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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 rent in Florida.
Search for Vacation Rental options here, then Book Securely on our partner site.
Siesta Key Home, Heated Pool, Spa, Near The Beach! - Talk To T
Siesta Key
Vacation Home
9.6 Star Review
7 Bedroom(s) Sleeps 14
Beautiful 5 Bedroom Home Directly On Siesta Key Beach!!
Siesta Key
Vacation Home
9.8 Star Review
5 Bedroom(s) Sleeps 14
NO Bunks-King Beds, Garage Parking, Private Beach Access-Less
Siesta Key
Vacation Home
10.0 Star Review
5 Bedroom(s) Sleeps 10
The Lookout - 891 “Siesta Key’
Siesta Key
Vacation Home
10.0 Star Review
5 Bedroom(s) Sleeps 10
Beach Dream | Home W/ Ocean Views, 2 Private Pools, Rooftop Lo
Siesta Key
Vacation Home
10.0 Star Review
6 Bedroom(s) Sleeps 22
Nearly Beachfront, One House From The Beach! Pool And Game Roo
Siesta Key
Vacation Home
9.8 Star Review
8 Bedroom(s) Sleeps 18
Large Pool Home- Blocks From Siesta Key Beach
Siesta Key
Vacation Home
10.0 Star Review
5 Bedroom(s) Sleeps 10
Isla Amor | Escape To A Luxury Waterfront Home With Heated Poo
Siesta Key
Vacation Home
9.6 Star Review
5 Bedroom(s) Sleeps 11
Gertrude's Siesta | 4-min Walk To Beach & Village, Tropical &
Siesta Key
Vacation Home
9.4 Star Review
6 Bedroom(s) Sleeps 22
#1 Rooftop Deck W/ Gulf Views - Steps To Beach
Siesta Key
Vacation Home
10.0 Star Review
6 Bedroom(s) Sleeps 14
16 Guest Pool House Walk To The Beach And Village
Siesta Key
Vacation Home
9.6 Star Review
6 Bedroom(s) Sleeps 16
Siesta Key Village Heated Pool
Siesta Key
Vacation Home
10.0 Star Review
6 Bedroom(s) Sleeps 14
Waterfront Siesta Key Home W/ Pool, HotTub & Mini Putt
Siesta Key
Vacation Home
10.0 Star Review
5 Bedroom(s) Sleeps 16
Gulf Views/Steps To Beach/Resort Pool W/Slide/Spa
Siesta Key
Vacation Home
10.0 Star Review
6 Bedroom(s) Sleeps 14
Steps To Beach - Resort Pool/Slide/Spa/Gulf Views
Siesta Key
Vacation Home
10.0 Star Review
6 Bedroom(s) Sleeps 14
Stunning Haven: 2 Pools & Hot Tubs ~ Walk To Beach
Siesta Key
Vacation Home
10.0 Star Review
6 Bedroom(s) Sleeps 24
Two Homes With Shared Backyard, Perfect Rental For Groups - Vi
Siesta Key
Vacation Home
6 Bedroom(s) Sleeps 28
Sandy Seahorse Cottage | Pet Friendly Home On Siesta Key W/ Pr
Siesta Key
Vacation Home
9.8 Star Review
6 Bedroom(s) Sleeps 16
Casa De Mariposa | Heated Pool, Gulf Views, Dual-Villa Duplex,
Siesta Key
Vacation Home
10.0 Star Review
6 Bedroom(s) Sleeps 16
The Solaster | Pet Friendly Home On Siesta Key W/ 2 Heated Poo
Siesta Key
Vacation Home
10.0 Star Review
6 Bedroom(s) Sleeps 20
Coastal Luxury • Pool • Spa • Fire Pit • Sun Decks •
Siesta Key
Vacation Home
10.0 Star Review
5 Bedroom(s) Sleeps 12
The Boat House Waterfront Pool Home Walk To Beach!
Siesta Key
Vacation Home
10.0 Star Review
5 Bedroom(s) Sleeps 12
Tropical Oasis | Luxury Home On Siesta Key W/ Private Heated P
Siesta Key
Vacation Home
9.8 Star Review
7 Bedroom(s) Sleeps 16
Siesta Home With Pool & Waterslide - Sunset Splash
Siesta Key
Vacation Home
10.0 Star Review
8 Bedroom(s) Sleeps 23
Sunset Gulf – Luxury Siesta Key Retreat With Pool! Beach Acc
Siesta Key
Vacation Home
9.6 Star Review
8 Bedroom(s) Sleeps 23
Ultimate Family Reunion: Pool, Game Room, 3 Mins To Beach - Su
Siesta Key
Vacation Home
9.4 Star Review
8 Bedroom(s) Sleeps 20
Spacious Siesta Key Paradise-Canal Front, Private Pool, Walk T
Siesta Key
Vacation Home
9.8 Star Review
5 Bedroom(s) Sleeps 10
Perfect Location. Roof Top Deck. Gulf Views. Heated Pool/Spa W
Siesta Key
Vacation Home
9.8 Star Review
6 Bedroom(s) Sleeps 18
The Hummingbird | Located In Siesta Key Village W/ Private Poo
Siesta Key
Vacation Home
10.0 Star Review
6 Bedroom(s) Sleeps 20
Garage Parking, King Beds-NO Bunks, Pool & Private Beach Acces
Siesta Key
Vacation Home
10.0 Star Review
5 Bedroom(s) Sleeps 10
Steps To Beach/Siesta Village-Resort Pool W/Slide
Siesta Key
Vacation Home
10.0 Star Review
7 Bedroom(s) Sleeps 18
High Tide - 170 “Siesta Key”
Siesta Key
Vacation Home
9.6 Star Review
5 Bedroom(s) Sleeps 10
Gertrude's Siesta | Oceanview, 12-steps Beach, 4-min Trolley T
Siesta Key
Vacation Home
9.6 Star Review
7 Bedroom(s) Sleeps 24
Luxurious Paradise With Tiki Bar And Heated Pool, Just Remodel
Siesta Key
Vacation Home
9.8 Star Review
5 Bedroom(s) Sleeps 10
Steps To Beach/Gulf Views/Pool Volleyball/Slide
Siesta Key
Vacation Home
9.8 Star Review
6 Bedroom(s) Sleeps 16
Pool Volleyball-Gulf Views-Steps To Beach-Rooftop
Siesta Key
Vacation Home
10.0 Star Review
6 Bedroom(s) Sleeps 16
Siesta Key Oceanfront Palace With Private Beach
Siesta Key
Vacation Home
9.6 Star Review
5 Bedroom(s) Sleeps 10
High Tide - Beautiful Pool With Waterslide, 2 Min Walk To The
Siesta Key
Vacation Home
9.6 Star Review
6 Bedroom(s) Sleeps 18
Beachfront Luxury - Resort Pool - Steps To Village
Siesta Key
Vacation Home
10.0 Star Review
5 Bedroom(s) Sleeps 12
5 STAR SIESTA KEY, 80 STEPS To BEACH, LUXURY POOL, 6 BEDROOMS,
Siesta Key
Vacation Home
10.0 Star Review
6 Bedroom(s) Sleeps 14
Sugar Sand Cottage – Gulf-View Siesta Key Escape
Siesta Key
Vacation Home
10.0 Star Review
5 Bedroom(s) Sleeps 19
Waterfront KEY Home W/ Pool, HotTub, Mins To Beach
Siesta Key
Vacation Home
8.8 Star Review
5 Bedroom(s) Sleeps 16
Sunshine On Siesta - Refreshed Duplex!
Siesta Key
Vacation Home
10.0 Star Review
5 Bedroom(s) Sleeps 12
Seashell Esta – Luxe Siesta Key Escape
Siesta Key
Vacation Home
10.0 Star Review
7 Bedroom(s) Sleeps 20
Luxury 6 Bedroom Near The Village
Siesta Key
Vacation Home
10.0 Star Review
6 Bedroom(s) Sleeps 14
Luxe Lagoon | Located In SK Village! Private Pool & Spa, Rooft
Siesta Key
Vacation Home
10.0 Star Review
7 Bedroom(s) Sleeps 22