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All Units
Surf View
Weekly $3,850 - $17,150
303 Calle
8 BR, 8 BA, 1 HF BA
Sleeps: 22
View: Rooftop Deck
Type: Single Family Home
Location: Siesta Key
Summer House
Weekly $3,150 - $14,000
99 Messina
6 BR, 6 BA
Sleeps: 22
View: Pool View
Type: Single Family Home
Location: Siesta Key
Beach Retreat
Weekly $1,813 - $6,650
5230 Navarra
3 BR, 3 BA
Sleeps: 8
View: Pool
Type: Single Family Home
Location: Siesta Key
Blue Lagoon
Weekly $1,813 - $7,000
322 Miramar
3 BR, 3 BA
Sleeps: 10
View: Pool
Type: Single Family Home
Location: Siesta Key
The Mahi
Weekly $1,120 - $4,200
110 Ven -179
2 BR, 2 BA
Sleeps: 8
View: Courtyard
Type: Condo
Location: Siesta Key
Sunset View
Weekly $3,850 - $19,250
547 Beach
8 BR, 5 BA, 1 HF BA
Sleeps: 25
View: Gorgeous Gulf Views
Type: Single Family Home
Location: Siesta Key
Summer Sun
Weekly $1,743 - $5,950
5204 Cortez
3 BR, 3 BA
Sleeps: 10
View:
Type: Condo
Location: Siesta Key
Lido Key Retreat
Weekly $3,150 - $12,600
1406 Westway
7 BR, 5 BA
Sleeps: 17
View: Pool. Garden
Type: Single Family Home
Location: Lido Key
Island House
Weekly $3,990 - $13,300
344 Canal
7 BR, 6 BA
Sleeps: 23
View: Pool and Canal
Type: Single Family Home
Location: Siesta Key
The Daiquiri Deck
Weekly $1,813 - $6,300
304 Canal
3 BR, 3 BA
Sleeps: 10
View: Pool and Village
Type: Condo
Location: Siesta Key
John Ringling House
Weekly $1,925 - $8,400
76 S Wash
3 BR, 3 BA, 1 HF BA
Sleeps: 14
View: Estate and Courtyard
Type: Single Family Home
Location: Lido Key
Dry Dock
Weekly $2,975 - $13,475
515 Canal B
6 BR, 6 BA, 1 HF BA
Sleeps: 18
View: Canal/Water
Type: Single Family Home
Location: Siesta Key
Aruba
Weekly $2,100 - $8,050
5255 Menorca
3 BR, 2 BA, 1 HF BA
Sleeps: 12
View: Pool
Type: Single Family Home
Location: Siesta Key
Aloft on Canal
Weekly $3,850 - $19,250
542 Canal
8 BR, 6 BA, 1 HF BA
Sleeps: 22
View: Perfect Gulf Views
Type: Single Family Home
Location: Siesta Key
Sunset Gulf
Weekly $3,850 - $20,300
551 Beach Rd
8 BR, 5 BA, 1 HF BA
Sleeps: 25
View: Gorgeous Gulf Views
Type: Single Family Home
Location: Siesta Key
Island Time West
Weekly $1,575 - $5,600
353 Miramar
3 BR, 2 BA, 1 HF BA
Sleeps: 13
View: City View
Type: Condo
Location: Siesta Key
Ringling Manor
Weekly $1,575 - $7,000
112 Fillmore
4 BR, 3 BA
Sleeps: 8
View: Estate and Courtyard
Type: Single Family Home
Location: Lido Key
Sea Spray
Weekly $3,850 - $19,250
538 Canal
8 BR, 6 BA, 1 HF BA
Sleeps: 22
View: Gorgeous Gulf Views
Type: Single Family Home
Location: Siesta Key
Salty Dog
Weekly $3,325 - $13,300
515 Canal A
6 BR, 5 BA, 1 HF BA
Sleeps: 17
View: Canal - Water
Type: Single Family Home
Location: Siesta Key
Sunset Splash
Weekly $5,250 - $19,250
95 Messina
8 BR, 7 BA, 1 HF BA
Sleeps: 24
View: Pool/Tiki
Type: Single Family Home
Location: Siesta Key
Private Beach House
Weekly $1,043 - $3,493
315
2 BR, 2 BA, 1 HF BA
Sleeps: 9
View: Street
Type: Condo
Location: Siesta Key
The Pool House
Weekly $3,675 - $12,600
98 Messina
5 BR, 4 BA
Sleeps: 16
View: Pool and Garden
Type: Single Family Home
Location: Siesta Key
Bimini Breeze
Weekly $1,680 - $7,000
5259 Menorca
2 BR, 2 BA
Sleeps: 8
View: Pool
Type: Single Family Home
Location: Siesta Key
Island Time East
Weekly $1,575 - $5,250
355 Miramar
3 BR, 2 BA, 1 HF BA
Sleeps: 13
View: Street and City
Type: Condo
Location: Siesta Key
Siesta Sun
Weekly $2,100 - $8,050
559 Beach A
3 BR, 3 BA, 1 HF BA
Sleeps: 10
View: Ocean View
Type: Condo
Location: Siesta Key
Fins Up
Weekly $1,225 - $5,775
110 Ven -279
3 BR, 2 BA
Sleeps: 10
View: Peaking Gulf Views
Type: Condo
Location: Siesta Key
Island Sun
Weekly $1,673 - $6,195
559 Beach B
3 BR, 2 BA
Sleeps: 10
View: Pool View
Type: Condo
Location: Siesta Key
*Pricing displayed excludes taxes, fees and travel insurance.
