Waterfront holiday rentals in Siesta Key
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Top-rated waterfront rentals in Siesta Key
Guests agree: these waterfront rentals 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 waterfront rentals in Siesta Key
Waterfront apartment rentals
Flat in Siesta Key
4.67 out of 5 average rating, 168 reviewsSiesta Key Condo. Sit by the water !
1–8 Dec
Flat in Longboat Key
4.82 out of 5 average rating, 124 reviewsOcean Front Studio Special From $99/night
19–26 Aug
Flat in Saint Pete Beach
4.77 out of 5 average rating, 200 reviewsSteps from Sand & Pool
7–14 Nov
Flat in Ruskin
4.85 out of 5 average rating, 104 reviewsSunset Del Mar (Studio with view of Tampa Bay)
26 Jul – 2 Aug
Flat in Bradenton Beach
4.88 out of 5 average rating, 204 reviewsLas Palmas Beach Rentals Unit 1
31 Jan – 7 Feb
Flat in Gulfport
4.99 out of 5 average rating, 107 reviewsSpacious Casa Marina in Gulfport
6–13 Nov
Flat in Siesta Key
5.0 out of 5 average rating, 4 reviewsSunset Sensation
4–11 Sep
Flat in Siesta Key
4.94 out of 5 average rating, 83 reviewsSiesta Premier Location - The 'Calm of Siesta'
20–27 Jul
Waterfront house rentals
Home in Siesta Key
4.91 out of 5 average rating, 122 reviewsSea Club II Garden House
27 Nov – 4 Dec
Home in Myakka City
4.98 out of 5 average rating, 134 reviewsCharming Country Stay (Near Lakewood Ranch)
4–11 Oct
Home in Siesta Key
4.89 out of 5 average rating, 100 reviewsSpacious & Modern Gem ~ Walk to Gated Beach ~ Pool
20–27 Apr
Home in Siesta Key
4.79 out of 5 average rating, 117 reviews3BR Unit with Pool & Hot Tub, 2 min walk to Beach
2–9 Oct
Home in Gulfport
4.89 out of 5 average rating, 118 reviewsThe Brenda Ann/Pet Friendly/Walk to downtown!
19–26 Sep
Home in Englewood
4.96 out of 5 average rating, 104 reviewsWaterfront Cottage by Manasota Key
12–19 Sep
Home in Longboat Key
4.87 out of 5 average rating, 106 reviewsSummer House longboat key
28 Feb – 7 Mar
Home in Sarasota
4.93 out of 5 average rating, 106 reviewsLake Front House with a Pool
31 Oct – 7 Nov
Waterfront apartment rentals
Apartment in Longboat Key
4.82 out of 5 average rating, 159 reviewsUpdated Beachfront Condo at Prestigious Long Boat
5–12 Jan
Apartment in Longboat Key
4.8 out of 5 average rating, 212 reviewsSRQ/Longboat Key Beach - kid friendly/romantic B1
30 Sep – 7 Oct
Apartment in Venice
4.87 out of 5 average rating, 141 reviewsThe Studio at the Beach 56
17–24 May
Apartment in Siesta Key
4.97 out of 5 average rating, 110 reviewsSiesta Key For Me @ The Palm Bay Club
14–21 Sep
Apartment in Venice
4.82 out of 5 average rating, 219 reviewsUpdated beachy condo - ready for you!
12–19 Dec
Apartment in Sarasota
4.83 out of 5 average rating, 147 reviewsBest Gulf Coast Condo in Siesta Key
3–10 Jul
Apartment in Siesta Key
4.82 out of 5 average rating, 131 reviewsThe Key to a Great Vacation!
23–30 Nov
Apartment in Bradenton Beach
4.91 out of 5 average rating, 129 reviewsBeachfront condo in paradise
14–21 Nov
Quick stats about waterfront rentals in Siesta Key
Total rentals
300 properties
Rentals with a pool
250 properties have a pool
Pet-friendly rentals
60 properties allow pets
Family-friendly rentals
240 properties are a good fit for families
Total number of reviews
8.3K reviews
Nightly prices starting at
€ 84 before taxes and fees
Destinations to explore
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