Siesta Key Luxury Rental Properties — Vacation Rentals

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27 of 27 listings

Treasure on the Canal — photo 1

Treasure on the Canal — photo 2

Treasure on the Canal — photo 3

Treasure on the Canal — photo 4

Treasure on the Canal — photo 5

Treasure on the Canal — photo 6

Treasure on the Canal — photo 7

Treasure on the Canal — photo 8

Treasure on the Canal

3 bedrooms · 5 beds · 2.5 bathrooms

From$515/ night

Island Sun — photo 1

Island Sun — photo 2

Island Sun — photo 3

Island Sun — photo 4

Island Sun — photo 5

Island Sun — photo 6

Island Sun — photo 7

Island Sun — photo 8

Island Sun

3 bedrooms · 3 beds · 2 bathrooms

From$290/ night

Casa Siesta — photo 1

Casa Siesta — photo 2

Casa Siesta — photo 3

Casa Siesta — photo 4

Casa Siesta — photo 5

Casa Siesta — photo 6

Casa Siesta — photo 7

Casa Siesta — photo 8

Casa Siesta

3 bedrooms · 4 beds · 3 bathrooms

From$500/ night

Three Sandy Sisters — photo 1

Three Sandy Sisters — photo 2

Three Sandy Sisters — photo 3

Three Sandy Sisters — photo 4

Three Sandy Sisters — photo 5

Three Sandy Sisters — photo 6

Three Sandy Sisters — photo 7

Three Sandy Sisters — photo 8

Three Sandy Sisters

2 bedrooms · 3 beds · 2 bathrooms

From$130/ night

Changing Channels — photo 1

Changing Channels — photo 2

Changing Channels — photo 3

Changing Channels — photo 4

Changing Channels — photo 5

Changing Channels — photo 6

Changing Channels — photo 7

Changing Channels — photo 8

Changing Channels

4 bedrooms · 5 beds · 4 bathrooms

From$375/ night

Siesta Sun — photo 1

Siesta Sun — photo 2

Siesta Sun — photo 3

Siesta Sun — photo 4

Siesta Sun — photo 5

Siesta Sun — photo 6

Siesta Sun — photo 7

Siesta Sun — photo 8

Siesta Sun

3 bedrooms · 4 beds · 3.5 bathrooms

From$325/ night

Penthouse Paradise — photo 1

Penthouse Paradise — photo 2

Penthouse Paradise — photo 3

Penthouse Paradise — photo 4

Penthouse Paradise — photo 5

Penthouse Paradise — photo 6

Penthouse Paradise — photo 7

Penthouse Paradise — photo 8

Penthouse Paradise

3 bedrooms · 3 beds · 3.5 bathrooms

From$275/ 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 — photo 6

Private Beach House — photo 7

Private Beach House — photo 8

Private Beach House

2 bedrooms · 3 beds · 2.5 bathrooms

From$175/ 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 — photo 6

The Midnight Turtle — photo 7

The Midnight Turtle — photo 8

The Midnight Turtle

3 bedrooms · 5 beds · 3 bathrooms

From$215/ 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 — photo 6

The Shaded Sanctuary — photo 7

The Shaded Sanctuary — photo 8

The Shaded Sanctuary

3 bedrooms · 4 beds · 3.5 bathrooms

From$165/ night

Casita West — photo 1

Casita West — photo 2

Casita West — photo 3

Casita West — photo 4

Casita West — photo 5

Casita West — photo 6

Casita West — photo 7

Casita West — photo 8

Casita West

2 bedrooms · 3 beds · 1 bathroom

From$125/ night

Casita East — photo 1

Casita East — photo 2

Casita East — photo 3

Casita East — photo 4

Casita East — photo 5

Casita East — photo 6

Casita East — photo 7

Casita East — photo 8

Casita East

2 bedrooms · 3 beds · 1 bathroom

From$125/ night

Casa Playa — photo 1

Casa Playa — photo 2

Casa Playa — photo 3

Casa Playa — photo 4

Casa Playa — photo 5

Casa Playa — photo 6

Casa Playa — photo 7

Casa Playa — photo 8

Casa Playa

5 bedrooms · 6 beds · 3 bathrooms

From$325/ night

Ocean Overlook — photo 1

Ocean Overlook — photo 2

Ocean Overlook — photo 3

Ocean Overlook — photo 4

Ocean Overlook — photo 5

Ocean Overlook — photo 6

Ocean Overlook — photo 7

Ocean Overlook — photo 8

Ocean Overlook

8 bedrooms · 8 beds · 9 bathrooms

From$925/ 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 — photo 6

Siesta Sunset Sanctuary — photo 7

Siesta Sunset Sanctuary — photo 8

Siesta Sunset Sanctuary

4 bedrooms · 4 beds · 5.5 bathrooms

From$500/ 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 — photo 6

Sun N Sea #1 — photo 7

Sun N Sea #1 — photo 8

Sun N Sea #1

2 bedrooms · 3 beds · 1 bathroom

From$135/ 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) — photo 6

The Hideaway (SKLRP) — photo 7

The Hideaway (SKLRP) — photo 8

The Hideaway (SKLRP)

4 bedrooms · 4 beds · 5 bathrooms

From$450/ night

The Big Dipper — photo 1

The Big Dipper — photo 2

The Big Dipper — photo 3

The Big Dipper — photo 4

The Big Dipper — photo 5

The Big Dipper — photo 6

The Big Dipper — photo 7

The Big Dipper — photo 8

The Big Dipper

4 bedrooms · 5 beds · 4 bathrooms

From$750/ 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 — photo 6

Sun N Sea #2 — photo 7

Sun N Sea #2 — photo 8

Sun N Sea #2

2 bedrooms · 3 beds · 1 bathroom

From$135/ 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 — photo 6

Dos Casitas Retreat — photo 7

Dos Casitas Retreat — photo 8

Dos Casitas Retreat

4 bedrooms · 6 beds · 2 bathrooms

From$225/ night

Surf View (SKLRP) — photo 1

Surf View (SKLRP) — photo 2

Surf View (SKLRP) — photo 3

Surf View (SKLRP) — photo 4

Surf View (SKLRP) — photo 5

Surf View (SKLRP) — photo 6

Surf View (SKLRP) — photo 7

Surf View (SKLRP) — photo 8

Surf View (SKLRP)

8 bedrooms · 8 beds · 8.5 bathrooms

From$725/ night

Blue Paradise — photo 1

Blue Paradise — photo 2

Blue Paradise — photo 3

Blue Paradise — photo 4

Blue Paradise — photo 5

Blue Paradise — photo 6

Blue Paradise — photo 7

Blue Paradise — photo 8

Blue Paradise

6 bedrooms · 7 beds · 6.5 bathrooms

From$720/ night

Sunset Gulf — photo 1

Sunset Gulf — photo 2

Sunset Gulf — photo 3

Sunset Gulf — photo 4

Sunset Gulf — photo 5

Sunset Gulf — photo 6

Sunset Gulf — photo 7

Sunset Gulf — photo 8

Sunset Gulf

8 bedrooms · 12 beds · 5.5 bathrooms

From$651/ night

Sunset View — photo 1

Sunset View — photo 2

Sunset View — photo 3

Sunset View — photo 4

Sunset View — photo 5

Sunset View — photo 6

Sunset View — photo 7

Sunset View — photo 8

Sunset View

8 bedrooms · 10 beds · 5.5 bathrooms

From$800/ night

Treasure on the Canal — photo 1

Treasure on the Canal — photo 2

Treasure on the Canal — photo 3

Treasure on the Canal — photo 4

Treasure on the Canal — photo 5

Treasure on the Canal — photo 6

Treasure on the Canal — photo 7

Treasure on the Canal — photo 8

Treasure on the Canal

3 bedrooms · 5 beds · 2.5 bathrooms

From$515/ night

Island Sun — photo 1

Island Sun — photo 2

Island Sun — photo 3

Island Sun — photo 4

Island Sun — photo 5

Island Sun — photo 6

Island Sun — photo 7

Island Sun — photo 8

Island Sun

3 bedrooms · 3 beds · 2 bathrooms

From$290/ night

Casa Siesta — photo 1

Casa Siesta — photo 2

Casa Siesta — photo 3

Casa Siesta — photo 4

Casa Siesta — photo 5

Casa Siesta — photo 6

Casa Siesta — photo 7

Casa Siesta — photo 8

Casa Siesta

3 bedrooms · 4 beds · 3 bathrooms

From$500/ night

Three Sandy Sisters — photo 1

Three Sandy Sisters — photo 2

Three Sandy Sisters — photo 3

Three Sandy Sisters — photo 4

Three Sandy Sisters — photo 5

Three Sandy Sisters — photo 6

Three Sandy Sisters — photo 7

Three Sandy Sisters — photo 8

Three Sandy Sisters

2 bedrooms · 3 beds · 2 bathrooms

From$130/ night

Changing Channels — photo 1

Changing Channels — photo 2

Changing Channels — photo 3

Changing Channels — photo 4

Changing Channels — photo 5

Changing Channels — photo 6

Changing Channels — photo 7

Changing Channels — photo 8

Changing Channels

4 bedrooms · 5 beds · 4 bathrooms

From$375/ night

Siesta Sun — photo 1

Siesta Sun — photo 2

Siesta Sun — photo 3

Siesta Sun — photo 4

Siesta Sun — photo 5

Siesta Sun — photo 6

Siesta Sun — photo 7

Siesta Sun — photo 8

Siesta Sun

3 bedrooms · 4 beds · 3.5 bathrooms

From$325/ night

Penthouse Paradise — photo 1

Penthouse Paradise — photo 2

Penthouse Paradise — photo 3

Penthouse Paradise — photo 4

Penthouse Paradise — photo 5

Penthouse Paradise — photo 6

Penthouse Paradise — photo 7

Penthouse Paradise — photo 8

Penthouse Paradise

3 bedrooms · 3 beds · 3.5 bathrooms

From$275/ 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 — photo 6

Private Beach House — photo 7

Private Beach House — photo 8

Private Beach House

2 bedrooms · 3 beds · 2.5 bathrooms

From$175/ 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 — photo 6

The Midnight Turtle — photo 7

The Midnight Turtle — photo 8

The Midnight Turtle

3 bedrooms · 5 beds · 3 bathrooms

From$215/ 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 — photo 6

The Shaded Sanctuary — photo 7

The Shaded Sanctuary — photo 8

The Shaded Sanctuary

3 bedrooms · 4 beds · 3.5 bathrooms

From$165/ night

Casita West — photo 1

Casita West — photo 2

Casita West — photo 3

Casita West — photo 4

Casita West — photo 5

Casita West — photo 6

Casita West — photo 7

Casita West — photo 8

Casita West

2 bedrooms · 3 beds · 1 bathroom

From$125/ night

Casita East — photo 1

Casita East — photo 2

Casita East — photo 3

Casita East — photo 4

Casita East — photo 5

Casita East — photo 6

Casita East — photo 7

Casita East — photo 8

Casita East

2 bedrooms · 3 beds · 1 bathroom

From$125/ night

Casa Playa — photo 1

Casa Playa — photo 2

Casa Playa — photo 3

Casa Playa — photo 4

Casa Playa — photo 5

Casa Playa — photo 6

Casa Playa — photo 7

Casa Playa — photo 8

Casa Playa

5 bedrooms · 6 beds · 3 bathrooms

From$325/ night

Ocean Overlook — photo 1

Ocean Overlook — photo 2

Ocean Overlook — photo 3

Ocean Overlook — photo 4

Ocean Overlook — photo 5

Ocean Overlook — photo 6

Ocean Overlook — photo 7

Ocean Overlook — photo 8

Ocean Overlook

8 bedrooms · 8 beds · 9 bathrooms

From$925/ 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 — photo 6

Siesta Sunset Sanctuary — photo 7

Siesta Sunset Sanctuary — photo 8

Siesta Sunset Sanctuary

4 bedrooms · 4 beds · 5.5 bathrooms

From$500/ 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 — photo 6

Sun N Sea #1 — photo 7

Sun N Sea #1 — photo 8

Sun N Sea #1

2 bedrooms · 3 beds · 1 bathroom

From$135/ 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) — photo 6

The Hideaway (SKLRP) — photo 7

The Hideaway (SKLRP) — photo 8

The Hideaway (SKLRP)

4 bedrooms · 4 beds · 5 bathrooms

From$450/ night

The Big Dipper — photo 1

The Big Dipper — photo 2

The Big Dipper — photo 3

The Big Dipper — photo 4

The Big Dipper — photo 5

The Big Dipper — photo 6

The Big Dipper — photo 7

The Big Dipper — photo 8

The Big Dipper

4 bedrooms · 5 beds · 4 bathrooms

From$750/ 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 — photo 6

Sun N Sea #2 — photo 7

Sun N Sea #2 — photo 8

Sun N Sea #2

2 bedrooms · 3 beds · 1 bathroom

From$135/ 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 — photo 6

Dos Casitas Retreat — photo 7

Dos Casitas Retreat — photo 8

Dos Casitas Retreat

4 bedrooms · 6 beds · 2 bathrooms

From$225/ night

Surf View (SKLRP) — photo 1

Surf View (SKLRP) — photo 2

Surf View (SKLRP) — photo 3

Surf View (SKLRP) — photo 4

Surf View (SKLRP) — photo 5

Surf View (SKLRP) — photo 6

Surf View (SKLRP) — photo 7

Surf View (SKLRP) — photo 8

Surf View (SKLRP)

8 bedrooms · 8 beds · 8.5 bathrooms

From$725/ night

Blue Paradise — photo 1

Blue Paradise — photo 2

Blue Paradise — photo 3

Blue Paradise — photo 4

Blue Paradise — photo 5

Blue Paradise — photo 6

Blue Paradise — photo 7

Blue Paradise — photo 8

Blue Paradise

6 bedrooms · 7 beds · 6.5 bathrooms

From$720/ night

Sunset Gulf — photo 1

Sunset Gulf — photo 2

Sunset Gulf — photo 3

Sunset Gulf — photo 4

Sunset Gulf — photo 5

Sunset Gulf — photo 6

Sunset Gulf — photo 7

Sunset Gulf — photo 8

Sunset Gulf

8 bedrooms · 12 beds · 5.5 bathrooms

From$651/ night

Sunset View — photo 1

Sunset View — photo 2

Sunset View — photo 3

Sunset View — photo 4

Sunset View — photo 5

Sunset View — photo 6

Sunset View — photo 7

Sunset View — photo 8

Sunset View

8 bedrooms · 10 beds · 5.5 bathrooms

From$800/ night

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