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From $432 per night (USD)
VRBO
Crystal Sands Tower Unit 1204 - Beachfront
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Crystal Sands Condominiums! We would love to have you stay with us in one of our luxury 2-bedroom 2-bath full ...
From $432 per night (USD)
VRBO
From $456 per night (USD)
Expedia
Crystal Sands Tower Unit 1004 - Beachfront
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Affectionately called "The Perch", unit #1004 has been in our family since the building was nothing more than a blueprin ...
From $456 per night (USD)
Expedia
From $432 per night (USD)
VRBO
Crystal Sands Tower Unit 404 - Beachfront
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Breathtaking Views - Beachfront Condo - Completely Renovated Enjoy breathtaking views of the Gulf of Mexico and world-f ...
From $432 per night (USD)
VRBO
From $432 per night (USD)
Expedia
Crystal Sands Tower Unit 305 - Beachfront
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Treat yourself to a completely remodeled and updated 3rd floor 2 bedroom 2 bath ocean front condo. Enjoy the beautiful ...
From $432 per night (USD)
Expedia
From $492 per night (USD)
VRBO
Crystal Sands Tower Unit 502 - Beachfront
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
SONG OF SIESTA KEY!! Located on Beautiful #1 Award Winning White Sands of Siesta Key Beach with panoramic views from 30 ...
From $492 per night (USD)
VRBO
From $432 per night (USD)
Expedia
Crystal Sands Tower Unit 506 - Beachfront
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Treat yourself to a completely remodeled and updated 5th floor 2 bedroom 2 bath ocean front condo. Enjoy the beautiful ...
From $432 per night (USD)
Expedia
From $472 per night (USD)
VRBO
Crystal Sands Tower Unit 704 - Beachfront
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
Enjoy the best of Crystal Sands in this beachy, contemporary 2-bedroom, 2 bath condo overlooking the 2011 and 2017 Best ...
From $472 per night (USD)
VRBO
From $432 per night (USD)
Expedia
Crystal Sands Tower Unit 710 - Beachfront
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Crystal Sands Condominiums! We would love to have you stay with us in one of our luxury 2-bedroom 2-bath full ...
From $432 per night (USD)
Expedia
From $468 per night (USD)
VRBO
Crystal Sands Villa 20 - Private Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
For more privacy we offer you this 2 bedroom 2 bath villa flanking our attractive palm lined boulevard. Gracious living ...
From $468 per night (USD)
VRBO
From $432 per night (USD)
Expedia
Crystal Sands Tower Unit 104 - Beachfront
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Welcome to Crystal Sands Condominiums! We would love to have you stay with us in one of our luxury 2-bedroom 2-bath full ...
From $432 per night (USD)
Expedia
From $479 per night (USD)
VRBO
Crystal Sands Tower Unit 205 - Beachfront
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Crystal Sands Condominiums! We would love to have you stay with us in one of our luxury 2-bedroom 2-bath full ...
From $479 per night (USD)
VRBO
From $302 per night (USD)
Expedia
Turtle Beach, Beachfront, B110 - First Floor, Free Boat Docks & WiFi
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
From the lanai and your private patio, you are directly on the beach where it is easy to keep an eye on the children pla ...
From $302 per night (USD)
Expedia
$Luxurious Living by Siesta Beach in this renovated 2b\/1b ground floor unit$
From $278 per night (USD)
VRBO
Luxurious Living by Siesta Beach in this renovated 2b\/1b ground floor unit
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
NOW WITH PRIVATE WiFi. Our condo is beautifully decorated with elegant touch & taste. It was recently renovated with st ...
From $278 per night (USD)
VRBO
From $338 per night (USD)
Expedia
Direct Gulf View from 3rd Floor - B307, Free Boat Docks & WiFi
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Enjoy our third floor upgraded apartment with new wood plank flooring, including on the lanai, new leather couches,upgra ...
From $338 per night (USD)
Expedia
From $378 per night (USD)
VRBO
Heated Pool, FREE WiFi, Short Stroll to Siesta Key Beach, America's Sweetheart!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
**ASK ABOUT LAST MINUTE DEALS! Fall in love with charming Gulf and Bay Club Bayside, a Key West-inspired vi ...
From $378 per night (USD)
VRBO
From $338 per night (USD)
Expedia
Luxurious Comfort with Gulf Views - B302 Free Boat Docks & WiFi
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This recently renovated 3rd floor unit has a new owner who has made many upgrades to the condo. In the newly renovated l ...
From $338 per night (USD)
Expedia
From $293 per night (USD)
VRBO
Romantic comfort from - B303, 3rd Floor and Gulf View, Free Boat Docks & WiFi
Bedrooms:
2
Bathrooms:
1
Sleeps:
4
The perfect place to spend a romantic vacation directly on the Gulf of Mexico. Enjoy breathtaking views from this lovely ...
From $293 per night (USD)
VRBO
From $347 per night (USD)
Expedia
Beach Front Sophistication and Comfort, 3rd Floor -B305, Free Boat Docks & WiFi
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Within just a few feet of the beach, our condominium home features a well equipped kitchen with granite counter tops, lu ...
From $347 per night (USD)
Expedia
From $303 per night (USD)
VRBO
Coastal Getaway minutes from Siesta Key, America’s #1 Beach
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Set back off the road on a quiet lane, enjoy this newly furnished, cozy modern coastal home. With this 3 bedroom, 2 bat ...
From $303 per night (USD)
VRBO
Click For Pricing
Expedia
Gulf Views of Turtle Beach on 3rd Floor - A301, Free Boat Docks & WiFi
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Location, location, location ~ and view. 3rd floor corner unit overlooks Turtle Beach. 2015 updates include new wood la ...
Click For Pricing
Expedia
Click For Pricing
VRBO
Beachfront Siesta Key! Listen to the surf! A205 -2nd floor free WiFi & Boat Dock
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Enjoy Gulf sunsets and the sounds of the surf from your 2nd floor beachfront condo - just one flight of steps - or use t ...
Click For Pricing
VRBO
From $254 per night (USD)
Expedia
Located across the street from Siesta Key Beach, Gulf and Pool View Condo!! #319
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
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 $254 per night (USD)
Expedia
From $269 per night (USD)
VRBO
Relax in this renovated 2 bedroom condo with Gulf Views. Great for families
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Now with private WiFi. Your perfect vacation awaits in this Two Bedroom / One Bath Condo right next to famous Siesta Key ...
From $269 per night (USD)
VRBO
$Charming Condo at La Siesta with Partial Beach Views \Your home away from home\$
From $250 per night (USD)
Expedia
Charming Condo at La Siesta with Partial Beach Views \"Your home away from home\"
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Now with private Wifi. This Two Bedroom, One Bath condo is just steps to the white, powdered sugar sand of Siesta Key. ...
From $250 per night (USD)
Expedia
From $215 per night (USD)
VRBO
Chic Sarasota Cottage: Near Beaches & Downtown!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Plan your next beach escape at this gorgeous 1-bedroom, 1-bath Sarasota vacation rental! Perfect for couples or small gr ...
From $215 per night (USD)
VRBO
$Siesta Keys Home w\/ Deck Half Mile to Turtle Beach$
From $348 per night (USD)
Expedia
Siesta Keys Home w\/ Deck Half Mile to Turtle Beach
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Begin your sunkissed adventures at this 2-bedroom, 1-bathroom vacation rental condo in Siesta Key. This coastal condo bo ...
From $348 per night (USD)
Expedia
From $338 per night (USD)
VRBO
Gulf View from Lanai or Master - B308 with Boat Dock & Free WiFi
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This lovely and colorful 3rd floor unit has an incredible view of the Gulf of Mexico to enjoy with your family members f ...
From $338 per night (USD)
VRBO
$Extraordinary Beach view! 2b\/1b Fully Renovated, Walk in shower, Custom Kitchen$
From $258 per night (USD)
Expedia
Extraordinary Beach view! 2b\/1b Fully Renovated, Walk in shower, Custom Kitchen
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Now with private WiFi. Your perfect vacation awaits in this Two Bedroom/One Bath condo right next to the famous Siesta K ...
From $258 per night (USD)
Expedia
From $302 per night (USD)
VRBO
Corner Unit, Privacy and Gulf front, First Floor - B114, Free Boat Docks & WiFi
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
High demand upgraded first floor corner unit which sleeps 6 features a king, twins and sleeper sofa. The south end offer ...
From $302 per night (USD)
VRBO
From $495 per night (USD)
Expedia
Sun, Sand and Savings Sarasota Deals Up to 15% Off
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 $495 per night (USD)
Expedia
From $302 per night (USD)
VRBO
Turtle Beach, A105 - Gulf front - perfect for couples! Free Boat Docks & WiFi
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This first floor colorful unit sleeps 6 and you will love the sandy beach just outside the lanai door with comfortable p ...
From $302 per night (USD)
VRBO
From $321 per night (USD)
Expedia
Beach View with Boat Docks, Lovely Condo - B203, Free Boat Docks & WiFi
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to Fisherman's Cove unit B203, this cozy beach house awaits your visit! Magnificent view of the Gulf of Mexico a ...
From $321 per night (USD)
Expedia
From $302 per night (USD)
VRBO
Beach front Fisherman's Cove - A109, 1st floor, Free Boat Dock & WiFi
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Newly remodeled kitchen with stainless appliances. Freshly painted throughout and casual furnishings for your family to ...
From $302 per night (USD)
VRBO
From $338 per night (USD)
Expedia
First Class with Gulf View & Sunsets - B213, Free Boat Docks & WiFi
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Gorgeous unit and beautifully furnished with an incredible 2nd floor view of the Gulf of Mexico. Sleeps six comfortably ...
From $338 per night (USD)
Expedia
From $338 per night (USD)
VRBO
Siesta Sand & Sunsets-Breathtaking Beach Views-B204-2 BR, 2 BA condo
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Enjoy the unrestricted views (no sea oats or berm) of the ocean and sunsets from our beach front condo just steps away f ...
From $338 per night (USD)
VRBO
From $338 per night (USD)
Expedia
Corner Unit, Gulf Front on 2nd floor - A214, Free Boat Docks & WiFi
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
A beautiful gulf view with wrap around, all screened sliding doors to enjoy the gulf breeze. This unit is on the south ...
From $338 per night (USD)
Expedia
$Villa Vista Mare | Gorgeous Home w\/ Views of Gulf, Heated Pool, & Across From Siesta Key Beach!$
From $785 per night (USD)
VRBO
Villa Vista Mare | Gorgeous Home w\/ Views of Gulf, Heated Pool, & Across From Siesta Key Beach!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Welcome to Villa Vista Mare, located just steps away from the world-renowned Siesta Key Beach! This 3 bedroom, 3 bathroo ...
From $785 per night (USD)
VRBO
From $302 per night (USD)
Expedia
Siesta Key Gulf Front-2 BR-B103, Beautiful Sunsets + Water Views
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Just bring your swimsuits, flip flops, and some groceries…everything that you might need is located in this totally upda ...
From $302 per night (USD)
Expedia
$Beach Condo on Siesta Key Beach w\/ Heated Pool$
From $270 per night (USD)
VRBO
Beach Condo on Siesta Key Beach w\/ Heated Pool
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
If you are going to visit the #1 beach in the country, then stay on the #1 beach! This two bedroom, two full bathroom be ...
From $270 per night (USD)
VRBO
Click For Pricing
Expedia
POOL VIEW King bed Walk to beach Covered porch overlooks pool DAILY RATES
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
We are a small resort on Siesta Key offering daily rentals Pool view is a 1 bedroom 1 bathroom ground floor rental wit ...
Click For Pricing
Expedia
$Crescent Cottage | Pet Friendly 🐶 w\/ Private Pool, Lounging Area,Short Walk to Crescent Beach$
From $673 per night (USD)
VRBO
Crescent Cottage | Pet Friendly 🐶 w\/ Private Pool, Lounging Area,Short Walk to Crescent Beach
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Crescent Cottage – Your Siesta Key Escape Recently Renovated! Welcome to Crescent Cottage, your ultimate island retrea ...
From $673 per night (USD)
VRBO
$Sand Dollar Cottage | Waterfront Home w\/ Private Pool & Kayaks! Minutes to Siesta Key Beach!$
From $721 per night (USD)
Expedia
Sand Dollar Cottage | Waterfront Home w\/ Private Pool & Kayaks! Minutes to Siesta Key Beach!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Welcome to Sand Dollar Cottage, your private tropical haven nestled in the heart of Siesta Key, where serenity meets adv ...
From $721 per night (USD)
Expedia
$Villa Champagne | Pet Friendly Waterfront Home w\/ Private Pool & Spa, Close to Beach & Village!$
From $754 per night (USD)
VRBO
Villa Champagne | Pet Friendly Waterfront Home w\/ Private Pool & Spa, Close to Beach & Village!
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Welcome to Villa Champagne – Your Dream Siesta Key Escape! Indulge in the perfect beach vacation at Villa Champagne, an ...
From $754 per night (USD)
VRBO
$Sandy Seahorse Cottage | Pet Friendly Home on Siesta Key w\/ Private Pool, Short Walk to Beach$
From $909 per night (USD)
Expedia
Sandy Seahorse Cottage | Pet Friendly Home on Siesta Key w\/ Private Pool, Short Walk to Beach
Bedrooms:
6
Bathrooms:
7
Sleeps:
16
Fully Remodeled Interior – Perfectly Prepared for Your Stay! Welcome to Sandy Seahorse Cottage, your perfect Sie ...
From $909 per night (USD)
Expedia
From $364 per night (USD)
VRBO
Updated and clean, two heated pool, tennis, and beach access
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Enjoy this updated townhome within walking distance to Siesta Key's main beach. The property is located within a resort ...
From $364 per night (USD)
VRBO
From $222 per night (USD)
Expedia
Enjoy the Siesta Key Beach Life to the fullest! Beach AND Pool Access
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
*** NEW *** Siesta Key beach has become known world wide for its incredible miles of soft white sand beaches and small v ...
From $222 per night (USD)
Expedia
$Sarasota House w\/ Backyard Oasis: 6 Mi to Beach!$
From $653 per night (USD)
VRBO
Sarasota House w\/ Backyard Oasis: 6 Mi to Beach!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Soak up the Sunshine State from this 2-bedroom, 2-bathroom Sarasota vacation rental. The home boasts a private backyard ...
From $653 per night (USD)
VRBO
Click For Pricing
Expedia
Waterfront Pool Home - Amazing Sunsets Included
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Beautiful property overlooking little Sarasota bay. Tucked away on a very quite street minutes from shopping, restaurant ...
Click For Pricing
Expedia
From $374 per night (USD)
VRBO
Well Appointed Home with Heated Pool Just Off Siesta Key Close Gulf Gate Area
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Come enjoy the relaxed but vibrant vibe of Sarasota, Florida. The beautiful white sand beaches of Siesta Key, named #1 b ...
From $374 per night (USD)
VRBO
$Oceanfront Home w\/ Sunset Views of Sarasota Bay - Snowbirds Welcome, Dogs OK$
From $309 per night (USD)
Expedia
Oceanfront Home w\/ Sunset Views of Sarasota Bay - Snowbirds Welcome, Dogs OK
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Sunsetter on Sapphire Shores Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ...
From $309 per night (USD)
Expedia
From $389 per night (USD)
VRBO
Walk to the Beach & Village, Heated Pool Oasis, Spacious
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Discover your dream vacation rental in the heart of Siesta Key, Florida, where coastal charm meets modern luxury. This s ...
From $389 per night (USD)
VRBO
From $331 per night (USD)
Expedia
The Coral Cottage close to all that Sarasota has to offer
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
We are Matt and Val, and we purchased this home with a vision to create a warm, inviting space for individuals, couples ...
From $331 per night (USD)
Expedia
From $399 per night (USD)
VRBO
Hidden Paradise Among Tropical Landscape on Lakefront Property on Siesta Key
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This is a one bedroom one bathroom unit furnished with king-size bed in the private bedroom and roll-a-ways available on ...
From $399 per night (USD)
VRBO
$Lakeside Hidden Paradise Among Tropical Landscape W\/ Heated Pool$
From $359 per night (USD)
Expedia
Lakeside Hidden Paradise Among Tropical Landscape W\/ Heated Pool
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Nestled along the serene waters of Heron Lagoon, our 1-bedroom suites at Siesta Heron Suites & Villas offer the perfect ...
From $359 per night (USD)
Expedia
$Lakefront Siesta Key Vacation Rental Home within Small Private Resort W\/ Pool$
From $650 per night (USD)
VRBO
Lakefront Siesta Key Vacation Rental Home within Small Private Resort W\/ Pool
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Spending time in sunny Siesta Key is always a treat for travelers. Those looking to enhance their stay with the inclusio ...
From $650 per night (USD)
VRBO
From $439 per night (USD)
Expedia
Spacious Renovated 1 Bedroom Siesta Key Beachside Vacation Rental Getaway
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Want to stay in a prime location and stay within budget? America's #1 rated beach is just a stones through away located ...
From $439 per night (USD)
Expedia
$4 Bedroom Key West Style Home W\/ Heated Pool, Close to Village and Beaches$
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VRBO
4 Bedroom Key West Style Home W\/ Heated Pool, Close to Village and Beaches
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Stay at this large Key West style Siesta Key vacation rental home minutes to Siesta Key village and beaches. The propert ...
Click For Pricing
VRBO
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Expedia
Veranda Beach Club, ( Week 2 ) Jan. 11 to 18, 2020
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Beautifully furnished beach front property, Second floor corner garden unit with two balconies. Private beach with umbr ...
Click For Pricing
Expedia
From $236 per night (USD)
VRBO
Great place to see the dolphins! And less than half a mile from Turtle Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Sunrise Bay is a 2BR, 1.5 bath, second floor apartment, in a 4-plex apartment property. It faces east and is on the wat ...
From $236 per night (USD)
VRBO
From $589 per night (USD)
Expedia
POOL VIEW V5 Luxury King Bedroom Siesta Key Walk to beach DAILY SPECIALS
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
We are a small resort on Siesta Key offering daily rentals Villa 5 is a ground floor luxury studio suite The entire stud ...
From $589 per night (USD)
Expedia
From $386 per night (USD)
VRBO
Siesta Key For Me @ The Palm Bay Club
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Newly Renovated Siesta Key Condo | Ocean & Bay Views | Sleeps 6 | The Palm Bay Club Exciting Updates Coming in May 2025! ...
From $386 per night (USD)
VRBO
From $459 per night (USD)
Expedia
Adorable Lido Beach Home- walk to beach and St. Armand's
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Enjoy a morning stroll on the beach collecting sea shells, walk to St. Armand's to experience great restaurants and shop ...
From $459 per night (USD)
Expedia
From $141 per night (USD)
VRBO
Sea Side Vacation Home - By 5 beaches
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Our remodeled Tropical Vacation Home has everything for your living needs. 3 Bedroom with Office/Den. We are only 5 mi ...
From $141 per night (USD)
VRBO
From $190 per night (USD)
Expedia
Charming Beach Cottage
Bedrooms:
1
Bathrooms:
2
Sleeps:
7
LOCATION!!! 3D Matterport scan of the house available!!! Getaway from the fast paced, high pressure life and slip on som ...
From $190 per night (USD)
Expedia
From $891 per night (USD)
VRBO
Casa Eulimia | Pet Friendly, Ping Pong Table, Private Heated Pool, Steps to Beach!
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
"Welcome to Casa Eulimia,, a gorgeous vacation rental duplex located on the Southern end of Siesta Key. This spacious an ...
From $891 per night (USD)
VRBO
$Seahorse Cabana | Pet Friendly Home on Siesta Key w\/ Heated Pool, Short Walk to Beach!$
From $407 per night (USD)
Expedia
Seahorse Cabana | Pet Friendly Home on Siesta Key w\/ Heated Pool, Short Walk to Beach!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Fully Remodeled Interior – Perfectly Prepared for Your Stay! Welcome to Seahorse Cottage, a beautiful duplex property n ...
From $407 per night (USD)
Expedia
From $1133 per night (USD)
VRBO
Casa Ohana | Pet Friendly, Ping Pong Table, Private Heated Pool, Steps to Beach!
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
🌴 Casa Ohana | A Laid-Back, Luxe Beach Escape on Siesta Key Welcome to Casa Ohana, your personal slice of paradise in t ...
From $1133 per night (USD)
VRBO
From $814 per night (USD)
Expedia
Casa Tegula | Pet Friendly 🐶 Ping Pong Table, Private Heated Pool, Steps to Beach!
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Welcome to Casa Tegula, your luxurious tropical oasis on the Southern end of Siesta Key. This stunning beach vacation re ...
From $814 per night (USD)
Expedia
From $806 per night (USD)
VRBO
Casa Antilles | Pet Friendly, Ping Pong Table, Private Heated Pool, Steps to Beach!
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Welcome to Casa Antilles: A Hidden Gem on the Southern End of Siesta Key Discover the perfect blend of luxury and tranq ...
From $806 per night (USD)
VRBO
From $833 per night (USD)
Expedia
Casa Junonia | Pet Friendly, Ping Pong Table, Private Heated Pool, Steps to Beach!
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Welcome to Casa Junonia, a gorgeous vacation rental duplex located on the Southern end of Siesta Key. This spacious and ...
From $833 per night (USD)
Expedia
From $326 per night (USD)
VRBO
Casita Mar | Pet Friendly, Siesta Key Home with Pool & Beach Access Included!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to Casita Mar, a beautifully renovated 2-bedroom, 1-bath vacation rental on Siesta Key, offering everything you ...
From $326 per night (USD)
VRBO
From $1008 per night (USD)
Expedia
Admirals Watch | Ocean Views from Spacious Balconies, Heated Pool and Steps to Siesta Key Beach
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Ultimate Siesta Key Beach Escape at Admiral's Watch – Steps from the Sand! Wake up to the sound of waves and the fresh G ...
From $1008 per night (USD)
Expedia
$La Contento Casa | Pet Friendly, Waterfront Home on Siesta Key w\/ Private Heated Pool & Kayaks!$
From $839 per night (USD)
VRBO
La Contento Casa | Pet Friendly, Waterfront Home on Siesta Key w\/ Private Heated Pool & Kayaks!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
La Contento Casa: Your Dream Beach Vacation Awaits! Welcome to La Contento Casa, a stunning waterfront retreat where the ...
From $839 per night (USD)
VRBO
$The Solaster | Pet Friendly Home on Siesta Key w\/ 2 Heated Pools, Walk to Beach & South Village!$
From $1161 per night (USD)
Expedia
The Solaster | Pet Friendly Home on Siesta Key w\/ 2 Heated Pools, Walk to Beach & South Village!
Bedrooms:
6
Bathrooms:
7
Sleeps:
20
Escape to The Solaster, a magnificent vacation rental duplex retreat that offers nothing but luxury and relaxation. This ...
From $1161 per night (USD)
Expedia
From $1597 per night (USD)
VRBO
The Abalone | Luxury Pet Friendly Home, 2 Heated Pools, Ping Pong Tables Steps to Beach!
Bedrooms:
6
Bathrooms:
9
Sleeps:
24
Welcome to The Abalone, a gorgeous vacation rental duplex located on the Southern end of Siesta Key. This spacious and a ...
From $1597 per night (USD)
VRBO
From $797 per night (USD)
Expedia
Peacock Villa | Spacious Outdoor Area, Cabana Room, Heated Pool, & Steps to Siesta Key Beach!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Welcome to Peacock Villa – Your Exclusive Siesta Key Retreat Step into Peacock Villa, an exquisite vacation property of ...
From $797 per night (USD)
Expedia
From $911 per night (USD)
VRBO
Casa Coquina | Pet Friendly, Ping Pong Table, Private Heated Pool, Steps to Beach!
Bedrooms:
3
Bathrooms:
5
Sleeps:
14
Welcome to Casa Coquina, a hidden gem vacation rental duplex located on the Southern end of Siesta Key. As you enter the ...
From $911 per night (USD)
VRBO
From $1473 per night (USD)
Expedia
The Nautilus | Luxury Pet Friendly Home, 2 Heated Pools, Ping Pong Tables Steps to Beach!
Bedrooms:
6
Bathrooms:
9
Sleeps:
24
"Welcome to the Nautilus, your luxurious tropical oasis on the Southern end of Siesta Key. This stunning beach vacation ...
From $1473 per night (USD)
Expedia
From $535 per night (USD)
VRBO
Casita Sun Star | Pet Friendly Home on Siesta Key, Heated Pool, Walk to Beach & South Village!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Escape to Casita Sun Star, a magnificent vacation rental duplex retreat that offers nothing but luxury and relaxation. T ...
From $535 per night (USD)
VRBO
From $1565 per night (USD)
Expedia
Casa De Mariposa | Private Heated Pool, Ping Pong, & Steps to Siesta Key Beach!
Bedrooms:
6
Bathrooms:
7
Sleeps:
16
Welcome to Casa De Mariposa – The Ultimate Siesta Key Escape Nestled in the heart of Siesta Key, Casa De Mariposa is a ...
From $1565 per night (USD)
Expedia
$Sol y Mar | Pet Friendly, Siesta Key Duplex Home w\/ Pool Access, Private Beach Access Included!$
From $615 per night (USD)
VRBO
Sol y Mar | Pet Friendly, Siesta Key Duplex Home w\/ Pool Access, Private Beach Access Included!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Welcome to Sol y Mar and experience the best of Siesta Key, a beautifully renovated vacation rental offering the unique ...
From $615 per night (USD)
VRBO
$Villa De Paradisio | Waterfront Home w\/ Private Pool, Fishing Dock, Close to Beach & Village!$
From $590 per night (USD)
Expedia
Villa De Paradisio | Waterfront Home w\/ Private Pool, Fishing Dock, Close to Beach & Village!
Bedrooms:
2
Bathrooms:
5
Sleeps:
12
Experience the pinnacle of waterfront luxury at Villa De Paradisio, a stunning Siesta Key rental home nestled along the ...
From $590 per night (USD)
Expedia
$Casita Sol | Pet Friendly, Siesta Key Duplex Home w\/ Pool & Private Beach Access Included!$
From $326 per night (USD)
VRBO
Casita Sol | Pet Friendly, Siesta Key Duplex Home w\/ Pool & Private Beach Access Included!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to Casita Sol, a charmingly updated 2-bedroom, 1-bathroom vacation rental nestled in the heart of Siesta Key. Ca ...
From $326 per night (USD)
VRBO
From $1032 per night (USD)
Expedia
Casa Mahalo | Pet Friendly, Ping Pong Table, Private Heated Pool, Steps to Beach!
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
"🌺 Casa Mahalo | Island Bliss in the Heart of Siesta Key Welcome to Casa Mahalo, your serene island escape perched on t ...
From $1032 per night (USD)
Expedia
$Sandy Cabana | Pet Friendly Home on Siesta Key w\/ Heated Pool, Short Walk to Beach!$
From $395 per night (USD)
VRBO
Sandy Cabana | Pet Friendly Home on Siesta Key w\/ Heated Pool, Short Walk to Beach!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Fully Remodeled Interior – Perfectly Prepared for Your Stay! Welcome to Sandy Cabana, a peaceful retreat tucked ...
From $395 per night (USD)
VRBO
From $2454 per night (USD)
Expedia
The Big Kahuna | SK Village, Pet Friendly, 2 Heated Pools, Elevator, Ping Pong Tables Steps to Beach
Bedrooms:
6
Bathrooms:
9
Sleeps:
24
🌞 The Big Kahuna | Siesta Key's Ultimate Beach Retreat Welcome to The Big Kahuna, your private, two-in-one beach haven ...
From $2454 per night (USD)
Expedia
$Serenity Cottage | Multilevel Home on Siesta Key w\/ Private Pool & Spa, Short Walk to Beach!$
From $621 per night (USD)
VRBO
Serenity Cottage | Multilevel Home on Siesta Key w\/ Private Pool & Spa, Short Walk to Beach!
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
Welcome to Serenity Cottage, a tranquil cottage located on the southern end of Siesta Key. This remarkable vacation rent ...
From $621 per night (USD)
VRBO
From $2085 per night (USD)
Expedia
The Conch | Luxury Pet Friendly Home, 2 Heated Pools, Ping Pong Tables Steps to Beach!
Bedrooms:
6
Bathrooms:
9
Sleeps:
26
Welcome to The Conch: Your Ultimate Luxury Retreat on the Southern End of Siesta Key Discover The Conch, an extraordina ...
From $2085 per night (USD)
Expedia
From $702 per night (USD)
VRBO
Casa Stolida | Pet Friendly 🐶 Ping Pong Table, Private Heated Pool, Steps to Beach!
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Welcome to Casa Stolida, your luxurious tropical oasis on the Southern end of Siesta Key. This stunning beach vacation r ...
From $702 per night (USD)
VRBO
From $572 per night (USD)
Expedia
Casita Morning Star | Pet Friendly Home on Siesta Key, Heated Pool, Walk to Beach & South Village!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Escape to Casita Morning Star, a magnificent vacation rental duplex retreat that offers nothing but luxury and relaxatio ...
From $572 per night (USD)
Expedia
From $730 per night (USD)
VRBO
Monarch Villa | Ocean Views, Cabana Room, Heated Pool, & Steps to Siesta Key Beach!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Welcome to Monarch Villa – Your Ideal Siesta Key Getaway Discover the perfect vacation retreat at Monarch Villa, an exq ...
From $730 per night (USD)
VRBO
$Topsail Cottage | Luxury Home on Siesta Key w\/ Heated Pool & Rooftop View of Gulf, Walk to Beach!$
From $748 per night (USD)
Expedia
Topsail Cottage | Luxury Home on Siesta Key w\/ Heated Pool & Rooftop View of Gulf, Walk to Beach!
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
Welcome to Topsail Cottage, a luxurious condo located on the southern end of Siesta Key. This exquisite 4-bedroom, 4-bat ...
From $748 per night (USD)
Expedia
$AMAZING 4 level SIESTA KEY home on large water with dock, crows nest, spa\/pool$
From $1488 per night (USD)
VRBO
AMAZING 4 level SIESTA KEY home on large water with dock, crows nest, spa\/pool
Bedrooms:
7
Bathrooms:
6
Sleeps:
10
Indulge in unbeatable waterfront living in this breathtaking Siesta Key vacation rental, nestled on the serene waters of ...
From $1488 per night (USD)
VRBO
$Beachfront Home on Gulf of Mexico w\/ Indoor Pool$
From $741 per night (USD)
Expedia
Beachfront Home on Gulf of Mexico w\/ Indoor Pool
Bedrooms:
3
Bathrooms:
5
Sleeps:
6
Pack your bags for a lavish getaway and stay at this chic oceanfront vacation rental in Englewood! Resting on a stunning ...
From $741 per night (USD)
Expedia
From $223 per night (USD)
VRBO
2 Bedroom 2 Bath home near Siesta Key Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Summary: Take a peek at the amazing open kitchen, dining room and living room. It's perfect to enjoy family time and mak ...
From $223 per night (USD)
VRBO
From $73 per night (USD)
Expedia
Adorable 1 Bedroom 1 Apartment
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Very nice and spacious 1 bedroom 1 bath apartment with a comfortable setting. Perfectly located only 3 min walking dista ...
From $73 per night (USD)
Expedia
From $482 per night (USD)
VRBO
Crystal Sands Tower Unit 903 - Beachfront
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Breathtaking, unobstructed, North to South, panoramic views of the Gulf of Mexico on renowned Crescent Beach; located o ...
From $482 per night (USD)
VRBO
From $437 per night (USD)
Expedia
Crystal Sands Tower Unit 1206 - Beachfront
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Penthouse Condo - Direct Beachfront -Million Dollar View This condo is in the most requested part of the Crystal Sands c ...
From $437 per night (USD)
Expedia
Click For Pricing
VRBO
Spectacular penthouse view over downtown Sarasota plus private beach access
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to paradise on Siesta Key! You will find this penthouse condo inviting and comfortable with everything you need ...
Click For Pricing
VRBO
From $690 per night (USD)
Expedia
Key West Suite - Steps to Siesta Key Beach - Just 60 Paces to Paradise!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Steps from Siesta Key Beach – Just 60 Paces to Paradise! Welcome to our recently updated, spacious 2-bedroom + DEN, 2-b ...
From $690 per night (USD)
Expedia

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