
Holiday houses in Siesta Key
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Top-rated holiday rentals in Siesta Key
Guests agree: these stays are highly rated for location, cleanliness and more.
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Holiday rentals for every style
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Popular amenities for Siesta Key holiday rentals
Other great holiday rentals in Siesta Key

Home in Siesta Key
5 out of 5 average rating, 3 reviewsLuxury 3BR Pool Near Beach | The Nest Siesta Key
Guest favourite

Condo in Siesta Key
4.91 out of 5 average rating, 64 reviewsEnchanting Coastal Ambiance & Breathtaking Sunsets
Superhost

Condo in Siesta Key
4.9 out of 5 average rating, 48 reviewsRomantic 1BR Suite, Private Balcony & Sunset Views
Top Guest favourite

Tiny home in Bradenton
5 out of 5 average rating, 40 reviewsRomantic Luxe Tiny Home+ Hot Tub
Top Guest favourite

Apartment in Longboat Key
5 out of 5 average rating, 51 reviewsCondo with a View 3: Open Wed Nite $150/nt!
Top Guest favourite

Home in Siesta Key
5 out of 5 average rating, 21 reviewsNewly Remodeled "Beach House on Siesta"
Guest favourite

Condo in Siesta Key
5 out of 5 average rating, 8 reviewsSpacious 2BR 2nd floor Siesta Key condo - GBB 1274
Superhost

Condo in Siesta Key
5 out of 5 average rating, 5 reviewsA New Listing - Siesta Key Beach Front!
Quick stats about holiday rentals in Siesta Key
Total rentals
2K properties
Total number of reviews
34K reviews
Family-friendly rentals
1.6K properties are a good fit for families
Pet-friendly rentals
360 properties allow pets
Rentals with a pool
1.6K properties have a pool
Rentals with dedicated workspaces
950 properties have a dedicated workspace
Destinations to explore
- Seminole Holiday rentals
- Central Florida Holiday rentals
- Miami Holiday rentals
- Saint Johns River Holiday rentals
- Orlando Holiday rentals
- Gold Coast Holiday rentals
- Miami Beach Holiday rentals
- Havana Holiday rentals
- Fort Lauderdale Holiday rentals
- Tampa Holiday rentals
- Kissimmee Holiday rentals
- Four Corners Holiday rentals
- Waterfront rentals Siesta Key
- Beach house rentals Siesta Key
- Luxury rentals Siesta Key
- Cottage rentals Siesta Key
- Rentals with a patio Siesta Key
- Rentals with a hot tub Siesta Key
- Rentals with outdoor seating Siesta Key
- Apartment rentals Siesta Key
- Beachfront rentals Siesta Key
- Pet-friendly rentals Siesta Key
- Rentals with a washing machine and dryer Siesta Key
- Rentals with pools Siesta Key
- Townhouse rentals Siesta Key
- Rentals with a kayak Siesta Key
- Condo rentals Siesta Key
- Beach condo rentals Siesta Key
- Rentals with breakfast Siesta Key
- Villa rentals Siesta Key
- Family-friendly rentals Siesta Key
- Rentals with lake access Siesta Key
- Rentals with a fire pit Siesta Key
- House rentals Siesta Key
- Rentals with a sauna Siesta Key
- Mansion rentals Siesta Key
- Rentals with beach access Siesta Key
- Rentals with an EV charger Siesta Key
- Rentals with a fireplace Siesta Key
- Fitness-friendly rentals Siesta Key
- Anna Maria Island
- Siesta Beach
- Crescent Beach
- John's Pass
- Turtle Beach
- Raymond James Stadium
- Caspersen Beach
- Bean Point Beach
- Anna Maria Public Beach
- Amalie Arena
- Coquina Beach
- Cortez Beach
- Lido Key Beach
- Gulfport Beach Recreation Area
- Vinoy Park
- Streamsong Resort
- Jannus Live
- Manasota Key Beach
- North Beach
- Splash Harbour Water Park
- River Strand Golf and Country Club
- North Beach At Fort DeSoto Park
- Fort De Soto Park
- Point Of Rocks