pinterest facebook instagram twitter youtube google my business
  • (305) 294-7358
Key West Time
April 23rd
8:01am · 73°F

Rooftop Renaissance ~ Monthly Rental

1BR 2BA ~ Monthly Rental
Sleeps 4

Rooftop Renaissance vacation rental falls into a distinctive design category of Heritage Victorian - Meets Modern Luxury. This one-of-a-kind monthly rental is situated on two floors of one side of a grand historic home on Caroline Street. An exquisite 1BR 2BA luxury accommodation, it was redesigned to offer all the accoutrements of a 5-Star condominium. It provides pleasing views of tin roofs and treetops, and a peaceful Zen-pool Garden below. Located in the Key West Historic Seaport neighborhood, it’s a short two blocks from the famous harbor walk. Within a few minutes’ walk enjoy a diversity of dockside restaurants, renowned bars, live music, and gaze at the sail and power boats.

The interior is modern, classical, and island style all at the same time. Festive Caribbean blue walls throughout are contrasted with bright white trim. Ocean themed artwork adds to the tropical Island vibe. A distinctive black metal staircase, with wooden risers, joins the two levels of the condominium. The first level accommodates the living room /kitchen/dining spaces, and one full bathroom. Level two is soley reserved for the master bedroom suite.


GREAT ROOM – First Level

The living room area has a stylish cream-colored L-shape sofa. On the wall opposite the sofa, is a handsome floor to ceiling storage cabinet that hides away a queen-size Murphy bed. This creates an additional sleeping space with its own bathroom.

Steps from the sofa, a doorless entrance leads to the U-Shape kitchen. Built-out with granite counter tops and white cottage style cabinets, the kitchen provides upscale stainless-steel appliances. It’s equipped to do some serious cooking, but a playful sign on the wall reminds you too, Relax, You’re in Key West! Two kitchen windows invite in the sunlight and provide pleasing views, including the outdoor private back deck.

Around the corner from the kitchen, the open-air back deck connects with the living room through French doors. Set for two, an adorable counter-height table with chairs and sun umbrella provides the perfect place for morning coffee and evening cocktails.

Returning to the living room, and facing the staircase, take note of the dining area, set with a tasteful white dining table and seafoam tone chairs. Now continue past the dining set, through the square arch, into the downstairs hall. Here you will find the laundry closet on one side of the hall, with full size stackable washer/dryer. On the opposite side there’s a full-size bathroom.

The downstairs bathroom is made elegant with a classic white marble top vanity and jade jewel tone tiled shower. A large sash window provides plenty of natural light. Storage under the vanity top provides a convenient place to stow your cosmetics. Stepping back into the hall, our tour proceeds to the spiral staircase ascending to the master bedroom suite.


MASTER SUITE – Second Level

At the top of the house, Rooftop Renaissance provides an exceptional romantic hideaway. Get ready for a WOWZA moment when you step into the bedroom. A masterfully reinvented attic, it’s an extraordinarily cool space. When I first walked into this room, I almost felt as if I could be in a tropical USS Starship Enterprise

Bold wing-shaped angular ceilings create a thrilling artistic space. Inset spotlights and twin shuttered skylights wash the blue and white room with light, creating intriguing shadows. The queen size bed commands the center of the room. A dressing bench is placed at the foot of the bed. Tidy nooks and crannies are expertly set with a desk, bureau, shelves, storage, and closets.

The full-size master bathroom is stunning with a double size shower with indigo jewel tone tiles and frameless glass doors. The white marble vanity top is extended out past the sink, to create additional counter and drawer space for personal items. A fanciful feature is the sash window in the shower that frames a picturesque treetop view. Between the window, ceiling, and vanity lights, the space is perfectly lit.


Bedding Summary:

• 1 Queen Size bed

• 1 Queen Size sleeper sofa

Amenities: 5 Star Resort Quality with Amenities. A shared Zen Garden swimming pool and in-ground spa are at the back of the property. Private open-air deck adjoining the living room. Stainless-steel kitchen appliances include oven with glass stove top, French door refrigerator with icemaker, dishwasher, microwave Keurig. Laundry closet with full-size w/d. Wi-Fi. Large TV. Lush tropical gardens and landscaping.

Area: Heart of Key West's designated Historic Seaport District. There is so much to do right on the harbor. Walk to all Old Town features, no need for a car. Just two short streets from Duval St. (remember it takes 3 to 4 Key West streets to make a city block); two streets from the harbor where the boats are docked. Close to Mallory Square Sunset Celebration and Old Town Key West retailers.

Activities: Close to adventures and activities including sailing, boating, diving, museums, nightlife, music. Conveniently located near gourmet grocery shopping with excellent wine selection, sushi deli, and butcher. Close to shopping, art galleries, and a variety of national and international restaurants, coffee shops. Close to Simonton Beach. Be sure to stop by the Schooner Wharf Bar, the oldest and most authentic bar on the harbor. You may want to dine at the Half Shell Raw Bar, the original seafood restaurant on the harbor.  If you want to come by boat, you can possibly arrange to dock here. Close to the beach.

Parking: There is no off-street parking available at the property. If you bring a car to Key West we suggest that you park it in the City of Key West Old Town Parking Garage just up the street on Caroline Street. From this location you do not need a car. Enjoy walking or biking everywhere—you'll see more that way. 

Book Direct For The Best Price Guaranteed

special rates available

1 BR 2 BA

Aug 1- Sept 30

Monthly $4500

view all specials

Dates Monthly
Apr 1, 2024 - Apr 30, 2024 $6175
May 1, 2024 - May 31, 2024 $4900
Jun 1, 2024 - Jun 30, 2024 $4900
Jul 1, 2024 - Jul 31, 2024 $4900
Aug 1, 2024 - Aug 31, 2024 $4900
Sep 1, 2024 - Sep 30, 2024 $4900
Oct 1, 2024 - Oct 31, 2024 $4900
Nov 1, 2024 - Nov 30, 2024 $4900
Dec 1, 2024 - Dec 31, 2024 $5700
Jan 1, 2025 - Jan 31, 2025 $9150
Feb 1, 2025 - Feb 28, 2025 $9150
Mar 1, 2025 - Mar 31, 2025 $9150
Apr 1, 2025 - Apr 30, 2025 $6175
May 1, 2025 - May 31, 2025 $4900
Jun 1, 2025 - Jun 30, 2025 $4900
Jul 1, 2025 - Jul 31, 2025 $4900
Aug 1, 2025 - Aug 31, 2025 $4900
Sep 1, 2025 - Sep 30, 2025 $4900
Oct 1, 2025 - Oct 31, 2025 $4900
Nov 1, 2025 - Nov 30, 2025 $4900
Dec 1, 2025 - Dec 31, 2025 $5700

Additional Notes:

  • Holiday, Festival, and Event Rates are 20% to 25% higher. These include, but are not limited to: Fantasy Fest, Thanksgiving, Christmas, New Years, Power Boat Races, Mini-Lobster Season, Labor Day, Parrot Heads Meeting of the Mind, 4th of July, Easter.
  • Future Dates not listed, please call 305-294-7358 for pricing.

Rates and Terms are subject to change without notice. Above rates do not include taxes and fees. Click here for more details on additional fees. Please contact us for specific pricing and to confirm rates. Rates in US Funds. (305) 294-7358 Ext 1 -

Apply here for Travel Guard Trip Cancellation and Interruption Insurance.

VHKW offers promotional specials for purchasing trip insurance for stays between Aug 10 and Oct 20. Please call for more details.

Bedding Summary:

  • Master bedroom - Queen size bed
  • Livingroom - Queen sleeper sofa
Inquire Availability for this property
* all fields are required.

Thank you for your inquiry. We will get back to you as soon as possible.

Sort Properties

Rental Period

Availability Calendar

* This property may not be available for the dates above due to other inquires and pending reservation.

Vacation Rental

Rentals For
Social Distancing

rentals for social distancing

Sunset Key

sunset key






town houses and condos







Truman Annex

truman annex