Mansion holiday rentals in Key West
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Top-rated mansion rentals in Key West
Guests agree: These mansions are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Key West mansion rentals
Luxury mansion rentals
Home in Marathon
5.0 out of 5 average rating, 11 reviewsWaterfront Escape -VACA-23-408
Home in Marathon
4.9 out of 5 average rating, 10 reviews4BR Sombrero Beach House on Canal w Dock & Pool
Home in Key Largo
4.97 out of 5 average rating, 63 reviewsLuxury Heated Pool/Jacuzzi, Games & Nice Backyard.
Home in Marathon
4.97 out of 5 average rating, 77 reviews4BR 3B, Heated Pool & Spa, 60' Dock
Home in Marathon
4.95 out of 5 average rating, 41 reviewsParadise Ocean front Fisherman’s choice
Home in Marathon
4.96 out of 5 average rating, 84 reviewsAngler’s Eden
Home in Marathon
4.92 out of 5 average rating, 24 reviewsSerenity Bay Estate-FL Keys Best Kept Secret! Beau
Home in Marathon
5.0 out of 5 average rating, 4 reviewsLuna Light ~ Waterfront ~ Pool ~ Dock ~ Views!
Pet-friendly mansion rentals
Home in Marathon
4.97 out of 5 average rating, 33 reviews2023 New Modern Private Dock+Heated Pool+Jacuzzi
Home in Marathon
4.82 out of 5 average rating, 66 reviewsWelcome to Luna Island in the Florida Keys
Home in Key Colony Beach
4.88 out of 5 average rating, 42 reviews*Newly Renovated Single Family Home w/Private Pool
Home in Marathon
4.97 out of 5 average rating, 79 reviewsCoco Plum Waterfront Hideaway Home in Marathon
Home in Marathon
5.0 out of 5 average rating, 9 reviewsWaterfront home w/4 Bedrooms, private pool & dock
Home in Marathon
4.86 out of 5 average rating, 72 reviewsWaterfront Private Pool & Dock Near Sombrero Beach
Home in Marathon
4.89 out of 5 average rating, 82 reviews4 Bed/3.5 bath with private pool, tiki hut & dock!
Apartment in Marathon
4.8 out of 5 average rating, 70 reviewsIt’s 5 o’clock somewhere!
Mansion rentals with a pool
Home in Key Largo
4.95 out of 5 average rating, 107 reviewsMariners Club Resort, Best in the Upper Keys
Home in Marathon
4.91 out of 5 average rating, 54 reviewsFlorida Gulf Paradise
Home in Marathon
4.91 out of 5 average rating, 11 reviewsBeautiful Home w/ Pool, Kayaks, & Golfcart
Home in Marathon
4.98 out of 5 average rating, 58 reviewsLuxury 4/3 Waterfront w/Private Heated Pool & Dock
Home in Marathon
4.92 out of 5 average rating, 25 reviewsVaca Cove (C) Reel Paradise, Ocean View with Dock
Home in Marathon
4.91 out of 5 average rating, 11 reviewsSale! Pool, Hot Tub, Dock & Putting Green!
Home in Marathon
5.0 out of 5 average rating, 17 reviewsPerla Blanca 4 Bed 5 Bath kayaks pool boat dock
Home in Key Largo
4.7 out of 5 average rating, 27 reviewsSeaside Escape
Destinations to explore
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