Currently displaying:
All Units
Island Time East
Weekly $1,393 - $8,400
355 Miramar
3 BR, 3 BA, 1 HF BA
Sleeps: 14
View: Street, Pool, City
Type: Condo
Location: Siesta Key
Blue Lagoon
Weekly $1,393 - $8,400
322 Miramar
3 BR, 3 BA
Sleeps: 9
View: Pool
Type: Single Family Home
Location: Siesta Key
Villa Marina
Weekly $903 - $6,720
5240 - 112
2 BR, 2 BA
Sleeps: 6
View: Pool and City
Type: Condo
Location: Siesta Key
Island Time West
Weekly $1,393 - $8,400
353 Miramar
3 BR, 3 BA, 1 HF BA
Sleeps: 14
View: Street, City, Pool
Type: Condo
Location: Siesta Key
The Daiquiri Deck
Weekly $1,323 - $7,700
304 Canal
3 BR, 3 BA
Sleeps: 10
View: Pool and Village
Type: Condo
Location: Siesta Key
Fins Up
Weekly $1,113 - $7,700
110 Ven -279
3 BR, 2 BA
Sleeps: 10
View: Peaking Gulf Views
Type: Condo
Location: Siesta Key
Tarpon Villa
Weekly $1,603 - $12,600
340 Canal
4 BR, 2 BA, 1 HF BA
Sleeps: 12
View: Pool
Type: Condo
Location: Siesta Key
The Pool House
Weekly $3,150 - $18,375
98 Messina
5 BR, 4 BA
Sleeps: 16
View: Pool and Garden
Type: Single Family Home
Location: Siesta Key
Bimini Breeze
Weekly $1,323 - $7,700
5259 Menorca
2 BR, 2 BA
Sleeps: 8
View: Pool
Type: Single Family Home
Location: Siesta Key
Island Sun
Weekly $1,253 - $7,700
559 Beach B
3 BR, 2 BA
Sleeps: 10
View: Pool View
Type: Condo
Location: Siesta Key
Dry Dock
Weekly $3,500 - $18,375
515 Canal B
6 BR, 6 BA, 1 HF BA
Sleeps: 18
View: Canal/Water
Type: Single Family Home
Location: Siesta Key
Modern Marvel
Weekly $3,500 - $18,550
150 Givens
4 BR, 4 BA, 1 HF BA
Sleeps: 12
View: Gulf of Mexico
Type: Single Family Home
Location: Siesta Key
Siesta Sun
Weekly $1,603 - $10,500
559 Beach A
3 BR, 3 BA, 1 HF BA
Sleeps: 10
View: Ocean View
Type: Condo
Location: Siesta Key
Bahama Mama
Weekly $3,150 - $17,500
5227 Menorca
5 BR, 5 BA
Sleeps: 14
View: Pool
Type: Single Family Home
Location: Siesta Key
Sunset View
Weekly $3,500 - $18,900
547 Beach
8 BR, 5 BA, 1 HF BA
Sleeps: 25
View: Gorgeous Gulf Views
Type: Single Family Home
Location: Siesta Key
The Mahi
Weekly $903 - $7,000
110 Ven -179
2 BR, 2 BA
Sleeps: 8
View: Courtyard
Type: Condo
Location: Siesta Key
Point Break
Weekly $3,850 - $19,600
336 De Mayo
8 BR, 8 BA, 1 HF BA
Sleeps: 24
View: Gulf and City View
Type: Single Family Home
Location: Siesta Key
Aloft on Canal
Weekly $3,850 - $19,600
542 Canal
8 BR, 6 BA, 1 HF BA
Sleeps: 22
View: Gulf and City Views
Type: Single Family Home
Location: Siesta Key
Sunset Gulf
Weekly $3,500 - $18,900
551 Beach Rd
8 BR, 5 BA, 1 HF BA
Sleeps: 25
View: Gorgeous Gulf Views
Type: Single Family Home
Location: Siesta Key
Beach Retreat
Weekly $1,463 - $9,800
5230 Navarra
3 BR, 3 BA
Sleeps: 8
View: Pool
Type: Single Family Home
Location: Siesta Key
Summer Salt
Weekly $973 - $6,720
308 Canal
2 BR, 2 BA
Sleeps: 8
View: City and Pool
Type: Condo
Location: Siesta Key
Blue Paradise
Weekly $3,850 - $19,600
5234 Navarra
6 BR, 6 BA, 1 HF BA
Sleeps: 18
View: Gulf Views
Type: Single Family Home
Location: Siesta Key
Summer House
Weekly $4,200 - $19,600
99 Messina
6 BR, 6 BA
Sleeps: 22
View: Pool View
Type: Single Family Home
Location: Siesta Key
Sugar Sand Cottage
Weekly $2,975 - $19,600
105 Beach
5 BR, 3 BA, 1 HF BA
Sleeps: 19
View: Beach and Gulf
Type: Single Family Home
Location: Siesta Key
Salty Dog
Weekly $3,500 - $18,200
515 Canal A
6 BR, 5 BA, 1 HF BA
Sleeps: 17
View: Canal - Water
Type: Single Family Home
Location: Siesta Key
Sea Spray
Weekly $3,850 - $19,600
538 Canal
8 BR, 6 BA, 1 HF BA
Sleeps: 22
View: Gorgeous Gulf Views
Type: Single Family Home
Location: Siesta Key
Tipsy Turtle
Weekly $973 - $5,600
412 Canal
2 BR, 2 BA
Sleeps: 6
View: Street and Courtyard
Type: Condo
Location: Siesta Key
Reel Lucky
Weekly $903 - $5,600
410 Canal
2 BR, 2 BA
Sleeps: 8
View: Peaking Gulf Views
Type: Condo
Location: Siesta Key
Island House
Weekly $3,500 - $18,200
344 Canal
7 BR, 6 BA
Sleeps: 23
View: Pool and Canal
Type: Single Family Home
Location: Siesta Key
Siesta Penthouse
Weekly $2,100 - $14,000
304 Miramar
4 BR, 3 BA, 1 HF BA
Sleeps: 10
View: Gulf and City Views
Type: Condo
Location: Siesta Key
Beach Club Breeze
Weekly $1,113 - $7,350
302 Canal
3 BR, 3 BA
Sleeps: 10
View: Pool and Village
Type: Condo
Location: Siesta Key
On The Rocks
Weekly $3,500 - $18,375
309 Miramar
5 BR, 5 BA
Sleeps: 15
View: City and Pool
Type: Single Family Home
Location: Siesta Key
Private Beach House
Weekly $903 - $6,650
315
2 BR, 2 BA, 1 HF BA
Sleeps: 9
View: Street
Type: Condo
Location: Siesta Key
Aruba
Weekly $1,743 - $10,500
5255 Menorca
3 BR, 2 BA, 1 HF BA
Sleeps: 12
View: Pool
Type: Single Family Home
Location: Siesta Key
Mainsail
Weekly $2,800 - $15,400
1245 Big Oak
4 BR, 3 BA, 1 HF BA
Sleeps: 10
View: Waterfront
Type: Single Family Home
Location: Siesta Key
Surf View
Weekly $3,500 - $18,900
303 Calle
8 BR, 8 BA, 1 HF BA
Sleeps: 22
View: Rooftop Deck
Type: Single Family Home
Location: Siesta Key
Siesta Palooza
Weekly $3,850 - $19,600
332 De Mayo
8 BR, 8 BA
Sleeps: 25
View: Gulf and City View
Type: Single Family Home
Location: Siesta Key
*Pricing displayed excludes taxes, fees and travel insurance.
