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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 places to stay in .
To book a selected property, follow the "Search Availability" button or "View Rental" for Pricing & Rates, which will take you directly on our partner website. All bookings are securely completed on our partner websites.
Siesta Key Home, Heated Pool, Spa, Near The Beach! - Talk To The Sand
9.6 Star Rating
Siesta Key Vacation Home
7 Bedroom(s) Sleeps 14 -- Pet Friendly 
Beautiful 5 Bedroom Home Directly On Siesta Key Beach!!
9.8 Star Rating
Siesta Key Vacation Home
5 Bedroom(s) Sleeps 14 -- Pet Friendly
NO Bunks-King Beds, Garage Parking, Private Beach Access-Less Crowded
10.0 Star Rating
Siesta Key Vacation Home
5 Bedroom(s) Sleeps 10
The Lookout - 891 “Siesta Key’
10.0 Star Rating
Siesta Key Vacation Home
5 Bedroom(s) Sleeps 10 -- Pet Friendly
Beach Dream | Home W/ Ocean Views, 2 Private Pools, Rooftop Lookout And Steps To Siesta Ke
10.0 Star Rating
Siesta Key Vacation Home
6 Bedroom(s) Sleeps 22
Nearly Beachfront, One House From The Beach! Pool And Game Room - Ocean Overlook
9.8 Star Rating
Siesta Key Vacation Home
8 Bedroom(s) Sleeps 18 -- Pet Friendly
Large Pool Home- Blocks From Siesta Key Beach
10.0 Star Rating
Siesta Key Vacation Home
5 Bedroom(s) Sleeps 10 -- Pet Friendly
Isla Amor | Escape To A Luxury Waterfront Home With Heated Pool & Stunning Views In Siesta
9.6 Star Rating
Siesta Key Vacation Home
5 Bedroom(s) Sleeps 11
Gertrude's Siesta | 4-min Walk To Beach & Village, Tropical & 100% Private!
9.4 Star Rating
Siesta Key Vacation Home
6 Bedroom(s) Sleeps 22 -- Pet Friendly
#1 Rooftop Deck W/ Gulf Views - Steps To Beach
10.0 Star Rating
Siesta Key Vacation Home
6 Bedroom(s) Sleeps 14 -- Pet Friendly
16 Guest Pool House Walk To The Beach And Village
9.6 Star Rating
Siesta Key Vacation Home
6 Bedroom(s) Sleeps 16
Siesta Key Village Heated Pool
10.0 Star Rating
Siesta Key Vacation Home
6 Bedroom(s) Sleeps 14 -- Pet Friendly
Waterfront Siesta Key Home W/ Pool, HotTub & Mini Putt
10.0 Star Rating
Siesta Key Vacation Home
5 Bedroom(s) Sleeps 16 -- Pet Friendly
Gulf Views/Steps To Beach/Resort Pool W/Slide/Spa
10.0 Star Rating
Siesta Key Vacation Home
6 Bedroom(s) Sleeps 14 -- Pet Friendly
Steps To Beach - Resort Pool/Slide/Spa/Gulf Views
10.0 Star Rating
Siesta Key Vacation Home
6 Bedroom(s) Sleeps 14 -- Pet Friendly
Stunning Haven: 2 Pools & Hot Tubs ~ Walk To Beach
10.0 Star Rating
Siesta Key Vacation Home
6 Bedroom(s) Sleeps 24 -- Pet Friendly
Two Homes With Shared Backyard, Perfect Rental For Groups - Village Time
Siesta Key Vacation Home
6 Bedroom(s) Sleeps 28 -- Pet Friendly
Sandy Seahorse Cottage | Pet Friendly Home On Siesta Key W/ Private Pool, Short Walk To Be
9.8 Star Rating
Siesta Key Vacation Home
6 Bedroom(s) Sleeps 16 -- Pet Friendly
Casa De Mariposa | Heated Pool, Gulf Views, Dual-Villa Duplex, 0.3 Miles To Siesta Key Bea
10.0 Star Rating
Siesta Key Vacation Home
6 Bedroom(s) Sleeps 16
The Solaster | Pet Friendly Home On Siesta Key W/ 2 Heated Pools, Walk To Beach & South Vi
10.0 Star Rating
Siesta Key Vacation Home
6 Bedroom(s) Sleeps 20 -- Pet Friendly
Coastal Luxury • Pool • Spa • Fire Pit • Sun Decks • Sunsets • Minutes To Beac
10.0 Star Rating
Siesta Key Vacation Home
5 Bedroom(s) Sleeps 12 -- Pet Friendly
The Boat House Waterfront Pool Home Walk To Beach!
10.0 Star Rating
Siesta Key Vacation Home
5 Bedroom(s) Sleeps 12
Tropical Oasis | Luxury Home On Siesta Key W/ Private Heated Pool/ Spa, Steps To Beach & V
9.8 Star Rating
Siesta Key Vacation Home
7 Bedroom(s) Sleeps 16
Siesta Home With Pool & Waterslide - Sunset Splash
10.0 Star Rating
Siesta Key Vacation Home
8 Bedroom(s) Sleeps 23 -- Pet Friendly
Sunset Gulf – Luxury Siesta Key Retreat With Pool! Beach Access!
9.6 Star Rating
Siesta Key Vacation Home
8 Bedroom(s) Sleeps 23
Ultimate Family Reunion: Pool, Game Room, 3 Mins To Beach - Surf View
9.4 Star Rating
Siesta Key Vacation Home
8 Bedroom(s) Sleeps 20 -- Pet Friendly
Spacious Siesta Key Paradise-Canal Front, Private Pool, Walk To SK Beach/Village
9.8 Star Rating
Siesta Key Vacation Home
5 Bedroom(s) Sleeps 10
Perfect Location. Roof Top Deck. Gulf Views. Heated Pool/Spa W/ Rain Curtain
9.8 Star Rating
Siesta Key Vacation Home
6 Bedroom(s) Sleeps 18
The Hummingbird | Located In Siesta Key Village W/ Private Pool, Walk To Beach!
10.0 Star Rating
Siesta Key Vacation Home
6 Bedroom(s) Sleeps 20
Garage Parking, King Beds-NO Bunks, Pool & Private Beach Access-No Crowds
10.0 Star Rating
Siesta Key Vacation Home
5 Bedroom(s) Sleeps 10
Steps To Beach/Siesta Village-Resort Pool W/Slide
10.0 Star Rating
Siesta Key Vacation Home
7 Bedroom(s) Sleeps 18 -- Pet Friendly
High Tide - 170 “Siesta Key”
9.6 Star Rating
Siesta Key Vacation Home
5 Bedroom(s) Sleeps 10 -- Pet Friendly
Gertrude's Siesta | Oceanview, 12-steps Beach, 4-min Trolley To Village, Tiki-bar, Ping-po
9.6 Star Rating
Siesta Key Vacation Home
7 Bedroom(s) Sleeps 24 -- Pet Friendly
Luxurious Paradise With Tiki Bar And Heated Pool, Just Remodeled!
9.8 Star Rating
Siesta Key Vacation Home
5 Bedroom(s) Sleeps 10
Steps To Beach/Gulf Views/Pool Volleyball/Slide
9.8 Star Rating
Siesta Key Vacation Home
6 Bedroom(s) Sleeps 16 -- Pet Friendly
Pool Volleyball-Gulf Views-Steps To Beach-Rooftop
10.0 Star Rating
Siesta Key Vacation Home
6 Bedroom(s) Sleeps 16 -- Pet Friendly
Siesta Key Oceanfront Palace With Private Beach
9.6 Star Rating
Siesta Key Vacation Home
5 Bedroom(s) Sleeps 10 -- Pet Friendly
High Tide - Beautiful Pool With Waterslide, 2 Min Walk To The Beach
9.6 Star Rating
Siesta Key Vacation Home
6 Bedroom(s) Sleeps 18 -- Pet Friendly
Beachfront Luxury - Resort Pool - Steps To Village
10.0 Star Rating
Siesta Key Vacation Home
5 Bedroom(s) Sleeps 12
5 STAR SIESTA KEY, 80 STEPS To BEACH, LUXURY POOL, 6 BEDROOMS, SPACIOUS LIVING
10.0 Star Rating
Siesta Key Vacation Home
6 Bedroom(s) Sleeps 14
Sugar Sand Cottage – Gulf-View Siesta Key Escape
10.0 Star Rating
Siesta Key Vacation Home
5 Bedroom(s) Sleeps 19
Waterfront KEY Home W/ Pool, HotTub, Mins To Beach
8.8 Star Rating
Siesta Key Vacation Home
5 Bedroom(s) Sleeps 16 -- Pet Friendly
Sunshine On Siesta - Refreshed Duplex!
10.0 Star Rating
Siesta Key Vacation Home
5 Bedroom(s) Sleeps 12 -- Pet Friendly
Seashell Esta – Luxe Siesta Key Escape
10.0 Star Rating
Siesta Key Vacation Home
7 Bedroom(s) Sleeps 20 -- Pet Friendly
Luxury 6 Bedroom Near The Village
10.0 Star Rating
Siesta Key Vacation Home
6 Bedroom(s) Sleeps 14
Luxe Lagoon | Located In SK Village! Private Pool & Spa, Rooftop, Pet Friendly ?️☀️?
10.0 Star Rating
Siesta Key Vacation Home
7 Bedroom(s) Sleeps 22 -- Pet Friendly