Stays for 4+ guests in Siesta Key & Sarasota, FL
Stays for 4+ guests in Siesta Key & Sarasota, FL, from $62 a night. Book direct on each manager's site, no OTA fee.
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Private Pool - Walk to Siesta Key Beach & Village!
House · 3 bed · 2 bath · sleeps 6
Siesta Key, FL
From $251 a night
- waterfront
- kitchen
- wifi
- free driveway parking on premises – 3 sp
Exact location
Book direct on HostWise Stays
Beach Retreat #2
House · 4 bed · 2 bath · sleeps 10
Sarasota, FL
From $324 a night
- dining table
- pool all year
- bathtub
- extra pillows and blankets
Exact location
Book direct on Trish's Beach Retreat
Beach Retreat #1
House · 4 bed · 2 bath · sleeps 10
Sarasota, FL
From $376 a night
- cleaning products
- dryer
- fridge
- toaster
Exact location
Book direct on Trish's Beach Retreat
Curtiss Ave
Condo · 2 bed · 2 bath · sleeps 4
Sarasota, FL
From $62 a night
- condo on the 1st floor
- entire home
- smart lock
- maximum occupancy: 4
Exact location
Book direct on Siesta Key Vacation Rentals
165 Vista Hermosa
Condo · 2 bed · 2 bath · sleeps 4
Siesta Key, FL
From $93 a night
- condo on the 1st floor
- entire home
- lockbox
- maximum occupancy: 4
Exact location
Book direct on Siesta Key Vacation Rentals
Sea Winds 118
Condo · 1 bed · 1 bath · sleeps 4
Siesta Key, FL
From $93 a night
- condo on the 1st floor
- entire home
- lockbox
- maximum occupancy: 4
Exact location
Book direct on Siesta Key Vacation Rentals
Siesta Harbor 302M
Condo · 2 bed · 2 bath · sleeps 4
Siesta Key, FL
From $109 a night
- condo on the 2nd floor
- entire home
- smart lock
- maximum occupancy: 4
Exact location
Book direct on Siesta Key Vacation Rentals
Provincial Gardens S5
Villa · 2 bed · 2 bath · sleeps 4
Siesta Key, FL
From $117 a night
- villa
- entire home
- smart lock
- maximum occupancy: 4
Exact location
Book direct on Siesta Key Vacation Rentals
Provincial Gardens N4
Villa · 2 bed · 2 bath · sleeps 4
Siesta Key, FL
From $119 a night
- villa
- entire home
- smart lock
- maximum occupancy: 4
Exact location
Book direct on Siesta Key Vacation Rentals
Harbour Town 211
Condo · 3 bed · 2 bath · sleeps 6
Siesta Key, FL
From $124 a night
- condo on the 2nd floor
- entire home
- lockbox
- maximum occupancy: 6
Exact location
Book direct on Siesta Key Vacation Rentals
Peppertree 1136
Condo · 2 bed · 2 bath · sleeps 4
Siesta Key, FL
From $124 a night
- condo on the 1st floor
- entire home
- lockbox
- maximum occupancy: 4
Exact location
Book direct on Siesta Key Vacation Rentals
SaraSea 7
Condo · 2 bed · 2 bath · sleeps 4
Siesta Key, FL
From $146 a night
- condo on the 1st floor
- entire home
- lockbox
- maximum occupancy: 4
Exact location
Book direct on Siesta Key Vacation Rentals
Your Perfect Beach Escape
Beach house · 2 bed · 2 bath · sleeps 6
Sarasota, FL
From $150 a night
- wifi
- air conditioning
- full kitchen
- washer/dryer
Exact location
Book direct on Siesta Key Vacation Rental
Bay Tree Club 404A
Condo · 2 bed · 2 bath · sleeps 4
Sarasota, FL
From $155 a night
- condo in a condo on the 4th floor
- entire home
- maximum occupancy: 4
- children welcome
Exact location
Book direct on Siesta Key Vacation Rentals
Provincial Gardens N9
Villa · 2 bed · 2 bath · sleeps 4
Siesta Key, FL
From $205 a night
- villa
- entire home
- lockbox
- maximum occupancy: 4
Exact location
Book direct on Siesta Key Vacation Rentals
Provincial Gardens S4
Villa · 2 bed · 2 bath · sleeps 5
Siesta Key, FL
From $205 a night
- villa
- entire home
- lockbox
- maximum occupancy: 5
Exact location
Book direct on Siesta Key Vacation Rentals
Provincial Gardens N3
Villa · 2 bed · 2 bath · sleeps 4
Siesta Key, FL
From $207 a night
- villa
- entire home
- smart lock
- maximum occupancy: 4
Exact location
Book direct on Siesta Key Vacation Rentals
Shark Unit, Pool Jacuzzi Steps to Siesta Key Beach
House · 3 bed · 2 bath · sleeps 12
Siesta Key, FL
From $313 a night
- air conditioning
- heating
- hot tub
- kitchen
Exact location
Book direct on CielStay
Trish's Beach Retreat W/ Pool/Spa by Siesta Keys#2
House · 4 bed · 2 bath · sleeps 10
Sarasota, FL
From $324 a night
- dining table
- pool all year
- bathtub
- extra pillows and blankets
Exact location
Book direct on Trish's Beach Retreat
Charlotte Chalet
Chalet · 3 bed · 2 bath · sleeps 6
Sarasota
From $338 a night
- air conditioning
- body soap
- conditioner
- dryer
Exact location
Book direct on BNB Breeze
Trish's Beach Retreat with Pool/Spa by Siesta Keys
House · 4 bed · 2 bath · sleeps 10
Sarasota, FL
From $376 a night
- cleaning products
- dryer
- fridge
- toaster
Exact location
Book direct on Trish's Beach Retreat
Sea Club II - 1B
Condo · 1 bed · 1 bath · sleeps 4
Siesta Key
From $379 a night
- bathtub
- body soap
- hair dryer
- shower
Exact location
Book direct on Siesta Key Vacation Rentals
CandyPop Retro Retreat
Bungalow · 2 bed · 2 bath · sleeps 4
Sarasota
From $380 a night
- air conditioning
- body soap
- conditioner
- dryer
Exact location
Book direct on BNB Breeze
Brookline Retreat
Bungalow · 4 bed · 2 bath · sleeps 8
Sarasota
From $384 a night
- air conditioning
- body soap
- conditioner
- dryer
Exact location
Book direct on BNB Breeze
The Olive Turtle
Bungalow · 3 bed · 2 bath · sleeps 6
Sarasota
From $396 a night
- air conditioning
- body soap
- conditioner
- dryer
Exact location
Book direct on BNB Breeze
Bianco Sands - 1118B
Villa · 1 bed · 1 bath · sleeps 4
Siesta Key
From $429 a night
- body soap
- hair dryer
- shower
- toilet paper
Exact location
Book direct on Siesta Key Vacation Rentals
Blue Ocean - Sand Dollar Suite
Condo · 1 bed · 1 bath · sleeps 4
Siesta Key
From $429 a night
- body soap
- hair dryer
- shower
- toilet paper
Exact location
Book direct on Siesta Key Vacation Rentals
Blue Ocean - Sandcastle Suite
Condo · 2 bed · 2 bath · sleeps 8
Siesta Key
From $429 a night
- body soap
- hair dryer
- shower
- toilet paper
Exact location
Book direct on Siesta Key Vacation Rentals
Casa Mar - 08
Condo · 1 bed · 1 bath · sleeps 6
Siesta Key
From $429 a night
- bathtub
- body soap
- hair dryer
- shower
Exact location
Book direct on Siesta Key Vacation Rentals
Casa Mar - 56
Condo · 1 bed · 1 bath · sleeps 4
Siesta Key
From $429 a night
- bathtub
- body soap
- hair dryer
- shower
Exact location
Book direct on Siesta Key Vacation Rentals
Lake House at the Beach - C117
House · 2 bed · 2 bath · sleeps 6
Siesta Key
From $429 a night
- body soap
- hair dryer
- shower
- toilet paper
Exact location
Book direct on Siesta Key Vacation Rentals
Lake House at the Beach - C127
House · 2 bed · 2 bath · sleeps 6
Siesta Key
From $429 a night
- bathtub
- body soap
- hair dryer
- shower
Exact location
Book direct on Siesta Key Vacation Rentals
Lake House at the Beach - C207
House · 2 bed · 2 bath · sleeps 7
Siesta Key
From $429 a night
- bathtub
- body soap
- hair dryer
- shower
Exact location
Book direct on Siesta Key Vacation Rentals
Sea Shell - 308
Condo · 2 bed · 2 bath · sleeps 7
Siesta Key
From $429 a night
- bathtub
- body soap
- hair dryer
- shower
Exact location
Book direct on Siesta Key Vacation Rentals
A Charming Beach Cottage - Unit A
Cottage · 1 bed · 1 bath · sleeps 4
Siesta Key
From $449 a night
- body soap
- hair dryer
- shower
- toilet paper
Exact location
Book direct on Siesta Key Vacation Rentals
Bianco Sands - 1108
Villa · 2 bed · 2 bath · sleeps 6
Siesta Key
From $449 a night
- bathtub
- body soap
- hair dryer
- shower
Exact location
Book direct on Siesta Key Vacation Rentals
Bianco Sands - 1110
Villa · 2 bed · 2 bath · sleeps 6
Siesta Key
From $449 a night
- bathtub
- body soap
- hair dryer
- shower
Exact location
Book direct on Siesta Key Vacation Rentals
Bianco Sands - 1114
Villa · 2 bed · 2 bath · sleeps 6
Siesta Key
From $449 a night
- bathtub
- body soap
- hair dryer
- shower
Exact location
Book direct on Siesta Key Vacation Rentals
Bianco Sands - 1116
Villa · 2 bed · 2 bath · sleeps 6
Siesta Key
From $449 a night
- bathtub
- body soap
- hair dryer
- shower
Exact location
Book direct on Siesta Key Vacation Rentals
Bianco Sands - 1118A
Villa · 2 bed · 2 bath · sleeps 6
Siesta Key
From $449 a night
- bathtub
- body soap
- hair dryer
- shower
Exact location
Book direct on Siesta Key Vacation Rentals
Palm Bay Club - 343 Bayside
Condo · 2 bed · 2 bath · sleeps 8
Siesta Key
From $449 a night
- bathtub
- body soap
- hair dryer
- shower
Exact location
Book direct on Siesta Key Vacation Rentals
Siesta Beach House - 210
Beach house · 2 bed · 1 bath · sleeps 7
Siesta Key
From $449 a night
- body soap
- hair dryer
- shower
- toilet paper
Exact location
Book direct on Siesta Key Vacation Rentals
Crescent Arms
Condo · 2 bed · 2 bath · sleeps 6
Siesta Key
From $459 a night
- bathtub
- body soap
- hair dryer
- shower
Exact location
Book direct on Siesta Key Vacation Rentals
Gulf & Bay Club - C301
Condo · 2 bed · 2 bath · sleeps 8
Siesta Key
From $459 a night
- gym/fitness room
- new property
- premium property
- bathtub
Exact location
Book direct on Siesta Key Vacation Rentals
Gulf & Bay Club - F306
Condo · 3 bed · 2 bath · sleeps 8
Siesta Key
From $459 a night
- bathtub
- body soap
- hair dryer
- shower
Exact location
Book direct on Siesta Key Vacation Rentals
Gulf & Bay Club - F402
Condo · 3 bed · 2 bath · sleeps 8
Siesta Key
From $459 a night
- bathtub
- body soap
- hair dryer
- toilet paper
Exact location
Book direct on Siesta Key Vacation Rentals
Bianco Sands - 1126
Villa · 2 bed · 2 bath · sleeps 7
Siesta Key
From $479 a night
- bathtub
- body soap
- hair dryer
- shower
Exact location
Book direct on Siesta Key Vacation Rentals
Bianco Sands - 1128
Villa · 3 bed · 2 bath · sleeps 8
Siesta Key
From $479 a night
- bathtub
- body soap
- hair dryer
- shower
Exact location
Book direct on Siesta Key Vacation Rentals
Crescent Cove - A Crescent Beach Villa
Villa · 2 bed · 2 bath · sleeps 6
Siesta Key
From $479 a night
- bathtub
- body soap
- hair dryer
- shower
Exact location
Book direct on Siesta Key Vacation Rentals
Living the Dream - Mermaid
Condo · 2 bed · 1 bath · sleeps 6
Siesta Key
From $479 a night
- bathtub
- body soap
- hair dryer
- shower
Exact location
Book direct on Siesta Key Vacation Rentals
Living the Dream - Pink Flamingo
Condo · 2 bed · 1 bath · sleeps 6
Siesta Key
From $479 a night
- body soap
- hair dryer
- shower
- toilet paper
Exact location
Book direct on Siesta Key Vacation Rentals
Living the Dream - Starfish
Condo · 2 bed · 1 bath · sleeps 6
Siesta Key
From $479 a night
- bathtub
- body soap
- hair dryer
- shower
Exact location
Book direct on Siesta Key Vacation Rentals
Our House at the Beach - 204W
House · 2 bed · 2 bath · sleeps 6
Siesta Key
From $479 a night
- bathtub
- body soap
- hair dryer
- shower
Exact location
Book direct on Siesta Key Vacation Rentals
Our House at the Beach - 501W
House · 2 bed · 2 bath · sleeps 8
Siesta Key
From $479 a night
- bathtub
- body soap
- hair dryer
- shower
Exact location
Book direct on Siesta Key Vacation Rentals
Our House at the Beach - 502E
House · 2 bed · 2 bath · sleeps 7
Siesta Key
From $479 a night
- bathtub
- body soap
- hair dryer
- shower
Exact location
Book direct on Siesta Key Vacation Rentals
Our House at the Beach - 604E
House · 2 bed · 2 bath · sleeps 6
Siesta Key
From $479 a night
- body soap
- hair dryer
- shower
- toilet paper
Exact location
Book direct on Siesta Key Vacation Rentals
Island Hideaway
Bungalow · 3 bed · 2 bath · sleeps 8
Sarasota
From $484 a night
- air conditioning
- body soap
- conditioner
- dryer
Exact location
Book direct on BNB Breeze
Cozy Coastal
Bungalow · 2 bed · 2 bath · sleeps 6
Sarasota
From $493 a night
- air conditioning
- body soap
- conditioner
- dryer
Exact location
Book direct on BNB Breeze
Pinecraft Pearl
Bungalow · 2 bed · 2 bath · sleeps 4
Sarasota
From $493 a night
- air conditioning
- body soap
- conditioner
- dryer
Exact location
Book direct on BNB Breeze
A Sea La Vie - Crystal Sands
Villa · 2 bed · 2 bath · sleeps 5
Siesta Key
From $499 a night
- body soap
- hair dryer
- shower
- toilet paper
Exact location
Book direct on Siesta Key Vacation Rentals
These are the cheapest; there are more. Narrow by facet above, or ask an agent through https://otaless.com/mcp.
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How prices are computed
Lowest rate the manager has published. Your dates may cost more; the real price is on their site. The "from" figure is the lowest nightly rate the manager published on that listing page when we last fetched it. It excludes taxes, cleaning and other fees, it is not a quote, and it is not live availability.
Updated 2026-10-31 08:45 UTC. Prices and facts are whatever the manager published on their own site.