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Middle Keys Properties

(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.


Property Name BR/BA Highest (Peak) Rate (Holidays/Events) Lowest (Fall) Rate
(Aug 15 to Dec 15)
A Heavenly Place 2/2 $3,100 $2,000
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
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 # 512-2 2/2 contact us contact us
Cottage # 526 1/1 $220 $1,550
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 # 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
On the Beach 3/2.5 $4,500 $3,000
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 # 100-2 3/3 $5,500 $4,500
Private Home # 102 4/3.5 $4,750 $3,000
Private Home # 108 2/2.5 $3,675 $2,500
Private Home # 1400-A 3/2 $3,835 $2,435
Private Home # 1400-B 2/2 $3,205 $1,805
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 # 417 1/1 $2,750 $2,000
Private Home # 500 4/3 $5,500 $3,000
Private Home # 508 2/2 $3,205 $1,805
Private Home # 509 3/3 $4,500 $3,500
Private Home # 509-S 5/4 $5,000 $8,500
Private Home # 514 3/3 $6,000 $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
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 # 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


Please contact us for rates on Monthly Rental properties.

Property Name BR/BA
A Perfect Ten 3/3
A Shady Place 1/1
A Sunny Place 1/1
Bella Vista 4/4.5
Captain's Folly 4/3.5
Captains Hideaway 3/2
Casa Olivia 3/2.5
Casablanca South 1/1
Classic Conch 4/3
Conch Manor 4/2
Cottage # 419 1/1
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
Key West Paradise 5/4
Maria's Conch House 2/2
Ocean Blue 3/3
Ocean Gallery 1/1
Old South 3/3.5
Out of Africa 2/2
Paradise Key 4/3
Private Haven 3/2
Private Home # 316W 2+Den/2
Private Home # 1118 2/2
Private Retreat 2/2
Sea View 3/2
Seaport Breeze 4/3
Seaport Gardens 4/3
Seaport Palms 3/2
Spanish Lime 2/2
Sunset Bay 2/2
Towering Palms 3/2
Under the Sea 2/2
Victorian Secret 4/2.5
Water's Edge 4/4
Winter Haven 3/2
Yesteryears 6/6




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 $6,000 $4,000
African Palms 7/4 $7,500 $4,500
Bay Breezes 2/2.5 $1,950 $1,250
Beach & Golf Retreat 3/3 $2,850 $1,850
Beach Chalet 3/2 $4,000 $2,400
Beach Haven 3/2 $4,000 $2,400
Beach Sanctuary 3/2 $4,000 $2,400
Beach House Resort 2/2.5 $4,500 $1,750
Beach House Resort 3/2.5 $6,600 $3,150
Blue View 2/2 $3,350 $1,200
Cabana Breeze 3/3 $2,850 $1,850
Caribbean Palms Estate 5/4 $5,500 $3,750
Emerald Dreams 3/3 $2,650 $1,650
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
Endless Views 3/2 $2,800 $1,600
Escape to Paradise 3/2 $2,100 $1,450
Fins to the Left 2/2 $2,850 $1,950
Fins to the Right 2/2 $2,850 $1,950
Fisherman's Friend 2/2 $2,100 $1,450
Grand Paradise 6/5 $12,000 $6,000
Gulf Breeze 3/2 $1,900 $1,400
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
Hidden Haven 3/2 $2,150 $1,450
Island Colors 3/2 $3,150 $2,150
Island Escape 2/2 $2,200 $1,500
Margarita Villa 2/2.5 $1,800 $1,300
Mariner's Hideaway 3/3 $2,800 $1,600
Mermaids & Dolphins 2/2 $2,100 $1,400
Moonlit Palms Studio $1,500 $1,000
Ocean Escape 1/1 $1,250 $750
Ocean Escape 2/2 $1,650 $1,000
Ocean Escape 3/3 $2,550 $1,650
Ocean Landing 3/3 $3,350 $2,150
Ocean Palms Studio $1,500 $1,000
Ocean Splendor 3/3 $3,500 $2,200
Ocean Treasure 3/2.5 $3,700 $2,450
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
Pool View 2/2.5 $1,500 $1,000
Reflections 4/2 $6,000 $3,000
Reunion Retreat 6/5 $6,000 $4,000
Sea Chalet 4/3 $5,000 $3,500
Seabreeze 4/2.5 $2,850 $1,850
Sombrero Escape 3/2 $2,950 $1,650
Sombrero Lane 4/3 $5,000 $2,650
Sombrero Splendor 4/3 $4,500 $2,250
Sombrero Treasure 4/2 $ $
Sombrero View Cottage 2/2 $1,600 $950
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
Two Fins 4/4 $5,900 $3,900
Water Hazard 4/3 $4,800 $2,200
Waterways 4/3 $3,600 $1,900


Dock at Bougainvillea House

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

Casa Valencia from the water


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.


Property Name BR/BA Highest (Peak) Rate (Holidays/Events) Lowest (Fall) Rate
(Aug 15 to Dec 15)
Beach Hideaway 3/3 $2,950 $1,950
Beach Rest 2/2 $1,800 $1,050
Casa Contenta 8/5 $9,000 $5,500
Crystal Cove 3/3 $6,000 $3,500
Emerald Views 6/4 $6,500 $4,000
Finding Nemo 4/3 $5,500 $3,000
Flamingo Beach 4/3 $6,000 $3,000
Flip-Flop Beach 2/2 $2,500 $1,500
Gulfside Harbour 3/3 $6,000 $3,500
High Expectations 4/4 $5,500 $3,500
Island Oasis 4/3 $5,500 $3,500
Mockingbird House 3/3 $2,150 $1,350
Ocean Perch 2/2 $2,250 $950
Ocean Roost 2/2 $2,250 $950
Oceanfront Oasis 4/4 $20,000 $4,200
Oceanpointe 1/1 $1,815 $835
Oceanpointe 2/2 $2,100 $900
Ocean's Edge 2/2 contact us contact us
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
Reef Motif 4/3 $5,000 $3,500
Sailfish Reef 2/2 $2,400 $1,150
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 $9,000 $6,000
Seaview Villa 3/3 $2,750 $1,750
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 $3,350 $1,200

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