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From $221 per night (USD)
VRBO
Cozy house near Siesta Key Beach
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to our newly furnished home. When you walk up to it, it looks like a cozy cottage too. The inside is fresh new a ...
From $221 per night (USD)
VRBO
From $595 per night (USD)
Expedia
Private Heated Pool, walk to St Armand's! Perfect for families!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Blue Palm by Lido Key Vacations Minimum stay duration of 7 days/nights #VR22-00132 Blue Palm by Lido Key Vacations ...
From $595 per night (USD)
Expedia
From $1026 per night (USD)
VRBO
Siesta Key Waterfront Estate heated Pool Privacy! 5 rooms
Bedrooms:
4
Bathrooms:
4
Sleeps:
14
This wooded property is unreal and our 5 star ratings agree! 1 acre on the water for your entire family or group to rela ...
From $1026 per night (USD)
VRBO
From $479 per night (USD)
Expedia
Charming 1940s Bungalow – 6 Mins to Beach + Private Pool Oasis!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Siesta Sunset Bungalows – Private Beachside Oasis with Heated Pool & Gazebo Welcome to Siesta Sunset Bungalows, your sec ...
From $479 per night (USD)
Expedia
From $260 per night (USD)
VRBO
Siesta Beach Condo Rental with direct beach and pool access
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Looking for quick easy access to the #1 beach in America? You've found the place! Enjoy the excellent location of the Si ...
From $260 per night (USD)
VRBO
From $634 per night (USD)
Expedia
Island House Beach Resort 6S
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This beautifully appointed 2-bedroom, 2-bathroom condo features a spacious primary ensuite with a king-size bed, along w ...
From $634 per night (USD)
Expedia
From $456 per night (USD)
VRBO
Beach Days, Home Nights 2BR w/ Kitchen-Beach Club at Siesta Key #103E by RVA
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
RVA offers beautiful turquoise waters and quartz-crystal white sands, which have been officially ranked as the “finest, ...
From $456 per night (USD)
VRBO
From $361 per night (USD)
Expedia
Relax & Unwind – 1BR Beach Club Siesta Key 110D RVA
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
RVA offers beautiful turquoise waters and quartz-crystal white sands, which have been officially ranked as the “finest, ...
From $361 per night (USD)
Expedia
From $169 per night (USD)
VRBO
Sarasota Home in the Gulf gate neighborhood 5 minutes from the beach
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Great little beach house within walking distance to shopping and 5 minutes from Siesta Key Beach. Quiet neighborhood, gr ...
From $169 per night (USD)
VRBO
From $361 per night (USD)
Expedia
Siesta Key 1-Bedroom Condo | Unit 102B at The Beach Club – Steps to the Beach
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Unit 102B at The Beach Club at Siesta Key | 1-Bedroom Luxury Vacation Rental Near Siesta Key Beach Welcome to Unit 102B ...
From $361 per night (USD)
Expedia
Click For Pricing
VRBO
Siesta Key Getaway – Pet Friendly & Steps to Beach: Siesta Bungalow by RVA
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Enjoy your Florida getaway in this lovely vacation home, just one block from both the world-famous Siesta Key Village an ...
Click For Pricing
VRBO
From $317 per night (USD)
Expedia
Condo w/ Pool Access < 4 Miles to Siesta Key Beach
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Explore the charm of sunny Sarasota with a getaway to this coastal condo! Boasting 2 bedrooms, 1.5 baths, and a private ...
From $317 per night (USD)
Expedia
From $995 per night (USD)
VRBO
Luxury Pool and Rooftop Deck, Walk to Siesta Key Beach and Village! - Casa Siest
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Casa Siesta by Siesta Key Luxury Rental Properties is a beautifully designed three-bedroom, three-bathroom private pool ...
From $995 per night (USD)
VRBO
From $177 per night (USD)
Expedia
Indulge at Harbor Towers, Easy Beach Access & Intracoastal Views at 50% Less than Beachfront
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to Harbor Towers 3rd Fl 2 Bedroom Bay View! This beautiful 3rd-floor, 2-bedroom, 2-bath condo at Harbor Tow ...
From $177 per night (USD)
Expedia
$Experience \Old Florida\ at the Coral Cottage$
From $385 per night (USD)
VRBO
Experience \"Old Florida\" at the Coral Cottage
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
BRAND NEW REMODEL AND BETTER THAN EVER! Designer furnished, cozy, stylish Vintage Florida home on Phillippi Creek. Fishi ...
From $385 per night (USD)
VRBO
From $250 per night (USD)
Expedia
The Perfect Shiny Condo
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Explore Sarasota, where the sunset on the most beautiful beach in the world always arrives on time and it's only 6 minut ...
From $250 per night (USD)
Expedia
From $449 per night (USD)
VRBO
Beachfront Ground Level Suite - Everything is Modern & New
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
The condo has just been completely redone from the studs, and turned out absolutely amazing!! (will have more new phones ...
From $449 per night (USD)
VRBO
From $307 per night (USD)
VRBO
Beautiful and elegant villa in the Gated Community of Gran Paradiso
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Beautiful recently built villa in Gran Paradiso, Venice Fl, in a gated community with 24 hour security. Villa sleeps 6 ...
From $307 per night (USD)
VRBO
From $192 per night (USD)
VRBO
Beautiful 1800 square foot Mid Century Home
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
My 1967 vintage Mid Century home is a one level gem set at the end of a cup-de-sac and quiet city easement. If you want ...
From $192 per night (USD)
VRBO
From $354 per night (USD)
Expedia
Beach & Pool Open! Direct Beachfront Condo! Sunsets!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Amazing direct Gulf view from this 4th floor front corner condo. Crescent Arms is a quiet, beach front, high r ...
From $354 per night (USD)
Expedia
From $139 per night (USD)
VRBO
Heritage Oaks 2 Bedroom with Golf Course and Water Views
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Heritage Oaks, a private gated golf & tennis country club community in Sarasota, Florida. Our Condo is located on the si ...
From $139 per night (USD)
VRBO
From $586 per night (USD)
Expedia
Beautiful, Spectacular view of the Ocean, new furniture, oversized deck/balcony
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Check out my other amazing VRBO property reviews: Vrbo.com/4802815 ! Location, location, location! This beautiful apar ...
From $586 per night (USD)
Expedia
From $369 per night (USD)
VRBO
Cozy & Relaxing Home next to Siesta Key
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
You'll have a great time at this cozy, peaceful house next to Siesta Key. Have fun with the whole family at this stylish ...
From $369 per night (USD)
VRBO
From $263 per night (USD)
Expedia
Private home- large lanai & heated pool. 7 mins to Manasota Key beach
Bedrooms:
1
Bathrooms:
3
Sleeps:
9
Recently renovated 3 bedroom home. Private master bedroom w/ attached master bath. 2 additional bedrooms are on the othe ...
From $263 per night (USD)
Expedia
From $426 per night (USD)
VRBO
Island Time: Open Sept 13th - 16th!
Bedrooms:
1
Bathrooms:
0
Sleeps:
4
This sublime oceanfront studio is directly on the pristine white sands and serene blue waters of the Gulf of Mexico in e ...
From $426 per night (USD)
VRBO
From $262 per night (USD)
Expedia
Old Floridian cottage in Historic Gulf Village
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Cozy and clean, close to the Gulf! One block to center of Olde Historic Dearborn St. & Englewood Framers market. Walking ...
From $262 per night (USD)
Expedia
From $229 per night (USD)
VRBO
Amazing well take care house in a great location.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Amazing well take care property, huge car garage, fresh painted and remodeled, just a short ride to Venice Historic Down ...
From $229 per night (USD)
VRBO
From $379 per night (USD)
Expedia
The Cottage Next Door Best Downtown location in Sarasota
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Recently restored 1925 cottage nestled in the heart of Sarasota's newest and most desirable downtown neighborhood and ju ...
From $379 per night (USD)
Expedia
From $219 per night (USD)
VRBO
Beautifully decorated, well-furnished Private Pool House-walk to great beach! On desirable Venice Island!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Location, location, location! Tastefully decorated 3 bedrooms, 2 modern bathrooms, attractive family room & open concep ...
From $219 per night (USD)
VRBO
From $189 per night (USD)
Expedia
Near Siesta Key Beach, Renovated Updated Condo, Pools | Tennis | Gym
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to Harbor Towers Yacht & Racquet Club 2nd FL Renovated Unit! Experience the best of Siesta Key from this be ...
From $189 per night (USD)
Expedia
From $1323 per night (USD)
VRBO
Beach Views - Family-Friendly, Steps to Lido Beach!
Bedrooms:
7
Bathrooms:
7
Sleeps:
12
Beach Views by Lido Key Vacations #VR22-00034 Minimum Stay Duration 7 days/nights Welcome to Beach Views, an ...
From $1323 per night (USD)
VRBO
From $332 per night (USD)
Expedia
Amazing house, 2 blocks from the beach (#1 in USA), close to the village.
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Family house, 2 rooms, dinner room, TV room, kitchen, living room, 2 bathrooms. Our house is amazing for a perfect relax ...
From $332 per night (USD)
Expedia
From $666 per night (USD)
VRBO
Oceanfront home
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Treat your family, friends, and beloved small dogs to an unforgettable oceanfront getaway in sunny Florida! Conveniently ...
From $666 per night (USD)
VRBO
From $288 per night (USD)
Expedia
Tropical 2-Bdr Condo with Pool on Siesta Key Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Stay on the Beach! Make yourself at home in one of Siesta Keys most exclusive luxury condominium complex The Gulf and B ...
From $288 per night (USD)
Expedia
From $242 per night (USD)
VRBO
Beachside Condo in Siesta Key
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Enjoy this ground-floor recently refurbished unit with two beautiful King bedrooms. The unit has a beachy, relaxed feel ...
From $242 per night (USD)
VRBO
Click For Pricing
Expedia
Siesta Key 5th Floor Center Front Condo on Crescent Beach 180' Panoramic Views
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Enjoy a spectacular, 180-degree view of the Gulf of Mexico and the world-famous Siesta Key white sand Crescent Beach. W ...
Click For Pricing
Expedia
From $313 per night (USD)
VRBO
Beach & Pool Open! Beachfront View All Rooms. Chairs, Wifi
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Summary: Our 6th floor condo has great gulf views from every room! Crescent Arms is a quiet, beach front, high rise con ...
From $313 per night (USD)
VRBO
From $289 per night (USD)
Expedia
Lanai + Community Pool Access: Sarasota Oasis!
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Step-Free Access | Resort-Style Perks | No Pets Allowed Unwind and rejuvenate in this 2-bedroom, 2-bath Sarasota vacati ...
From $289 per night (USD)
Expedia
From $302 per night (USD)
VRBO
Spacious South Venice Home
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Beautiful! Recently updated 1700 sq’ home in quiet community of South Venice. Walking distance to Shamrock Park that con ...
From $302 per night (USD)
VRBO
From $320 per night (USD)
Expedia
Beachcomber unit 403
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Our building is located on the beach, this unit has an ISLAND view. Beach front units are available to rese ...
From $320 per night (USD)
Expedia
From $323 per night (USD)
VRBO
Beachcomber unit 503
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Our building is located on the beach, this unit has an ISLAND view. Beach front units are available to rese ...
From $323 per night (USD)
VRBO
From $321 per night (USD)
Expedia
Beachcomber unit 405
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Our building is located on the beach, this unit has an ISLAND view. Beach front units are available to rese ...
From $321 per night (USD)
Expedia
From $428 per night (USD)
VRBO
Home in quiet Bird Sanctuary Neighborhood, close to Beach
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Enjoy your stay in the comfort of our modern house in the quiet surrounding of our bird sanctuary neighborhood. Enjoy be ...
From $428 per night (USD)
VRBO
From $323 per night (USD)
Expedia
Beachcomber unit 303
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Our building is located on the beach, this unit has an ISLAND view. Enjoy upscale Longboat Key in the elega ...
From $323 per night (USD)
Expedia
From $496 per night (USD)
VRBO
Beachcomber unit 204
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This is a great location directly on the beach with a spectacular view of the Gulf of Mexico. This Gulf fro ...
From $496 per night (USD)
VRBO
From $491 per night (USD)
Expedia
Beachcomber unit 208
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to The Beachcomber, a Longboat Key beach resort located right on the Gulf of Mexico. Just a few steps from your ...
From $491 per night (USD)
Expedia
From $323 per night (USD)
VRBO
Beachcomber unit 305
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Our building is located on the beach, this unit has an ISLAND view. Pack your bags, invite your family and ...
From $323 per night (USD)
VRBO
From $553 per night (USD)
Expedia
Beach Walk Cottage | Private Pool, Ping Pong Table + Walk to Siesta Beach
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
🌴 Beach Walk Cottage | Private Pool, Ping Pong Table + Walk to Siesta Beach 💖 Why You'll Love This Home Tucked in a q ...
From $553 per night (USD)
Expedia
From $702 per night (USD)
VRBO
Longboat Key Luxury Condo - walking to St. Armand's Circle!
Bedrooms:
1
Bathrooms:
3
Sleeps:
4
This luxurious COVID free top floor end unit condo was newly furnished in 2022 and features an elevator. Taking in v ...
From $702 per night (USD)
VRBO
From $815 per night (USD)
Expedia
Steps from Beach. Roof Top Deck-Gulf Views. Shared Heated Pool
Bedrooms:
3
Bathrooms:
3
Sleeps:
10
Siesta Sun by Siesta Key Luxury Rental Properties is a stunning 3 bedroom, 3. and a half bath Siesta Key luxury rental l ...
From $815 per night (USD)
Expedia
From $156 per night (USD)
VRBO
Siesta Harbor, 6 Min Walk to Beach, Pool/Hot Tub, King Ensuite Master with Water Canal Views
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to Siesta Harbor Portofino Canal View! Beautiful property across the street from Crescent beach with canal ...
From $156 per night (USD)
VRBO
From $900 per night (USD)
Expedia
400 yards to Siesta Key Village, 800 yard To The public Beach Access 2 and 7.
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
ONE OF A KIND PROPERTY four blocks from SIESTA KEY Beach so,pack up your cooler, and all your beach supplies, and take t ...
From $900 per night (USD)
Expedia
From $270 per night (USD)
VRBO
Private heated pool. Shark teeth, close to beaches, downtown, shopping, biking…
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Premier Host! Wonderful private Heated pool area. Great for families, premier location. Renovated with a new AC system, ...
From $270 per night (USD)
VRBO
From $410 per night (USD)
Expedia
Serene vacation villa just 7 minute drive from Siesta Key
Bedrooms:
2
Bathrooms:
2
Sleeps:
7
2 Bedroom/2 Bath Villa with one-car garage and screened in lanai Peaceful and tastefully decorated villa in Village de ...
From $410 per night (USD)
Expedia
From $328 per night (USD)
VRBO
Pet-Friendly Home w/ Pool, Close to Venice Beaches
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Free WiFi | Private Heated Pool Instantly feel relaxed when you arrive at this beautiful 2-bedroom, 2-bath Venice home ...
From $328 per night (USD)
VRBO
From $487 per night (USD)
Expedia
Location, location! Private Beach, Gulf Views from Balcony, Heated Pool, Siesta Sands with King Bed
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to Siesta Sands Beach Resort 4th Floor with Elevator! This gorgeous south-end Siesta Key condo sits on the ...
From $487 per night (USD)
Expedia
From $1516 per night (USD)
VRBO
Resort Pool w/Slide - Walk to Beach & Village
Bedrooms:
6
Bathrooms:
5
Sleeps:
14
Summary: Vunique Vacations was built for the discerning traveler who’s seeking a truly unforgettable experience! Each h ...
From $1516 per night (USD)
VRBO
From $2184 per night (USD)
Expedia
Steps to Beach/Pool w/Slide and Chipping Green
Bedrooms:
8
Bathrooms:
8
Sleeps:
19
Summary: Vunique Vacations was built for the discerning traveler who’s seeking a truly unforgettable experience! Each h ...
From $2184 per night (USD)
Expedia
From $1535 per night (USD)
VRBO
Resort Pool w/Slide - Walk to Beach & Village
Bedrooms:
5
Bathrooms:
5
Sleeps:
14
Summary: Vunique Vacations was built for the discerning traveler who’s seeking a truly unforgettable experience! Each h ...
From $1535 per night (USD)
VRBO
From $1802 per night (USD)
Expedia
Pool Volleyball-Gulf Views-Steps to Beach-Rooftop
Bedrooms:
6
Bathrooms:
6
Sleeps:
16
Summary: Vunique Vacations was built for the discerning traveler who’s seeking a truly unforgettable experience! Each h ...
From $1802 per night (USD)
Expedia
From $1789 per night (USD)
VRBO
Steps to Beach/Gulf Views/Pool Volleyball/Slide
Bedrooms:
7
Bathrooms:
6
Sleeps:
16
Summary: Vunique Vacations was built for the discerning traveler who’s seeking a truly unforgettable experience! Each h ...
From $1789 per night (USD)
VRBO
From $232 per night (USD)
Expedia
Florida home for your perfect stay away from cold
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
House is located in a good neighborhood 15 min away from Siesta Key which was voted nr.1 beach in USA for 10 years in a ...
From $232 per night (USD)
Expedia
From $496 per night (USD)
VRBO
Beachcomber unit 202
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Staying on Longboat Key means you get to experience what Heaven on Earth feels like. A place where you can walk on prist ...
From $496 per night (USD)
VRBO
From $320 per night (USD)
Expedia
Beachcomber unit 501
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Our building is located on the beach, this unit has an ISLAND view. Relax and Enjoy the Beach, Pool & Longb ...
From $320 per night (USD)
Expedia
From $233 per night (USD)
VRBO
Tropical, private, downtown
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
You’ll more than enjoy your accommodations and be very glad you chose to stay here. Your apartment is well appointed, co ...
From $233 per night (USD)
VRBO
From $492 per night (USD)
Expedia
4 bed 3 bath Waterfront Home by Ralph Twitchell
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Originally designed by Ralph Twitchell, one of the founding members of the Sarasota School of Architecture, this midcent ...
From $492 per night (USD)
Expedia
From $268 per night (USD)
VRBO
Condo# 409 Steps from Siesta Key Beach Condo
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
** This unit offers reservations with a 4-night minimum from April/11/2026 through December/11/26 and April/10/27 throu ...
From $268 per night (USD)
VRBO
From $276 per night (USD)
Expedia
Studio Retreat Across the Street from Beautiful Siesta Key Beach
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Just knowing you have a scenic trip to Siesta Key on the calendar is exciting. Knowing you've booked your stay in Beach ...
From $276 per night (USD)
Expedia
From $526 per night (USD)
VRBO
Luxury Home W/ Pool, Spa, and Walking Distance to Beach
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Come enjoy the relaxed vibe of Siesta Key! The beautiful white sand beaches that make Siesta Key the #1 beach in the US ...
From $526 per night (USD)
VRBO
From $486 per night (USD)
Expedia
Fully Renovated Beachside Getaway with Heated Pool – Walk to Restaurants
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Never miss a beach-scape sunset when you are just a couple hundred meters from Americans #1 beach, Siesta Key Beach. Enj ...
From $486 per night (USD)
Expedia
From $493 per night (USD)
VRBO
Luxury Home w/ Heated Pool and Private Beach Access
Bedrooms:
3
Bathrooms:
4
Sleeps:
11
When a beach getaway infused with luxury and style sounds like a refreshing change of pace, you'll find everything you n ...
From $493 per night (USD)
VRBO
From $435 per night (USD)
Expedia
Romantic Lakefront Two bedroom unit W/ access to Heated Pool and More
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
When a vacation focused on fun under the sun is your goal and you're looking for amazing accommodations to meet the mome ...
From $435 per night (USD)
Expedia
From $193 per night (USD)
VRBO
Walk to the Beach and More from this Fully Renovated Unit W/ Heated Pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Making the most of a sunny getaway starts with booking Holiday House 1 the next time travel plans bring you to scenic Si ...
From $193 per night (USD)
VRBO
From $302 per night (USD)
Expedia
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
A sunny Siesta Key adventure is made even better for those who book a stay in beautiful Beach Road. This welcoming 2-bed ...
From $302 per night (USD)
Expedia
From $443 per night (USD)
VRBO
Updated unit with easy beach access on Siesta Key
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
When a beach-focused getaway is exactly your style and you can't wait to enjoy time in Siesta Key, booking One Ocean-A p ...
From $443 per night (USD)
VRBO
From $392 per night (USD)
Expedia
Renovated Siesta Key Vacation Rental W/ Heated Pool Walking Distance to Beach
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Spending time in Siesta Key is always an exciting experience. However, those who choose to book a stay in Holiday House ...
From $392 per night (USD)
Expedia
From $450 per night (USD)
VRBO
Renovated condo with easy beach access on Siesta
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Taking time to kick back and relax in beach-focused style is easy to do when you make your way to Siesta Key and book On ...
From $450 per night (USD)
VRBO
From $202 per night (USD)
VRBO
Walk to Downtown or Southside Village and Waterfront!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Charming Retreat in the Heart of it All. – Perfect Location for Exploring Downtown Sarasota, Bay fishing Siesta Key and ...
From $202 per night (USD)
VRBO
From $574 per night (USD)
VRBO
Beachside Private Vacation Home w/ Large Heated Pool
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Come and enjoy a stress free vacation at this island paradise three bedroom two bath private home with heated pool. The ...
From $574 per night (USD)
VRBO
From $212 per night (USD)
Expedia
Venice Gardens Getaway, A Guest Favorite
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
BEAUTIFULLY decorated with a beach/ocean theme, you will LOVE this vacation home! Master Bedroom: King Size Bed Bedro ...
From $212 per night (USD)
Expedia
From $263 per night (USD)
VRBO
Beachside Studio Located Across from Main Beach and Half Mile to Village
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
When taking time to unwind with a healthy dose of sand, sun, and surf is exactly your style, Siesta Key is the place to ...
From $263 per night (USD)
VRBO
From $497 per night (USD)
Expedia
Siesta Key Beachside Vacation Rental W/ Heated Pool – Walk to Beach and More
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Come and enjoy this two bedroom two bathroom condo style vacation rental located just a short walk to Siesta Key beach. ...
From $497 per night (USD)
Expedia
From $320 per night (USD)
VRBO
Beachcomber unit 201
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Our building is located on the beach, this unit has an ISLAND view. Welcome Snow Birds and Florida locals l ...
From $320 per night (USD)
VRBO
From $1410 per night (USD)
Expedia
🌴 Island Escape | Home on Siesta Key w/ Private Heated Pool & Ping Pong Table!
Bedrooms:
2
Bathrooms:
4
Sleeps:
12
🌴 Island Escape | Heated Saltwater Pool + 2 Min Walk to Siesta Beach 💖 Why You'll Love This Home Step into Island Esc ...
From $1410 per night (USD)
Expedia
From $193 per night (USD)
VRBO
Sarasota Downtown, Best Location For Your Vacation !!!
Bedrooms:
1
Bathrooms:
2
Sleeps:
7
Located in the heart of Sarasota City, just minutes to shopping, dining, golf courses and of course the #1 Beach in the ...
From $193 per night (USD)
VRBO
From $265 per night (USD)
Expedia
Tropical vacation house with large, heated pool and spacious, open floor plan
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Charming, tropical 3-bedroom, 2-bathroom home in Venice Gardens with a large, private HEATED pool that is 5 minutes from ...
From $265 per night (USD)
Expedia
From $327 per night (USD)
VRBO
Private Beach Access | Ocean Views | Pool | Full Views of the Gulf of Mexico | Bay Tree Bliss
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to Bay Tree Club Beach Side! Enjoy a 5-star stay at Bay Tree Club, a premier beach property on the south en ...
From $327 per night (USD)
VRBO
From $189 per night (USD)
Expedia
Super Clean Vacation Villa with Pool
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
1250 sqf. 3 bedroom all tile Villa with pool in super quiet and nice aerea in North Port Fl. The house has everything yo ...
From $189 per night (USD)
Expedia
From $143 per night (USD)
VRBO
Gulf View Condo-5 minute walk to village!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Completely updated 2 bedroom 1 bath gulf view villa in Sandy Cove. This is a quiet ground floor unit with a loft, and n ...
From $143 per night (USD)
VRBO
From $418 per night (USD)
Expedia
Serene Resort-style Villa minutes to Siesta Key, in popular Village des Pins
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Located in South Sarasota, this newly renovated villa with a large open living/dining area and serene lanai is close to ...
From $418 per night (USD)
Expedia
From $342 per night (USD)
VRBO
Hot Tub, Game Room, Fire Pit, Rays/Braves Spring
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome Home! BobcatBnB is the premier vacation property if you want to visit the world champion Atlanta Braves and Ta ...
From $342 per night (USD)
VRBO
From $440 per night (USD)
Expedia
*** FULLY UPDATED *** On the Beach, Walk to Village, Watch the Sunsets from Balcony
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
*** FULLY UPDATED December 2025*** This 3 story unit is a 3 Bedroom / 3.5 Bathroom house with spectacular views from eve ...
From $440 per night (USD)
Expedia
From $468 per night (USD)
VRBO
Beach Front and Walking Distance to Village
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
This 3 story unit is a 3 Bedroom / 3.5 Bathroom house with spectacular views from every bedroom and private beach access ...
From $468 per night (USD)
VRBO
From $211 per night (USD)
Expedia
Luxury-Gran Paradiso 3 Bedroom/ 2.5 Bath Townhouse /High End Amenities
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Check out this New Construction, 2022, Gated Community, 3 Bedroom, 2 1/2 Bath Townhome with private Lanai. Park like se ...
From $211 per night (USD)
Expedia
From $342 per night (USD)
VRBO
Beautiful Florida Home 3 Miles to Venice Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
9
Relax with the whole family at this peaceful place to stay. Lots of space with bright decor. Venice has so much to offer ...
From $342 per night (USD)
VRBO
From $268 per night (USD)
Expedia
Completely remodeled 3bdrm/2.5bath heated pool
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Our house was completely remodeled and we’re excited to share it with you! It’s located in the quiet suburbs of Venice, ...
From $268 per night (USD)
Expedia
From $197 per night (USD)
VRBO
A spacious condo in beautiful Siesta Key, Heated Pool, Tennis, Waterfront Picnic
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Recently fully renovated and tastefully decorated 2-bedroom 2 bathroom 3rd floor condo in the very desirable island comm ...
From $197 per night (USD)
VRBO
From $439 per night (USD)
Expedia
Crystal Sands Tower Unit 309 - Beachfront
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to Crystal Sands newest rental, Unit 309. The relaxing color scheme of this beautifully renovated condominium ...
From $439 per night (USD)
Expedia
From $408 per night (USD)
VRBO
Fully renovated Siesta Key Condo | Walk to Beach | Pool | Perfect Location in SK Village
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Siesta Key Village Retreat – Steps to Pool & Beach! Experience the ultimate beach getaway in this newly remodeled 2 ...
From $408 per night (USD)
VRBO
From $130 per night (USD)
Expedia
4th floor condominium, Pool, and short walk to Siesta Key with America's #1 Beach
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Finding time to unwind in style is a gift. For those with their travel sights set in the Sarasota and Siesta Key area of ...
From $130 per night (USD)
Expedia

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