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
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Popular amenities for Key West mansion rentals
Luxury mansion rentals
Home in Key Largo
4.95 out of 5 average rating, 106 reviewsMariners Club Resort, Best in the Upper Keys
13–20 Jun
Home in Marathon
5.0 out of 5 average rating, 17 reviewsDirect Oceanfront Private Paradise - Pool/Spa/Dock
1–8 Feb
Home in Marathon
4.98 out of 5 average rating, 48 reviewsIsland Dreamz Bay House -Modern 5 Star, Pool/Dock
17–24 Jan
Home in Marathon
5.0 out of 5 average rating, 16 reviewsAmazing Bayfront Newer House with Dock and Pool!
2–9 Sep
Home in Marathon
5.0 out of 5 average rating, 8 reviewsWaterfront Escape -VACA-23-408
31 Mar – 7 Apr
Home in Marathon
4.89 out of 5 average rating, 9 reviews4BR Sombrero Beach House on Canal w Dock & Pool
11–18 Feb
Home in Cudjoe Key
5.0 out of 5 average rating, 3 reviewsLatitudes-Ocean Front Pool
9–16 Nov
Home in Marathon
4.92 out of 5 average rating, 24 reviewsSerenity Bay Estate-FL Keys Best Kept Secret! Beau
31 Aug – 7 Sep
Pet-friendly mansion rentals
Home in Marathon
4.97 out of 5 average rating, 79 reviewsCoco Plum Waterfront Hideaway Home in Marathon
21–28 Sep
Home in Marathon
4.82 out of 5 average rating, 66 reviewsWelcome to Luna Island in the Florida Keys
20–27 Aug
Home in Key Colony Beach
4.87 out of 5 average rating, 39 reviews*Newly Renovated Single Family Home w/Private Pool
1–8 Mar
Home in Marathon
4.86 out of 5 average rating, 71 reviewsWaterfront Private Pool & Dock Near Sombrero Beach
16–23 Dec
Home in Marathon
5.0 out of 5 average rating, 4 reviewsPool & Spa, Walk to Beach, Dock, Tiki, Lux Home
25 Jan – 1 Feb
Serviced apartment in Marathon
4.8 out of 5 average rating, 66 reviewsIt’s 5 o’clock somewhere!
22–29 Oct
Home in Marathon
4.82 out of 5 average rating, 87 reviewsBeautiful Waterfront Gulf of Mexico View
2–9 Nov
Home in Key Largo
4.92 out of 5 average rating, 71 reviewsTropicasa
9–16 Sep
Mansion rentals with a pool
Home in Marathon
4.91 out of 5 average rating, 54 reviewsFlorida Gulf Paradise
23–30 Jan
Home in Marathon
4.97 out of 5 average rating, 75 reviews4BR 3B, Heated Pool & Spa, 60' Dock
7–14 Dec
Home in Marathon
4.98 out of 5 average rating, 58 reviewsLuxury 4/3 Waterfront w/Private Heated Pool & Dock
1–8 Feb
Home in Marathon
4.95 out of 5 average rating, 22 reviewsVaca Cove (C) Reel Paradise, Ocean View with Dock
4–11 Jan
Home in Key Largo
4.69 out of 5 average rating, 26 reviewsSeaside Escape
27 Sep – 4 Oct
Home in Marathon
4.67 out of 5 average rating, 3 reviewsSombrero- Waterfront 4 BR Luxury Pool Home- M#9
17–24 Aug
Villa in Marathon
4.87 out of 5 average rating, 107 reviewsDuck Key 4 BR Villa Dock Behind & Cabana Club
18–25 Dec
Home in Key Largo
5.0 out of 5 average rating, 5 reviewsSeaside Elegance with Pool & Boat Dock
29 Jul – 5 Aug
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