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  • Welcome to Paradise!  Pet Friendly!  Walk to acclaimed Siesta Beach!
    From $286 per night (USD)

    VRBO

    Welcome to Paradise! Pet Friendly! Walk to acclaimed Siesta Beach!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    9

    **** APRIL IS THE BEST MONTH TO BE IN PARADISE !!! **** Ahhh, welcome to Paradise — where sunny, warm ...

    From $286 per night (USD)

    VRBO

    Details
  • Beachside Villa 2 bedroom A- 1
    From $178 per night (USD)

    Expedia

    Beachside Villa 2 bedroom A- 1

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Horizons West 2 bedroom, 2 bath villa A-1 is just steps from the beach. It has a updated kitchen (with stainless steel ...

    From $178 per night (USD)

    Expedia

    Details
  • Beach View 2 bedroom 307
    From $265 per night (USD)

    VRBO

    Beach View 2 bedroom 307

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Horizons West unit 307 is a lovely 2 bedroom, 2 bath unit with a fantastic Gulf view. There is a king-size bed in the m ...

    From $265 per night (USD)

    VRBO

    Details
  • BEACHFRONT CONDO - THREE BEDROOM - HEATED POOL - FREE BOAT DOCKS - RENOVATED
    From $215 per night (USD)

    Expedia

    BEACHFRONT CONDO - THREE BEDROOM - HEATED POOL - FREE BOAT DOCKS - RENOVATED

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Beachfront Condo - Three Bedroom - Heated Pool - Free Boat Docks - Upscale - Siesta KeyLocated Next to Turtle Beach on t ...

    From $215 per night (USD)

    Expedia

    Details
  • Charming Cottage ~ 5 Miles to Siesta Key Beach!
    From $123 per night (USD)

    VRBO

    Charming Cottage ~ 5 Miles to Siesta Key Beach!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Run from the cold and escape to paradise at this 1-bed, 1-bath vacation rental nestled just off the coast in Sarasota. W ...

    From $123 per night (USD)

    VRBO

    Details
  • Beachside Villa 2 bedroom C- 3
    From $170 per night (USD)

    Expedia

    Beachside Villa 2 bedroom C- 3

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    This nicely appointed beach villa is one of the very closest to Horizons West’s spectacular amenities....just steps to t ...

    From $170 per night (USD)

    Expedia

    Details
  • Beach View 1 bedroom 111
    From $219 per night (USD)

    VRBO

    Beach View 1 bedroom 111

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    Unit 111 is an oversized 1 bedroom hi-rise, beachfront unit in Horizon West, Siesta Key Florida. Recently updated open- ...

    From $219 per night (USD)

    VRBO

    Details
  • Bayside Villa 2 bedroom E- 7
    From $195 per night (USD)

    Expedia

    Bayside Villa 2 bedroom E- 7

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    Horizons West Villa E-7 is located on the Bay-Side of Midnight Pass Road. The unit is a very nice, well equipped 2 bedr ...

    From $195 per night (USD)

    Expedia

    Details
  • Updated Single Family close to Shamrock Park and Beaches
    From $97 per night (USD)

    VRBO

    Updated Single Family close to Shamrock Park and Beaches

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Spacious! Highly convenient located 1/2 block from Shamrock Park and close to 4 different beaches, you'll enjoy this com ...

    From $97 per night (USD)

    VRBO

    Details
  • Beachside Villa 2 bedroom A- 6
    From $178 per night (USD)

    Expedia

    Beachside Villa 2 bedroom A- 6

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    Horizons West unit A-6 is an updated 2 bedroom, 2 bath gulfside villa and is convenient to both pools and the beach. It ...

    From $178 per night (USD)

    Expedia

    Details
  • Beach View 1 bedroom 110
    From $214 per night (USD)

    VRBO

    Beach View 1 bedroom 110

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    Horizons West unit 110 has a beautiful Gulf view. It is a lovely, updated one bedroom with a King bed. Very well-equip ...

    From $214 per night (USD)

    VRBO

    Details
  • Siesta Key 4 Bedroom, Walk to Siesta Key Beach in 7 mins, Canal Home, Heated Splash Pool, WiFi, BBQ
    From $397 per night (USD)

    Expedia

    Siesta Key 4 Bedroom, Walk to Siesta Key Beach in 7 mins, Canal Home, Heated Splash Pool, WiFi, BBQ

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    Upscale Spanish Mediterranean style beautiful custom home on the canal with a private area to launch a kayak, walk to Si ...

    From $397 per night (USD)

    Expedia

    Details
  • Beachside Villa 2 bedroom A-10
    From $186 per night (USD)

    VRBO

    Beachside Villa 2 bedroom A-10

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Horizons West villa A-10 is an open concept 2 bedroom, 2 bath gulfside villa, has been beautifully updated throughout an ...

    From $186 per night (USD)

    VRBO

    Details
  • Beach View 3 bedroom 201
    From $433 per night (USD)

    Expedia

    Beach View 3 bedroom 201

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Horizons West unit 201 is an updated 3 bedroom, 2 bath corner unit in the high-rise building with a beautiful view. Wel ...

    From $433 per night (USD)

    Expedia

    Details
  • QUIET RELAXING HOME IN SARASOTA
    From $250 per night (USD)

    VRBO

    QUIET RELAXING HOME IN SARASOTA

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Your stay in Sarasota couldn't get any better when you settle into this 3-bedroom, 2-bathroom vacation rental house. Boa ...

    From $250 per night (USD)

    VRBO

    Details
  • PARADISE MEETS PRIVACY WITH AMAZING WATER VIEW & HEATED POOL
    From $183 per night (USD)

    VRBO

    PARADISE MEETS PRIVACY WITH AMAZING WATER VIEW & HEATED POOL

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Situated in the West Villages, one of the best master-planned communities in the country, this nearly new build in Gran ...

    From $183 per night (USD)

    VRBO

    Details
  • Best Location!  Right next to St Armands Circle and Lido Key!
    From $143 per night (USD)

    VRBO

    Best Location! Right next to St Armands Circle and Lido Key!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    **Update** New (very comfortable) Flexsteel couches purchased.*** Location Location Location. This is the best locati ...

    From $143 per night (USD)

    VRBO

    Details
  • Nice Retreat - Professionally Decorated & renovated
    From $350 per night (USD)

    Expedia

    Nice Retreat - Professionally Decorated & renovated

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Vibrant, active 55+ gated community (not an RV Park). Pet-friendly mfg. home in central Sarasota - minutes from bike tra ...

    From $350 per night (USD)

    Expedia

    Details
  • Fisherman's Cove B306 - The Maarten  Private Beach is Open!
    From $201 per night (USD)

    VRBO

    Fisherman's Cove B306 - The Maarten Private Beach is Open!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Siesta Key Sunset Family Rentals is family-owned and proud to offer our beach-front Siesta Key (Sarasota) vacation rent ...

    From $201 per night (USD)

    VRBO

    Details
  • Shell House retreat
    From $189 per night (USD)

    Expedia

    Shell House retreat

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Situated a short 5 miles drive from the cool emerald waters of Number 1. Siesta Key Beach. The community offers the very ...

    From $189 per night (USD)

    Expedia

    Details
  • Grand accomdation on USA #1 Beach  - Siesta Key Fl
    From $134 per night (USD)

    VRBO

    Grand accomdation on USA #1 Beach - Siesta Key Fl

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    Two master suite condo on the island of Siesta Key with unparalleled beautiful views on the fifth floor! This lovely ...

    From $134 per night (USD)

    VRBO

    Details
  • Arden Garden - Family Friendly Close to Siesta Key
    From $341 per night (USD)

    Expedia

    Arden Garden - Family Friendly Close to Siesta Key

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    The Arden Garden is a modern retreat, situated in a residential neighborhood while maintaining the feeling of cool isola ...

    From $341 per night (USD)

    Expedia

    Details
  • Beach Access, Heated Pool, Boat Docks, and MORE for the perfect beach getaway
    From $104 per night (USD)

    VRBO

    Beach Access, Heated Pool, Boat Docks, and MORE for the perfect beach getaway

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Siesta Key has grown in popularity over recent years due to its beautiful miles of pure white quartz sand beaches, vibra ...

    From $104 per night (USD)

    VRBO

    Details
  • Siesta Key - 2BR - Beachfront Condo on Crescent Beach - Heated Pool - Tennis Ct
    From $196 per night (USD)

    Expedia

    Siesta Key - 2BR - Beachfront Condo on Crescent Beach - Heated Pool - Tennis Ct

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    SIESTA BREAKERS - Siesta Key Beachfront Vacation Rental Condo on Crescent Beach (Two Bedroom Vacation Units for Rent) L ...

    From $196 per night (USD)

    Expedia

    Details
  • Sarasota Downtown All Inclusive Town house !!!
    From $159 per night (USD)

    VRBO

    Sarasota Downtown All Inclusive Town house !!!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    8

    Located in the heart of Sarasota City, just minutes to shopping, dining, golf courses and of course the #1 Beach in the ...

    From $159 per night (USD)

    VRBO

    Details
  • *** OCEAN FRONT SPECIAL ***  From $99/night
    From $144 per night (USD)

    Expedia

    *** OCEAN FRONT SPECIAL *** From $99/night

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    *** OCEAN FRONT SPECIAL *** From $99/night . Longboat Key - Ocean Front Condo ~ DIRECT BEACH FRONT CONDO ~ ~ Beautifull ...

    From $144 per night (USD)

    Expedia

    Details
  • 2/2 Vaulted Ceiling 10 Min to beach on golf course
    From $73 per night (USD)

    VRBO

    2/2 Vaulted Ceiling 10 Min to beach on golf course

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    This Venice vacation rental 2nd floor condo has 2 bedrooms, 2 baths and room for 6 guests It features 2 separate lanais ...

    From $73 per night (USD)

    VRBO

    Details
  • Siesta Key  2 Bed/1Bath Villa,1500 ft from Beach, Barefoot Bungalows -GULL
    From $189 per night (USD)

    Expedia

    Siesta Key 2 Bed/1Bath Villa,1500 ft from Beach, Barefoot Bungalows -"GULL"

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    "Gull" unit at Barefoot Bungalows is a 2 bedroom /1 full bath villa, spacious living area, fully furnished, located 100 ...

    From $189 per night (USD)

    Expedia

    Details
  • ON BEACH! ALL Remodeled!! Nice pool. Free beach chairs,lots of activities area
    From $290 per night (USD)

    VRBO

    ON BEACH! ALL Remodeled!! Nice pool. Free beach chairs,lots of activities area

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    We are Thankful Our condo and Siesta Key Beach did not have significant damage from Hurricane Ian . New UV Germicidal li ...

    From $290 per night (USD)

    VRBO

    Details
  • Cozy nest for snowbirds!
    From $90 per night (USD)

    Expedia

    Cozy nest for snowbirds!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    6

    Come stay at our unit in Royal Coachman Resort. We are just a five or so minute drive to Nokomis beach and near Venice, ...

    From $90 per night (USD)

    Expedia

    Details
  • Sarasota Villa w/ Pool Access ~ 4 Mi to Beach!
    From $171 per night (USD)

    VRBO

    Sarasota Villa w/ Pool Access ~ 4 Mi to Beach!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Sun, sand, and beach fun await at this Sarasota vacation rental! Located in the Pinetree-Village Des Pins neighborhood, ...

    From $171 per night (USD)

    VRBO

    Details
  • Ground Floor, Snowbird-Friendly Home w/ High-Speed WiFi & Central AC
    From $193 per night (USD)

    Expedia

    Ground Floor, Snowbird-Friendly Home w/ High-Speed WiFi & Central AC

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    The Hemingway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...

    From $193 per night (USD)

    Expedia

    Details
  • Cozy, Screen porch, Near Beach & Shopping, Non-fenced,
    From $175 per night (USD)

    VRBO

    Cozy, Screen porch, Near Beach & Shopping, Non-fenced,

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Spacious and cozy home with a screen back porch great for sunning, dinner at sunset or looking at the stars. The many wi ...

    From $175 per night (USD)

    VRBO

    Details
  • Bay Isle Bliss | Pet Friendly Home w/ Private Pool & Walking Distance to Shell Beach
    From $478 per night (USD)

    Expedia

    Bay Isle Bliss | Pet Friendly Home w/ Private Pool & Walking Distance to Shell Beach

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Bay Isle Bliss is a newly updated, single-family home residing on Siesta Key's north end. Three bedrooms and two bathroo ...

    From $478 per night (USD)

    Expedia

    Details
  • Great Location w/ Private Beach, 2 Pools, 2 Jaccuzi & More! Excelsior101-5
    From $231 per night (USD)

    VRBO

    Great Location w/ Private Beach, 2 Pools, 2 Jaccuzi & More! Excelsior101-5

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Spacious Condo in a Great Location at Excelsior Beach to Bay. Private Beach, 2 Pools, 2 Jaccuzi, Fishing Deck & More! S ...

    From $231 per night (USD)

    VRBO

    Details
  • NEW! Mid-Mod Coastal Home w/ Pool: 1 Mi to Beach
    From $443 per night (USD)

    Expedia

    NEW! Mid-Mod Coastal Home w/ Pool: 1 Mi to Beach

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Located in the museum district, this 2-bedroom, 2-bathroom vacation rental offers guests an upscale taste of Sarasota! S ...

    From $443 per night (USD)

    Expedia

    Details
  • Gorgeous 3/3 pool home on water Lido Key!
    From $793 per night (USD)

    VRBO

    Gorgeous 3/3 pool home on water Lido Key!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    This beautifully decorated 3 bed/3 bath, is 2,320 Sq Ft with a private heated pool & Jacuzzi. Enjoy your luxurious vacat ...

    From $793 per night (USD)

    VRBO

    Details
  • 💕Beach Comber Pool home with Free Bikes & Kayaks and private beach !
    From $250 per night (USD)

    Expedia

    💕Beach Comber Pool home with Free Bikes & Kayaks and private beach !

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Welcome to our family vacation home in Venice Florida. This is one of our homes away from home and we enjoy sharing it ...

    From $250 per night (USD)

    Expedia

    Details
  • Newly Remodeled-150 Yards to Beach and Restaurants!
    From $200 per night (USD)

    VRBO

    Newly Remodeled-150 Yards to Beach and Restaurants!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Located just 150 yards from Crescent beach, one side of this duplex offers a 2 bedroom and 1 bath villa, and is in the h ...

    From $200 per night (USD)

    VRBO

    Details
  • Crystal Sands Tower Unit 311 - Beachfront
    From $375 per night (USD)

    Expedia

    Crystal Sands Tower Unit 311 - Beachfront

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Enjoy a luxurious vacation in this spacious, completely renovated two bedroom, two bath high rise condo with spectacular ...

    From $375 per night (USD)

    Expedia

    Details
  • Jamaica Royale 91, 3 Heated Pools, 2 Bedrooms, WiFi, Sleeps 6
    From $248 per night (USD)

    VRBO

    Jamaica Royale 91, 3 Heated Pools, 2 Bedrooms, WiFi, Sleeps 6

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    In this handy ground-floor condo, you're just a short walk away from gorgeous Crescent Beach, the jewel in Siesta Key's ...

    From $248 per night (USD)

    VRBO

    Details
  • Amazing view on the golf course and near the beach. Fully remodeled and new
    From $209 per night (USD)

    Expedia

    Amazing view on the golf course and near the beach. Fully remodeled and new

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Located in the Farmington Vista community of the Plantation Golf and Country Club, is a sunny, bright, first floor treas ...

    From $209 per night (USD)

    Expedia

    Details
  • A Gem in Siesta Key FL - #1 beach in US
    From $180 per night (USD)

    VRBO

    A Gem in Siesta Key FL - #1 beach in US

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    WELCOME TO PARADAISE!!! Light, bright, beachy and welcoming! A slice of old Florida just steps away from private beach a ...

    From $180 per night (USD)

    VRBO

    Details
  • Casa Freedom - Walkable Central location, Less than 3 miles to Siesta Beach!
    From $369 per night (USD)

    Expedia

    Casa Freedom - Walkable Central location, Less than 3 miles to Siesta Beach!

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    10

    NOTE: BOOKING JANUARY, FEBRUARY OR MARCH? Please book whole months only NOT mid-month to mid-month. This time frame is a ...

    From $369 per night (USD)

    Expedia

    Details
  • Steps to Water! Sunsets, Dock, Hot Tub!  Englewood, Fl. The Best Kept Secret!
    From $231 per night (USD)

    VRBO

    Steps to Water! Sunsets, Dock, Hot Tub! Englewood, Fl. The Best Kept Secret!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Beauty Beyond Belief!! Englewood, A little less people. A lot more fun! Clean, Fresh, Inviting! An AMAZING Water View E ...

    From $231 per night (USD)

    VRBO

    Details
  • Cozy Sarasota Retreat - 3 Blocks to the Coast!
    From $228 per night (USD)

    Expedia

    Cozy Sarasota Retreat - 3 Blocks to the Coast!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Escape to this top-floor Sarasota unit for a trip filled with enough sun, sand, and surf to last a lifetime! Offering 2 ...

    From $228 per night (USD)

    Expedia

    Details
  • Manasota Key Retreat with free use of bikes and beach supplies
    From $190 per night (USD)

    VRBO

    Manasota Key Retreat with free use of bikes and beach supplies

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Come as you are, kick off your shoes, and immerse yourself into this tropical Paradise. The locally known Lemon Bay Park ...

    From $190 per night (USD)

    VRBO

    Details
  • Pool/Waterfront Home 5 min walk to Siesta Key Village and  Beach
    From $690 per night (USD)

    Expedia

    Pool/Waterfront Home 5 min walk to Siesta Key Village and Beach

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Located 5 minutes walk to #1 Siesta Key Beach, famous bar and restaurants. This beauty has a private court yard with a f ...

    From $690 per night (USD)

    Expedia

    Details
  • COMFY APT(2 BR/1 BATH)  IN SQR DOWNTOWN LIDO SIESTA BEACH 5 mins (5 People)
    From $84 per night (USD)

    VRBO

    COMFY APT(2 BR/1 BATH) IN SQR DOWNTOWN LIDO SIESTA BEACH 5 mins (5 People)

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Private Apartment at Downtown Area, 2 bedrooms(1 queen, 2 full beds), 1 bath, 1 futon, living room, kitchen equipped, ...

    From $84 per night (USD)

    VRBO

    Details
  • Spacious Beachfront Condo with a Fantastic Pool
    From $329 per night (USD)

    Expedia

    Spacious Beachfront Condo with a Fantastic Pool

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

    Located on the quiet south end of Lido Key, this fantastic beachfront condo has it all. Premium 4th floor location show ...

    From $329 per night (USD)

    Expedia

    Details
  • 4 bedroom, 6 bath, 10 min from Siesta Beach
    From $262 per night (USD)

    VRBO

    4 bedroom, 6 bath, 10 min from Siesta Beach

    Bedrooms:
    6
    Bathrooms:
    4
    Sleeps:
    6

    Location!!! Incredible 4 bed, 6 bath house with Lanai and pool/jacuzzi. Outstanding location: 10 min from Siesta Beach, ...

    From $262 per night (USD)

    VRBO

    Details
  • Beautiful Condo- ideal location
    From $110 per night (USD)

    Expedia

    Beautiful Condo- ideal location

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Beautifully decorated and spacious condo 8 minutes from the beach and downtown Venice. Screened in deck overlooking foun ...

    From $110 per night (USD)

    Expedia

    Details
  • Downtown Modern Home Close to Beach and Dining
    From $138 per night (USD)

    VRBO

    Downtown Modern Home Close to Beach and Dining

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    A charming single-family 2-bedroom Bungalow in the heart of Sarasota, Florida, with all new designer furnishings and lin ...

    From $138 per night (USD)

    VRBO

    Details
  • Easy Living Incredible Location Perfect for getting a feel of area
    From $100 per night (USD)

    Expedia

    Easy Living Incredible Location Perfect for getting a feel of area

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    2

    Beautifully appointed home 3.2 Miles to Siesta Key, close to downtown, Interstate 75. One level living, two bedrooms one ...

    From $100 per night (USD)

    Expedia

    Details
  • Sun & Beach
    From $110 per night (USD)

    VRBO

    Sun & Beach

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    2 full furnished bedrooms , king and queen sizes beds. Sofa bed and a twin chair bed . 2 full bathrooms. Kitchen with al ...

    From $110 per night (USD)

    VRBO

    Details
  • Paradise Vacation Condo Steps from Siesta Beach
    From $345 per night (USD)

    Expedia

    Paradise Vacation Condo Steps from Siesta Beach

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Located right on Siesta Key, you will have private access to Siesta Beach, the #1 beach in the USA. Inside this condo y ...

    From $345 per night (USD)

    Expedia

    Details
  • Sarasota creekside pool home oasis, close to beaches and activities.
    From $335 per night (USD)

    VRBO

    Sarasota creekside pool home oasis, close to beaches and activities.

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Welcome to Sarasota Florida. A premier: vacation, adventure, retirement destination. Located on the best (West) coast of ...

    From $335 per night (USD)

    VRBO

    Details
  • Downtown Sarasota Home By Siesta Key and Golfing
    From $103 per night (USD)

    Expedia

    Downtown Sarasota Home By Siesta Key and Golfing

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Beautiful remodeled apartment in a quiet neighborhood. 10min to Dwtn, 15min to Siesta & Lido Beach. Unit has 1 bedroom w ...

    From $103 per night (USD)

    Expedia

    Details
  • Englewood Villa - 3 BR, 2 BA, Pet Friendly
    From $171 per night (USD)

    VRBO

    Englewood Villa - 3 BR, 2 BA, Pet Friendly

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    10

    Summary: Completely renovated and remodeled house in downtown historic Englewood area. Experience "Old Florida" at it's ...

    From $171 per night (USD)

    VRBO

    Details
  • Gorgeous newly remodeled pool home on St. Armand's Circle for 10
    From $699 per night (USD)

    Expedia

    Gorgeous newly remodeled pool home on St. Armand's Circle for 10

    Bedrooms:
    6
    Bathrooms:
    5
    Sleeps:
    10

    Please see COVID and Standard Cancellation Policy below - it is different from VRBO policy options, as are payment opti ...

    From $699 per night (USD)

    Expedia

    Details
  • Centrally located to Beaches and Downtown Sarasota
    From $355 per night (USD)

    VRBO

    Centrally located to Beaches and Downtown Sarasota

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    4.92 rating on Airbnb. "Paradise in Sarasota" Come experience this beautiful, renovated home centrally located to all ...

    From $355 per night (USD)

    VRBO

    Details
  • 1/1 Tower Gulf N (034)
    From $257 per night (USD)

    Expedia

    1/1 Tower Gulf N (034)

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Unit 34 is a one bedroom one bathroom located on the north side of the building. The unit is tiled throughout the unit. ...

    From $257 per night (USD)

    Expedia

    Details
  • Noko Life on Shore T
    From $140 per night (USD)

    VRBO

    Noko Life on Shore T

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Enjoy Noko Life at this cozy vacation rental duplex. Located just a short walk or bike ride (.4 mile) to beautiful Nokom ...

    From $140 per night (USD)

    VRBO

    Details
  • Ground Floor, Snowbird-Friendly Cottage with High-Speed WiFi!
    From $105 per night (USD)

    Expedia

    Ground Floor, Snowbird-Friendly Cottage with High-Speed WiFi!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    The Love Shack Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...

    From $105 per night (USD)

    Expedia

    Details
  • “Over the Rainbow!” Vacation Rental Relaxing retreat 5 miles from everything!
    From $300 per night (USD)

    VRBO

    “Over the Rainbow!” Vacation Rental Relaxing retreat 5 miles from everything!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Paradise in a single family home awaits you. Only 5 miles to Siesta Key Beach parking, Siesta Key Village (restaurants, ...

    From $300 per night (USD)

    VRBO

    Details
  • Modern North Port Gem Bear Beaches, Golf & Shops!
    From $256 per night (USD)

    Expedia

    Modern North Port Gem Bear Beaches, Golf & Shops!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Bring your family of beach lovers to this charming 3-bedroom, 2-bathroom vacation rental situated in North Port. Conveni ...

    From $256 per night (USD)

    Expedia

    Details
  • Luxury Waterfront Views / Pool / 1400sf / 2 min to Beach
    From $349 per night (USD)

    VRBO

    Luxury Waterfront Views / Pool / 1400sf / 2 min to Beach

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Our home, located on Siesta Key, with breathtaking intercostal water views is fully furnished with all the amenities you ...

    From $349 per night (USD)

    VRBO

    Details
  • Siesta Key Beach Front Condo! Breathtaking view!
    From $236 per night (USD)

    Expedia

    Siesta Key Beach Front Condo! Breathtaking view!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    This beautiful 2 bedroom, 2 full bath condo sleeps 6 and is located directly on one of the TOP 10 BEACHES IN THE WORLD! ...

    From $236 per night (USD)

    Expedia

    Details
  • Harbor Towers Yacht & Racquet Club
    From $136 per night (USD)

    VRBO

    Harbor Towers Yacht & Racquet Club

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Harbor Towers Yacht and Racquet Club is located on the intercostal waterway on Siesta Key in Sarasota, Florida. From the ...

    From $136 per night (USD)

    VRBO

    Details
  • Walk to Downtown King bed FREE parking near beach
    From $84 per night (USD)

    Expedia

    Walk to Downtown King bed FREE parking near beach

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Travel back into the roaring 20s at our Purple studio apartment. Originally built in 1926, this landmark property in the ...

    From $84 per night (USD)

    Expedia

    Details
  • NEW! Classic Sarasota Home < 4 Mi to Public Beach
    From $127 per night (USD)

    VRBO

    NEW! Classic Sarasota Home < 4 Mi to Public Beach

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    5

    Your perfect Florida vacation is waiting for you at this well-appointed 3-bedroom, 2-bathroom home in Sarasota. Start yo ...

    From $127 per night (USD)

    VRBO

    Details
  • A beautifully updated 3 bedroom, 2 bath near beach
    From $275 per night (USD)

    Expedia

    A beautifully updated 3 bedroom, 2 bath near beach

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Relax and enjoy this recently updated and beautifully decorated 3-bedroom duplex within walking distance to the fabulous ...

    From $275 per night (USD)

    Expedia

    Details
  • Siesta Key Village-Suite #1: A block to the Beach!
    From $189 per night (USD)

    VRBO

    Siesta Key Village-Suite #1: A block to the Beach!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    Looking for the Ultimate Siesta Key Experience? This is it! Located in the Center of the Iconic Siesta Key Village, Sies ...

    From $189 per night (USD)

    VRBO

    Details
  • 3 Bed / 2 Bath, Contemporary Waterfront Home w/Heated Pool
    From $617 per night (USD)

    Expedia

    3 Bed / 2 Bath, Contemporary Waterfront Home w/Heated Pool

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    We are centrally located 10 minutes from Tampa Bay Ray's Spring Training Stadium in one direction, and 10 minutes from t ...

    From $617 per night (USD)

    Expedia

    Details
  • LUXURY BEACH CABANA ON SIESTA KEY!
    From $327 per night (USD)

    VRBO

    LUXURY BEACH CABANA ON SIESTA KEY!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Newly Acquired and Renovated Luxury Beach Cabana! View America’s #1 Beach from your Bedroom! Fully Stocked! The newly ...

    From $327 per night (USD)

    VRBO

    Details
  • Siesta Cooler: Only Minutes Walk to Siesta Beach!
    From $272 per night (USD)

    Expedia

    Siesta Cooler: Only Minutes Walk to Siesta Beach!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    Light, bright and cozy in the HEART of Siesta Key Village! Open floor plan including queen-sized murphy bed, Smart TVs, ...

    From $272 per night (USD)

    Expedia

    Details
  • Gulf and Bay Club 102B, Sleeps 4, Lagoon View, Ground Floor, 2 Bedrooms
    From $242 per night (USD)

    VRBO

    Gulf and Bay Club 102B, Sleeps 4, Lagoon View, Ground Floor, 2 Bedrooms

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Ready to spend twenty-eight days or more in paradise? If so, Gulf & Bay Club 102B is waiting for you. This ground-floor ...

    From $242 per night (USD)

    VRBO

    Details
  • One Bed Room Condo In Sarasota - Professionally Cleaned
    From $219 per night (USD)

    Expedia

    One Bed Room Condo In Sarasota - Professionally Cleaned

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    A beautiful condo first floor fully fenced backyard in the sunny state of Florida, it houses all amenities you could pos ...

    From $219 per night (USD)

    Expedia

    Details
  • Siesta Cool : Only Minutes Walk to Siesta Beach!
    From $279 per night (USD)

    VRBO

    Siesta Cool : Only Minutes Walk to Siesta Beach!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    Light, bright and cozy in the HEART of Siesta Key Village! Open floor plan including queen-sized murphy bed, Smart TVs, ...

    From $279 per night (USD)

    VRBO

    Details
  • Siesta Key Village -Suite #2: A Block to the Beach, In the HEART of the Village!
    From $239 per night (USD)

    Expedia

    Siesta Key Village -Suite #2: A Block to the Beach, In the HEART of the Village!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    Looking for the Ultimate Siesta Key Experience? This is it! Located in the Center of the Iconic Siesta Key Village, Sies ...

    From $239 per night (USD)

    Expedia

    Details
  • Private Villa steps to Lido Beach
    From $225 per night (USD)

    VRBO

    Private Villa steps to Lido Beach

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Beautiful private villa located across the street from Lido Beach and a 10 minute walk to St. Armands Circle. Villa has ...

    From $225 per night (USD)

    VRBO

    Details
  • Unit 21 - Two Bedroom Two Bathroom Condominium With Full Gulf Views
    From $569 per night (USD)

    Expedia

    Unit 21 - Two Bedroom Two Bathroom Condominium With Full Gulf Views

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    New changes as of 2021; This renovated two bedroom two bathroom condo is located on the second floor of our Grand Tower ...

    From $569 per night (USD)

    Expedia

    Details
  • 5 star upscale 1 bed condo near Siesta Key Beach!
    From $100 per night (USD)

    VRBO

    5 star upscale 1 bed condo near Siesta Key Beach!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Stay in a beautiful mini condo on the Oaks golf course and country club in Osprey that is super close to Siesta Key beac ...

    From $100 per night (USD)

    VRBO

    Details
  • NEW Vacation Home Minutes away from Siesta Key Beach & St. Armands Circle
    From $235 per night (USD)

    Expedia

    NEW Vacation Home Minutes away from Siesta Key Beach & St. Armands Circle

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Brand new 3 Bedroom, 2 Bathroom home in Sarasota, FL. Located minutes away from Siesta Key Beach as well as numerous res ...

    From $235 per night (USD)

    Expedia

    Details
  • Siesta Key Village-Suite #3: A Block to the Beach!
    From $239 per night (USD)

    VRBO

    Siesta Key Village-Suite #3: A Block to the Beach!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    Looking for the Ultimate Siesta Key Experience? This is it! Located in the Center of the Iconic Siesta Key Village, Sies ...

    From $239 per night (USD)

    VRBO

    Details
  • Tranquil  St. Armand's Updated Pool Home
    From $572 per night (USD)

    Expedia

    Tranquil St. Armand's Updated Pool Home

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    PLEASE SEE CANCELLATION POLICIES BELOW - Please note that the minimum lease period is (7) nights due to City Code rest ...

    From $572 per night (USD)

    Expedia

    Details
  • Luxury Estate Chalet Heated pool/spa Prime Location
    From $343 per night (USD)

    VRBO

    Luxury Estate Chalet Heated pool/spa Prime Location

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    10

    Welcome to the paradise! With over 3 acres this estate house in Sarasota-North Port Florida has a unique privacy surroun ...

    From $343 per night (USD)

    VRBO

    Details
  • Modern&FreshlyRenovated 2 bed/2 bath Heated Pool Home, 3 miles from Siesta
    From $204 per night (USD)

    Expedia

    Modern&FreshlyRenovated 2 bed/2 bath Heated Pool Home, 3 miles from Siesta

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    Modern&Freshly Renovated 2 bedrooms / 2 bathrooms Heated Pool Home, 3 miles from #1 Siesta Key Beach. Located in Florenc ...

    From $204 per night (USD)

    Expedia

    Details
  • 2BR close to downtown w/Game room & PURPLE(r) beds
    From $206 per night (USD)

    VRBO

    2BR close to downtown w/Game room & PURPLE(r) beds

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    This comfortable, modern duplex house is only minutes to Beaches and downtown Sarasota. We're walking distance to Payne ...

    From $206 per night (USD)

    VRBO

    Details
  • Newly Remodeled!  Directly Across from Beach ~ Condo
    From $178 per night (USD)

    VRBO

    Newly Remodeled! Directly Across from Beach ~ Condo

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    The location of the condo is fantastic as you will have access to the luxurious Longboat Key Beach nearly to yourself. T ...

    From $178 per night (USD)

    VRBO

    Details
  • Bright and Airy 4th floor condo at Fisherman's Haven with Private Beach and Stunning Water Views! FH
    From $214 per night (USD)

    VRBO

    Bright and Airy 4th floor condo at Fisherman's Haven with Private Beach and Stunning Water Views! FH

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Bright and Airy 4th floor condo at Fisherman's Haven with private beach and stunning water views! Spacious, open-conce ...

    From $214 per night (USD)

    VRBO

    Details
  • 2 Bed/2 bath Condo Steps to Siesta Key Beach!
    From $196 per night (USD)

    Expedia

    2 Bed/2 bath Condo Steps to Siesta Key Beach!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    The unit is newly furnished in a beachy style perfect for a vacation on Siesta Key, consistently rated one of the 10 bes ...

    From $196 per night (USD)

    Expedia

    Details
  • Stylish escape near the beach with free WiFi, pool, two balconies, & AC
    From $194 per night (USD)

    VRBO

    Stylish escape near the beach with free WiFi, pool, two balconies, & AC

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Salt & Serenity Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...

    From $194 per night (USD)

    VRBO

    Details
  • Freshly Renovated Siesta Key Getaway ~ Your Dream Vacation!
    From $237 per night (USD)

    Expedia

    Freshly Renovated Siesta Key Getaway ~ Your Dream Vacation!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    A brand new remodeled condo at Harbor Towers Yacht & Racquet Club! Don't miss out on the beautiful Florida sunrise righ ...

    From $237 per night (USD)

    Expedia

    Details
  • Crescent Street 1138 B, Walk to the beach, Pool, 1 Bedroom, Pet Friendly
    From $177 per night (USD)

    VRBO

    Crescent Street 1138 B, Walk to the beach, Pool, 1 Bedroom, Pet Friendly

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Half-hidden by lush tropical foliage, Crescent Street 1138 B is paradise for anyone who longs to relax in time-honored F ...

    From $177 per night (USD)

    VRBO

    Details
  • Siesta Dunes Beach 201, Completely Renovated, 2 Bedrooms, Sleeps 6, Spa, Large H
    From $216 per night (USD)

    VRBO

    Siesta Dunes Beach 201, Completely Renovated, 2 Bedrooms, Sleeps 6, Spa, Large H

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    This unit has been newly renovated. Stunning seaside decor, new kitchen, baths, paint, and luxury vinyl plank flooring t ...

    From $216 per night (USD)

    VRBO

    Details
  • BEAUTIFULY DECORATED CONDO 3 MILES FROM SIESTA KEY BEACH
    From $126 per night (USD)

    VRBO

    BEAUTIFULY DECORATED CONDO 3 MILES FROM SIESTA KEY BEACH

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Beautiful vacation villa located in the popular Village Des Pins complex, only a short drive to Siesta Key Beach, voted ...

    From $126 per night (USD)

    VRBO

    Details
  • Our House at the Beach 222, Sleeps 4, 2 Bedroom, Tennis, Heated Pool
    From $230 per night (USD)

    VRBO

    Our House at the Beach 222, Sleeps 4, 2 Bedroom, Tennis, Heated Pool

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    There's plenty of room for everyone here at Our House. We have a split-level living/dining area, with a large living roo ...

    From $230 per night (USD)

    VRBO

    Details
  • Vista Hermosa 189, Wireless Internet, 2 Bedrooms, Pool, Sleeps 6
    From $166 per night (USD)

    VRBO

    Vista Hermosa 189, Wireless Internet, 2 Bedrooms, Pool, Sleeps 6

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    When booking a Florida rental for a stay of at least two weeks, you want a place that has it all: a convenient location, ...

    From $166 per night (USD)

    VRBO

    Details
  • Updated Home w/ Pvt Pool < 10 Mins to Siesta Key
    From $519 per night (USD)

    Expedia

    Updated Home w/ Pvt Pool < 10 Mins to Siesta Key

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    From the nearby Sniki Tiki bar to restaurants in Siesta Key Village and white-sand beaches, you can enjoy it all with ea ...

    From $519 per night (USD)

    Expedia

    Details