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From $405 per night (USD)
VRBO
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 $405 per night (USD)
VRBO
From $405 per night (USD)
Expedia
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 $405 per night (USD)
Expedia
From $240 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 $240 per night (USD)
VRBO
From $405 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 $405 per night (USD)
Expedia
From $1994 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 $1994 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 $215 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 $215 per night (USD)
VRBO
From $275 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. Thi ...
From $275 per night (USD)
Expedia
From $115 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 $115 per night (USD)
VRBO
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 $982 per night (USD)
VRBO
Bird's eye beach view 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 ...
From $982 per night (USD)
VRBO
From $481 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 $481 per night (USD)
Expedia
From $149 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 $149 per night (USD)
VRBO
From $300 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 $300 per night (USD)
Expedia
From $366 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 $366 per night (USD)
VRBO
From $449 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 $449 per night (USD)
Expedia
From $942 per night (USD)
VRBO
Tasteful 2brm Beachfront luxury
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
FL Vacation Connection offers this 2brm luxury condo. 3rd floor. 1700 sq ft. 52' beachfront balcony. Large living area. ...
From $942 per night (USD)
VRBO
From $60 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 $60 per night (USD)
Expedia
From $328 per night (USD)
VRBO
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 $328 per night (USD)
VRBO
From $360 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 $360 per night (USD)
Expedia
From $115 per night (USD)
VRBO
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 $115 per night (USD)
VRBO
From $131 per night (USD)
Expedia
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 $131 per night (USD)
Expedia
From $196 per night (USD)
VRBO
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 $196 per night (USD)
VRBO
From $375 per night (USD)
Expedia
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 $375 per night (USD)
Expedia
From $189 per night (USD)
VRBO
Great Siesta Key Location! Short Walk to the Beach, Shopping, Dining & More!. Vista Hermosa 312A
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Great Island Location - Walk to the Beach, Shopping & Dining and more! Beautifully updated condo at Vista Hermosa locat ...
From $189 per night (USD)
VRBO
From $577 per night (USD)
Expedia
Boaters dream! Deep water canal on Buttonwood Harbour LBK
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
PLEASE SEE COVID 19 AND STANDARD POLICIES BELOW - it is different from VRBO policy options as are payment options. Arriv ...
From $577 per night (USD)
Expedia
From $321 per night (USD)
VRBO
New Lower Pricing! Villa w/garage & private beach, 2 heated pools, WiFi, Cable/streaming
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 $321 per night (USD)
VRBO
From $300 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 $300 per night (USD)
Expedia
From $189 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 $189 per night (USD)
VRBO
From $240 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 $240 per night (USD)
Expedia
From $275 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 $275 per night (USD)
VRBO
From $350 per night (USD)
Expedia
Adorable 2 bedroom condo on Lido, 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 $350 per night (USD)
Expedia
From $299 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 $299 per night (USD)
VRBO
From $265 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 bathroom co ...
From $265 per night (USD)
VRBO
From $134 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
A charming coastal cottage home that epitomizes coastal living at its finest. Situated walking distance from the sh ...
From $134 per night (USD)
VRBO
From $173 per night (USD)
Expedia
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 $173 per night (USD)
Expedia
From $140 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. Enjoy the sunset over Siesta key from just a short block away. Two ...
From $140 per night (USD)
VRBO
From $215 per night (USD)
Expedia
🦩Discover 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 $215 per night (USD)
Expedia
From $802 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 $802 per night (USD)
VRBO
From $275 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 $275 per night (USD)
Expedia
From $123 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 $123 per night (USD)
VRBO
From $448 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 home located right on the pristine shores of Siesta Key Beach. This ...
From $448 per night (USD)
Expedia
From $520 per night (USD)
VRBO
Siesta Dreams 1- OceanViews, Roof Deck, Private Beach Path, in the Village!
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Siesta Dreams 1- OceanViews, Roof Deck, Private Beach Path, in the Village! This is “The Siesta Dreams”, a Gertrude Ren ...
From $520 per night (USD)
VRBO
From $1331 per night (USD)
Expedia
Siesta Dreams 6BR - Two large 3BR Units, Ocean-views, 100% Private.
Bedrooms:
4
Bathrooms:
6
Sleeps:
16
Siesta Dreams 6BR - Two large 3BR Units, Ocean-views, 100% Private! This is “The Siesta Dreams” a Gertrude Rentals prop ...
From $1331 per night (USD)
Expedia
From $1087 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
Welcome to Floritas Key, a vibrant yet coastal bungalow located on the northern end of Siesta Key. This delightful retre ...
From $1087 per night (USD)
VRBO
From $752 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 $752 per night (USD)
Expedia
From $225 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 $225 per night (USD)
VRBO
From $466 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 $466 per night (USD)
Expedia
From $793 per night (USD)
VRBO
Coconut Cottage | Home on Lido Key w/ Private Heated Pool/Spa, Walk to Lido Beach & St. Armands!
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Escape to the enchanting Coconut Cottage, a hidden gem nestled on the barrier island of Lido Key. This quaint and coasta ...
From $793 per night (USD)
VRBO
From $135 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 $135 per night (USD)
Expedia
From $302 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! This is The Village Breeze, a Gertrude Rent ...
From $302 per night (USD)
VRBO
From $276 per night (USD)
Expedia
The Village Breeze II - White-sand, Heated Pool, Beaches, Daiquiris, Seafood.
Bedrooms:
2
Bathrooms:
2
Sleeps:
7
The Village Breeze - Heated Pool, Beaches, Daiquiris, Seafood, White-sand! This is The Village Breeze, a Gertrude Rent ...
From $276 per night (USD)
Expedia
From $499 per night (USD)
VRBO
The Village Breeze (2 units) 4BR/4Bath Pool, Beach - Siesta Village Living!
Bedrooms:
4
Bathrooms:
4
Sleeps:
14
This is The Village Breeze 4BR, a Gertrude Rentals property. No car required! Two side by side 2BR/2Bath units in an e ...
From $499 per night (USD)
VRBO
From $192 per night (USD)
Expedia
Sunny Daze Near Siesta Key (2 miles)
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Amazing home located near the #1 rated Siesta Key Beach (2 miles), shopping, and restaurants. Plenty of space to spread ...
From $192 per night (USD)
Expedia
From $235 per night (USD)
VRBO
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 $235 per night (USD)
VRBO
From $158 per night (USD)
Expedia
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 $158 per night (USD)
Expedia
From $147 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 $147 per night (USD)
VRBO
From $181 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 $181 per night (USD)
Expedia
From $91 per night (USD)
VRBO
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 $91 per night (USD)
VRBO
From $167 per night (USD)
Expedia
Luminous 2 beds/2 baths w/ Balcony LIDO BEACH TOWERS
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This comfortable condo is in the Lido Key towers. it's a beachfront residence with pool and amenities. Perfect location ...
From $167 per night (USD)
Expedia
From $120 per night (USD)
VRBO
LAKEFRONT-FREE KAYAKS, BICYCLES, STANDUP PADDLEBOARDS-WALK 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 $120 per night (USD)
VRBO
From $200 per night (USD)
Expedia
Quiet pool house on a lake - 7 min. from beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Please note that hurricane Ian has destroyed our pool cage and a patio overhang roof. This beautiful 1600 Sq. Ft single ...
From $200 per night (USD)
Expedia
From $202 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 $202 per night (USD)
VRBO
From $217 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 $217 per night (USD)
Expedia
From $1950 per night (USD)
VRBO
Nearly Beachfront, Gulf/Beach Views, Private Heated Pool, Family/Pet Friendly
Bedrooms:
4
Bathrooms:
5
Sleeps:
19
Sugar Sand Cottage by Siesta Key Luxury Rental Properties Home in Siesta Key, FL At A Glance • Ground Level Home w/ 5 ...
From $1950 per night (USD)
VRBO
From $130 per night (USD)
Expedia
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 $130 per night (USD)
Expedia
From $259 per night (USD)
VRBO
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 $259 per night (USD)
VRBO
From $296 per night (USD)
Expedia
Just 130 steps from your walk-out balcony to the Beautiful White Sand Beach!!!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Tasteful and very clean 1500sq ft. 1st Floor 2 bedroom/2bath condo with all the amenities of home! Enjoy the ability to ...
From $296 per night (USD)
Expedia
From $175 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 $175 per night (USD)
VRBO
From $130 per night (USD)
Expedia
BIG COZY CONDO 2bed/2bath. 7 minutes to SIESTA 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 $130 per night (USD)
Expedia
From $221 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 $221 per night (USD)
VRBO
Click For Pricing
Expedia
Florida home near beaches golf boating and Dearborn St .
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Close to beach 3.5 miles but a wonderful neighborhood. Enjoy those Florida breezes in your 3 bedroom 2 bath home with a ...
Click For Pricing
Expedia
From $170 per night (USD)
VRBO
Cozy Heated pool retreat, updated house with new kitchen, 25 min to beach.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This 3-bedroom villa offers screened pool, fully fenced backyard, BBQ, Wi-Fi, 3 smart TVs with Disney Plus and Roku TV, ...
From $170 per night (USD)
VRBO
From $110 per night (USD)
VRBO
Booking Now for June 2023 and Spring/Summer 2024!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This stunning, COMPLETELY RENOVATED townhome is overlooking the pool and near the beach. The modern-coastal style decor ...
From $110 per night (USD)
VRBO
From $249 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 $249 per night (USD)
VRBO
From $293 per night (USD)
Expedia
Villa Fiesta | Pet Friendly Home In Siesta Village, Heated Pool and Hot Tub, Walk to the Beach!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to Villa Fiesta, your ultimate island retreat nestled in the heart of Siesta Key Village. This stunning property ...
From $293 per night (USD)
Expedia
From $548 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:
4
Sleeps:
12
Welcome to Casa De Siesta, your ultimate island retreat nestled in the heart of Siesta Key Village. This stunning proper ...
From $548 per night (USD)
VRBO
From $425 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 villag ...
From $425 per night (USD)
Expedia
From $335 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 $335 per night (USD)
VRBO
From $843 per night (USD)
Expedia
NEW! Siesta Key-Luxury 4 BR Home w/Heated Pool
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Sprawling ranch retreat on cul-de-sac with private pool and less than 5 minutes to the beach! Private master suite opens ...
From $843 per night (USD)
Expedia
From $159 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 $159 per night (USD)
VRBO
From $644 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 *Features include* * Heated Pool * ...
From $644 per night (USD)
Expedia
From $158 per night (USD)
VRBO
A true mid-century Florida bungalow located 1 block from Sarasota Bay.
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 $158 per night (USD)
VRBO
From $310 per night (USD)
Expedia
Oceanside 603 1BR - Beach-front in the world-famous Siesta Key Village!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
“Beachside 603” is a Gertrude Rentals property right on Beach Rd at Access 10. Large, Fully Renovated, 1BR Apartment, j ...
From $310 per night (USD)
Expedia
From $146 per night (USD)
VRBO
Updated, Community Heated Pool/Spa, WiFi, Smart TV’s, Lanai, Tennis, Putting Green, Garage/Driveway
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 $146 per night (USD)
VRBO
From $404 per night (USD)
Expedia
Crystal Sands Villa 12A
Bedrooms:
4
Bathrooms:
3
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 $404 per night (USD)
Expedia
From $475 per night (USD)
VRBO
Entire private house
Bedrooms:
5
Bathrooms:
5
Sleeps:
13
Enjoy Full master suite with Jacuzzi tub w/private access to pool with built in hot tub.There are 4 more bedrooms throug ...
From $475 per night (USD)
VRBO
From $222 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 $222 per night (USD)
Expedia
From $275 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 $275 per night (USD)
VRBO
From $550 per night (USD)
VRBO
Penthouse timeshare
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
A rare opportunity to escape to your four bedroom penthouse on the beach in Longboat Key or for a week in February (2/5/ ...
From $550 per night (USD)
VRBO
From $129 per night (USD)
VRBO
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 $129 per night (USD)
VRBO
Click For Pricing
Expedia
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
Expedia
From $85 per night (USD)
VRBO
COMFY COZY PLACE. Open room with kitchenette. Close to beaches with 3 miles
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Comfy cozy cute private drive studio with queen bed. Small fridge, coffee maker, toaster oven and microwave if you decid ...
From $85 per night (USD)
VRBO
From $198 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 $198 per night (USD)
Expedia
From $315 per night (USD)
VRBO
Gorgeous Beach Cottage in Sunny Sarasota
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Larger group? Inquire about our adorable adjacent 1/1 Coconut Cottage for your group's stay. Perfect for in-laws, famili ...
From $315 per night (USD)
VRBO
From $100 per night (USD)
Expedia
*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 $100 per night (USD)
Expedia
From $836 per night (USD)
VRBO
The Sun Dial | Waterfront Home on Siesta Key w/ Private Pool & Large Backyard, Close to Beach!
Bedrooms:
4
Bathrooms:
4
Sleeps:
12
Welcome to The Sun Dial, your very own tropical paradise nestled on the water's edge! Step inside this magnificent home ...
From $836 per night (USD)
VRBO
From $140 per night (USD)
Expedia
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 $140 per night (USD)
Expedia
From $169 per night (USD)
VRBO
🌴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 $169 per night (USD)
VRBO
From $235 per night (USD)
Expedia
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 $235 per night (USD)
Expedia

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