Stays for 10+ guests in Siesta Key & Sarasota, FL
Stays for 10+ guests in Siesta Key & Sarasota, FL, from $253 a night. Book direct on each manager's site, no OTA fee.
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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
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
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
Olive Tree Oasis
Bungalow · 4 bed · 2 bath · sleeps 10
Sarasota
From $635 a night
- air conditioning
- body soap
- conditioner
- dryer
Exact location
Book direct on BNB Breeze
A Somewhere is Here - Changes in Attitude
Condo · 3 bed · 2 bath · sleeps 10
Siesta Key
From $699 a night
- bathtub
- body soap
- hair dryer
- shower
Exact location
Book direct on Siesta Key Vacation Rentals
A Tide that Binds Us - 600
Townhome · 3 bed · 2 bath · sleeps 13
Siesta Key
From $699 a night
- bathtub
- body soap
- hair dryer
- shower
Exact location
Book direct on Siesta Key Vacation Rentals
Breezemont Bungalow
Bungalow · 4 bed · 2 bath · sleeps 10
Sarasota
From $764 a night
- air conditioning
- body soap
- conditioner
- dryer
Exact location
Book direct on BNB Breeze
Costa del Ray
Bungalow · 4 bed · 2 bath · sleeps 10
Sarasota
From $887 a night
- air conditioning
- body soap
- conditioner
- dryer
Exact location
Book direct on BNB Breeze
Apres Sea at Cinco Siesta
Townhome · 5 bed · 3 bath · sleeps 14
Siesta Key
From $1,200 a night
- bathtub
- body soap
- hair dryer
- shower
Exact location
Book direct on Siesta Key Vacation Rentals
Casa Tropicana | 4BR Luxury Pool & Spa Retreat
House · 4 bed · 3.5 bath · sleeps 10
Siesta Key, FL
From $1,200 a night
- body soap
- cleaning products
- conditioner
- hot water
Exact location
Book direct on Luxury Furnished Vacation Rentals & Property Management
Hibiscus Haven
Bungalow · 4 bed · 3 bath · sleeps 10
Sarasota
From $1,206 a night
- air conditioning
- body soap
- conditioner
- dryer
Exact location
Book direct on BNB Breeze
A Charming Beach Cottage
Cottage · 3 bed · 3 bath · sleeps 10
Siesta Key
From $1,299 a night
- bathtub
- body soap
- hair dryer
- shower
Exact location
Book direct on Siesta Key Vacation Rentals
A Somewhere is Here - Changes in Latitude
Condo · 3 bed · 2 bath · sleeps 10
Siesta Key
From $1,311 a night
- bathtub
- body soap
- hair dryer
- shower
Exact location
Book direct on Siesta Key Vacation Rentals
Sarasota's Gem
Bungalow · 4 bed · 2 bath · sleeps 10
Sarasota
From $1,387 a night
- air conditioning
- body soap
- conditioner
- dryer
Exact location
Book direct on BNB Breeze
Blossom Bay
Bungalow · 4 bed · 3 bath · sleeps 10
Sarasota
From $1,446 a night
- air conditioning
- body soap
- conditioner
- dryer
Exact location
Book direct on BNB Breeze
Sapphire Shores
Bungalow · 5 bed · 5 bath · sleeps 10
Sarasota
From $1,638 a night
- air conditioning
- body soap
- conditioner
- dryer
Exact location
Book direct on BNB Breeze
Pelican's Perch
Bungalow · 4 bed · 3 bath · sleeps 10
Sarasota
From $1,730 a night
- air conditioning
- body soap
- conditioner
- dryer
Exact location
Book direct on BNB Breeze
Salty Sailfish
Bungalow · 4 bed · 3 bath · sleeps 10
Sarasota
From $1,820 a night
- air conditioning
- body soap
- conditioner
- dryer
Exact location
Book direct on BNB Breeze
Lulu's Key House: Private Heated Pool, Steps To Siesta Key Beach & Perfectly Located In The Village!
House · 6 bed · 2 bath · sleeps 20
Siesta Key
From $1,825 a night
- air conditioning
- dryer
- fire extinguisher
- garden
Exact location
Book direct on Niranar
Beach | Family & Pet Friendly | Garage & Balcony | Walk or Bike | Downtown
House · 3 bed · 3 bath · sleeps 10
Sarasota
From $253 a night
Exact location
Book direct on Beach, Pet-Friendly, Pool, Siesta Key, Sarasota, Florida Vacation Rentals
Flamingo on Siesta
Townhome · 3 bed · 3 bath · sleeps 10
Siesta Key
From $360 a night
Exact location
Book direct on Siesta Key Vacation Rentals
Osprey on Siesta
Townhome · 3 bed · 1 bath · sleeps 10
Siesta Key
From $499 a night
Exact location
Book direct on Siesta Key Vacation Rentals
Sea Horse on Siesta
House · 4 bed · 3 bath · sleeps 10
Siesta Key
From $550 a night
Exact location
Book direct on Siesta Key Vacation Rentals
Walk to Siesta Key Beach • Family & Pet Friendly • Saltwater Pool • EV Charging Station
Beach house · 4 bed · 3 bath · sleeps 12
Siesta Key
From $645 a night
Exact location
Book direct on Beach, Pet-Friendly, Pool, Siesta Key, Sarasota, Florida Vacation Rentals
3615 Flores
House · 4 bed · 3 bath · sleeps 10
Sarasota
From $700 a night
Exact location
Book direct on siesta-retreats.com
Coral House on Siesta
Townhome · 4 bed · 5 bath · sleeps 12
Siesta Key
From $1,000 a night
Exact location
Book direct on Siesta Key Vacation Rentals
Sea Jewel on Siesta
House · 3 bed · 3 bath · sleeps 10
Siesta Key
From $1,050 a night
Exact location
Book direct on Siesta Key Vacation Rentals
Coastal Breeze Siesta: Waterfront 4-unit Retreat Walk To Turtle Beach, Boat Dock & Free Beach Gear
4 bed · 4 bath · sleeps 16
Siesta Key
From $1,182 a night
- air conditioning
- dryer
- fire extinguisher
- garden
Exact location
Book direct on Niranar
Sand Dollar on Siesta
House · 6 bed · 7 bath · sleeps 14
Siesta Key
From $1,500 a night
Exact location
Book direct on Siesta Key Vacation Rentals
Walk to Siesta Key Beach • Family & Pet Friendly • Saltwater Pool • EV Charging Station
Beach house · 3 bath · sleeps 12
Siesta Key
From $645 a night
Exact location
Book direct on Beach, Pet-Friendly, Pool, Siesta Key, Sarasota, Florida Vacation Rentals
Lido Beach Family Complex
Beach house · 4 bed · 3 bath · sleeps 10
Sarasota, FL
No nightly rate published
- air conditioning
- central heating
- linens provided
- clothes dryer
Exact location
Book direct on P
Sarasota Coastal Retreat
Bungalow · 5 bed · 5.5 bath · sleeps 14
Sarasota, FL
No nightly rate published
- air conditioning
- fireplace
- central heating
- baking sheet
Exact location
Book direct on P
Sea La Vie
Bungalow · 3 bed · 2 bath · sleeps 10
Siesta Key, FL
No nightly rate published
- air conditioning
- central heating
- baking sheet
- blender
Exact location
Book direct on P
Siesta Sea Life
Bungalow · 6 bed · 4 bath · sleeps 20
Siesta Key, FL
No nightly rate published
- air conditioning
- central heating
- baking sheet
- blender
Exact location
Book direct on P
Siesta Sweet Spot
Townhome · 3 bed · 2.5 bath · sleeps 10
Sarasota, FL
No nightly rate published
- air conditioning
- fireplace
- central heating
- baking sheet
Exact location
Book direct on P
Temple of Time
Bungalow · 5 bed · 7 bath · sleeps 12
Sarasota, FL
No nightly rate published
- air conditioning
- fireplace
- central heating
- baking sheet
Exact location
Book direct on P
Waldemere's Wonderland
Bungalow · 5 bed · 5 bath · sleeps 12
Sarasota, FL
No nightly rate published
- air conditioning
- fireplace
- central heating
- baking sheet
Exact location
Book direct on P
A Las Palmas
Condo · 7 bed · 7 bath · sleeps 16
Siesta Key
No nightly rate published
- bathtub
- body soap
- hair dryer
- shower
Exact location
Book direct on Siesta Key Vacation Rentals
Canopy Heights
Bungalow · 7 bed · 6 bath · sleeps 18
Sarasota
No nightly rate published
- air conditioning
- body soap
- conditioner
- dryer
Exact location
Book direct on BNB Breeze
Casey Key Luxe Paradise~Private Beach~Gulf to Bay
House · 3 bed · 5 bath · sleeps 10
Nokomis, FL
No nightly rate published
- tv
- air conditioning
- desk
- office
Exact location
Book direct on Manage your vacation home with Fairly.
Coastal Lodge
Lodge · 6 bed · 6 bath · sleeps 15
Sarasota
No nightly rate published
- air conditioning
- body soap
- conditioner
- dryer
Exact location
Book direct on BNB Breeze
Fanta-Sea 49
Townhome · 5 bed · 4 bath · sleeps 14
Siesta Key
No nightly rate published
- bathtub
- body soap
- hair dryer
- shower
Exact location
Book direct on Siesta Key Vacation Rentals
Fanta-Sea 53
Townhome · 4 bed · 4 bath · sleeps 12
Siesta Key
No nightly rate published
- bathtub
- body soap
- hair dryer
- shower
Exact location
Book direct on Siesta Key Vacation Rentals
Fanta-Sea 55
Townhome · 4 bed · 4 bath · sleeps 12
Siesta Key
No nightly rate published
- bathtub
- body soap
- hair dryer
- shower
Exact location
Book direct on Siesta Key Vacation Rentals
Jellyfish-Flamingo House, Amazing Location On Beach & Walk To Village
House · 4 bed · 3 bath · sleeps 20
Siesta Key, FL
No nightly rate published
- air conditioning
- cleaning products
- dishes and silverware
- dryer
Exact location
Book direct on Siesta Key Gem: Vibrant Retreats with Pools & Hot Tubs
Lookout
Condo · 4 bed · 4 bath · sleeps 10
Siesta Key
No nightly rate published
- bathtub
- body soap
- hair dryer
- shower
Exact location
Book direct on Siesta Key Vacation Rentals
MERMAID HOUSE WITH POOL JACUZZI STEPS to SIESTA KEY BEACH
House · 3 bed · 2 bath · sleeps 12
Siesta Key, FL
No nightly rate published
- air conditioning
- cleaning products
- dishes and silverware
- dryer
Exact location
Book direct on Siesta Key Gem: Vibrant Retreats with Pools & Hot Tubs
Mermaid-Shark 6BR House With Pool, Jacuzzi - Steps to Siesta Key Beach
House · 6 bed · 4 bath · sleeps 24
Siesta Key, FL
No nightly rate published
- air conditioning
- cleaning products
- dishes and silverware
- dryer in the unit, free
Exact location
Book direct on Siesta Key Gem: Vibrant Retreats with Pools & Hot Tubs
Spacious & Unique: Heated Pool ~ 2 Hot Tubs ~ Pkg!
House · 4 bed · 3 bath · sleeps 16
Sarasota, FL
No nightly rate published
- air conditioning
- cleaning products
- dishes and silverware
- dryer
Exact location
Book direct on Siesta Key Gem: Vibrant Retreats with Pools & Hot Tubs
Beach House Residences Unit 1
Beach house · 4 bed · 3 bath · sleeps 10
Sarasota, FL
No nightly rate published
Exact location
Book direct on Gulf Coast Vacation Rentals
Heated Pool - Near Beach - Outdoor Games for Family - Close to DT
House · 3 bath · sleeps 12
Sarasota
No nightly rate published
- shampoo
- air conditioning
- central heating
- stove
Exact location
Book direct on TrustFirst Management
Island Sol - 4845
Hotel · 4 bed · 4 bath · sleeps 13
Sarasota, FL
No nightly rate published
Exact location
Book direct on Westgate Park City
Palm Paradise - 156
Hotel · 5 bed · 5 bath · sleeps 10
Sarasota, FL
No nightly rate published
Exact location
Book direct on Westgate Park City
Pickleball- Heated Pool - Game Room - Themed Rooms
House · 4 bath · sleeps 12
Sarasota
No nightly rate published
- air conditioning
- central heating
- fireplace
- linens provided
Exact location
Book direct on TrustFirst Management
Siesta Keys Neighbor 5min to Beach - Entire Suite Apartment
Apartment · 1 bath · sleeps 12
Sarasota
No nightly rate published
- air conditioning
- central heating
- linens provided
- extra pillows & blankets
Exact location
Book direct on TrustFirst Management
Tiki Tide Villa
Villa · 4 bed · 2 bath · sleeps 10
Sarasota
No nightly rate published
- air conditioning
- dryer
- garage
- heating
Exact location
Book direct on BNB Breeze
TropiCool Retreat
Bungalow · 4 bed · 2 bath · sleeps 10
Sarasota
No nightly rate published
- air conditioning
- body soap
- conditioner
- dryer
Exact location
Book direct on BNB Breeze
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 07:39 UTC. Prices and facts are whatever the manager published on their own site.