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From $390 per night (USD)
VRBO
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 $390 per night (USD)
VRBO
From $135 per night (USD)
Expedia
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 $135 per night (USD)
Expedia
From $391 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 $391 per night (USD)
VRBO
From $391 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 $391 per night (USD)
Expedia
From $236 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 $236 per night (USD)
VRBO
From $374 per night (USD)
Expedia
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 $374 per night (USD)
Expedia
From $776 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 $776 per night (USD)
VRBO
From $328 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 $328 per night (USD)
VRBO
From $263 per night (USD)
VRBO
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 $263 per night (USD)
VRBO
From $428 per night (USD)
Expedia
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 $428 per night (USD)
Expedia
From $167 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 $167 per night (USD)
VRBO
From $250 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 $250 per night (USD)
Expedia
From $280 per night (USD)
VRBO
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 $280 per night (USD)
VRBO
From $157 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 $157 per night (USD)
VRBO
From $349 per night (USD)
VRBO
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 $349 per night (USD)
VRBO
From $221 per night (USD)
Expedia
Great Siesta Key Location with Deeded Beach Access at The Anchorage 308
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Great Siesta Key Location at The Anchorage. Deeded Beach Access, Walk to Shopping & Dining! Spacious 2 bedroom, 2 bath, ...
From $221 per night (USD)
Expedia
From $261 per night (USD)
VRBO
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 $261 per night (USD)
VRBO
From $249 per night (USD)
Expedia
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 $249 per night (USD)
Expedia
From $96 per night (USD)
VRBO
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 $96 per night (USD)
VRBO
From $236 per night (USD)
Expedia
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 $236 per night (USD)
Expedia
From $120 per night (USD)
VRBO
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 $120 per night (USD)
VRBO
Click For Pricing
Expedia
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
Expedia
From $369 per night (USD)
VRBO
Penthouse suite with ocean views 2Br 2 Bath “Great sunsets from lanai”
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 $369 per night (USD)
VRBO
From $176 per night (USD)
Expedia
Renovated Bahia Vista 2nd floor 2 bedroom garden condo with partial Gulf views
Bedrooms:
1
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)
Expedia
From $278 per night (USD)
VRBO
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 $278 per night (USD)
VRBO
From $148 per night (USD)
Expedia
Relaxat at Lovely home by the Warm Mineral Springs in Sunshine Florida.
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Welcome to our cozy retreat! We’re absolutely delighted to have you as our guest! As you settle in, please feel right ...
From $148 per night (USD)
Expedia
Click For Pricing
VRBO
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 ...
Click For Pricing
VRBO
From $267 per night (USD)
Expedia
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 $267 per night (USD)
Expedia
From $112 per night (USD)
VRBO
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 $112 per night (USD)
VRBO
From $302 per night (USD)
Expedia
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 $302 per night (USD)
Expedia
From $3274 per night (USD)
VRBO
The Coral Reef | Pet Friendly 🐶 Located in Siesta Key Village, Steps to Siesta Key Beach!
Bedrooms:
3
Bathrooms:
3
Sleeps:
12
Welcome to The Coral Reef, the perfect destination for small to medium sized families or groups looking for an intimate ...
From $3274 per night (USD)
VRBO
From $925 per night (USD)
Expedia
Sea Breeze | Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Welcome to Sea Breeze, the perfect destination for small families or couples looking for an intimate yet unforgettable v ...
From $925 per night (USD)
Expedia
From $881 per night (USD)
VRBO
Sea Foam | Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Welcome to Sea Foam, the perfect destination for small families or couples looking for an intimate yet unforgettable vac ...
From $881 per night (USD)
VRBO
From $3236 per night (USD)
Expedia
The Beachy Keen | Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!
Bedrooms:
3
Bathrooms:
3
Sleeps:
10
Welcome to The Beachy Keen, the perfect destination for small to medium sized families or groups looking for an intimate ...
From $3236 per night (USD)
Expedia
From $881 per night (USD)
VRBO
Sea Coast | Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Welcome to Sea Coast, the perfect destination for small families or couples looking for an intimate yet unforgettable va ...
From $881 per night (USD)
VRBO
From $925 per night (USD)
Expedia
Sea Dream | Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Welcome to Sea Dream, the perfect destination for small families or couples looking for an intimate yet unforgettable va ...
From $925 per night (USD)
Expedia
From $881 per night (USD)
VRBO
Sea Escape | Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Welcome to Sea Escape, the perfect destination for small families or couples looking for an intimate yet unforgettable v ...
From $881 per night (USD)
VRBO
From $881 per night (USD)
Expedia
Sea Angel | Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Welcome to Sea Angel, the perfect destination for small families or couples looking for an intimate yet unforgettable va ...
From $881 per night (USD)
Expedia
From $1832 per night (USD)
VRBO
CJs on Siesta | Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!
Bedrooms:
6
Bathrooms:
6
Sleeps:
24
Welcome to CJ's on Siesta, the perfect destination for large families and groups seeking an unforgettable vacation exper ...
From $1832 per night (USD)
VRBO
Click For Pricing
Expedia
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
Expedia
From $353 per night (USD)
VRBO
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 $353 per night (USD)
VRBO
From $226 per night (USD)
Expedia
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. Th ...
From $226 per night (USD)
Expedia
From $131 per night (USD)
VRBO
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)
VRBO
From $409 per night (USD)
Expedia
Oceanfront home w/sunset views of Sarasota Bay
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Treat your family, friends, and beloved small dogs to an unforgettable oceanfront getaway in sunny Florida! Convenientl ...
From $409 per night (USD)
Expedia
From $541 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 $541 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 $411 per night (USD)
VRBO
Experience paradise steps away from Siesta Key Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Escape to the sun-drenched shores of Siesta Key and experience the ultimate in coastal living at our charming 2-bedroom ...
From $411 per night (USD)
VRBO
From $632 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 $632 per night (USD)
Expedia
From $884 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 $884 per night (USD)
VRBO
From $312 per night (USD)
VRBO
Sarasota Modern Home minutes to Siesta & Downtown
Bedrooms:
1
Bathrooms:
4
Sleeps:
9
This modern home will be your ultimate vacation retreat. Three spacious bedrooms, office/den, two bathrooms and a modern ...
From $312 per night (USD)
VRBO
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 $261 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 $261 per night (USD)
Expedia
From $298 per night (USD)
VRBO
Siesta Key - Gulf-Front Retreat - 2 BR – Free Boat Docks - Upscale
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Siesta Key - Gulf-Front Retreat - 2 BR - Free Boat Docks - Upscale Located Next to Turtle Beach on the Southern End of ...
From $298 per night (USD)
VRBO
From $195 per night (USD)
Expedia
Great Siesta Key Location! Short Walk to the Beach, Shopping, Dining & More!. Vista Hermosa 312A
Bedrooms:
2
Bathrooms:
2
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 $195 per night (USD)
Expedia
From $355 per night (USD)
VRBO
Sun, Sand and Savings Sarasota Deals
Bedrooms:
2
Bathrooms:
2
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 $355 per night (USD)
VRBO
From $194 per night (USD)
Expedia
Specious and renovated 2 bed 2 bath house
Bedrooms:
1
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 $194 per night (USD)
Expedia
From $280 per night (USD)
VRBO
Private Entrance Condo - Large patio with direct pool access!
Bedrooms:
2
Bathrooms:
2
Sleeps:
7
Paradise on Siesta Key is our way of describing this wonderful ground-floor unit with a private patio. The beautiful vie ...
From $280 per night (USD)
VRBO
$Adorable two bedroom condo\nwalk to the beach and st Armand’s circle$
From $245 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 $245 per night (USD)
Expedia
From $132 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 $132 per night (USD)
VRBO
Click For Pricing
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 $383 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 $383 per night (USD)
VRBO
From $360 per night (USD)
Expedia
100 STEPS YOU'RE ON USA's #1 BEACH,RENTING SINCE 1998, SLEEP 6 IN BEDS
Bedrooms:
2
Bathrooms:
2
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)
Expedia
From $471 per night (USD)
VRBO
Sarasota Getaway w/ Private Pool & Backyard Oasis!
Bedrooms:
3
Bathrooms:
3
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 $471 per night (USD)
VRBO
From $152 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 $152 per night (USD)
Expedia
From $204 per night (USD)
VRBO
Unique Nokomis Home ~ 2 Mi to Beach Access!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Nestled a short distance from oceanfront relaxation, this 2-bedroom, 2-bath vacation rental offers serenity during your ...
From $204 per night (USD)
VRBO
From $166 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 $166 per night (USD)
Expedia
From $299 per night (USD)
VRBO
Beachcomber unit 205
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Our building is located on the beach, this unit has an ISLAND view. Beautifully renovated 1 bedroom, 1 bath ...
From $299 per night (USD)
VRBO
From $672 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 $672 per night (USD)
Expedia
From $275 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 $275 per night (USD)
VRBO
From $174 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 $174 per night (USD)
Expedia
From $429 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 $429 per night (USD)
VRBO
From $461 per night (USD)
Expedia
Villa Castile | Pet Friendly Home on Siesta Key w/ Private Heated Pool, Walk to Beach & Village!
Bedrooms:
3
Bathrooms:
3
Sleeps:
10
Welcome to Villa Castile, a luxurious retreat located just outside the vibrant Siesta Key Village. This stunning vacatio ...
From $461 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 $363 per night (USD)
Expedia
Lovely Heated Pool Home ❤ Walk to Beach, Restaurants, Bike & Boat Rentals & More
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Location! Location! Location! -- Stunning pool home with over 2600 sf of living space located steps from the South bridg ...
From $363 per night (USD)
Expedia
From $714 per night (USD)
VRBO
Coconut Cottage | Home on Lido Key w/ Private Heated Pool/Spa, Walk to Lido Beach & St. Armands!
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
Escape to the Charm of Coconut Cottage – Your Private Lido Key Retreat Discover your perfect getaway at Coconut Cottage, ...
From $714 per night (USD)
VRBO
From $159 per night (USD)
Expedia
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 $159 per night (USD)
Expedia
From $120 per night (USD)
VRBO
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 $120 per night (USD)
VRBO
From $280 per night (USD)
Expedia
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 $280 per night (USD)
Expedia
From $175 per night (USD)
VRBO
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 $175 per night (USD)
VRBO
From $304 per night (USD)
Expedia
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 ...
From $304 per night (USD)
Expedia
From $206 per night (USD)
VRBO
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 $206 per night (USD)
VRBO
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 $373 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 $373 per night (USD)
VRBO
From $350 per night (USD)
Expedia
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 $350 per night (USD)
Expedia
From $2129 per night (USD)
VRBO
Nearly Beachfront, Gulf Views, Heated Pool & Pet-Friendly - Sugar Sand Cottage
Bedrooms:
3
Bathrooms:
5
Sleeps:
19
Sugar Sand Cottage by Siesta Key Luxury Rental Properties Home in Siesta Key, Florida Siesta Key Luxury Rental Proper ...
From $2129 per night (USD)
VRBO
From $137 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 $137 per night (USD)
VRBO
From $856 per night (USD)
VRBO
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. We have place for 8 people to ...
From $856 per night (USD)
VRBO
From $435 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 $435 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 $157 per night (USD)
Expedia
Lake view spacious 2bdr CONDO 7 min by the BEACH
Bedrooms:
2
Bathrooms:
2
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 $157 per night (USD)
Expedia
From $208 per night (USD)
VRBO
One Bedroom - Ground Floor Condo - Heated Pool - Siesta Key Village
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
VILLAGE WEST - Deluxe Ground Floor Vacation Condo in Siesta Key Village with Heated Pool Located right in the Heart of ...
From $208 per night (USD)
VRBO
From $180 per night (USD)
Expedia
Cozy Heated Pool Home, 3 bed 2 bath, 25 min 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 $180 per night (USD)
Expedia
From $261 per night (USD)
VRBO
Unit 401 Beautiful view of the Gulf of Mexico
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Schedule your escape to Siesta Key Beach in the bright and clean Unit 401. This top floor, end unit has an open floor pl ...
From $261 per night (USD)
VRBO
From $279 per night (USD)
Expedia
Villa Fiesta | Pet Friendly Home In Siesta Village, Heated Pool and Hot Tub, Walk to the Beach!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Welcome to Villa Fiesta, your ultimate island retreat nestled in the heart of Siesta Key Village. This stunning property ...
From $279 per night (USD)
Expedia
From $568 per night (USD)
VRBO
Casa De Siesta | Pet Friendly Home In Siesta Village, Private Pool and Hot Tub, Walk to the Beach!
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Welcome to Casa De Siesta, your ultimate island retreat nestled in the heart of Siesta Key Village. This stunning proper ...
From $568 per night (USD)
VRBO
From $572 per night (USD)
Expedia
Siesta Sunrise-Just steps to the beach and village
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Location, location, location! Siesta Sunrise is just steps to beautiful Siesta Key beach and a short walk to the village ...
From $572 per night (USD)
Expedia
From $262 per night (USD)
VRBO
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 $262 per night (USD)
VRBO
From $203 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 $203 per night (USD)
VRBO
From $441 per night (USD)
VRBO
Myakka River
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Bring your small boat or kayaks. Located in Venice near Wellen Park. This area is fisherman’s paradise. Tarpon, Redfish, ...
From $441 per night (USD)
VRBO
From $680 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 $680 per night (USD)
Expedia

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