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From $288 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 $288 per night (USD)
VRBO
From $289 per night (USD)
Expedia
Steps to Water! Sunsets, Hot Tub! Englewood, Fl. The Best Kept Secret!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Listing Description: Welcome to 20 Steps to Water! Sunsets, and Hot tub! The dock is being replaced and is not usable ...
From $289 per night (USD)
Expedia
From $167 per night (USD)
VRBO
Cozy Sarasota Retreat - 3 Blocks to the Coast!
Bedrooms:
1
Bathrooms:
3
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 $167 per night (USD)
VRBO
From $137 per night (USD)
Expedia
Manasota Key Retreat with free use of bikes and beach supplies
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
Come as you are, kick off your shoes, and immerse yourself into this tropical Paradise. The locally known Lemon Bay Park ...
From $137 per night (USD)
Expedia
$Waterfront\/Pool Home under 5 min walk to Siesta Key Village and Beach$
From $799 per night (USD)
VRBO
Waterfront\/Pool Home under 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 $799 per night (USD)
VRBO
From $328 per night (USD)
Expedia
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 $328 per night (USD)
Expedia
From $113 per night (USD)
VRBO
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 $113 per night (USD)
VRBO
Click For Pricing
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 ...
Click For Pricing
Expedia
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VRBO
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 ...
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VRBO
From $137 per night (USD)
Expedia
Downtown Sarasota Home By Siesta Key and Golfing
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Beautiful remodeled apartment in a quiet neighborhood. 10min to Dwtn, 15min to Siesta & Lido Beach. Unit has 1 bedroom w ...
From $137 per night (USD)
Expedia
From $271 per night (USD)
VRBO
Englewood Villa - 3 BR, 2 BA, Pet Friendly
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
*** 47% Discount when you book 28 or more nights during non-winter months *** Summary: Completely renovated and remodele ...
From $271 per night (USD)
VRBO
$1\/1 Tower Gulf N (034)$
From $426 per night (USD)
Expedia
1\/1 Tower Gulf N (034)
Bedrooms:
1
Bathrooms:
2
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 $426 per night (USD)
Expedia
From $206 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 $206 per night (USD)
VRBO
Click For Pricing
Expedia
“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, ...
Click For Pricing
Expedia
$Luxury Waterfront Views \/ Pool \/ 1400sf \/ Minutes to Beach$
From $426 per night (USD)
VRBO
Luxury Waterfront Views \/ Pool \/ 1400sf \/ Minutes to Beach
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Our home, located on Siesta Key, with breathtaking intercostal water views is fully furnished with all the amenities you ...
From $426 per night (USD)
VRBO
From $392 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 $392 per night (USD)
Expedia
From $138 per night (USD)
VRBO
Harbor Towers Yacht & 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 $138 per night (USD)
VRBO
From $223 per night (USD)
Expedia
Siesta Key Village-Suite #1: A block to the Beach!
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
Looking for the Ultimate Siesta Key Experience? This is it! Located in the Center of the Iconic Siesta Key Village, Sies ...
From $223 per night (USD)
Expedia
From $359 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 $359 per night (USD)
VRBO
From $422 per night (USD)
Expedia
Siesta Cooler: Only Minutes Walk to Siesta Beach!
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
Light, bright and cozy in the HEART of Siesta Key Village! Open floor plan including queen-sized murphy bed, Smart TVs, ...
From $422 per night (USD)
Expedia
From $412 per night (USD)
VRBO
Siesta Cool : Only Minutes Walk to Siesta Beach!
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
Light, bright and cozy in the HEART of Siesta Key Village! Open floor plan including queen-sized murphy bed, Smart TVs, ...
From $412 per night (USD)
VRBO
From $202 per night (USD)
Expedia
Siesta Key Village -Suite #2: A Block to the Beach, In the HEART of the Village!
Bedrooms:
1
Bathrooms:
3
Sleeps:
3
Looking for the Ultimate Siesta Key Experience? This is it! Located in the Center of the Iconic Siesta Key Village, Sies ...
From $202 per night (USD)
Expedia
From $229 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 $229 per night (USD)
VRBO
From $209 per night (USD)
Expedia
Siesta Key Village-Suite #3: A Block to the Beach!
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
Looking for the Ultimate Siesta Key Experience? This is it! Located in the Center of the Iconic Siesta Key Village, Sies ...
From $209 per night (USD)
Expedia
From $830 per night (USD)
VRBO
Tranquil St. Armand's Pool Home
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
This is a fabulous 4 bedroom 3 bath home with a light and bright open floor plan. You will enjoy the new kitchen with gr ...
From $830 per night (USD)
VRBO
From $132 per night (USD)
Expedia
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 $132 per night (USD)
Expedia
$2 Bed\/2 bath Condo Steps to Siesta Key Beach!$
From $281 per night (USD)
VRBO
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 $281 per night (USD)
VRBO
From $288 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 $288 per night (USD)
Expedia
From $165 per night (USD)
VRBO
BEAUTIFUL UPDATED CONDO CLOSE TO 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 $165 per night (USD)
VRBO
From $321 per night (USD)
Expedia
Private Beachfront on Siesta Key
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Paradise and convenience await you at this newly renovated, spacious 2 bedroom, 2 bath condo. This full furnished unit ...
From $321 per night (USD)
Expedia
From $235 per night (USD)
VRBO
Great Siesta Key Location with Deeded Beach Access at The Anchorage 308
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Great Siesta Key Location at The Anchorage. Deeded Beach Access, Walk to Shopping & Dining! Spacious 2 bedroom, 2 bath, ...
From $235 per night (USD)
VRBO
From $213 per night (USD)
Expedia
GORGEOUS NOKOMIS BEACH HOME
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Beautifully appointed 2 bedroom (king bed in the master and queen bed in the second bedroom) /2 bath, plus DEN (den has ...
From $213 per night (USD)
Expedia
From $488 per night (USD)
VRBO
A few steps from the beach with community pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Enjoy beach and pool days to the fullest at this two bedroom two bath updated vacation rental on Siesta Key. No need to ...
From $488 per night (USD)
VRBO
$Peaceful 1bed\/1bath Condo Golf & Lake views in the Meadows$
From $101 per night (USD)
Expedia
Peaceful 1bed\/1bath Condo Golf & Lake views in the Meadows
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Great condo in the Meadows, Longwater Chase Community, on the 2nd floor (no elevator), 1 parking spot included. This is ...
From $101 per night (USD)
Expedia
From $271 per night (USD)
VRBO
Pet-friendly condo a short walk from private beach & fishing dock on bay
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Get your second wind at A Second Wind! Roomy, quiet and comfortable third-floor condo at beautiful Island Reef. Beach-to ...
From $271 per night (USD)
VRBO
From $139 per night (USD)
Expedia
Country Club Living close to Siesta Key Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Fully Furnished and Totally Updated 2 bed with a den or 3 bed (currently set up as), 2 bath, 1414 sq ft condo with garag ...
From $139 per night (USD)
Expedia
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VRBO
Sarasota Best Place, Siesta key only 7 ml, BBQ+, family friendly
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
House being remodeled in 2020, New appliances, City Water! (sure not well funky egg smell!) Two New Air Conditioner unit ...
Click For Pricing
VRBO
From $415 per night (USD)
Expedia
Penthouse suite with ocean views 2Br 2 Bath DISCOUNT FOR JANUARY RENTERS
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Newly renovated and Decorated Penthouse with ocean views. This 5th floor unit is located Two blocks from the famous MTV ...
From $415 per night (USD)
Expedia
From $176 per night (USD)
VRBO
Renovated Bahia Vista 2nd floor 2 bedroom garden condo with partial Gulf views
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Fully furnished beach side condo on Venice Island in the Bahia Vista community amongst the canopy of BaynanTrees, Palms ...
From $176 per night (USD)
VRBO
From $214 per night (USD)
Expedia
NEW REDUCED PRICES Pool Home in South Venice - Close to Beaches
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Comfortable in Quiet Neighborhood. The open airy living room features comfortable furnishings, and fantastic floors. I ...
From $214 per night (USD)
Expedia
From $174 per night (USD)
VRBO
Emerald Palms Unit 6
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Updated cottage with beautiful Lemon Bay view. 2 bedroom, 2 bathroom with full kitchen. Enjoy amazing sunsets on the wat ...
From $174 per night (USD)
VRBO
From $129 per night (USD)
Expedia
Relaxat at Lovely home by the Warm Mineral Springs in Sunshine Florida.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to our cozy retreat! We’re absolutely delighted to have you as our guest! As you settle in, please feel right ...
From $129 per night (USD)
Expedia
From $1122 per night (USD)
VRBO
Downtown Main Street Loft
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Enjoy a stylish experience at this centrally-located place. Perfect for friends or family. Walking distance to all downt ...
From $1122 per night (USD)
VRBO
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Expedia
Location, Location- Walk to Nokomis Beach!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Nokomis offers you beautiful beaches to enjoy with plenty of recreational areas to relax, have picnics or just watch th ...
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Expedia
From $308 per night (USD)
VRBO
Heated Pool ❤ Home- Close to Beaches, Restaurants
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Beautiful 3/2 single-level Heated Pool home with almost 1600 sf of living space. Located in Southgate & close to everyt ...
From $308 per night (USD)
VRBO
$Adorable1\/1 - Walk to Siesta Key!$
From $121 per night (USD)
Expedia
Adorable1\/1 - Walk to Siesta Key!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Fully remodeled duplex apartment in one of the most desirable neighborhoods in Sarasota, just over the bridge from Siest ...
From $121 per night (USD)
Expedia
From $372 per night (USD)
VRBO
Imagine living in luxury at the Magnificent Venetian Golf and River Club!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Beautiful appointed update home with 2-2 split plan overlooking a private lake. 15 min to 7 gulf beaches.. Incredible re ...
From $372 per night (USD)
VRBO
From $1093 per night (USD)
Expedia
The Coral Reef | Pet Friendly 🐶 Located in Siesta Key Village, Steps to Siesta Key Beach!
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Welcome to The Coral Reef, the perfect destination for small to medium sized families or groups looking for an intimate ...
From $1093 per night (USD)
Expedia
From $804 per night (USD)
VRBO
Sea Breeze | Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to Sea Breeze, the perfect destination for small families or couples looking for an intimate yet unforgettable v ...
From $804 per night (USD)
VRBO
From $784 per night (USD)
Expedia
Sea Foam | Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to Sea Foam, the perfect destination for small families or couples looking for an intimate yet unforgettable vac ...
From $784 per night (USD)
Expedia
From $2268 per night (USD)
VRBO
The Beachy Keen | Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Welcome to The Beachy Keen, the perfect destination for small to medium sized families or groups looking for an intimate ...
From $2268 per night (USD)
VRBO
From $804 per night (USD)
Expedia
Sea Coast | Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to Sea Coast, the perfect destination for small families or couples looking for an intimate yet unforgettable va ...
From $804 per night (USD)
Expedia
From $831 per night (USD)
VRBO
Sea Dream | Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to Sea Dream, the perfect destination for small families or couples looking for an intimate yet unforgettable va ...
From $831 per night (USD)
VRBO
From $871 per night (USD)
Expedia
Sea Escape | Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to Sea Escape, the perfect destination for small families or couples looking for an intimate yet unforgettable v ...
From $871 per night (USD)
Expedia
From $775 per night (USD)
VRBO
Sea Angel | Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to Sea Angel, the perfect destination for small families or couples looking for an intimate yet unforgettable va ...
From $775 per night (USD)
VRBO
From $2198 per night (USD)
Expedia
CJs on Siesta | Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!
Bedrooms:
6
Bathrooms:
7
Sleeps:
24
Welcome to CJ's on Siesta, the perfect destination for large families and groups seeking an unforgettable vacation exper ...
From $2198 per night (USD)
Expedia
Click For Pricing
VRBO
Beautiful Single Family Home
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
We have a 3 bedroom, 2 bathroom fully furnished home for rent, for the month of February or March of 2021 in the gated c ...
Click For Pricing
VRBO
From $371 per night (USD)
Expedia
Luxurious Private Villa,Heated pool, walk to beach,2 King suites,Free wi fi
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
This luxurious villa, built on a very private 3/4 acre lot, sits well back from the road. Mature oak and palm trees line ...
From $371 per night (USD)
Expedia
From $228 per night (USD)
VRBO
Vacation delight! Cozy condo just steps from the beach and St. Armands circle.
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
If you are looking for a quiet island beach community that offers alot to do then you've come to the right place. Thi ...
From $228 per night (USD)
VRBO
From $131 per night (USD)
Expedia
Near Siesta Key beaches, Many resurants, malls of condo on Tamiani trail
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Apartment has washer dryer. Parking on grounds for tenants and guests . not public. Nice Gym near heated pool with Jac ...
From $131 per night (USD)
Expedia
Click For Pricing
VRBO
Inn on the Beach 3007 by FVC
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Offered by FL Vacation Connection, this island getaway is located on the southern tip of Longboat Key with beautiful bea ...
Click For Pricing
VRBO
$Oceanfront home w\/sunset views of Sarasota Bay$
From $616 per night (USD)
Expedia
Oceanfront home w\/sunset views of Sarasota Bay
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Treat your family, friends, and beloved small dogs to an unforgettable oceanfront getaway in sunny Florida! Convenientl ...
From $616 per night (USD)
Expedia
From $520 per night (USD)
VRBO
Walk to beach Heated POOL King bed DAILY WEEKLY Villa 1 SPECIALS
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Enjoy Siesta Key in style! We are a small resort on Siesta Key offering daily rentals Brand new high end ground floor lu ...
From $520 per night (USD)
VRBO
From $351 per night (USD)
Expedia
PARADISE ! 2 bedroom 2 bathroom with incredible views
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This spacious large ground floor corner unit is just steps away from the pool, hot-tub, fishing pier and poolside BBQ's. ...
From $351 per night (USD)
Expedia
From $526 per night (USD)
VRBO
Clean Perfectly Remodeled Townhome, Steps From the Private Beach. 3 night min
Bedrooms:
3
Bathrooms:
2
Sleeps:
5
Impeccably Clean, the reviews speak for themselves! Located at Siesta Beach House, 5950 Midnight Pass Road, this luxuri ...
From $526 per night (USD)
VRBO
From $645 per night (USD)
Expedia
Siesta Key Beach Resort Jamaica Royale
Bedrooms:
3
Bathrooms:
2
Sleeps:
4
The unit is a 2 bedroom, 2 bath with a King Posturpedic bed in the master bedroom, Second bedroom has a Queen bed .Eac ...
From $645 per night (USD)
Expedia
From $929 per night (USD)
VRBO
Luxury 2 bedroom Beachfront Condo by FVC
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
FL Vacation Connection offers this 2brm luxury condo. 3rd floor. 1700 sq ft. 52' beachfront balcony. Large Living, dini ...
From $929 per night (USD)
VRBO
From $292 per night (USD)
Expedia
Sarasota Modern Home minutes to Siesta & Downtown
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
This modern home will be your ultimate vacation retreat. Three spacious bedrooms, office/den, two bathrooms and a modern ...
From $292 per night (USD)
Expedia
From $83 per night (USD)
VRBO
Family Friendly Cottage @ Sun N Fun Resort
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Family friendly, beautiful vacation home rental at the best resort in sunny Sarasota! Guest access Guests have full ac ...
From $83 per night (USD)
VRBO
From $291 per night (USD)
Expedia
NEWLY RENOVATED!!!!! directly across from the world famous Siesta Key Beach.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
NEWLY RENOVATED!!!!!!!! Your vacation awaits you in this lovely two bedroom, two bath condo directly across from the wo ...
From $291 per night (USD)
Expedia
From $313 per night (USD)
VRBO
Siesta Key - Gulf-Front Retreat - 2 BR – Free Boat Docks - Upscale
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Siesta Key - Gulf-Front Retreat - 2 BR - Free Boat Docks - Upscale Located Next to Turtle Beach on the Southern End of S ...
From $313 per night (USD)
VRBO
From $218 per night (USD)
Expedia
Great Siesta Key Location! Short Walk to the Beach, Shopping, Dining & More!. Vista Hermosa 312A
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Beautifully updated condo at Vista Hermosa located on the quieter Southern end of Siesta Key. Just a short walk to the b ...
From $218 per night (USD)
Expedia
From $487 per night (USD)
VRBO
Modern Crystal Sands Villa: Private Beach, 2 Heated Pools, Steps to Crescent Beach & Siesta Key Fun
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Looking for a great deal? Discounts are automatically applied based on your length of stay! No need for promo codes or r ...
From $487 per night (USD)
VRBO
From $348 per night (USD)
Expedia
Specious and renovated 2 bed 2 bath house
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Hello and thank you for visiting our listing of our freshly renovated house with brand new kitchen and new bathrooms! ...
From $348 per night (USD)
Expedia
From $370 per night (USD)
VRBO
Sparkling Rental Close to Beaches and Downtown
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This charming home has sparkling restored Terrazzo floors that lend a beautiful shine throughout this 3 bed/ 2 bath beac ...
From $370 per night (USD)
VRBO
From $290 per night (USD)
Expedia
Private Entrance Condo - Large patio with direct pool access!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Paradise on Siesta Key is our way of describing this wonderful ground-floor unit with a private patio. The beautiful vie ...
From $290 per night (USD)
Expedia
$Charming 2\/2 Villa in Village des Pins - 15 min from SIESTA KEY$
From $156 per night (USD)
VRBO
Charming 2\/2 Villa in Village des Pins - 15 min from SIESTA KEY
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Agreeable villa with lanai in the Village des Pins Community (with an outdoor pool!), only at a 15 min drive from the #1 ...
From $156 per night (USD)
VRBO
$Adorable two bedroom condo\nwalk to the beach and st Armand’s circle$
From $254 per night (USD)
Expedia
Adorable two bedroom condo\nwalk to the beach and st Armand’s circle
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Be sure to check out our other properties 512091- Living the Dream on Lido I ***************************************** ...
From $254 per night (USD)
Expedia
From $391 per night (USD)
VRBO
Sunset Boulevard - One Bedroom Condo on Casey Key with Great view
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Updated one bedroom one bath condo located on beautiful Casey Key. Fully furnished kitchen and dining area. Great view f ...
From $391 per night (USD)
VRBO
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Expedia
Cozy vacation home 5 mins from downtown!!!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Keep it simple at this peaceful and centrally-located place. A perfect place to bring your family to vacation. Close to ...
Click For Pricing
Expedia
From $360 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 $360 per night (USD)
VRBO
From $321 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 $321 per night (USD)
Expedia
$Sarasota Getaway w\/ Private Pool & Backyard Oasis!$
From $479 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 $479 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 $203 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 $203 per night (USD)
VRBO
From $137 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 $137 per night (USD)
Expedia
From $717 per night (USD)
VRBO
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 $717 per night (USD)
VRBO
From $318 per night (USD)
Expedia
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 $318 per night (USD)
Expedia
From $174 per night (USD)
VRBO
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 $174 per night (USD)
VRBO
$Siesta Sunset | Luxurious Beach Front Penthouse w\/ Views of Gulf, Minutes to Siesta Key Village$
From $612 per night (USD)
Expedia
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 $612 per night (USD)
Expedia
$Villa Castile | Pet Friendly Home on Siesta Key w\/ Private Heated Pool, Walk to Beach & Village!$
From $802 per night (USD)
VRBO
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 $802 per night (USD)
VRBO
From $281 per night (USD)
Expedia
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)
Expedia
From $375 per night (USD)
VRBO
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 $375 per night (USD)
VRBO
$Coconut Cottage | Home on Lido Key w\/ Private Heated Pool\/Spa, Walk to Lido Beach & St. Armands!$
From $863 per night (USD)
Expedia
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 Charm of Coconut Cottage – Your Private Lido Key Retreat Discover your perfect getaway at Coconut Cottage, ...
From $863 per night (USD)
Expedia
From $162 per night (USD)
VRBO
Ideal location Siesta Key
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
2 week minimum rental from April through December. Currently available for the month of January 2026 select the first da ...
From $162 per night (USD)
VRBO
From $700 per night (USD)
Expedia
LUXURY HOUSE BY THE CANAL , Pets welcome 😀🐕.
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Our beautiful 3 bedroom / 2 bathroom house is located in the heart of Siesta Key Village. The house features outdoor po ...
From $700 per night (USD)
Expedia
From $239 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 $239 per night (USD)
VRBO
From $127 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 $127 per night (USD)
Expedia
$Harbor Towers Yacht & Racquet Club - Gulf Facing 2\/2 Condo - Fully Upgraded!$
From $279 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 $279 per night (USD)
VRBO
From $184 per night (USD)
Expedia
Tiny House Siesta- perfect tiny house for two!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Just enough room for two. This cozy Tiny House was handcrafted in Florida and has found its way to us. You will ...
From $184 per night (USD)
Expedia

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