Florida Keys Vacation Rentals

Luxurious Vacation Homes in Key West

If you have any questions about rentals in Key West, please call 305-296-0011.

Find the perfect vacation home rental for your Key West, Florida vacation getaway! When you find a vacation rental of interest to you, simply check the box in front of the property listing and fill in the form at the bottom of the page. One of our reservation coordinators will be in contact with you as soon as possible. We look forward to seeing you in the Florida Keys!

$$$$$ $8,000 +
$$$$ $6,000 - $7,999
$$$ $3,000 - $5,999
$$ $1,750 - $2,999
$ Less than $1,750

New Featured Property

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Tranquil Palms Retreat — $$$$$ MM 31, 3 bedrooms, 4 baths, sleeps 8. Beautiful home on Big Pine Key on acres of protected Keys Habitat; heart-of-pine wood floors and marble baths; sleeps 8 comfortably; larger parties considered. Over 250 feet of ocean frontage, large natural beach, lots of Keys deer, elegantly decorated (upscale tropical décor), 2 master bedrooms with king beds, third bedroom with queen and 4 baths (jetted tub), additional private den with queen sleeper sofa; panoramic views, very tranquil and private. High speed internet access. Bring your tents — the kids would love it! Drive to Key West or Marathon. Kayaks and baby items available upon request; 16 room fishing lodge/grocery store/boat rentals at end of road. Incredible property, truly the best of the Keys.
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Homes

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Treetop — $$$$ 5 bedrooms, 5 baths, sleeps 12, no pets. Magnificent historic home two blocks from Duval Street in the heart of Old Town Key West. Heated pool & spa, off-street parking, 3 kings + 3 queens, TV/ cable ea.BR, decks, gardens, terraces, wireless internet, central A/C, ceiling fans, washer/dryer. Please call for rates and availability.
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Turtle Crawl — $$$$ 4 bedrooms, 4 baths, sleeps 8, no pets. Wonderful secluded private home in Truman Annex, with all the amenities, great furnishing and decor. Private pool and deck, wireless DSL, walking distance to both downtown and the beach. Call for rates and availability.
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A Key Location — $$$ 2 bedrooms, 2½ baths, sleeps 6, no pets. Two-story Townhouse one block from Duval. Private heated pool. Elegant but comfortable. Covered porch. Next to Amelia House. Please call for rates and availability.
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A Key Retreat — $$$ 3 bedrooms, 3 baths, sleeps 6-8, no pets. Built in the 1920's, this bungalow-style home has 12 ft. ceilings and large rooms. There are two bedrooms in the main house, each with a tiled bath. The third bedroom with bath is in the cottage by the pool. Please call for rates and availability.
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Amelia House — $$$ 2 bedrooms, 2½ baths, sleeps 6, no pets. Two-story Townhouse one block from Duval. Private heated pool. Antiques and local art. Orchid garden. Sophisticated. Next to A Key Location.
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Bahama Dreaming — $$$ 3 bedrooms, 2 baths, sleeps 8, no pets. Historic Private Home, one block from Duval. Modern Art, Antiques and Stylish Decor. Large windows and high ceilings. Heated pool with waterfall and tropical gardens. Please call for rates and availability.
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The English House — $$$ 3 bedrooms, 3 baths, sleeps 6, no pets. Elegant home with antiques and art. Heated pool. 1 block from Duval. Please call for rates and availability.
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Tropical Dreaming — $$$ 2 bedrooms, 2½ baths, sleeps 6, no pets. Beautifully furnished, this elegant home is sophisticated but comfortable. Only one half block away from Duval Street and close to world-class restaurants, galleries and nightclubs. Please call for rates and availability.
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Monthly Rentals

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Casa Invierno — $$$$ 3 bedrooms, 2 baths, sleeps 6, no pets. Large home in quiet area, beauitful private pool; well appointed with hardwood floors, ceramic tile, updated furnishings. Privacy is well afforded. Call for rates and availability. Monthly rentals only.
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The Verandas — $$$$$ 2 bedrooms, 2 baths, sleeps 6, no pets. Beautiful private old town home- well appointed with french doors that lead you to a charming outdoor area which features a private pool. Call for rates and availability. Monthly rental only.
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United House — $$$$$ 3 bedrooms, 2½ baths, sleeps 6, no pets. Stunning home with all the amenities, great attention to detail, unique art and decor, 3rd bedroom in a separate cottage, wonderful private deck and yard with both pool and Jacuzzi. Truly an upscale retreat. Call for rates and availability. Monthly rentals only.
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Villa Da Vinci — $$$$$ 5½ bedrooms, 4½ baths, sleeps 10, no pets. Amazing Gulf side property with all the amenities, unique in both decor and furnishings, great views, this beautiful property offers both pool and Jacuzzi, dockage and tennis court. Monthly rentals only.
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Villa Tropical — $$$$$ 3 bedrooms, 4 baths, sleeps 6, no pets. Elegant two story home, lush private garden and heated pool. French doors open from living room and dining room to deck overlooking pool and gardens. Truly an upscale retreat. Call for rates and availability. Monthly rentals only.
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Island Treasure — $$$ 1 bedroom, 2 baths, sleeps 4, no pets. Private historic home, beautifully restored, charmingly decorated with art and antiques, wonderful private deck with cocktail pool, perfect for a couple's getaway. Monthly only. Please call for rates and availability.
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Southard Square — $$$ 2 bedrooms, 2 baths, sleeps 4, no pets. Nice Condominium in a gated complex. 8 blocks to Duval. Balcony overlooking tropical gardens and nice shared pool area. Casual and comfortable. Monthly only. Please call for rates and availability.
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Southard Street — $$$ 2 bedrooms, 2 baths, sleeps 4, no pets. Charming home in old town Key West just blocks off Duval Street. Cozy two bedroom. Please call for rates and availability. Monthly rentals only.
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Theopolus Pinder House — $$$ 2 bedrooms, 2 baths, sleeps 4, no pets. Private historic home, beautifully restored, overstuffed with great art and antiques, wonderful private deck with Jacuzzi, a true and treasured piece of Key West history. Please call for rates and availability. Monthly rentals only.
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Condominiums and Townhomes

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Gallup Arms — $$$ 3 bedrooms, 2 baths, sleeps 6, no pets. Three story condominium in a four condominium complex. 8 blocks to Duval. 16 x 40 shared pool and large terrace. Casual and comfortable. Tropical Gardens and Quiet Neighborhood. Please call for rates and availability.
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Villa Soleil — $$$ 2 bedrooms, 2½ baths, sleeps 6, no pets. Wonderful three level home in Truman Annex; blocks from Duval and minutes from the beaches, private, gated community with shared pool, French doors open to small garden with beautiful foliage. Balcony off master bedroom, DSL available. Please call Sanne at 305-296-0011 ext. 119 for rates and availability.
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Sunset View — $$$ 2 bedrooms, 2 baths, sleeps 4, no pets. Upscale two story condo in Truman Annex, elegantly furnished, beautiful views over the gulf from the living room and master bedroom balcony. Large shared pool, peaceful and secluded yet minutes from downtown. Call Sanne at 305-296-0011 ext. 119 for rates and availability.
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Azure Vista — $$ 2 bedrooms, 3 baths, sleeps 6, no pets. There is no more lovely way to enjoy America's tropics than at Azure Vista, an exceptional, Luxury Condominium located in the prestigious 1800 Atlantic Condominium on the Atlantic Ocean. This unit offers incredible ocean vistas from the private terrace. Please call for further details and availability.
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More information:

Select any of the above properties which interest you. Fill in the form below and one of our rental managers will contact you ASAP. Thank you for visiting.
All of our properties are smoke-free.

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