Compass Realty Vacation Home Rentals & Management

Compass Realty Vacation Home Rentals & Management Compass Realty in Key West, Florida! We specialize in privately owned vacation rentals and sales of

The original vacation home rental and management company of Key West.

🌴✨ AN ISLAND RETREAT — Brand New, Renovated & Reimagined! ✨🌴Escape to this charming 2-bedroom, 2.5-bath townhome in hist...
08/16/2026

🌴✨ AN ISLAND RETREAT — Brand New, Renovated & Reimagined! ✨🌴

Escape to this charming 2-bedroom, 2.5-bath townhome in historic Mills Place at Truman Annex, freshly renovated, painted and beautifully refurnished.

🏡 Highlights:
• 🛏️ King primary suite with ensuite bath & private cocktail deck
• 🛏️ Queen guest bedroom with ensuite bath
• 🌿 Lovely rear deck & gardens
• 🏊 Large community pool with sunny & shaded areas
• 🚗 Assigned off-street parking
• 🚲 Bike racks
• 📍 Quiet location in gated Truman Annex, right in the heart of Old Town Key West

A peaceful island retreat just steps from the pool and close to everything Key West has to offer! 🌴☀️

Monthly rental — 28-night minimum stay required.

📞 305-292-1881
📧 [email protected]


https://www.compass-realty.com/vrp/unit/An_Island_Retreat-2698-266044-1

🌴✨ AFTERNOON DELIGHT — Breathtaking Views in Truman Annex! 🌅Enjoy some of the best waterfront views in Key West from thi...
08/15/2026

🌴✨ AFTERNOON DELIGHT — Breathtaking Views in Truman Annex! 🌅

Enjoy some of the best waterfront views in Key West from this beautiful 2-bedroom, 2-bath condo in historic Mills Place.

🌊 Gulf views & ships passing by
🌅 Sunset views every evening
🏡 Two private balconies
✨ Soaring 18-ft ceilings & windows on three sides
🛏️ 2 bedrooms with private baths
🍽️ Full kitchen, dining area & spacious living room
📍 Convenient Truman Annex location near Duval Street, dining & Old Town attractions

Relax, watch the boats come and go, and enjoy unforgettable Key West sunsets from your own private retreat. 🌴⛵

Monthly rental — 28-night minimum stay required.

📞 305-292-1881
📧 [email protected]


https://www.compass-realty.com/vrp/unit/Afternoon_Delight_in_the_Truman_Annex-2698-219331-1

🌴✨ GYPSY’S PALACE — Waterfront Living in Truman Annex! 🌅Escape to this fabulous 2-level waterfront condo in the historic...
08/14/2026

🌴✨ GYPSY’S PALACE — Waterfront Living in Truman Annex! 🌅

Escape to this fabulous 2-level waterfront condo in the historic Mills Place Hospital Building at Truman Annex.

🌊 Stunning water & sunset views
🏡 Spacious 2-level layout with tall ceilings
🌅 Covered deck overlooking Truman Waterfront Park
🛏️ 2 bedrooms with ensuite baths & private decks
🏊 Large community pool
🚗 Assigned street parking
📍 Close to Duval Street, dining, shopping & Fort Zachary Taylor Park & Beach

Relax indoors or swing away in the hammock while enjoying beautiful Key West sunsets! 🌴☀️

Monthly rental — contact our office for details.

📞 305-292-1881
📧 [email protected]


https://www.compass-realty.com/vrp/unit/Gypsys_Palace_in_the_Truman_Annex-2698-193299-1

🌴🌊 BEACHY KEEN TOO — Your Key West Beach Escape! ☀️Weekly rentals available! Enjoy endless open-water views and immediat...
08/14/2026

🌴🌊 BEACHY KEEN TOO — Your Key West Beach Escape! ☀️

Weekly rentals available! Enjoy endless open-water views and immediate access to the Atlantic Ocean from this beautiful 2-bedroom waterfront condo at Beach Club.

✨ Highlights:
• 🌊 Stunning ocean views & covered balcony
• 🛏️ King primary suite with spa-like shower
• 🛏️ Guest room with twins or king
• 🏊 Two heated oceanfront pools
• 🎾 Tennis court & fitness center
• 🍹 Outdoor cooking & covered dining areas
• 🚗 Reserved garage parking
• 📍 Walking/biking distance to beaches, restaurants, shopping, bars & Duval Street

Relax, soak up the sunshine, and enjoy your own tropical Key West getaway! 🌴🌅

Weekly rental — up to 4 adults comfortably.
Sorry, no pets.

📞 305-292-1881
📧 [email protected]


https://www.compass-realty.com/vrp/unit/Beachy_Keen_Too-2698-259724-1

🌴✨ A GULFSTREAM DRIFT — Your Key West Paradise! 🌅Watch the sunset over the ocean from the huge penthouse balcony at this...
08/13/2026

🌴✨ A GULFSTREAM DRIFT — Your Key West Paradise! 🌅

Watch the sunset over the ocean from the huge penthouse balcony at this beautiful 3-bedroom, 3-bath Harbour Place condo in Truman Annex.

🌊 Ocean views from all 3 bedrooms
🛏️ Spacious bedrooms with ensuite baths
🌅 Huge private penthouse balcony
🏝️ 2,000 sq. ft. of tropical comfort
🏊 Nearby community pool
🚗 Covered private parking
📍 Just 3 blocks from Duval Street & ¼ mile from Fort Zachary Taylor State Park

Experience the best of Old Town Key West in this tropical retreat! 🌴☀️

28-night minimum stay required.

📞 305-292-1881
📧 [email protected]


https://www.compass-realty.com/vrp/unit/BREATHTAKING_VIEWS_ASK_ABOUT_OUR_SPECIAL_RATES-2698-193298-1

🌴✨ SWEET’S SPOT — Your Key West Penthouse Escape! 🌅Enjoy breathtaking open-water and sunset views from this luxurious 3-...
08/13/2026

🌴✨ SWEET’S SPOT — Your Key West Penthouse Escape! 🌅

Enjoy breathtaking open-water and sunset views from this luxurious 3-bedroom, 4.5-bath penthouse in Harbour Place at Truman Annex.

🌊 Stunning water views
🛏️ 3 bedrooms, each with a private bath
🌅 Spacious decks with harbor & sunset views
🏊 Beautiful waterfront pool
🚗 Covered parking for 2 vehicles
📍 Just 2 blocks from Duval Street

Relax in luxury and enjoy the very best of Old Town Key West! 🌴☀️

28-night minimum stay required.

📞 305-292-1881
📧 [email protected]


https://www.compass-realty.com/vrp/unit/Sweets_Spot_At_The_Harbour_Place-2698-228970-1

🌴🌊 AQUA BREEZE — Waterfront Living in Key West! 🌅Enjoy breathtaking open-water views from Aqua Breeze, a beautifully fur...
08/12/2026

🌴🌊 AQUA BREEZE — Waterfront Living in Key West! 🌅

Enjoy breathtaking open-water views from Aqua Breeze, a beautifully furnished 2-bedroom, 2.5-bath condo in Harbour Place at Truman Annex.

✨ Highlights:
• 🌊 Direct oceanfront location where the Gulf of Mexico & Atlantic Ocean meet
• 🌅 Waterfront plaza with chaise lounges & front-row sunset seating
• 🏊 Beautiful community pool
• 🚗 Covered off-street parking
• 📍 Gated Truman Annex in the heart of Old Town
• 🛍️ Quick walk to Duval Street, Mallory Square, shopping, dining & watersports

Relax, soak up the sunshine, and enjoy a front-row seat to some of the most spectacular sunsets in Key West! 🌴☀️⛵

28-night minimum stay required.

📞 305-292-1881
📧 [email protected]


https://www.compass-realty.com/vrp/unit/Ocean_Breeze_the_Truman_Annex-2698-193316-1

🌴🌊 PARADISE ON THE OCEAN — Key West Waterfront Living! 🌅Escape to Paradise on the Ocean, a beautiful 2-bedroom waterfron...
08/12/2026

🌴🌊 PARADISE ON THE OCEAN — Key West Waterfront Living! 🌅

Escape to Paradise on the Ocean, a beautiful 2-bedroom waterfront condo in Truman Annex. Enjoy breathtaking ocean views and spectacular Key West sunsets from every room and the private balcony!

✨ Highlights:
• 🛏️ King primary suite with beautifully appointed bath
• 🛏️ Guest room with twins that can convert to a king
• 🌅 Incredible waterfront views & sunsets
• 🏊 Large heated oceanfront pool
• 🚗 Assigned covered parking
• 📍 Just blocks from Duval Street, Mallory Square & Fort Zachary Taylor Beach
• 📶 Complimentary Wi-Fi

Relax, watch the sailing ships drift by, and enjoy the best of Key West from this incredible waterfront retreat! 🌴⛵

28-night minimum stay required.

📞 305-292-1881
📧 [email protected]


https://www.compass-realty.com/vrp/unit/Paradise_on_the_Ocean_the_Truman_Annex-2698-193319-1

🌴✨ SUBLIME SUNSETS — Luxury Waterfront Living in Key West! ✨🌴Ready for an unforgettable Key West getaway? Sublime Sunset...
08/11/2026

🌴✨ SUBLIME SUNSETS — Luxury Waterfront Living in Key West! ✨🌴

Ready for an unforgettable Key West getaway? Sublime Sunsets, a stunning 4-bedroom, 4.5-bath condominium at Harbour Place in Truman Annex, offers breathtaking waterfront views, luxurious accommodations, and plenty of space to relax and unwind. 🌊🌅

Recently completely renovated, this one-of-a-kind residence features an expansive floor plan with endless views of the Atlantic Ocean and Gulf of Mexico.

🏝️ Property Highlights:
• 🌊 Spectacular waterfront views throughout
• 🛏️ 4 luxurious king-size bedrooms, each with its own gorgeous ensuite bathroom
• 👨‍🍳 Fully equipped chef’s kitchen with modern conveniences
• 🍽️ Large 8-seat bar and island — perfect for gathering with family and friends
• 🛋️ Multiple spacious lounging areas for relaxing and entertaining
• 🍷 Spectacular waterfront dining room
• 🌅 4 private decks — 2 facing the ocean and 2 offering additional private outdoor space
• 🏊 Refreshing waterfront pool complex
• 📍 Located in historic Truman Annex, with immediate access to downtown and Duval Street
• ✨ Completely renovated for a luxurious and comfortable stay

Whether you're gathering with family, celebrating with friends, or simply looking for the perfect place to slow down and enjoy Key West, Sublime Sunsets is an exceptional waterfront retreat. 🌴☀️🐚

Come unwind, soak up the views, and stay long enough to experience the sunsets that will keep you coming back for more. 🌅💙

Please note: This property has a 28-night minimum stay.

📞 Contact our office for availability and rental details:
305-292-1881
📧 [email protected]



https://www.compass-realty.com/vrp/unit/Waterfront_4_bedroom_4.5_bath_luxurious_condo-2698-209734-1

🌴✨ Your Key West Escape Awaits at Truman Annex! ✨🌴Imagine waking up to breathtaking views of the Atlantic Ocean and Gulf...
08/11/2026

🌴✨ Your Key West Escape Awaits at Truman Annex! ✨🌴

Imagine waking up to breathtaking views of the Atlantic Ocean and Gulf of Mexico, relaxing on your private balcony, and ending the day with one of Key West’s legendary sunsets. 🌅

This beautifully updated Harbour Place condominium in Truman Annex puts you right in the heart of Old Town Key West — just about 3 blocks from Duval Street’s fabulous restaurants, shops, galleries, and nightlife.

🏝️ Property Highlights:
• 🌊 Stunning waterfront views from both bedrooms
• 🛏️ Primary bedroom with a king-size bed
• 🛏️ Second bedroom offers 2 twins or converts to a king
• ✨ Tastefully updated countertops, appliances, furniture & linens
• 🌅 Relaxing balconies off the living room and primary suite
• 🏊 Beautiful waterfront pool complex & lush gardens
• 🚗 Covered parking for one vehicle
• 📍 Prime location in historic Truman Annex / Old Town Key West

Whether you're looking for a peaceful waterfront retreat or want to experience everything Key West has to offer, this condo provides the perfect home base. 🌴☀️🐚

Please note: This property has a 28-night minimum stay.

📞 Contact our office for availability and rental details:
305-292-1881
📧 [email protected]



https://www.compass-realty.com/vrp/unit/Sunset_Dalite_the_Truman_Annex-2698-193338-1

Address

200 Front Street, Bldg 45
Key West, FL
33040

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