Sarasota Area Rentals
From $225 per night (USD)VRBO
Private Beachfront on Siesta Key
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
Paradise and convenience await you at this newly renovated, spacious 2 bedroom, 2 bath condo. This full furnished unit ...
From $225 per night (USD)VRBO
From $191 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 $191 per night (USD)Expedia
From $263 per night (USD)VRBO
BS 1305 - Family Friendly updated and Spacious! A short walk to the #1 Beach in
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Enjoy your vacation on Siesta Key in this spacious three bedroom / two bathroom vacation rental located in the the very ...
From $263 per night (USD)VRBO
From $450 per night (USD)Expedia
Close to 3 Beaches, Private Gated Waterfront Tropical Oasis Heated Pool Estate
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
As you come thru your own private gated paver brick driveway you enter into a tropical paradise filled with lush landsca ...
From $450 per night (USD)Expedia
From $200 per night (USD)VRBO
GORGEOUS NOKOMIS BEACH HOME
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Beautifully appointed 2 bedroom/2 bath, plus DEN. Maintenance-free single family home. Interiors have multiple upgrades ...
From $200 per night (USD)VRBO
From $180 per night (USD)VRBO
NEW! Cozy Gem near Mineral Springs & Beaches
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Welcome to a relaxing get-away at our 3-bedroom/2-bath well-maintained vacation house. Designed and situated with a ‘slo ...
From $180 per night (USD)VRBO
From $125 per night (USD)VRBO
Screened Private Pool, 2 Mi. to Crescent Beach Access, WiFi/Cable, Walk to Cafes, Dog Friendly
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Plan your getaway at Red Truck Pool Home! It's a cool, modern & spacious ranch style home in popular Gulf Gate neighbor ...
From $125 per night (USD)VRBO
From $149 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 $149 per night (USD)Expedia
From $109 per night (USD)VRBO
Peaceful 1bed/1bath Condo Golf & Lake views in the Meadows
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This is a nicely furnished 676 sqft, 1 bedroom, 1 bathroom, on the golf, with a great view on the course and a pond. **w ...
From $109 per night (USD)VRBO
From $194 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 $194 per night (USD)Expedia
From $199 per night (USD)VRBO
70-Foot Houseboat, Secluded Beach, Onsite Bikes & Golf carts to tour the Key!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
70 foot houseboat featuring two bedrooms and two bathrooms. Living room and dining room spacious with a pull out sleeper ...
From $199 per night (USD)VRBO
From $110 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 $110 per night (USD)Expedia
From $180 per night (USD)VRBO
Beachfront Venice Casa de Villa
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
Location! Location! Location! Beautiful Beachfront Condo conveniently located on the Private Venice Beach, 1.0 mile away ...
From $180 per night (USD)VRBO
From $130 per night (USD)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 ...
From $130 per night (USD)Expedia
From $300 per night (USD)VRBO
Penthouse suite with ocean views <br>2 Bed 2 Bath heated pool<br>Very clean UPDATED
- 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 $300 per night (USD)VRBO
From $401 per night (USD)Expedia
Crystal Sands1107 Exquisite Gulf & Sand Views, Luxury
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
1107 is definitely a slice of heaven on Siesta Key. It's fresh and new with beautiful new beachy furnishings, new linens ...
From $401 per night (USD)Expedia
From $110 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 $110 per night (USD)VRBO
From $312 per night (USD)Expedia
Newly renovated and updated home just 1 mile from Venice Beach.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Located on the south end of Venice, only 3.2 miles to Manasota Key Beach, this charming Vacation Home has just in been u ...
From $312 per night (USD)Expedia
From $110 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 $110 per night (USD)VRBO
From $143 per night (USD)Expedia
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 $143 per night (USD)Expedia
From $200 per night (USD)VRBO
Lovely home by the Warm Mineral Springs Florida
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
ATTENTION!!! Please follow the link below for the site of new host/new owner http://airbnb.com/h/suite-b-florida Ne ...
From $200 per night (USD)VRBO
From $950 per night (USD)Expedia
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 $950 per night (USD)Expedia
From $125 per night (USD)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 ...
From $125 per night (USD)VRBO
From $172 per night (USD)Expedia
The Pattison Place
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This home is truly "one of a kind!" A perfect open floor plan to create a very spacious home for you and your family! Th ...
From $172 per night (USD)Expedia
From $210 per night (USD)VRBO
Unit 121- Newly Renovated- Convenient 1st Floor- Palm Bay Club - Gulf Side In
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Unit 121- Newly Renovated- Convenient 1st Floor- Palm Bay Club - Gulf Side Interior- 2BR/2BA With Washer/Dryer. | Come ...
From $210 per night (USD)VRBO
From $125 per night (USD)Expedia
Last Minute Availability Minutes from Siesta Key
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Last Minute Availability, Jan/Feb 2021 near Siesta Key, Pool, Gym, Pets Allowed. Water, Sewer, trash and pest control in ...
From $125 per night (USD)Expedia
From $295 per night (USD)VRBO
Heated Pool ❤ Home- Close to Beaches, Restaurants
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
NOTE: BOOKING JANUARY, FEBRUARY OR MARCH? Please book whole months only NOT mid-month to mid-month. This time frame is a ...
From $295 per night (USD)VRBO
From $100 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 $100 per night (USD)Expedia
From $375 per night (USD)VRBO
Dream House
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Beautiful and a favorable house.This property is perfect for a big family and group of friends is near restaurant’s, gro ...
From $375 per night (USD)VRBO
From $113 per night (USD)Expedia
Live 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. Close to gulf beaches..Great community l ...
From $113 per night (USD)Expedia
From $139 per night (USD)VRBO
Elegant 3-Bed condo with intracoastal views
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 4
Enjoy the gorgeous amber sunsets from your expansive balcony offering panoramic views of the Intracoastal Waterway and t ...
From $139 per night (USD)VRBO
From $1043 per night (USD)Expedia
New Listing! | Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Welcome to The Coral Reef! This group of 3 private units is perfect for families and groups, with the ability to accommo ...
From $1043 per night (USD)Expedia
From $348 per night (USD)VRBO
New Listing! Sea Breeze | Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to Sea Breeze! This private unit is perfect for small families, with the ability to accommodate up to 4 guests, ...
From $348 per night (USD)VRBO
From $348 per night (USD)Expedia
New Listing! Sea Foam | Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to Sea Foam! This private unit is perfect for small families, with the ability to accommodate up to 4 guests, wi ...
From $348 per night (USD)Expedia
From $1043 per night (USD)VRBO
New Listing! | Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Welcome to The Beachy Keen! This group of 3 private units is perfect for families and groups, with the ability to accomm ...
From $1043 per night (USD)VRBO
From $348 per night (USD)Expedia
New Listing! Sea Coast | Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to Sea Coast! This private unit is perfect for small families, with the ability to accommodate up to 4 guests, w ...
From $348 per night (USD)Expedia
From $348 per night (USD)VRBO
New Listing! Sea Dream | Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to Sea Dream! This private unit is perfect for small families, with the ability to accommodate up to 4 guests, w ...
From $348 per night (USD)VRBO
From $348 per night (USD)Expedia
New Listing! Sea Escape | Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to Sea Escape! This private unit is perfect for small families, with the ability to accommodate up to 4 guests, ...
From $348 per night (USD)Expedia
From $180 per night (USD)VRBO
Seeing is believing!!!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Come enjoy our 3 bedroom/3 bath home located one block from the bay on a quiet, friendly street in the Indian Beach neig ...
From $180 per night (USD)VRBO
From $348 per night (USD)Expedia
New Listing! Sea Angel | Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to Sea Angel! This private unit is perfect for small families, with the ability to accommodate up to 4 guests, w ...
From $348 per night (USD)Expedia
From $2086 per night (USD)VRBO
New Listing! 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! This group of 6 private units is perfect for large families and groups, with the ability to a ...
From $2086 per night (USD)VRBO
From $215 per night (USD)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 ...
From $215 per night (USD)Expedia
From $239 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 $239 per night (USD)VRBO
From $180 per night (USD)Expedia
Cozy beach house in quiet neighborhood
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Cozy house with tropical backyard. Screened porch and hammock to enjoy the tropical warm weather. 8 minute drive to Sies ...
From $180 per night (USD)Expedia
From $250 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 $250 per night (USD)VRBO
From $115 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 $115 per night (USD)Expedia
From $215 per night (USD)VRBO
Summer Cove, beautiful luxury 3 bedroom 2 1/2 bath condo on Siesta Key, Florida
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Summer Cove on Siesta is the ultimate getaway! This intimate gated community of 45 luxury residences sits on Little Sara ...
From $215 per night (USD)VRBO
From $115 per night (USD)Expedia
Recently Remodeled 3 Bdrm-2 Bath In Quiet Neighborhood, Close to Beaches
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to our recently remodeled home with spacious floor plan. All new kitchen with brand new appliances, cookware, d ...
From $115 per night (USD)Expedia
From $906 per night (USD)VRBO
Inn on the Beach 3007
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Offered by FL Vacation Connection, this perfect island getaway is located on the southern tip of Longboat Key with a bea ...
From $906 per night (USD)VRBO
From $228 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 $228 per night (USD)Expedia
From $99 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 $99 per night (USD)VRBO
From $304 per night (USD)Expedia
Paradise! Remodeled 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 $304 per night (USD)Expedia
From $399 per night (USD)VRBO
Clean and Perfectly Remodeled Townhome, Steps From the Private Beach
- 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 $399 per night (USD)VRBO
From $409 per night (USD)Expedia
Siesta Key Beach Front 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 $409 per night (USD)Expedia
From $1143 per night (USD)VRBO
Inn on the Beach 1307
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
FL Vacation Connection looks forward to welcoming you to this luxury beachfront getaway located on the southern tip of L ...
From $1143 per night (USD)VRBO
From $109 per night (USD)Expedia
Fairy-Tale Getaway Private Entry Near Siesta Key
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
About this space: Newly remodeled, spacious bedroom/bath with a private entrance. Luxuriate in a comfortable queen bed, ...
From $109 per night (USD)Expedia
From $1445 per night (USD)VRBO
2700 sq ft home/guest home w/ private pool 200 steps to Crescent Beach - dogs OK
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Siesta Key Reverie Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $1445 per night (USD)VRBO
From $1100 per night (USD)Expedia
2,700 sq. ft. home with private pool 200 steps to Crescent Beach - dog welcome
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Seashell Sanctuary Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $1100 per night (USD)Expedia
From $222 per night (USD)VRBO
900-square-foot home with WiFi 200 steps from Crescent Beach - dog welcome
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Crescent Beach Casita Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter y ...
From $222 per night (USD)VRBO
From $405 per night (USD)Expedia
Island 3/2 home, WALK to the Beach, Shops & Dining
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Cast your cares aside and engage with who you are or who you want to be. Tell tales of yesterday and laugh until the tea ...
From $405 per night (USD)Expedia
From $355 per night (USD)VRBO
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 $355 per night (USD)VRBO
From $242 per night (USD)Expedia
#Siestakeying new designer one story bungalow 5 mi. to Siesta Key beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Siestakeying.com - a peaceful designer vacation rental home - just 5 miles away from #1 rated Siesta Key Beac ...
From $242 per night (USD)Expedia
From $105 per night (USD)VRBO
Cosy log cabin close to Downtown and Beaches
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
All new furnishings including a queen bed and a convertible sofa to accommodate up to 4 guests. Great location, 5 minute ...
From $105 per night (USD)VRBO
From $158 per night (USD)Expedia
Cozy and classic 2 bed.apartment, close to Siesta
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Enjoy beautiful Sarasota while staying in our cozy, fully renovated 2 bedroom apartment in duplex home . Close to many a ...
From $158 per night (USD)Expedia
From $109 per night (USD)VRBO
Family Friendly Cottage @ Sun N Fun Resort
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Family friendly, beautiful vacation home rental at the best resort in sunny Sarasota! Guest access Guests have full ac ...
From $109 per night (USD)VRBO
From $171 per night (USD)Expedia
LOCATION! LOCATION! directly across from the world famous Siesta Key Beach.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
LOCATION! LOCATION! LOCATION! Your vacation awaits you in this perfect two bedroom, two bath condo directly across from ...
From $171 per night (USD)Expedia
From $194 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 S ...
From $194 per night (USD)VRBO
From $162 per night (USD)Expedia
Great Island Location - Walk to Beach, Shopping & Dining. Vista Hermosa 312A
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Great Island Location - Walk to Beach, Shopping & Dining. Vista Hermosa 312A Beautifully remodeled condo just completed ...
From $162 per night (USD)Expedia
From $577 per night (USD)VRBO
Boaters dream! Deep water canal on Buttonwood Harbour LBK
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
PLEASE SEE COVID 19 / STANDARD POLICIES BELOW - it is different from VRBO policy options as are payment options. Arrival ...
From $577 per night (USD)VRBO
From $254 per night (USD)Expedia
Villa With Garage & Private Beach, 2 Heated Pools, WiFi., Cable/Stream, Garage w/Opener, Modern!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Spend your beach vacation in this beautiful, modern updated villa in the popular Crystal Sands Complex with Private Beac ...
From $254 per night (USD)Expedia
From $290 per night (USD)VRBO
Awesome Location! Walk to restaurants, short drive to beaches and downtown fun!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Lovely Mediterranean style Home with newly renovated guest house! This pristine Spanish Mission Style home has 2 bedroom ...
From $290 per night (USD)VRBO
From $250 per night (USD)Expedia
Prime Long Boat Key Location - Bay and Marina Views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Recently remodeled beautiful 2 Bedroom condo located on the top floor of a 3 floor building overlooking the Bay Harbour ...
From $250 per night (USD)Expedia
From $303 per night (USD)VRBO
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 $303 per night (USD)VRBO
From $154 per night (USD)Expedia
Crescent Beach - 2 Bedroom - Beachfront Condo Complex - Heated Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
CRESCENT ARMS - Siesta Key Beachfront Vacation Condos on Crescent Beach(Two Bedroom Beachview Unit for Rent) Located Di ...
From $154 per night (USD)Expedia
From $237 per night (USD)VRBO
Sparkling New 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 $237 per night (USD)VRBO
From $250 per night (USD)Expedia
Private Entrance Condo - Large patio with direct pool access!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
NOTICE: There are limited accessible features available for disabled guests at the present time at Harbor Towers Yacht & ...
From $250 per night (USD)Expedia
From $145 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 heated pool!), only at a 15 min drive from ...
From $145 per night (USD)VRBO
From $200 per night (USD)Expedia
Available in Nov. cute 2 bedroom condo, walk to beach and st Armand’s
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Be sure to check out our other properties 512091- Living the Dream on Lido I ***************************************** ...
From $200 per night (USD)Expedia
From $307 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 $307 per night (USD)VRBO
From $167 per night (USD)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 ...
From $167 per night (USD)Expedia
From $349 per night (USD)VRBO
REMODELED,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 $349 per night (USD)VRBO
From $210 per night (USD)Expedia
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 bathroom co ...
From $210 per night (USD)Expedia
From $229 per night (USD)VRBO
Luxury home, close to Manasota beach, 3 king bedrooms, private heated pool wi-fi
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Relax and enjoy a 5 star luxury home, built in 2011, which is not overlooked by any other homes. Manasota Beach, with fr ...
From $229 per night (USD)VRBO
From $479 per night (USD)Expedia
NEW! Sarasota Home w/ Pool ~ 5 Miles to the Beach!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Pack your bags, the perfect vacation is just a click away! This 3-bedroom, 3-bathroom vacation rental is perfect for a g ...
From $479 per night (USD)Expedia
From $138 per night (USD)VRBO
Walk to the beach! Clean and new, remodeled cozy 3 bedroom 2 bath cottage house
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Enjoy the gorgeous sunsets at the beach, just .8 mile away from this 3 bedroom 2 bath ranch home on Venice island. This ...
From $138 per night (USD)VRBO
From $241 per night (USD)Expedia
NEW! 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 $241 per night (USD)Expedia
From $130 per night (USD)VRBO
Spacious Villa with Lush Tropical Garden Very Close to Siesta Key!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Your warm relaxing subtropical vacation begins here. Renovated in 2019. Enjoy the sunset over Siesta key from just a sho ...
From $130 per night (USD)VRBO
From $399 per night (USD)Expedia
Casa Liberty - Modern & Clean, Less than 3 miles to Siesta Beach!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
NOTE: BOOKING JANUARY, FEBRUARY OR MARCH? Please book whole months only NOT mid-month to mid-month. This time frame is a ...
From $399 per night (USD)Expedia
From $215 per night (USD)VRBO
🦩Discover The Perfect Snowbird Nest on Siesta Key! Minimum 30-Day Rental🦩
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Pinkie Flamingo Welcomes You to The Tortuga #105B! King/Queen A rare find indeed! Come prepared to leave impressed.Thi ...
From $215 per night (USD)VRBO
From $814 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 $814 per night (USD)Expedia
From $165 per night (USD)VRBO
Coastal Cozy Retreat
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Beautiful monthly vacation rental a short drive from downtown Sarasota and from Siesta Key! RECENTLY remodeled & sharply ...
From $165 per night (USD)VRBO
From $238 per night (USD)Expedia
Siesta Key Waterfront Condo, Beachfront, Pool, Sunset View
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Fully Furnished, 2 Bedroom Gulf Side Waterfront Condo on South Siesta Key, walking distance to Turtle Beach. Very small, ...
From $238 per night (USD)Expedia
From $265 per night (USD)VRBO
Mellow Mermaid - Two Bedroom Apartment, Sleeps 5
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
An Ascendia Group Property ** Enhanced Cleaning Protocol ** Lovely 2 bedroom, 2 bath vacation condo (sleeps 5) located ...
From $265 per night (USD)VRBO
From $125 per night (USD)Expedia
Lido Beach Walk! One block to beach, easy 10 min stroll to St Armand's Circle.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Sarasota Certificate of Registration # VR22-00027 Lovely, well appointed one bedroom guest house with fully equipped kit ...
From $125 per night (USD)Expedia
From $65 per night (USD)VRBO
3/2 spotless turnkey-furnished Sarasota condo just 8 miles from Siesta Key Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Beautiful 3 bed, 2 bath, turnkey-furnished condo, located in the gated community of Stoneridge. First floor, wheel chair ...
From $65 per night (USD)VRBO
From $647 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
This stunning modern home offers all the amenities you need for your most memorable Siesta Key vacation! Siesta Sunset o ...
From $647 per night (USD)Expedia
From $1155 per night (USD)VRBO
Siesta Dreams #1- OceanViews, Roof Deck, Private Beach Path, in the Village!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Siesta Dreams #1- OceanViews, Roof Deck, Private Beach Path, in the Village! - This is “The Siesta Dreams”, a Gertrude ...
From $1155 per night (USD)VRBO
From $3276 per night (USD)Expedia
Siesta Dreams 6BR - Private penthouse Rooftop, Private BeachPath, Ocean-views
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 16
This is “The Siesta Dreams” a Gertrude Rentals property. Two large 3BR Units including Penthouse. 100% Private with Ocea ...
From $3276 per night (USD)Expedia
From $441 per night (USD)VRBO
Floritas Key | Pet Friendly Home on Siesta Key w/ Large Heated Private Pool & Outdoor Area!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
This coastal 5-bedroom/3-bathroom home features all the amenities you can think of for your beach vacation and offers an ...
From $441 per night (USD)VRBO
From $1042 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
This captivating 3-bedroom/3-bathroom townhome features all the amenities you can think of for your beach vacation and o ...
From $1042 per night (USD)Expedia