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Pet Friendly Key West Rentals

Over 140 of our nearly 200 Key West vacation rentals allow pets! Please make sure to check our vacation rental policies page for information on breeds that are not allowed, as well as rules to follow when bringing your pet to Key West. There is a $20 per night/per pet fee for nightly and weekly rentals, and a $200 per month/per pet fee for monthly rentals. Key West is a very dog-friendly town, so please feel free to bring your furry friend along, if your rental allows it!

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Poolside Paradise - Nightly Group Unit

Key West Vacation Rentals
3 Bedrooms
2 Bathrooms

Poolside Paradise is a beautiful home on the 500 block of Olivia Street, one-half block off world famous Duval Street! Enjoy the private pool in prime location! Great for larger groups and parties. Sleeps up to 10 comfortably!

Key Lime Cottage - Nightly Rental

Key West Vacation Rentals
Studio
1 Bathroom

Part of Banana's Foster Guest House. Beautifully updated studio w/ king bed, huge flat screen TV, balcony, mini fridge, and shared "plunge" pool. Located on the corner of Simonton and Caroline St - 1 block from all the Duval St action!

Helen`s Hideaway - Nightly Rental

Key West Vacation Rentals
2 Bedrooms
2 Bathrooms

This unique house and large private heated pool is surrounded by mature palms, Spanish lime trees, scheffeleras and other magnificent foliage. Completely gated and fenced, you will experience privacy in Key West that is unrivaled anywhere else on our small

Seaport Suite - Nightly Rental

Key West Vacation Rentals
4 Bedrooms
2 Bathrooms

Four bed two bath in the best location you could ask for. Private hot tub and gas grill in the back courtyard. Huge flat screen TV in the living room complete with two sofas - One a Queen Size Sleeper Sofa - and bean bags. Balcony overlooks Simonton St.

Sweet Caroline - Nightly Rental

Key West Vacation Rentals
2 Bedrooms
2.5 Bathrooms

Part of Banana's Foster Guest House. Beautifully updated 2 bedroom rental w/ 2 king beds, 3 huge flat screen TVs, full kitchen, and shared "plunge" pool. Located on the corner of Simonton and Caroline St - 1 block from all the Duval St action!

Shark Key Chateau - Monthly Rental

Key West Vacation Rentals
5 Bedrooms
5 Bathrooms

Château - Merriam-Webster defines it as a "large impressive residence". This does not do the 'Shark Key Chateau' justice! Very impressive, very large, very luxurious! Set apart from any residence you have experienced. But this property does not rest on

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