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Middle Keys Properties

Key West Properties in Alphabetical Order

(Click here to see Key West Properties
in order of # of Bedrooms)

Upper Keys Properties

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.

Click Here to learn more About Rates & Availability.


Key West weekly rentals.

Property Name BR/BA Highest (Peak) Rate (Holidays/Events) Lowest (Fall) Rate
(Aug 15 to Dec 15)
Atlantic Breeze 2 BR 2/2 $3,000 $1,350
Atlantic Breeze 4 BR 4/2 $5,500 $2,650
Atlantic Breeze Estate 6/4 $7,500 $3,750
Beach Front Villa 3/2.5 $4,500 $3,000
Conch Lane 2/1.5 $2,450 $1,400
Conch Lane 2/2.5 $2,650 $1,600
Conch Lane 3/2 $3,675 $2,500
Conch Row 2/2.5 $2,850 $1,800
Conch Village 2/2 $2,650 $1,200
Conch Village 3/3 $3,000 $1,500
Coral Palms 4/3 $6,000 $3,000
Cottage # 108 2/2 $2,650 $1,600
Cottage # 202-1 2/2 $2,650 $1,600
Cottage # 204-1 2/2 $2,650 $1,600
Cottage # 516-1 1/1 contact us contact us
Cottage # 516-2 1/1 contact us contact us
Cottage # 516-3 2/2 contact us contact us
Cottage # 516-4 1/1 contact us contact us
Cottage # 512-5 1/1 contact us contact us
Cottage # 512-5A studio contact us contact us
Cottage # 512-6 2/2 contact us contact us
Cottage # 706-1 1/1 $2,785 $1,385
Cottage # 706-2 2/1 $2,785 $1,385
Cottage # 708-1 1/1 $2,365 $1,105
Cottage # 708-2 2/2 $3,205 $1,805
Cottage # 714-2 1/1 $2,715 $1,315
Cottage # 714-9 2/2 $3,205 $1,805
Cottage # 729 Rear Studio $2,575 $1,385
Cottage # 729 Up Studio $2,435 $1,175
Duval Village 2/2.5 $2,450 $1,550
Harborfront Retreat 2/2 $3,135 $1,735
Harborfront Retreat 3/3 $3,835 $2,435
Harborfront Retreat 4/4 $4,535 $3,135
Margaritavillas 1/1 $1,800 $1,000
Margaritavillas 2/1 $2,000 $1,200
Margaritavillas 2/2 $2,200 $1,400
Margaritavillas 3/2 $3,675 $2,500
Paradise Island Villas 2/2 $2,650 $1,650
Paradise Island Villas 3/2 $2,950 $1,950
Poolside Court 2/1.5 $2,850 $1,800
Poolside Court 2/2.5 $2,850 $1,800
Private Home # 100-1 4/3 $6,500 $4,500
Private Home # 102 4/3.5 $4,750 $3,000
Private Home # 118-A 4/4 $7,500 $4,500
Private Home # 314 3/4 $6,500 $4,500
Private Home # 316 4/4 $7,500 $5,500
Private Home # 318 3/3.5 $6,500 $4,500
Private Home # 320 4/4 $7,500 $5,500
Private Home # 500 4/3 $5,500 $3,500
Private Home # 508 2/2 $3,205 $1,805
Private Home # 509-N 3/3 contact us contact us
Private Home # 509-S 5/4 $5,000 $8,500
Private Home # 514 4/3 $6,500 $4,500
Private Home # 535 3/2.5 $5,165 $3,065
Private Home # 611 2/2.5 $4,185 $2,785
Private Home # 729 3/2 $4,255 $2,855
Private Home # 830 2/1 $3,065 $1,665
Private Home # 1011-3 3/2.5 $4,250 $2,850
Private Home # 1400-A 3/2 $3,835 $2,435
Private Home # 1400-B 2/2 $3,205 $1,805
Sand Cabana 3/2 $4,500 $2,500
Sand Castle 5/3.5 $8,000 $4,500
Sea Watch 4/3.5 $5,500 $3,500
Southernmost Studios Studio $2,085 $1,105
Spring Fling 2/2 $2,450 $1,400
Summertime 5/4 $8,000 $4,500
Sunset Harbor 2/2 $3,675 $2,400
Sunset Harbor 2/2.5 $3,675 $2,400
Sunset Harbor 3/2 $4,750 $3,000
Sunset Harbor 3/.25 $4,750 $3,000
Sunset Harbor 3/3 $4,750 $3,000
Townhome # 108 2/2.5 $3,675 $2,500
Townhome # 219 4/2 $3,835 $2,435
Townhome #411-B 2/2 $3,150 $2,000
Townhome #413-B 2/2 $3,150 $2,000
Townhome #921-4 1/1 $2,435 $1,245
Townhome #921-8 1/1 $2,435 $1,245


Key West Monthly Rentals.
Please contact us for rates on Monthly Rental properties.

Property Name BR/BA
Bella Vista 4/4.5
Captain's Folly 4/3.5
Captains Hideaway 3/2
Conch Manor 4/2
Dolphin Beach Retreat 2/2
Emerald Vista 2/2
Front Row Seats 3/2
Gulf Retreat 4/2
Island Bungalow 1/1
Island House 2/2
Key Lime Pie 3/2
Key West Charm 1/1 and 2/2
Ocean Blue 3/3
Ocean Gallery 1/1
Paradise Key 4/3
Private Haven 3/2
Private Home # 316W 2+Den/2
Sea View 3/2
Seaport Palms 3/2
Sunset Bay 2/2
Towering Palms 3/2
Truly Conch 3/2
Under the Sea 2/2
Victorian Secret 4/2.5
Water's Edge 4/4
Winter Haven 3/2



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.

Click Here to learn more About Rates & Availability.


(Click here to see Middle Keys Properties in Order of Bedrooms)


Upper Keys

Key West

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
Admiral's Landing 5/3 $7,500 $4,500
Admiral's Playground 6/5 $6,500 $4,500
African Palms 7/4 $7,500 $4,500
Bay Breezes 2/2.5 $1,950 $1,250
Beach Chalet 3/2 $4,000 $2,400
Beach Haven 3/2 $4,000 $2,400
Beach Sanctuary 3/2 $4,000 $2,400
Blue View 2/2 $3,350 $1,200
Emerald Isle 3/2.5 $2,150 $1,450
Emerald Palms 3/2 $2,650 $1,550
Emerald Playground 3/3 $3,000 $1,800
Grand Paradise 6/5 $12,000 $6,000
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
Gulf Watch 4/3 $5,500 $3,250
Havana Daydreamin' 3/2 $4,000 $2,400
Heart of Paradise 3/2.5 $2,400 $1,250
Island Colors 3/2 $3,150 $2,150
Margarita Villa 2/2.5 $1,800 $1,300
Mariner's Hideaway 3/3 $2,800 $1,600
On Green Dolphin Street 4/4 $6,000 $2,500
Palm Oasis 3/2 $3,350 $1,800
Palm View 2/2.5 $1,500 $1,000
Private Home # 4-I 4/3 $5,000 $3,500
Pool View 2/2.5 $1,500 $1,000
Reflections 4/2 $6,000 $3,000
Sea Chalet 4/3 $5,000 $3,500
Sombrero Lane 4/3 $5,000 $2,650
Sombrero Splendor 4/3 $4,500 $2,250
Southern Comfort 3/2 $2,950 $1,950
The Blue Lagoon 5/4 $10,000 $5,000
Tiki Terrace 2/2 $1,850 $1,250


Upper Keys Properties in Alphabetical Order

(Click here to see Upper Keys Properties in order of Bedrooms)



Middle Keys

Key West

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.

Click Here to learn more About Rates & Availability.


Upper Keys Weekly Rentals.
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
Beach Rest 2/2 $1,800 $900
Casa Contenta 8/5 $9,000 $5,500
Finding Nemo 4/3 $5,000 $3,000
Flamingo Beach 4/3 $5,000 $3,000
Flip-Flop Beach 2/2 $2,500 $1,500
Island Oasis 4/3 $5,500 $3,500
Keys Safari 3/3 $3,750 $2,500
Mockingbird House 3/3 $2,250 $1,350
Ocean Mural 3/3 $2,500 $1,800
Ocean Perch 2/2 $2,100 $975
Ocean Roost 2/2 $2,100 $975
Oceanfront Oasis 4/4 $20,000 $4,200
Oceanpointe 1/1 $1,815 $835
Oceanpointe 2/2 $2,100 $900
Ocean's Edge 3/3 $3,500 $2,500
On The Bay 1/1 $2,100 $1,050
On The Bay 2/2 $2,600 $1,950
Plantation Palms 4/3.5 $5,500 $3,500
Plantation Palms 2/2 $3,500 $2,500
Private Home # 22-A 4/4 $10,000 $6,000
Private Home # 74-0 3/2 $5,000 $3,850
Private Home # 75-90 3/3 $8,500 $6,500
Private Home # 75-94 4/4 $8,500 $6,500
Private Home # 82-5 4/3 $7,000 $5,000
Private Home # 85-2 4/3 $4,200 $3,200
Private Home # 95-4 2/2 $4,500 $3,000
Private Home # 105-S 5/3 $6,000 $4,500
Private Home # 121-N 3/3 $4,500 $3,000
Private Home # 134-C 2/2 $2,100 $1,600
Private Home # 209-O 5/4 $5,000 $3,500
Private Home # 402-G 3/3 $6,000 $4,500
Private Home # MB-1 4/4 $7,000 $5,500
Reef Motif 4/3 $5,000 $3,500
Sailfish Reef 2/2 $2,250 $1,050
Sand Piper 2/1.5 $2,200 $1,350
Sea Gulls 1/1 $1,600 $1,000
Sea Gulls 2/2 $1,800 $1,200
Sea World 2/2 $1,850 $1,250
Seashells & Starfish 7/6 $8,500 $5,000
Seaview Villa 3/3 $2,500 $1,800
Ship Ahoy! 4/4 $5,500 $4,000
Sun Flower 2/1.5 $2,200 $1,350
The View 2/2 $1,650 $1,050
Treasure Chest 3/2 $3,500 $1,800

Upper Keys Monthly Rentals.
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
Crystal Cove 3/3 $15,000 $12,000
Gulfside Harbour 3/3 $10,000 $6,000
High Expectations 4/4 $8,500 $4,500
Private Home # 16-A 5/4 $12,000 $8,000
Private Home # 24-C 3/2 $4,200 $3,200
Private Home # 34-S 2/1 $3,600 $2,600
Private Home # 35 M 3/3 $15,000 $10,000
Private Home # 40-B 4/3 $8,500 $6,500
Private Home # 57-S 3/2 $6,000 $4,000
Private Home # 58-S 4/3 $18,000 $14,000
Private Home # 108 5/6 please call please call
Private Home # 109-8 4/3 $10,000 $8,000
Private Home # 243-S 4/2 $7,000 $5,500
Private Home # 254-A 4/2 $9,000 $7,000
Private Home # 258-G 3/2 $7,000 $5,000
Private Home # 352-S 4/3.5 $17,000 $14,000
Private Home # 356-S 4/3 $10,000 $8,000
Private Home #425-L 4/3.5 $10,000 $8,000
Private Home # 87-P 3/2 $5,500 $4,500

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