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From $383 per night (USD)
VRBO
100 STEPS YOU'RE ON USA's #1 BEACH,RENTING SINCE 1998, SLEEP 6 IN BEDS
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
'#1 beach in the USA' !! You are looking at our Sea Shell Condominium on beautiful Siesta Key, Florida. Our Family is ...
From $383 per night (USD)
VRBO
From $335 per night (USD)
Expedia
Beachcomber unit 205
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Our building is located on the beach, this unit has an ISLAND view. Beautifully renovated 1 bedroom, 1 bath ...
From $335 per night (USD)
Expedia
$Sarasota Getaway w\/ Private Pool & Backyard Oasis!$
From $404 per night (USD)
VRBO
Sarasota Getaway w\/ Private Pool & Backyard Oasis!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Pack your bags for fun in the Florida sun while you stay at this 3-bedroom, 3-bathroom Sarasota vacation rental. Boastin ...
From $404 per night (USD)
VRBO
From $161 per night (USD)
Expedia
Walk to the beach! Clean and new, remodeled cozy 3 bedroom 2 bath cottage house
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
A charming coastal cottage home that epitomizes coastal living at its finest. Situated walking distance from the sh ...
From $161 per night (USD)
Expedia
From $222 per night (USD)
VRBO
Unique Nokomis Home ~ 2 Mi to Beach Access!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Nestled a short distance from oceanfront relaxation, this 2-bedroom, 2-bath vacation rental offers serenity during your ...
From $222 per night (USD)
VRBO
From $183 per night (USD)
Expedia
Spacious Villa with Lush Tropical Garden Very Close to Siesta Key!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Your warm relaxing subtropical vacation begins here. Enjoy the sunset over Siesta key from just a short block away. Two ...
From $183 per night (USD)
Expedia
From $255 per night (USD)
VRBO
🦩The Perfect Snowbird Nest on Siesta Key! Minimum 30-Day Rental🦩
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Pinkie Flamingo Welcomes You to The Tortuga #105B! King/Queen A rare find indeed! Come prepared to leave impressed.This ...
From $255 per night (USD)
VRBO
From $516 per night (USD)
Expedia
Best Location Siesta Key Village Beach, Restaurants, Bars10% Friends Discount
Bedrooms:
3
Bathrooms:
3
Sleeps:
7
Welcome to Endless Summer, a private Apartment “2nd Floor” right in the heart of the Siesta Village with the style, eleg ...
From $516 per night (USD)
Expedia
From $405 per night (USD)
VRBO
Siesta Key Waterfront Condo, Beachfront, Pool, Sunset View
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to Day Dreaming! This 2 bedroom 1 bath rental offers everything you could dream of and more. Located just 300 ya ...
From $405 per night (USD)
VRBO
From $225 per night (USD)
Expedia
Lido Beach Walk! One block to beach!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Sarasota Certificate of Registration # VR22-00027 Minimum 7 night stay Lovely, well appointed one bedroom guest house wi ...
From $225 per night (USD)
Expedia
$Siesta Sunset | Luxurious Beach Front Penthouse w\/ Views of Gulf, Minutes to Siesta Key Village$
From $1305 per night (USD)
VRBO
Siesta Sunset | Luxurious Beach Front Penthouse w\/ Views of Gulf, Minutes to Siesta Key Village
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Siesta Sunset, a breathtaking beachfront rental home located right on the pristine shores of Siesta Key Beach ...
From $1305 per night (USD)
VRBO
$Villa Castile | Pet Friendly Home on Siesta Key w\/ Private Heated Pool, Walk to Beach & Village!$
From $1178 per night (USD)
Expedia
Villa Castile | Pet Friendly Home on Siesta Key w\/ Private Heated Pool, Walk to Beach & Village!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Welcome to Villa Castile, a luxurious retreat located just outside the vibrant Siesta Key Village. This stunning vacatio ...
From $1178 per night (USD)
Expedia
From $281 per night (USD)
VRBO
5th Floor Siesta Key Luxury Condo -, Heated Pool - Views Of Beach and Gulf
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Breathtaking Bay and Gulf views from this stunning fifth floor, end residence. Located in sought-after Siesta Key, close ...
From $281 per night (USD)
VRBO
From $783 per night (USD)
Expedia
Lovely Heated Pool Home ❤ Walk to Beach, Restaurants, Bike & Boat Rentals & More
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Location! Location! Location! -- Stunning pool home with over 2600 sf of living space located steps from the South bridg ...
From $783 per night (USD)
Expedia
$Coconut Cottage | Home on Lido Key w\/ Private Heated Pool\/Spa, Walk to Lido Beach & St. Armands!$
From $1168 per night (USD)
VRBO
Coconut Cottage | Home on Lido Key w\/ Private Heated Pool\/Spa, Walk to Lido Beach & St. Armands!
Bedrooms:
4
Bathrooms:
5
Sleeps:
9
Escape to the enchanting Coconut Cottage, a hidden gem nestled on the barrier island of Lido Key. This quaint and coasta ...
From $1168 per night (USD)
VRBO
From $182 per night (USD)
Expedia
Ideal location Siesta Key
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
2 week rental minimum Ideal location Siesta Key Beach located diagonally across the street. Hop on the free trolley ...
From $182 per night (USD)
Expedia
From $1562 per night (USD)
VRBO
The Village Breeze I - Heated Pool, Beaches, Daiquiris, Seafood, White-sand!
Bedrooms:
2
Bathrooms:
2
Sleeps:
7
The Village Breeze - Heated Pool, Beaches, Daiquiris, Seafood, White-sand! A Gertrude Rentals property. No car required! ...
From $1562 per night (USD)
VRBO
From $1580 per night (USD)
Expedia
The Village Breeze II - White-sand, Pool, Beaches, Daiquiris, Seafood!
Bedrooms:
2
Bathrooms:
2
Sleeps:
7
The Village Breeze - Heated Pool, Beaches, Daiquiris, Seafood, White-sand! A Gertrude Rentals property. No car required! ...
From $1580 per night (USD)
Expedia
$The Village Breeze (2 units) 4BR\/4Bath Pool, Beach - Siesta Village Living!$
From $3393 per night (USD)
VRBO
The Village Breeze (2 units) 4BR\/4Bath Pool, Beach - Siesta Village Living!
Bedrooms:
4
Bathrooms:
4
Sleeps:
14
The Village Breeze 4BR, a Gertrude Rentals property. No car required! Two side by side 2BR/2Bath units in an enviable ...
From $3393 per night (USD)
VRBO
From $573 per night (USD)
Expedia
LUXURY HOUSE BY THE CANAL , Pets welcome 😀🐕.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Our beautiful 3 bedroom / 2 bathroom house is located in the heart of Siesta Key Village. The house features outdoor po ...
From $573 per night (USD)
Expedia
From $264 per night (USD)
VRBO
Cozy, Clean & Crazily Convenient
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
If you're looking for a great vacation getaway and prefer the style of a single-story cottage over a high-rise condo, yo ...
From $264 per night (USD)
VRBO
From $187 per night (USD)
Expedia
Cheerful modern, minutes to beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Fully renovated 2 bedroom, 2 bath, new kitchen, great location. Sleeps 4 (1 child can sleep on the couch), a/c, on Legac ...
From $187 per night (USD)
Expedia
$Harbor Towers Yacht & Racquet Club - Gulf Facing 2\/2 Condo - Fully Upgraded!$
From $301 per night (USD)
VRBO
Harbor Towers Yacht & Racquet Club - Gulf Facing 2\/2 Condo - Fully Upgraded!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This condo is located at Harbor Towers Yacht and Racquet Club on Siesta Key! It is condo #626, gulf facing on the 6th f ...
From $301 per night (USD)
VRBO
From $198 per night (USD)
Expedia
Tiny House SIesta- perfect tiny house for two!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Just enough room for two. This cozy Tiny House was handcrafted in Florida and has found its way to us. You will love the ...
From $198 per night (USD)
Expedia
$Beachfront 2 beds\/2 baths w\/ Balcony LIDO BEACH TOWERS$
Click For Pricing
VRBO
Beachfront 2 beds\/2 baths w\/ Balcony LIDO BEACH TOWERS
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to your beachfront getaway at St. Armands Towers (North) on Lido Key! This spacious 2-bed, 2-bath condo is spre ...
Click For Pricing
VRBO
From $207 per night (USD)
Expedia
LAKEFRONT-FREE KAYAKS, BICYCLES, PADDLEBOARDS-WALK, BICYCLE, OR PADDLE TO BEACH
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Lakefront home feels like a remote cottage but is actually located in a beautifully landscaped, secure, family-friendly, ...
From $207 per night (USD)
Expedia
From $216 per night (USD)
VRBO
Quiet pool house on a lake - 7 min. from beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
This beautiful 1600 Sq. Ft single family home is located on Lake Shamrock, in the quiet neighborhood of Venice Gardens, ...
From $216 per night (USD)
VRBO
From $460 per night (USD)
VRBO
Newly Remodeled Luxury Beach Villa! Nearest Stand-Alone Villa on Siesta Key!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The newly remodeled 2 bedroom / 2 bath Villa sleeps up to 6 people. The Master bedroom features a king-size bed with an ...
From $460 per night (USD)
VRBO
From $362 per night (USD)
VRBO
Beachfront Condo - 3 BR- Heated Pool - Free Boat Docks – Upscale – Siesta Key
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Beachfront Condo - Three Bedroom - Heated Pool - Free Boat Docks - Upscale - Siesta Key Located Next to Turtle Beach on ...
From $362 per night (USD)
VRBO
From $2451 per night (USD)
Expedia
Nearly Beachfront, Gulf Views, Heated Pool & Pet-Friendly - Sugar Sand Cottage
Bedrooms:
4
Bathrooms:
6
Sleeps:
19
Sugar Sand Cottage by Siesta Key Luxury Rental Properties Home in Siesta Key, Florida Siesta Key Luxury Rental Proper ...
From $2451 per night (USD)
Expedia
From $156 per night (USD)
VRBO
Downtown, Mins away from Lido Beach, Siesta Key, St Armands Cir
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Rest and relax in this beautiful first-floor condo while being close to everything downtown Sarasota has to offer includ ...
From $156 per night (USD)
VRBO
From $339 per night (USD)
Expedia
Direct Siesta Key Beachfront condo!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Our beautiful fully remodeled condo is located directly across the street from world famous Siesta Key Beach! Whether yo ...
From $339 per night (USD)
Expedia
From $356 per night (USD)
VRBO
Clean Family Friendly 2 Bed, Private Beach Access, Renovated, GREAT LOCATION!
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Welcome to 9E at Sea Club II, our home away from home in the beach village of Siesta Key. Walk right in to our ground fl ...
From $356 per night (USD)
VRBO
From $231 per night (USD)
Expedia
Lake view spacious 2bdr CONDO 7 min by the BEACH
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This bright and cozy condo is very clean and feels like home, with amenities needed to stay a night, week or a month. T ...
From $231 per night (USD)
Expedia
From $167 per night (USD)
VRBO
One Bedroom - Ground Floor Condo - Heated Pool - Siesta Key Village
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
VILLAGE WEST - Deluxe Ground Floor Vacation Condo in Siesta Key Village with Heated Pool Located right in the Heart of ...
From $167 per night (USD)
VRBO
From $218 per night (USD)
Expedia
Cozy Solar Heated pool retreat, updated house with new kitchen, 25 min to beach.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This 3-bedroom villa offers screened solar heated recently resurfaced pool, fully fenced backyard, BBQ, Wi-Fi, 3 smart ...
From $218 per night (USD)
Expedia
From $400 per night (USD)
VRBO
Unit 401 Beautiful view of the Gulf of Mexico
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
• Enjoy your escape to Siesta Key in the bright and clean Unit 401. This top floor, end unit has an open floor plan wi ...
From $400 per night (USD)
VRBO
From $866 per night (USD)
Expedia
Villa Fiesta | Pet Friendly Home In Siesta Village, Heated Pool and Hot Tub, Walk to the Beach!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Villa Fiesta, your ultimate island retreat nestled in the heart of Siesta Key Village. This stunning property ...
From $866 per night (USD)
Expedia
From $1752 per night (USD)
VRBO
Casa De Siesta | Pet Friendly Home In Siesta Village, Private Pool and Hot Tub, Walk to the Beach!
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
Welcome to Casa De Siesta, your ultimate island retreat nestled in the heart of Siesta Key Village. This stunning proper ...
From $1752 per night (USD)
VRBO
From $348 per night (USD)
Expedia
Bright Coastal Condo: Walk to Lido Key Beach!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
On Lido Key in Sarasota, this sunny beachside condo awaits. Boasting beautiful views of the ocean and a fully equipped k ...
From $348 per night (USD)
Expedia
From $209 per night (USD)
VRBO
Enjoy your stay
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to our house! It's located in a quiet neighbourhood in North Port FL - a fast growing community close to the sho ...
From $209 per night (USD)
VRBO
From $879 per night (USD)
Expedia
Beachfront Condo on Famous Siesta Key!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to Siesta Breakers, a beautiful beachfront 2 bedroom condo on Siesta Key 🏡 Property Highlights: ✨ Heated pool ...
From $879 per night (USD)
Expedia
From $260 per night (USD)
VRBO
The Alameda - Historic SRQ Getaways, Central SRQ
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
The Space Welcome to the Indian Beach Sapphire Shores neighborhood of Sarasota, one of Sarasota's most desirable neighb ...
From $260 per night (USD)
VRBO
From $825 per night (USD)
Expedia
Oceanside! Large 1BR in VIllage, 15-steps to Path of Best Beach. Free Bikes and Paddle-boards!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Oceanside 603 is a Gertrude Rentals property right on Beach Rd at Access 10. Large, Fully Renovated, 1BR Apartment, jus ...
From $825 per night (USD)
Expedia
$Community Heated Pool\/Spa, Lanai, Tennis, Putting Green, Ready to Book!$
From $565 per night (USD)
VRBO
Community Heated Pool\/Spa, Lanai, Tennis, Putting Green, Ready to Book!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to the community of Village Des Pins! Come vacation at Yellow Pine Villa, a single story (half of a duplex) upd ...
From $565 per night (USD)
VRBO
From $474 per night (USD)
Expedia
Crystal Sands Villa 12A
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
One of a kind at Crystal Sands just steps from one of our two heated pools and only 100 yards from the white sand of Cre ...
From $474 per night (USD)
Expedia
From $599 per night (USD)
VRBO
Entire private house
Bedrooms:
5
Bathrooms:
7
Sleeps:
10
Enjoy Full master suite with Jacuzzi tub w/private access to pool with built in hot tub.There are 4 more bedrooms throug ...
From $599 per night (USD)
VRBO
From $155 per night (USD)
Expedia
The Flamingo House at Indian Beach Sapphire Shores
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Enjoy your stay in Sarasota at this charming "Old Florida" West of Trail home with fenced yard, minutes to downtown, att ...
From $155 per night (USD)
Expedia
From $290 per night (USD)
VRBO
Stand alone villa
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Stand alone villa with private patio and garden, just steps to the pool and beach. Putting green and shuffle board. Qui ...
From $290 per night (USD)
VRBO
From $567 per night (USD)
Expedia
Walk to beach Heated POOL King bed DAILY WEEKLY Villa 4 SPECIALS
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
We are a small resort on Siesta Key offering daily rentals Enjoy Siesta Key in style! Brand new high end ground floor lu ...
From $567 per night (USD)
Expedia
Click For Pricing
VRBO
Veranda Beach Club, beachfront Longboat Key, Florida
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Unit #309, a beach front condo, is available Weeks #51 & #52 2019, and Week #1 2020. Unit #306, with a partial ocean vi ...
Click For Pricing
VRBO
From $418 per night (USD)
Expedia
Pool ❤ Home - Close to Beaches, Food, Downtown, Parks, St. Armand's, etc
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
NOTE: BOOKING JANUARY, FEBRUARY OR MARCH? Please book whole months only NOT mid-month to mid-month. This time frame is a ...
From $418 per night (USD)
Expedia
From $159 per night (USD)
VRBO
*NEW LISTING* Incredible Lake View!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Looking for the perfect get-away location? Welcome to Serenata, one of Sarasota’s most sought after resort communities i ...
From $159 per night (USD)
VRBO
$The Sun Dial | Waterfront Home on Siesta Key w\/ Private Pool & Large Backyard, Close to Beach!$
From $1623 per night (USD)
Expedia
The Sun Dial | Waterfront Home on Siesta Key w\/ Private Pool & Large Backyard, Close to Beach!
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
Step inside this magnificent Siesta Key rental home and discover a world of luxury and tranquility. Nestled on the water ...
From $1623 per night (USD)
Expedia
From $176 per night (USD)
VRBO
Sarasota-Indian Beach Zen Home (private-pet friendly)
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
You’ll love this private home, centrally located to everything when you stay at this zen space 2 blocks to the local bay ...
From $176 per night (USD)
VRBO
From $310 per night (USD)
Expedia
🌴Tropical Retreat in Sarasota
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
This completely renovated home with full kitchen 3 bedrooms 2 bath split plan has a large Florida room with a attached s ...
From $310 per night (USD)
Expedia
From $345 per night (USD)
VRBO
Beautiful Coastal Home located within 2 miles to the beach!!
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Located ONLY 2 MILES FROM MANASOTA BEACH this fully furnished adorable beach themed place is available for you to come a ...
From $345 per night (USD)
VRBO
From $383 per night (USD)
Expedia
REOPENED now for DECEMBER! Over 50% discount!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
You want a perfect location. You want a clean, fresh vacation rental with quality furnishings. You want more - not less ...
From $383 per night (USD)
Expedia
From $584 per night (USD)
VRBO
Two Beautiful Cottages Side By Side - Private Pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Pricing is for BOTH cottages (Two 1 bedroom/1 bath cottages). All touch surfaces and floors are being cleaned with an E ...
From $584 per night (USD)
VRBO
From $352 per night (USD)
Expedia
Waterfront Beach House- Pool - Kayaks - Bikes - Boat Ramp
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Over 150 ft of private waterfront is the most majestic feature of this unique 2 bed/2 bath home. The property is complet ...
From $352 per night (USD)
Expedia
From $588 per night (USD)
VRBO
Siesta Key beach house
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Nice house with private pool with tree bedrooms and tree bath close to Siesta Key Village resturants and Beach. Canal o ...
From $588 per night (USD)
VRBO
From $696 per night (USD)
Expedia
Beachside Retreat with Pool and Beach Access
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
Service Highlights: - Professionally laundered linens & towels with each reservation. - Exceptional clean rating. - No k ...
From $696 per night (USD)
Expedia
From $571 per night (USD)
VRBO
Walk to Beach, Updated Condo, Private Patio and Grill
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Service Highlights: - Professionally laundered linens & towels with each reservation. - Exceptional clean rating. - No k ...
From $571 per night (USD)
VRBO
From $685 per night (USD)
Expedia
Spacious Updated Condo Just 2 Blocks to Siesta Key Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Service Highlights: - Professionally laundered linens & towels with each reservation. - Exceptional clean rating. - No k ...
From $685 per night (USD)
Expedia
From $571 per night (USD)
VRBO
Newly Fully Updated and Modern, Short Walk to BEACH
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Service Highlights: - Professionally laundered linens & towels with each reservation. - Exceptional clean rating. - No k ...
From $571 per night (USD)
VRBO
From $1915 per night (USD)
Expedia
Massive Mediterranean Beachside Bliss
Bedrooms:
6
Bathrooms:
7
Sleeps:
18
Across the street from the #1 Beach, two fabulous 3 bedroom, 3 bath townhomes with a shared pool and in unit elevator th ...
From $1915 per night (USD)
Expedia
From $1887 per night (USD)
VRBO
*** NEW *** Rent the WHOLE building! Sleeps 16
Bedrooms:
4
Bathrooms:
5
Sleeps:
16
Service Highlights: - Professionally laundered linens & towels with each reservation. - Exceptional clean rating. - No k ...
From $1887 per night (USD)
VRBO
From $624 per night (USD)
Expedia
The Beachside Retreat you have been looking for
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
Service Highlights: - Professionally laundered linens & towels with each reservation. - Exceptional clean rating. - No k ...
From $624 per night (USD)
Expedia
$Margaritaville - Pool ❤ w\/ Hot Tub, Close to Beaches, Restaurants, Shopping +++$
From $328 per night (USD)
VRBO
Margaritaville - Pool ❤ w\/ Hot Tub, Close to Beaches, Restaurants, Shopping +++
Bedrooms:
2
Bathrooms:
5
Sleeps:
8
Phenomenal, 4/2, 1894 sf home with all the amenities: Huge heated pool, Smart TVs in every room, Large kitchen with Isla ...
From $328 per night (USD)
VRBO
From $202 per night (USD)
VRBO
AMAZING 3 bedroom -15 miles from Venice beach.
Bedrooms:
2
Bathrooms:
4
Sleeps:
4
Amazing 3 bedroom, great for a couple looking to get away for a month or two to the Beautiful West Coast of Florida. Stu ...
From $202 per night (USD)
VRBO
From $321 per night (USD)
VRBO
Siesta Key Condo- walk to beautiful beaches, ride a free trolley around the key
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Come enjoy this adorable 2-Bedroom, 2-Bathroom centrally located Siesta Key Condo with large heated pool! The condo is a ...
From $321 per night (USD)
VRBO
From $184 per night (USD)
Expedia
Get To the Beach! Only 5 miles to Siesta Key Beach!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Charming updated duplex villa where you can enjoy beaches, shopping, restaurants and downtown Sarasota nightlife! Recen ...
From $184 per night (USD)
Expedia
From $390 per night (USD)
VRBO
Beautiful Getaway ~ 4 Miles to Venice Beach!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Florida is a beautiful state with amazing beaches and this 3-bedroom, 2.5-bath vacation rental gives you access to the b ...
From $390 per night (USD)
VRBO
From $329 per night (USD)
Expedia
Discounted rates for gorgeous one bdrm directly across from beach, near village!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
MUCH IN DEMAND AND POPULAR weeks in March are now available (Saturday to Saturday bookings). Gorgeous updated, just reno ...
From $329 per night (USD)
Expedia
From $172 per night (USD)
VRBO
Siesta Key Waterfront Condo on Turtle Beach Inlet. Fish, Swim & Boat just Steps from Your Door. The
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
Siesta Key Waterfront Condo on Turtle Beach Inlet. Fish, Swim & Boat just Steps from Your Door! Perfect location to rel ...
From $172 per night (USD)
VRBO
$Sarasota Bungalow w\/ Pergola, Garden & Waterfalls!$
From $224 per night (USD)
Expedia
Sarasota Bungalow w\/ Pergola, Garden & Waterfalls!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Book your coastal retreat to this quaint 1-bedroom, 1-bath Sarasota vacation rental cottage located just a short drive f ...
From $224 per night (USD)
Expedia
From $216 per night (USD)
VRBO
Quiet, Cozy, Bungalow with a Pool. Near Venice Beach and Warm Mineral Springs
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Open floor plan, 3 bedroom home with a breakfast bar and spacious living room that opens to a large screened in, in grou ...
From $216 per night (USD)
VRBO
From $444 per night (USD)
Expedia
Crystal Sands Tower Unit 602 - Beachfront
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Crystal Sands Condominiums! We would love to have you stay with us in one of our luxury 2-bedroom 2-bath full ...
From $444 per night (USD)
Expedia
From $263 per night (USD)
VRBO
Relax at Private Sandy Beach Aqua Pool House with FREE Bikes & Kayaks for Two!
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Welcome to our family vacation home in Venice Florida. This is one of our homes away from home and we enjoy sharing it ...
From $263 per night (USD)
VRBO
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Expedia
Modern 2 Bedroom House Near Siesta Key
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Our home is fully renovated with nearly brand new furniture. With 2 bedrooms, 2 bathrooms, and 3 beds total, we can comf ...
Click For Pricing
Expedia
From $194 per night (USD)
VRBO
Tiny House Pelican - near the beach with Free wifi!
Bedrooms:
1
Bathrooms:
2
Sleeps:
2
Amy was the first house to arrive at Tiny House Siesta. She is one of our smallest as she comfortably sleeps 3 people. S ...
From $194 per night (USD)
VRBO
From $205 per night (USD)
Expedia
Tiny Aqua Oasis- Tiny House that sleeps 6 comfortably & Free WiFi
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
It will be love at first sight with our tiny Blue Oasis; her cerulean color with bright white trim tells you you have ar ...
From $205 per night (USD)
Expedia
From $203 per night (USD)
VRBO
Tiny House modeled after the yellow lifeguard stand on famous Siesta Key Beach
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Located just over the bridge from Siesta Key and minutes away from Sarasota's thriving dining and arts districts, our su ...
From $203 per night (USD)
VRBO
From $205 per night (USD)
Expedia
Lemon Cottage in Tranquil Olde Englewood!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Exciting new! Total refurbishment of Dearborn Street is complete and looks beautiful! $14m has been spent on this. Th ...
From $205 per night (USD)
Expedia
From $215 per night (USD)
VRBO
Tiny House Sand Dollar - beachy tiny house living
Bedrooms:
1
Bathrooms:
3
Sleeps:
4
Experience compact living in Tiny House Sand dollar. Roughly 350 sq feet and designed for simplicity and efficiency. You ...
From $215 per night (USD)
VRBO
Click For Pricing
Expedia
Delightful Pool House 3 Miles to Siesta Key Beaches
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Our private pool home is fully set up with brand new furniture. With 3 bedrooms, 2 bathrooms, and 4 total beds, we can c ...
Click For Pricing
Expedia
Click For Pricing
VRBO
Tiny House Piña Colada- bright & beautiful near the beach with Free WiFi
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
This Tiny House was built by Tumbleweed. Once you walk thru the door, you know you are at the beach. Eleanor has bright ...
Click For Pricing
VRBO
From $205 per night (USD)
Expedia
Tiny Coral Oasis- sleeps 6 comfortably & Free WiFi
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
It will be love at first sight with our tiny Blue Oasis; her cerulean color with bright white trim tells you you have ar ...
From $205 per night (USD)
Expedia
From $471 per night (USD)
VRBO
Beach Front Condo On Siesta Key #1 Beach In The USA, With Gulf Views, Top Floor!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Recently renovated to include open concept living with a brand new Gourmet Kitchen and island. Granite counter tops, ...
From $471 per night (USD)
VRBO
From $204 per night (USD)
Expedia
Red Lifeguard Stand - Living large in a Tiny House with FREE WiFi
Bedrooms:
1
Bathrooms:
3
Sleeps:
4
Located just over the bridge from Siesta Key and minutes away from Sarasota's thriving dining and arts districts, our su ...
From $204 per night (USD)
Expedia
From $291 per night (USD)
VRBO
Perfect home away, modern amenities, ~ Heated Pool ~ Close to S. Venice Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Come and enjoy our Lemon Tree House! Virtual Tour: https://www.youtube.com/embed/Y68OcyA9tv8?rel=0.  Escape to your ...
From $291 per night (USD)
VRBO
$Lakefront Property on Siesta Key Among Tropical Landscape W\/ Heated Pool$
From $312 per night (USD)
Expedia
Lakefront Property on Siesta Key Among Tropical Landscape W\/ Heated Pool
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This is a one bedroom one bathroom unit furnished with king-size bed in the private bedroom and queen-size sleeper sofa ...
From $312 per night (USD)
Expedia
From $208 per night (USD)
VRBO
Beachfront Sarasota Resort Condo: Siesta Key View!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Sink your toes into Siesta Key's white sand beaches and swim in the crystal clear waters of the Gulf of Mexico during yo ...
From $208 per night (USD)
VRBO
From $345 per night (USD)
Expedia
Hidden Paradise on Lakefront Property Among Tropical Landscape on Siesta Key
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This is a one bedroom one bathroom unit furnished with king-size bed in the private bedroom and queen-size sleeper sofa ...
From $345 per night (USD)
Expedia
$Small and Quiet Lakefront Resort on Siesta Key W\/ Heated Pool and Kayaks$
From $263 per night (USD)
VRBO
Small and Quiet Lakefront Resort on Siesta Key W\/ Heated Pool and Kayaks
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This is a two bedroom two bathroom unit furnished with king-size bed in one private bedroom, two twin-size beds in the o ...
From $263 per night (USD)
VRBO
From $245 per night (USD)
Expedia
1 Block to the Beach on Siesta Key Vacation Rental Home with Swimming Pool
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Welcome to Cape Aqua! This single family vacation rental home on Siesta Key has 3 bedrooms 2 1/2 baths and pool. Located ...
From $245 per night (USD)
Expedia
From $276 per night (USD)
VRBO
Spacious vacation rental condo with lagoon views, beach access, and pool
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
When you're overdue for a refreshing vacation, a trip to Siesta Key is always a good idea. Making the experience even mo ...
From $276 per night (USD)
VRBO
$Sarasota House w\/ Private Pool - 4 Mi to Beach!$
From $263 per night (USD)
Expedia
Sarasota House w\/ Private Pool - 4 Mi to Beach!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Whether you're looking to spend time by the pool or at the beach, 'Siesta Jewel’ is perfect for travelers on a memorable ...
From $263 per night (USD)
Expedia
$Downtown. Sleeps 2. Mins to Beaches & Airport \/ Ground Floor Unit$
From $96 per night (USD)
VRBO
Downtown. Sleeps 2. Mins to Beaches & Airport \/ Ground Floor Unit
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Ground floor unit (No Stairs). Sleeps two (2). Renting this unit will place you within walking distance of Sarasota’s do ...
From $96 per night (USD)
VRBO
From $335 per night (USD)
Expedia
Vacation Rental on Siesta Key
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to this modern and spacious tropical getaway. This newly renovated two bedroom, two bathroom, and den Condo is l ...
From $335 per night (USD)
Expedia

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