S | 3/2 | $6,000 | $4,000
| Private Home # 258-G | 3/2 | $7,000 | $5,000
| Private Home # 87-P | 3/2 | $5,500 | $4,500
| Crystal Cove | 3/3 | $15,000 | $12,000
| Gulfside Harbour | 3/3 | $10,000 | $6,000
| Private Home # 35 M | 3/3 | $15,000 | $10,000
| Private Home # 243-S | 4/2 | $7,000 | $5,500
| Private Home # 254-A | 4/2 | $9,000 | $7,000
| Private Home # 40-B | 4/3 | $8,500 | $6,500
| Private Home # 58-S | 4/3 | $18,000 | $14,000
| Private Home # 109-8 | 4/3 | $10,000 | $8,000
| Private Home # 356-S | 4/3 | $10,000 | $8,000
| Private Home # 352-S | 4/3.5 | $17,000 | $14,000
| Private Home #425-L | 4/3.5 | $10,000 | $8,000
| High Expectations | 4/4 | $8,500 | $4,500
| Private Home # 16-A | 5/4 | $12,000 | $8,000
| Private Home # 108 | 5/6 | please call | please call
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