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5+ Bedroom Large Vacation Rentals in Siesta Key
We offer Vacation Rentals: Book your 5+ Bedroom Home securely here and save!
Stay steps from the sand in a Siesta Key rentals designed for convenience, coastal style, and those perfect Gulf sunsets — ideal for couples, families, and anyone who wants a seamless beach getaway.
Vacation Rentals by Owner in Florida.
We have partnered with a major provider for Vacation Rentals by Owner directly through Florida Vacation Rental Homes. With hundreds of short term rentals to choose from, we now have the selection and value to offer our visitors searching for .
For Pricing & Rates, follow the "Search Availability" or "View Rental" button, which will take you directly on our partner website.......All bookings are securely completed on our partners website!
9.6 Star Rating
Beachfront 5br On Siesta Key W/ Sunset Views
Vacation Home in Siesta Key
5 Bedrooms -- Sleeps 14 -- Pet Friendly 
10.0 Star Rating
Siesta Coastal Oasis - 5 Min Paved Walk To The Private Beach
Vacation Home in Siesta Key
5 Bedrooms -- Sleeps 10
9.8 Star Rating
The Lookout - 891 “siesta Key’
Vacation Home in Siesta Key
5 Bedrooms -- Sleeps 10 -- Pet Friendly
10.0 Star Rating
Beautiful Siesta Key
Vacation Home in Siesta Key
5 Bedrooms -- Sleeps 10
10.0 Star Rating
Beach Dream | Home W/ Ocean Views, 2 Private Pools, Rooftop Lookout And Steps To Siesta Ke
Vacation Home in Siesta Key
6 Bedrooms -- Sleeps 22
10.0 Star Rating
Nearly Beachfront, One House From The Beach! Pool And Game Room - Ocean Overlook
Vacation Home in Siesta Key
8 Bedrooms -- Sleeps 18 -- Pet Friendly
10.0 Star Rating
Large Pool Home- Blocks From Siesta Key Beach
Vacation Home in Siesta Key
5 Bedrooms -- Sleeps 10 -- Pet Friendly
9.4 Star Rating
? Isla Amor | Escape To A Luxury Waterfront Home With Heated Pool & Stunning Views In Sies
Vacation Home in Siesta Key
5 Bedrooms -- Sleeps 11
9.4 Star Rating
Gertrude's Siesta | 4-min Walk To Beach & Village, Tropical & 100% Private!
Vacation Home in Siesta Key
6 Bedrooms -- Sleeps 22 -- Pet Friendly
10.0 Star Rating
#1 Rooftop Deck W/ Gulf Views - Steps To Beach
Vacation Home in Siesta Key
6 Bedrooms -- Sleeps 14 -- Pet Friendly
9.6 Star Rating
16 Guest Pool House Walk To The Beach And Village
Vacation Home in Siesta Key
6 Bedrooms -- Sleeps 16
10.0 Star Rating
Siesta Key Village Heated Pool
Vacation Home in Siesta Key
6 Bedrooms -- Sleeps 14 -- Pet Friendly
10.0 Star Rating
Waterfront Siesta Key Home W/ Pool, Hottub & Mini Putt
Vacation Home in Siesta Key
5 Bedrooms -- Sleeps 16 -- Pet Friendly
10.0 Star Rating
Gulf Views/steps To Beach/resort Pool W/slide/spa
Vacation Home in Siesta Key
6 Bedrooms -- Sleeps 14 -- Pet Friendly
10.0 Star Rating
Steps To Beach - Resort Pool/slide/spa/gulf Views
Vacation Home in Siesta Key
6 Bedrooms -- Sleeps 14 -- Pet Friendly
10.0 Star Rating
Stunning Haven: 2 Pools & Hot Tubs ~ Walk To Beach
Vacation Home in Siesta Key
6 Bedrooms -- Sleeps 24 -- Pet Friendly
9.8 Star Rating
Sandy Seahorse Cottage | Pet Friendly Home On Siesta Key W/ Private Pool, Short Walk To Be
Vacation Home in Siesta Key
6 Bedrooms -- Sleeps 16 -- Pet Friendly
10.0 Star Rating
? Casa De Mariposa | Heated Pool, Gulf Views, Dual-villa Duplex, Walk To Siesta Key Beach
Vacation Home in Siesta Key
6 Bedrooms -- Sleeps 16
10.0 Star Rating
Solaster | A Luxury Island Escape, 2 Private Pools + 3-min Walk To Crescent Beach
Vacation Home in Siesta Key
6 Bedrooms -- Sleeps 20 -- Pet Friendly
10.0 Star Rating
Coastal Luxury*pool*hot Tub*sunsets*close To Beach
Vacation Home in Siesta Key
5 Bedrooms -- Sleeps 12 -- Pet Friendly
10.0 Star Rating
The Boat House Waterfront Pool Home Walk To Beach!
Vacation Home in Siesta Key
5 Bedrooms -- Sleeps 12
10.0 Star Rating
Tropical Oasis | Private Pool, Spa + Walk To Siesta Beach & Village
Vacation Home in Siesta Key
7 Bedrooms -- Sleeps 16
9.8 Star Rating
Siesta Home With Pool & Waterslide - Sunset Splash
Vacation Home in Siesta Key
8 Bedrooms -- Sleeps 23 -- Pet Friendly
9.6 Star Rating
Sunset Gulf – Luxury Siesta Key Retreat With Pool! Beach Access!
Vacation Home in Siesta Key
8 Bedrooms -- Sleeps 23
9.4 Star Rating
Ultimate Family Reunion: Pool, Game Room, 3 Mins To Beach - Surf View
Vacation Home in Siesta Key
8 Bedrooms -- Sleeps 20 -- Pet Friendly
9.8 Star Rating
Spacious Siesta Key Paradise-canal Front, Private Pool, Walk To Sk Beach/village
Vacation Home in Siesta Key
5 Bedrooms -- Sleeps 10
9.8 Star Rating
Perfect Location. Roof Top Deck. Gulf Views. Heated Pool/spa W/ Rain Curtain
Vacation Home in Siesta Key
6 Bedrooms -- Sleeps 18
10.0 Star Rating
The Hummingbird | Private Heated Pool & In The Heart Of Siesta Key Village
Vacation Home in Siesta Key
6 Bedrooms -- Sleeps 20
10.0 Star Rating
Luxury Oasis - 5 Min Walk To Private Beach - Avoid Crowded Public Beach
Vacation Home in Siesta Key
5 Bedrooms -- Sleeps 10
10.0 Star Rating
Steps To Beach/siesta Village-resort Pool W/slide
Vacation Home in Siesta Key
7 Bedrooms -- Sleeps 18 -- Pet Friendly
9.6 Star Rating
High Tide - 170 “siesta Key”
Vacation Home in Siesta Key
5 Bedrooms -- Sleeps 10 -- Pet Friendly
9.4 Star Rating
Gertrude's Siesta | Oceanview, 12-steps Beach, 4-min Trolley To Village, Tiki-bar, Ping-po
Vacation Home in Siesta Key
7 Bedrooms -- Sleeps 24 -- Pet Friendly
9.8 Star Rating
Luxurious Paradise With Tiki Bar And Heated Pool, Just Remodeled!
Vacation Home in Siesta Key
5 Bedrooms -- Sleeps 10
9.8 Star Rating
Steps To Beach/gulf Views/pool Volleyball/slide
Vacation Home in Siesta Key
6 Bedrooms -- Sleeps 16 -- Pet Friendly
10.0 Star Rating
Pool Volleyball-gulf Views-steps To Beach-rooftop
Vacation Home in Siesta Key
6 Bedrooms -- Sleeps 16 -- Pet Friendly
9.6 Star Rating
Siesta Key Oceanfront Palace With Private Beach
Vacation Home in Siesta Key
5 Bedrooms -- Sleeps 10 -- Pet Friendly
9.2 Star Rating
High Tide - Beautiful Pool With Waterslide, 2 Min Walk To The Beach
Vacation Home in Siesta Key
6 Bedrooms -- Sleeps 18 -- Pet Friendly
10.0 Star Rating
Beachfront Luxury - Resort Pool - Steps To Village
Vacation Home in Siesta Key
5 Bedrooms -- Sleeps 12
10.0 Star Rating
5 Star Siesta Key, 80 Steps To Beach, Luxury Pool, 6 Bedrooms, Spacious Living
Vacation Home in Siesta Key
6 Bedrooms -- Sleeps 14
9.8 Star Rating
Sugar Sand Cottage – Gulf-view Siesta Key Escape
Vacation Home in Siesta Key
5 Bedrooms -- Sleeps 19 -- Pet Friendly
9.2 Star Rating
Waterfront Key Home W/ Pool, Hottub, Mins To Beach
Vacation Home in Siesta Key
5 Bedrooms -- Sleeps 16 -- Pet Friendly
10.0 Star Rating
Seashell Esta – Luxe Siesta Key Escape
Vacation Home in Siesta Key
7 Bedrooms -- Sleeps 20 -- Pet Friendly
10.0 Star Rating
Luxury 6 Bedroom Near The Village
Vacation Home in Siesta Key
6 Bedrooms -- Sleeps 14
10.0 Star Rating
Luxe Lagoon | Located In Sk Village! Private Pool & Spa, Rooftop, Pet Friendly ?️☀️?
Vacation Home in Siesta Key
7 Bedrooms -- Sleeps 22 -- Pet Friendly
8.0 Star Rating
Island House – Walk To Siesta Key Beach!
Vacation Home in Siesta Key
7 Bedrooms -- Sleeps 19 -- Pet Friendly
10.0 Star Rating
The Pool House~steps To Beach & Siesta Key Village
Vacation Home in Siesta Key
5 Bedrooms -- Sleeps 16
10.0 Star Rating
7br Home W/ Private Pool & Hot Tub
Vacation Home in Siesta Key
7 Bedrooms -- Sleeps 16 -- Pet Friendly