Park City Resort Rentals - Vacation Rentals in Southernmost Point

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From US $1,350

         

New

Resort

Premier resort overlooking the Gulf. Walk to Mallory Square, restaurants, beach.

• Air Conditioner
• Security/Safety
• Bedding/Linens

• Key West
• Historic Seaport

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From US $1,688

         

|

9.5 (508 Reviews)

Resort

H2O Suites- Adults Only

• Air Conditioner
• Parking
• Pool

• Key West
• Uptown - Upper Duval

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From US $640

         

|

9.6 (1007 Reviews)

Resort

Santa Maria Suites

• Air Conditioner
• Parking
• Pool

• Key West
• Uptown - Upper Duval

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From US $473

         

New

Resort

Hyatt Sunset Harbor 1-bedroom suite w/AC, WiFi, Pool, Walk to Duval & Mallory

• Air Conditioner
• Parking
• Security/Safety

• Key West
• Historic Seaport

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From US $432

         

|

9.3 (681 Reviews)

Resort

Santa Maria Suites Resort

• Air Conditioner
• Parking
• Pool

• Key West
• Uptown - Upper Duval

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From US $598

         

|

9.2 (1008 Reviews)

Resort

Ocean Key Resort - A Noble House Resort

• Air Conditioner
• Parking
• Pool

• Key West
• Historic Seaport

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From US $444

         

New

Resort

Waterfront Resort, Songwriter’s Fest, Old Town, Sleeps 2, Swimming Pool, Hot Tub

• Air Conditioner
• Pool
• TV

• Key West
• Truman Annex

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From US $716

         

|

8.6 (1146 Reviews)

Resort

Opal Key Resort & Marina

• Air Conditioner
• Parking
• Pet Friendly

• Key West
• Truman Annex

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From US $516

         

|

9.0 (1024 Reviews)

Resort

Pier House Resort & Spa

• Air Conditioner
• Parking
• Pool

• Key West
• Historic Seaport

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From US $368

         

New

Resort

Charming 2-bedroom condo at the spectacular Coconut Beach Resort Nov 15-22-2025

• Air Conditioner
• Parking
• Pool

• Key West
• Uptown - Upper Duval

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From US $1,941

         

10.0 (1 Review)

Resort

Sunset Harbor Resort & Spa, Hot Tub, Pool

• Air Conditioner
• Parking
• Pool

• Key West
• Truman Annex

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New

From US $11,498

         

New

Resort

2 Sunset Harbor Resort Key West Florida

• Air Conditioner
• Pool
• Balcony/Terrace

• Key West
• Truman Annex

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New

From US $11,498

         

New

Resort

2 Sunset Harbor Resort Key West Florida

• Air Conditioner
• Pool
• Balcony/Terrace

• Key West
• Truman Annex

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From US $2,440

         

New

Resort

Galleon Resort, Pool/Hot Tub, In Town, Marina

• Air Conditioner
• Parking
• Pool

• Florida
• Key West

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New

From US $1,624

         

New

Resort

2 Sunset Harbor Resort, Pool, Hot Tub, In Town!

• Air Conditioner
• Pool
• Balcony/Terrace

• Key West
• Truman Annex

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New

From US $1,600

         

New

Resort

1/1 Galleon Resort, Hot Tub, Pool, Marina, Gym

• Air Conditioner
• Pool
• TV

• Key West
• Historic Seaport

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New

From US $1,600

         

New

Resort

@/2 Galleon Resort, Hot Tub, Pool, Marina, Gym

• Air Conditioner
• TV
• Balcony/Terrace

• Key West
• Historic Seaport

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From US $1,505

         

New

Resort

2 Banyan Resort, Beach, Pool, Hot Tub, In Town!

• Air Conditioner
• Parking
• Pool

• Key West
• Historic Seaport

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From US $1,463

         

New

Resort

Sunset Harbor Resort, Marina, In Town, Hot Tub, Pool, Balcony

• Air Conditioner
• Parking
• Pool

• Key West
• Truman Annex

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From US $956

         

New

Resort

Sunset Harbor Resort & Spa, In Town, Marina, Hot Tub.

• Air Conditioner
• Parking
• Pool

• Key West
• Truman Annex

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From US $908

         

New

Resort

Hyatt Sunset Harbour Resort-Prime location on Key West!

• Air Conditioner
• Parking
• Pool

• Key West
• Truman Annex

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From US $887

         

New

Resort

Sunset Harbor Resort+Key West-Hemingway Days 2 BR townhome-July 19-25, 2026

• Air Conditioner
• Security/Safety
• Bedding/Linens

• Key West
• Truman Annex

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New

From US $731

         

New

Resort

Galleon Resort - Waterfront Key West

• Air Conditioner
• Security/Safety
• Bedding/Linens

• Key West
• Historic Seaport

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From US $338

         

New

Resort

Hyatt Vacation Club in Key West- Studio

• Security/Safety
• Child Friendly

• Key West
• Truman Annex

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