The 2026 Lineup is HERE!

Key West, United States

Two Bedroom Vacation Homes & Condos

All of these properties are reserved for SEVEN NIGHTS - Monday to Monday!

WindwardBreeze

Overview

We have partnered with Last Key Realty and Rent Key West, two of Key West's Premier Property Management Offices to offer some of Key West's finest properties in our packages. We have larger units, too. All condos and homes have fully stocked kitchens, most have shared or private pools, some have private parking, and ALL are beautifully maintained and ready for your group! Enjoy more privacy and space! For more property info or for large grroup bookings, you can give us a call at 305.363.5899.

Sunrise Suites 203

Two Bedroom Vacation Homes & Condos $514.29/night Sleeps 6

Sunrise Suites 203

  • 2BR\2BA Condo in New Town
  • King + Queen + Sofa Sleeper
  • Shared Pool + Hot Tub Access

Utopia @ Tropical Village

Two Bedroom Vacation Homes & Condos $614.29/night Sleeps 4

Utopia @ Tropical Village

  • 1BR\1BA 2nd floor Condo in Old Town
  • 2 Queens
  • Shared Pool Access

Tropical Hideaway @ Tropical Village

Two Bedroom Vacation Homes & Condos $614.29/night Sleeps 4

Tropical Hideaway @ Tropical Village

  • 2BR\1BA Duplex near Southernmost Point
  • 2 Queens
  • Shared Pool Access

Hidden Treasure @ Colony

Two Bedroom Vacation Homes & Condos $614.29/night Sleeps 4

Hidden Treasure @ Colony

  • 2BR\2BA Cottage in Old Town
  • 2 King Beds + Sofa Sleeper
  • Private Deck w/ Outdoor Dining + Grill

Eyebrow Suite @ Eyebrow House

Two Bedroom Vacation Homes & Condos $685.71/night Sleeps 4

Eyebrow Suite @ Eyebrow House

  • 2BR\1.5BA Apartment near Duval Street
  • 2 Queen Beds
  • Large Hot Tub & Grill

La Casa de Luces

Two Bedroom Vacation Homes & Condos $685.71/night Sleeps 4

La Casa de Luces

  • 2BR\2BA Condo near Southernmost Point
  • King + Queen Bed
  • Shared Pool Access

Cuban Paradise @ Cuban Club

Two Bedroom Vacation Homes & Condos $685.71/night Sleeps 4

Cuban Paradise @ Cuban Club

  • 2BR\2BA Condo on Duval Street
  • King + Queen + Sofa Sleeper
  • Shared Balcony overlooking Duval

Tropical Cottage @ Tropical Village

Two Bedroom Vacation Homes & Condos $685.71/night Sleeps 4

Tropical Cottage @ Tropical Village

  • 2BR\2BA Cottage near Southernmost Point
  • King + King or 2 Twins + Sofa Sleeper
  • Shared Pool Access

Cuban Club Suite

Two Bedroom Vacation Homes & Condos $685.71/night Sleeps 4

Cuban Club Suite

  • 2BR\2BA Condo on Duval Street
  • King + Queen + Sofa Sleeper
  • Private Balcony overlooking Southern Duval

Fleming-O

Two Bedroom Vacation Homes & Condos $742.86/night Sleeps 6

Fleming-O

  • 2BR\1BA Private Home in Old Town
  • Queen + King or 2 Twins + Sofa Sleeper
  • Fenced Back Deck with Outdoor Dining Area

Catherine House

Two Bedroom Vacation Homes & Condos $971.43/night Sleeps 6

Catherine House

  • 2BR/2BA Cottage in Old Town
  • 2 King Beds
  • Private Conversation Pool

Villa Cubana

Two Bedroom Vacation Homes & Condos $971.43/night Sleeps 6

Villa Cubana

  • 2BR/2BA Townhome with Pool & Parking
  • King + King or Two Twins
  • Access to Community Pool and Parking Lot

Casita Angelita

Two Bedroom Vacation Homes & Condos $1,000.00/night Sleeps 4

Casita Angelita

  • 2BR/2BA Condo near the Amphitheater!
  • King + King or Two Twins
  • Off-Street Parking in Driveway

Top of Old Town

Two Bedroom Vacation Homes & Condos $1,171.43/night Sleeps 6

Top of Old Town

  • 2BR/2.5BA Condo at Duval Square
  • King + King or Two Twins + Queen sleeper sofa
  • Private Balcony & Shared Pool

Darling of Duval

Two Bedroom Vacation Homes & Condos $1,314.29/night Sleeps 6

Darling of Duval

  • 2BR/2BA Cottage near Duval Street
  • Two King Suites with walk-in showers
  • Private Patio with Jacuzzi Hot Tub

Puerta Coralina

Two Bedroom Vacation Homes & Condos $1,357.14/night Sleeps 6

Puerta Coralina

  • 2BR/3BA Cottage on a quiet street in Old Town
  • King + King or Two Twins
  • Private Pool with Waterfall and Outdoor Shower