Stays for 8+ guests in Siesta Key & Sarasota, FL
Stays for 8+ guests in Siesta Key & Sarasota, FL, from $200 a night. Book direct on each manager's site, no OTA fee.
Find stays in Siesta Key & Sarasota, FL
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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
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
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
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
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
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 - 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
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
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
Siesta Beach House - Cottage C
Beach house · 3 bed · 2 bath · sleeps 8
Siesta Key
From $499 a night
- new property
- semi adjacent property
- single level home
- bathtub
Exact location
Book direct on Siesta Key Vacation Rentals
Splish Splash Retreat
Bungalow · 3 bed · 2 bath · sleeps 8
Sarasota
From $508 a night
- air conditioning
- body soap
- conditioner
- dryer
Exact location
Book direct on BNB Breeze
Sunny Shores Retreat
Bungalow · 3 bed · 2 bath · sleeps 8
Sarasota
From $546 a night
- air conditioning
- body soap
- conditioner
- dryer
Exact location
Book direct on BNB Breeze
The Palms
Bungalow · 3 bed · 2 bath · sleeps 8
Sarasota
From $564 a night
- air conditioning
- body soap
- conditioner
- dryer
Exact location
Book direct on BNB Breeze
Sapphire Cove
Bungalow · 2 bed · 2 bath · sleeps 8
Sarasota
From $570 a night
- air conditioning
- body soap
- conditioner
- dryer
Exact location
Book direct on BNB Breeze
Mallory Squared- Unit A
Condo · 2 bed · 2 bath · sleeps 8
Siesta Key
From $578 a night
- body soap
- hair dryer
- shower
- toilet paper
Exact location
Book direct on Siesta Key Vacation Rentals
Paradise Getaway
Bungalow · 4 bed · 4 bath · sleeps 8
Sarasota
From $590 a night
- air conditioning
- body soap
- conditioner
- dryer
Exact location
Book direct on BNB Breeze
Coastal Surfside - 304
Condo · 3 bed · 2 bath · sleeps 8
Siesta Key
From $599 a night
- bathtub
- body soap
- hair dryer
- shower
Exact location
Book direct on Siesta Key Vacation Rentals
Coastal Surfside Swank
Condo · 3 bed · 2 bath · sleeps 8
Siesta Key
From $599 a night
- bathtub
- body soap
- hair dryer
- shower
Exact location
Book direct on Siesta Key Vacation Rentals
Bay Bliss Bungalow
Bungalow · 3 bed · 2 bath · sleeps 8
Sarasota
From $617 a night
- air conditioning
- body soap
- conditioner
- dryer
Exact location
Book direct on BNB Breeze
The Palmy Pickle
Bungalow · 1 bed · 2 bath · sleeps 8
Sarasota
From $618 a night
- air conditioning
- body soap
- conditioner
- dryer
Exact location
Book direct on BNB Breeze
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
Casa Louise
Bungalow · 4 bed · 2 bath · sleeps 8
Sarasota
From $644 a night
- air conditioning
- body soap
- conditioner
- dryer
Exact location
Book direct on BNB Breeze
Lemon Drop Cottage
Cottage · 3 bed · 3 bath · sleeps 8
Sarasota
From $659 a night
- air conditioning
- body soap
- conditioner
- dryer
Exact location
Book direct on BNB Breeze
Endless Summer
Bungalow · 3 bed · 1 bath · sleeps 8
Sarasota
From $672 a night
- air conditioning
- body soap
- conditioner
- dryer
Exact location
Book direct on BNB Breeze
Kiwi Cove
Bungalow · 3 bed · 2 bath · sleeps 8
Sarasota
From $672 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
Aloha Skies
Bungalow · 4 bed · 2 bath · sleeps 8
Sarasota
From $729 a night
- air conditioning
- body soap
- conditioner
- dryer
Exact location
Book direct on BNB Breeze
Kokomo Keys
Bungalow · 3 bed · 3 bath · sleeps 8
Sarasota
From $733 a night
- air conditioning
- body soap
- conditioner
- dryer
Exact location
Book direct on BNB Breeze
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
The Airy Bungalow
Bungalow · 4 bed · 2 bath · sleeps 9
Sarasota
From $770 a night
- air conditioning
- body soap
- conditioner
- dryer
Exact location
Book direct on BNB Breeze
Lakeview Oasis
Bungalow · 3 bed · 2 bath · sleeps 8
Sarasota
From $771 a night
- air conditioning
- body soap
- conditioner
- dryer
Exact location
Book direct on BNB Breeze
Living The Dream
Bungalow · 3 bed · 2 bath · sleeps 8
Sarasota
From $794 a night
- air conditioning
- body soap
- conditioner
- dryer
Exact location
Book direct on BNB Breeze
Royal Palms Oasis
Bungalow · 3 bed · 2 bath · sleeps 8
Sarasota
From $825 a night
- air conditioning
- body soap
- conditioner
- dryer
Exact location
Book direct on BNB Breeze
Bahama Breeze
Bungalow · 3 bed · 2 bath · sleeps 8
Sarasota
From $845 a night
- air conditioning
- body soap
- conditioner
- dryer
Exact location
Book direct on BNB Breeze
Southern Haven
Bungalow · 3 bed · 2 bath · sleeps 8
Sarasota
From $845 a night
- air conditioning
- body soap
- conditioner
- dryer
Exact location
Book direct on BNB Breeze
Sea Pointe
Bungalow · 3 bed · 2 bath · sleeps 8
Sarasota
From $873 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
A Tide that Binds Us - 602
Townhome · 3 bed · 2 bath · sleeps 9
Siesta Key
From $899 a night
- bathtub
- body soap
- hair dryer
- shower
Exact location
Book direct on Siesta Key Vacation Rentals
Jamaica Royale Beach View Tower - T32
Condo · 2 bed · 2 bath · sleeps 8
Siesta Key
From $899 a night
- bathtub
- body soap
- hair dryer
- shower
Exact location
Book direct on Siesta Key Vacation Rentals
Jamaica Royale Beachfront Tower - 305
Condo · 2 bed · 2 bath · sleeps 8
Siesta Key
From $899 a night
- body soap
- hair dryer
- shower
- toilet paper
Exact location
Book direct on Siesta Key Vacation Rentals
Riviera Retreat
Bungalow · 4 bed · 2 bath · sleeps 8
Sarasota
From $906 a night
- air conditioning
- body soap
- conditioner
- dryer
Exact location
Book direct on BNB Breeze
Roselawn St
Bungalow · 4 bed · 3 bath · sleeps 8
Sarasota
From $919 a night
- air conditioning
- body soap
- conditioner
- dryer
Exact location
Book direct on BNB Breeze
Raya House
House · 3 bed · 2 bath · sleeps 9
Sarasota
From $948 a night
- air conditioning
- body soap
- conditioner
- dryer
Exact location
Book direct on BNB Breeze
Seahorse Cove
Townhome · 3 bed · 2 bath · sleeps 8
Siesta Key
From $949 a night
- bathtub
- body soap
- hair dryer
- shower
Exact location
Book direct on Siesta Key Vacation Rentals
Moonlight Villa
Villa · 3 bed · 4 bath · sleeps 8
Sarasota
From $986 a night
- air conditioning
- body soap
- conditioner
- dryer
Exact location
Book direct on BNB Breeze
Coastal Cottage
Cottage · 3 bed · 3 bath · sleeps 9
Sarasota
From $1,043 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
House of Agape
House · 4 bed · 3 bath · sleeps 8
Sarasota
From $1,221 a night
- air conditioning
- body soap
- conditioner
- dryer
Exact location
Book direct on BNB Breeze
Cobalt Cove
Bungalow · 3 bed · 2 bath · sleeps 8
Sarasota
From $1,277 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
Sandy Feet Retreat
Bungalow · 3 bed · 2 bath · sleeps 8
Sarasota
From $1,306 a night
- air conditioning
- body soap
- conditioner
- dryer
Exact location
Book direct on BNB Breeze
A Somewhere is Here - Changes in Latitude
Condo · 3 bed · 2 bath · sleeps 10
Siesta Key
From $1,313 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
These are the cheapest; there are more. Narrow by facet above, or ask an agent through https://otaless.com/mcp.
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Managers here
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 2026-10-30 08:16 UTC. Prices and facts are whatever the manager published on their own site.