Siesta Key Luxury Rental Properties — Vacation Rentals

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36 of 36 listings

Talk To The Sand — photo 1

Talk To The Sand — photo 2

Talk To The Sand — photo 3

Talk To The Sand — photo 4

Talk To The Sand — photo 5

Talk To The Sand

7 bedrooms · 7 beds · 7.5 bathrooms

From$1,193/ night

Island Time East — photo 1

Island Time East — photo 2

Island Time East — photo 3

Island Time East — photo 4

Island Time East — photo 5

Island Time East

3 bedrooms · 4 beds · 3.5 bathrooms

From$294/ night

Island Sun — photo 1

Island Sun — photo 2

Island Sun — photo 3

Island Sun — photo 4

Island Sun — photo 5

Island Sun

3 bedrooms · 3 beds · 2 bathrooms

From$290/ night

Casita West — photo 1

Casita West — photo 2

Casita West — photo 3

Casita West — photo 4

Casita West — photo 5

Casita West

2 bedrooms · 3 beds · 1 bathroom

From$125/ night

Private Beach House — photo 1

Private Beach House — photo 2

Private Beach House — photo 3

Private Beach House — photo 4

Private Beach House — photo 5

Private Beach House

2 bedrooms · 3 beds · 2.5 bathrooms

From$135/ night

Island Time West — photo 1

Island Time West — photo 2

Island Time West — photo 3

Island Time West — photo 4

Island Time West — photo 5

Island Time West

3 bedrooms · 4 beds · 3.5 bathrooms

From$315/ night

Casita East — photo 1

Casita East — photo 2

Casita East — photo 3

Casita East — photo 4

Casita East — photo 5

Casita East

2 bedrooms · 3 beds · 1 bathroom

From$125/ night

Sun N Sea #1 — photo 1

Sun N Sea #1 — photo 2

Sun N Sea #1 — photo 3

Sun N Sea #1 — photo 4

Sun N Sea #1 — photo 5

Sun N Sea #1

2 bedrooms · 3 beds · 1 bathroom

From$100/ night

Sunset — photo 1

Sunset — photo 2

Sunset — photo 3

Sunset — photo 4

Sunset — photo 5

Sunset

2 bedrooms · 3 beds · 1 bathroom

From$135/ night

Siesta Sun — photo 1

Siesta Sun — photo 2

Siesta Sun — photo 3

Siesta Sun — photo 4

Siesta Sun — photo 5

Siesta Sun

3 bedrooms · 3 beds · 3.5 bathrooms

From$346/ night

The Midnight Turtle — photo 1

The Midnight Turtle — photo 2

The Midnight Turtle — photo 3

The Midnight Turtle — photo 4

The Midnight Turtle — photo 5

The Midnight Turtle

3 bedrooms · 4 beds · 3 bathrooms

From$215/ night

Dos Casitas Retreat — photo 1

Dos Casitas Retreat — photo 2

Dos Casitas Retreat — photo 3

Dos Casitas Retreat — photo 4

Dos Casitas Retreat — photo 5

Dos Casitas Retreat

4 bedrooms · 6 beds · 2 bathrooms

From$225/ night

Sun N Sea #2 — photo 1

Sun N Sea #2 — photo 2

Sun N Sea #2 — photo 3

Sun N Sea #2 — photo 4

Sun N Sea #2 — photo 5

Sun N Sea #2

2 bedrooms · 3 beds · 1 bathroom

From$135/ night

Changing Channels — photo 1

Changing Channels — photo 2

Changing Channels — photo 3

Changing Channels — photo 4

Changing Channels — photo 5

Changing Channels

4 bedrooms · 5 beds · 4 bathrooms

From$400/ night

Sunrise — photo 1

Sunrise — photo 2

Sunrise — photo 3

Sunrise — photo 4

Sunrise — photo 5

Sunrise

2 bedrooms · 3 beds · 1 bathroom

From$150/ night

The Shaded Sanctuary — photo 1

The Shaded Sanctuary — photo 2

The Shaded Sanctuary — photo 3

The Shaded Sanctuary — photo 4

The Shaded Sanctuary — photo 5

The Shaded Sanctuary

3 bedrooms · 4 beds · 3.5 bathrooms

From$165/ night

Casa Playa — photo 1

Casa Playa — photo 2

Casa Playa — photo 3

Casa Playa — photo 4

Casa Playa — photo 5

Casa Playa

5 bedrooms · 5 beds · 3 bathrooms

From$285/ night

Casa Siesta — photo 1

Casa Siesta — photo 2

Casa Siesta — photo 3

Casa Siesta — photo 4

Casa Siesta — photo 5

Casa Siesta

3 bedrooms · 3 beds · 3 bathrooms

From$1,135/ night

Blue Paradise — photo 1

Blue Paradise — photo 2

Blue Paradise — photo 3

Blue Paradise — photo 4

Blue Paradise — photo 5

Blue Paradise

6 bedrooms · 7 beds · 6.5 bathrooms

From$1,032/ night

The Hideaway (SKLRP) — photo 1

The Hideaway (SKLRP) — photo 2

The Hideaway (SKLRP) — photo 3

The Hideaway (SKLRP) — photo 4

The Hideaway (SKLRP) — photo 5

The Hideaway (SKLRP)

4 bedrooms · 4 beds · 5 bathrooms

From$450/ night

Sunset Gulf — photo 1

Sunset Gulf — photo 2

Sunset Gulf — photo 3

Sunset Gulf — photo 4

Sunset Gulf — photo 5

Sunset Gulf

8 bedrooms · 12 beds · 5.5 bathrooms

From$1,049/ night

Sunset Splash — photo 1

Sunset Splash — photo 2

Sunset Splash — photo 3

Sunset Splash — photo 4

Sunset Splash — photo 5

Sunset Splash

8 bedrooms · 8 beds · 7.5 bathrooms

From$1,024/ night

Sundown Sanctuary — photo 1

Sundown Sanctuary — photo 2

Sundown Sanctuary — photo 3

Sundown Sanctuary — photo 4

Sundown Sanctuary — photo 5

Sundown Sanctuary

4 bedrooms · 4 beds · 3.5 bathrooms

From$350/ night

Siesta Sunset Sanctuary — photo 1

Siesta Sunset Sanctuary — photo 2

Siesta Sunset Sanctuary — photo 3

Siesta Sunset Sanctuary — photo 4

Siesta Sunset Sanctuary — photo 5

Siesta Sunset Sanctuary

4 bedrooms · 4 beds · 5.5 bathrooms

From$1,031/ night

Talk To The Sand — photo 1

Talk To The Sand — photo 2

Talk To The Sand — photo 3

Talk To The Sand — photo 4

Talk To The Sand — photo 5

Talk To The Sand

7 bedrooms · 7 beds · 7.5 bathrooms

From$1,193/ night

Island Time East — photo 1

Island Time East — photo 2

Island Time East — photo 3

Island Time East — photo 4

Island Time East — photo 5

Island Time East

3 bedrooms · 4 beds · 3.5 bathrooms

From$294/ night

Island Sun — photo 1

Island Sun — photo 2

Island Sun — photo 3

Island Sun — photo 4

Island Sun — photo 5

Island Sun

3 bedrooms · 3 beds · 2 bathrooms

From$290/ night

Casita West — photo 1

Casita West — photo 2

Casita West — photo 3

Casita West — photo 4

Casita West — photo 5

Casita West

2 bedrooms · 3 beds · 1 bathroom

From$125/ night

Private Beach House — photo 1

Private Beach House — photo 2

Private Beach House — photo 3

Private Beach House — photo 4

Private Beach House — photo 5

Private Beach House

2 bedrooms · 3 beds · 2.5 bathrooms

From$135/ night

Island Time West — photo 1

Island Time West — photo 2

Island Time West — photo 3

Island Time West — photo 4

Island Time West — photo 5

Island Time West

3 bedrooms · 4 beds · 3.5 bathrooms

From$315/ night

Casita East — photo 1

Casita East — photo 2

Casita East — photo 3

Casita East — photo 4

Casita East — photo 5

Casita East

2 bedrooms · 3 beds · 1 bathroom

From$125/ night

Sun N Sea #1 — photo 1

Sun N Sea #1 — photo 2

Sun N Sea #1 — photo 3

Sun N Sea #1 — photo 4

Sun N Sea #1 — photo 5

Sun N Sea #1

2 bedrooms · 3 beds · 1 bathroom

From$100/ night

Sunset — photo 1

Sunset — photo 2

Sunset — photo 3

Sunset — photo 4

Sunset — photo 5

Sunset

2 bedrooms · 3 beds · 1 bathroom

From$135/ night

Siesta Sun — photo 1

Siesta Sun — photo 2

Siesta Sun — photo 3

Siesta Sun — photo 4

Siesta Sun — photo 5

Siesta Sun

3 bedrooms · 3 beds · 3.5 bathrooms

From$346/ night

The Midnight Turtle — photo 1

The Midnight Turtle — photo 2

The Midnight Turtle — photo 3

The Midnight Turtle — photo 4

The Midnight Turtle — photo 5

The Midnight Turtle

3 bedrooms · 4 beds · 3 bathrooms

From$215/ night

Dos Casitas Retreat — photo 1

Dos Casitas Retreat — photo 2

Dos Casitas Retreat — photo 3

Dos Casitas Retreat — photo 4

Dos Casitas Retreat — photo 5

Dos Casitas Retreat

4 bedrooms · 6 beds · 2 bathrooms

From$225/ night

Sun N Sea #2 — photo 1

Sun N Sea #2 — photo 2

Sun N Sea #2 — photo 3

Sun N Sea #2 — photo 4

Sun N Sea #2 — photo 5

Sun N Sea #2

2 bedrooms · 3 beds · 1 bathroom

From$135/ night

Changing Channels — photo 1

Changing Channels — photo 2

Changing Channels — photo 3

Changing Channels — photo 4

Changing Channels — photo 5

Changing Channels

4 bedrooms · 5 beds · 4 bathrooms

From$400/ night

Sunrise — photo 1

Sunrise — photo 2

Sunrise — photo 3

Sunrise — photo 4

Sunrise — photo 5

Sunrise

2 bedrooms · 3 beds · 1 bathroom

From$150/ night

The Shaded Sanctuary — photo 1

The Shaded Sanctuary — photo 2

The Shaded Sanctuary — photo 3

The Shaded Sanctuary — photo 4

The Shaded Sanctuary — photo 5

The Shaded Sanctuary

3 bedrooms · 4 beds · 3.5 bathrooms

From$165/ night

Casa Playa — photo 1

Casa Playa — photo 2

Casa Playa — photo 3

Casa Playa — photo 4

Casa Playa — photo 5

Casa Playa

5 bedrooms · 5 beds · 3 bathrooms

From$285/ night

Casa Siesta — photo 1

Casa Siesta — photo 2

Casa Siesta — photo 3

Casa Siesta — photo 4

Casa Siesta — photo 5

Casa Siesta

3 bedrooms · 3 beds · 3 bathrooms

From$1,135/ night

Blue Paradise — photo 1

Blue Paradise — photo 2

Blue Paradise — photo 3

Blue Paradise — photo 4

Blue Paradise — photo 5

Blue Paradise

6 bedrooms · 7 beds · 6.5 bathrooms

From$1,032/ night

The Hideaway (SKLRP) — photo 1

The Hideaway (SKLRP) — photo 2

The Hideaway (SKLRP) — photo 3

The Hideaway (SKLRP) — photo 4

The Hideaway (SKLRP) — photo 5

The Hideaway (SKLRP)

4 bedrooms · 4 beds · 5 bathrooms

From$450/ night

Sunset Gulf — photo 1

Sunset Gulf — photo 2

Sunset Gulf — photo 3

Sunset Gulf — photo 4

Sunset Gulf — photo 5

Sunset Gulf

8 bedrooms · 12 beds · 5.5 bathrooms

From$1,049/ night

Sunset Splash — photo 1

Sunset Splash — photo 2

Sunset Splash — photo 3

Sunset Splash — photo 4

Sunset Splash — photo 5

Sunset Splash

8 bedrooms · 8 beds · 7.5 bathrooms

From$1,024/ night

Sundown Sanctuary — photo 1

Sundown Sanctuary — photo 2

Sundown Sanctuary — photo 3

Sundown Sanctuary — photo 4

Sundown Sanctuary — photo 5

Sundown Sanctuary

4 bedrooms · 4 beds · 3.5 bathrooms

From$350/ night

Siesta Sunset Sanctuary — photo 1

Siesta Sunset Sanctuary — photo 2

Siesta Sunset Sanctuary — photo 3

Siesta Sunset Sanctuary — photo 4

Siesta Sunset Sanctuary — photo 5

Siesta Sunset Sanctuary

4 bedrooms · 4 beds · 5.5 bathrooms

From$1,031/ night