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 Key Largo
4.95 out of 5 average rating, 105 reviewsMariners Club Resort, Best in the Upper Keys
11–18 Aug
Home in Marathon
5.0 out of 5 average rating, 47 reviewsIsland Dreamz Bay House -Modern 5 Star, Pool/Dock
18–25 Nov
Home in Marathon
5.0 out of 5 average rating, 8 reviewsWaterfront Escape -VACA-23-408
7–14 Nov
Home in Marathon
4.9 out of 5 average rating, 20 reviewsModern Pool Home with Stunning Open Water Views!
21–28 Sept
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
12–19 Oct
Home in Marathon
4.95 out of 5 average rating, 39 reviewsParadise Ocean front Fisherman’s choice
20–27 Aug
Home in Key Largo
4.97 out of 5 average rating, 59 reviewsLuxury Heated Pool/Jacuzzi, Games & Nice Backyard.
23–30 Mar
Pet-friendly mansion rentals
Home in Marathon
4.97 out of 5 average rating, 79 reviewsCoco Plum Waterfront Hideaway Home in Marathon
21–28 Sept
Home in Marathon
4.82 out of 5 average rating, 66 reviewsWelcome to Luna Island in the Florida Keys
31 Aug – 7 Sept
Home in Marathon
4.86 out of 5 average rating, 71 reviewsWaterfront Private Pool & Dock Near Sombrero Beach
11–18 Nov
Flat in Marathon
4.8 out of 5 average rating, 65 reviewsIt’s 5 o’clock somewhere!
14–21 Dec
Home in Key Largo
4.92 out of 5 average rating, 71 reviewsTropicasa
2–9 Sept
Home in Marathon
4.82 out of 5 average rating, 87 reviewsBeautiful Waterfront Gulf of Mexico View
24–31 Jan
Villa in Marathon
5.0 out of 5 average rating, 8 reviewsWaterfront Home w/Dock, Pool, Bikes & SO MUCH MORE
24–31 Jan
Home in Marathon
4.89 out of 5 average rating, 82 reviews4 Bed/3.5 bath with private pool, tiki hut & dock!
4–11 Jan
Mansion rentals with a pool
Home in Marathon
5.0 out of 5 average rating, 9 reviewsBeautiful Home w/ Pool, Kayaks, & Golfcart
8–15 Jan
Home in Marathon
4.97 out of 5 average rating, 74 reviews4BR 3B, Heated Pool & Spa, 60' Dock
8–15 Feb
Home in Marathon
4.98 out of 5 average rating, 58 reviewsLuxury 4/3 Waterfront w/Private Heated Pool & Dock
20–27 Apr
Home in Marathon
4.95 out of 5 average rating, 21 reviewsVaca Cove (C) Reel Paradise, Ocean View with Dock
14–21 Feb
Home in Marathon
4.9 out of 5 average rating, 10 reviewsSale! Pool, Hot Tub, Dock & Putting Green!
17–24 Nov
Home in Marathon
4.91 out of 5 average rating, 54 reviewsFlorida Gulf Paradise
16–23 Jan
Home in Marathon
4.67 out of 5 average rating, 3 reviewsSombrero- Waterfront 4 BR Luxury Pool Home- M#9
10–17 Aug
Villa in Marathon
4.87 out of 5 average rating, 107 reviewsDuck Key 4 BR Villa Dock Behind & Cabana Club
31 Aug – 7 Sept
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