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From $426 per night (USD)
VRBO
Crystal Sands Tower Unit 506 - Beachfront
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Treat yourself to a completely remodeled and updated 5th floor 2 bedroom 2 bath ocean front condo. Enjoy the beautiful ...
From $426 per night (USD)
VRBO
From $432 per night (USD)
Expedia
Crystal Sands Tower Unit 704 - Beachfront
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Enjoy the best of Crystal Sands in this beachy, contemporary 2-bedroom, 2 bath condo overlooking the 2011 and 2017 Best ...
From $432 per night (USD)
Expedia
From $454 per night (USD)
VRBO
Crystal Sands Tower Unit 710 - Beachfront
Bedrooms:
2
Bathrooms:
2
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 $454 per night (USD)
VRBO
From $392 per night (USD)
Expedia
Crystal Sands Villa 20 - Private Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
For more privacy we offer you this 2 bedroom 2 bath villa flanking our attractive palm lined boulevard. Gracious living ...
From $392 per night (USD)
Expedia
From $492 per night (USD)
VRBO
Crystal Sands Tower Unit 104 - Beachfront
Bedrooms:
2
Bathrooms:
2
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 $492 per night (USD)
VRBO
From $426 per night (USD)
Expedia
Crystal Sands Tower Unit 205 - Beachfront
Bedrooms:
2
Bathrooms:
2
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 $426 per night (USD)
Expedia
From $316 per night (USD)
VRBO
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 $316 per night (USD)
VRBO
From $241 per night (USD)
Expedia
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 $241 per night (USD)
Expedia
From $302 per night (USD)
VRBO
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 $302 per night (USD)
VRBO
From $378 per night (USD)
Expedia
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)
Expedia
From $302 per night (USD)
VRBO
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 $302 per night (USD)
VRBO
From $254 per night (USD)
Expedia
Romantic comfort from - B303, 3rd Floor and Gulf View, Free Boat Docks & WiFi
Bedrooms:
1
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 $254 per night (USD)
Expedia
From $294 per night (USD)
VRBO
Coastal Getaway minutes from Siesta Key, America’s #1 Beach
Bedrooms:
3
Bathrooms:
4
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 $294 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
Expedia
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
Expedia
From $241 per night (USD)
Expedia
Located across the street from Siesta Key Beach, Gulf and Pool View Condo!! #319
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Updated 2BR Condo | Pool & Ocean Views | Steps to Beach & Village | Sleeps 6 Escape to paradise at La Siesta 319, a beau ...
From $241 per night (USD)
Expedia
From $256 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 $256 per night (USD)
VRBO
$Charming Condo at La Siesta with Partial Beach Views \Your home away from home\$
From $237 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 $237 per night (USD)
Expedia
From $212 per night (USD)
VRBO
Chic Sarasota Cottage: Near Beaches & Downtown!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Plan your next beach escape at this gorgeous 1-bedroom, 1-bath Sarasota vacation rental! Perfect for couples or small gr ...
From $212 per night (USD)
VRBO
From $359 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 $359 per night (USD)
Expedia
From $302 per night (USD)
Expedia
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 $302 per night (USD)
Expedia
From $250 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 $250 per night (USD)
Expedia
From $316 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 $316 per night (USD)
VRBO
From $377 per night (USD)
Expedia
Fall Into Paradise Your Endless Summer Starts Now
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 $377 per night (USD)
Expedia
From $432 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 $432 per night (USD)
VRBO
From $300 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 $300 per night (USD)
Expedia
From $347 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 $347 per night (USD)
VRBO
From $300 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 $300 per night (USD)
Expedia
From $300 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 $300 per night (USD)
VRBO
From $300 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 $300 per night (USD)
Expedia
From $1088 per night (USD)
VRBO
Villa Vista Mare | Gorgeous Home w/ Views of Gulf, Heated Pool, & Across From Siesta Key Beach!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
🌴Villa Vista Mare | Gulf Views, Heated Pool + Steps to Siesta Beach 💖 Why You'll Love This Home Wake up to sweeping G ...
From $1088 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
From $301 per night (USD)
VRBO
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 ...
From $301 per night (USD)
VRBO
From $678 per night (USD)
Expedia
Crescent Cottage | Pet Friendly 🐶 w/ Private Pool, Lounging Area, Short Walk to Crescent Beach
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Crescent Cottage – Your Siesta Key Escape Welcome to Crescent Cottage, your ultimate island retreat where comfort, luxu ...
From $678 per night (USD)
Expedia
From $634 per night (USD)
VRBO
Sand Dollar Cottage | Waterfront Home w/ Private Pool & Kayaks! Minutes to Siesta Key Beach!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
🌴 Sand Dollar Cottage | Canal-Front Oasis + Private Heated Pool 💖 Why You'll Love This Home Float into coastal sereni ...
From $634 per night (USD)
VRBO
From $624 per night (USD)
Expedia
🍾Villa Champagne | Pet Friendly Waterfront Home w/ Private Pool & Spa, Close to Beach & Village!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
"🍾Villa Champagne | Rooftop Sunsets + Walk to Siesta Beach 💖 Why You'll Love This Home Imagine sunrise yoga on your p ...
From $624 per night (USD)
Expedia
From $816 per night (USD)
VRBO
Sandy Seahorse Cottage | Pet Friendly Home on Siesta Key w/ Private Pool, Short Walk to Beach
Bedrooms:
5
Bathrooms:
6
Sleeps:
16
Fully Remodeled Interior – Perfectly Prepared for Your Stay! Welcome to Sandy Seahorse Cottage, your perfect Sie ...
From $816 per night (USD)
VRBO
From $306 per night (USD)
Expedia
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 $306 per night (USD)
Expedia
From $222 per night (USD)
VRBO
Enjoy the Siesta Key Beach Life to the fullest! Beach AND Pool Access
Bedrooms:
2
Bathrooms:
2
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)
VRBO
From $653 per night (USD)
Expedia
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)
Expedia
Click For Pricing
VRBO
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
VRBO
From $318 per night (USD)
Expedia
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 $318 per night (USD)
Expedia
From $382 per night (USD)
VRBO
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 $382 per night (USD)
VRBO
From $332 per night (USD)
Expedia
Walk to the Beach & Village, Heated Pool Oasis, Spacious
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Discover your dream vacation rental in the heart of Siesta Key, Florida, where coastal charm meets modern luxury. This s ...
From $332 per night (USD)
Expedia
From $334 per night (USD)
VRBO
The Coral Cottage close to all that Sarasota has to offer
Bedrooms:
1
Bathrooms:
2
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 $334 per night (USD)
VRBO
From $330 per night (USD)
Expedia
Hidden Paradise Among Tropical Landscape on Lakefront Property on Siesta Key
Bedrooms:
1
Bathrooms:
1
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 $330 per night (USD)
Expedia
From $344 per night (USD)
VRBO
Lakeside Hidden Paradise Among Tropical Landscape W/ Heated Pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Nestled along the serene waters of Heron Lagoon, our 1-bedroom suites at Siesta Heron Suites & Villas offer the perfect ...
From $344 per night (USD)
VRBO
From $616 per night (USD)
Expedia
Lakefront Siesta Key Vacation Rental Home within Small Private Resort W/ Pool
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Spending time in sunny Siesta Key is always a treat for travelers. Those looking to enhance their stay with the inclusio ...
From $616 per night (USD)
Expedia
From $366 per night (USD)
VRBO
Spacious Renovated 1 Bedroom Siesta Key Beachside Vacation Rental Getaway
Bedrooms:
1
Bathrooms:
1
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 $366 per night (USD)
VRBO
Click For Pricing
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:
1
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 $212 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 $212 per night (USD)
Expedia
From $369 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 May 2025! Our condo ...
From $369 per night (USD)
VRBO
From $336 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 $336 per night (USD)
Expedia
From $135 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 $135 per night (USD)
VRBO
From $182 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 $182 per night (USD)
Expedia
From $712 per night (USD)
VRBO
Casa Eulimia | Pet Friendly, Ping Pong Table, Private Heated Pool, Steps to Beach!
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
"Welcome to Casa Eulimia,, a gorgeous vacation rental duplex located on the Southern end of Siesta Key. This spacious an ...
From $712 per night (USD)
VRBO
From $388 per night (USD)
Expedia
Seahorse Cabana | Pet Friendly Home on Siesta Key w/ Heated Pool, Short Walk to Beach!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Fully Remodeled Interior – Perfectly Prepared for Your Stay! Welcome to Seahorse Cottage, a beautiful duplex property n ...
From $388 per night (USD)
Expedia
From $848 per night (USD)
VRBO
Casa Ohana | Pet Friendly, Ping Pong Table, Private Heated Pool, Steps to Beach!
Bedrooms:
3
Bathrooms:
4
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 $848 per night (USD)
VRBO
From $755 per night (USD)
Expedia
Casa Tegula | Pet Friendly 🐶 Ping Pong Table, Private Heated Pool, Steps to Beach!
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Welcome to Casa Tegula, your luxurious tropical oasis on the Southern end of Siesta Key. This stunning beach vacation re ...
From $755 per night (USD)
Expedia
From $724 per night (USD)
VRBO
Casa Antilles | Pet Friendly, Ping Pong Table, Private Heated Pool, Steps to Beach!
Bedrooms:
3
Bathrooms:
4
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 $724 per night (USD)
VRBO
From $727 per night (USD)
Expedia
Casa Junonia | Pet Friendly, Ping Pong Table, Private Heated Pool, Steps to Beach!
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Welcome to Casa Junonia, a gorgeous vacation rental duplex located on the Southern end of Siesta Key. This spacious and ...
From $727 per night (USD)
Expedia
From $325 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 $325 per night (USD)
VRBO
From $844 per night (USD)
Expedia
Admirals Watch | Ocean Views from Spacious Balconies, Heated Pool, and Steps to Siesta Key Beach
Bedrooms:
3
Bathrooms:
3
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 $844 per night (USD)
Expedia
From $731 per night (USD)
VRBO
La Contento Casa | Pet Friendly, Waterfront Home on Siesta Key w/ Private Heated Pool & Kayaks!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
"🌴 La Contento Casa | Private Heated Pool, Walk to Siesta Key Village and Beach 💖 Why You'll Love This Home Awaken to ...
From $731 per night (USD)
VRBO
From $1091 per night (USD)
Expedia
The Solaster | Pet Friendly Home on Siesta Key w/ 2 Heated Pools, Walk to Beach & South Village!
Bedrooms:
6
Bathrooms:
6
Sleeps:
20
Escape to The Solaster, a magnificent vacation rental duplex retreat that offers nothing but luxury and relaxation. This ...
From $1091 per night (USD)
Expedia
From $1571 per night (USD)
VRBO
The Abalone | Luxury Pet Friendly Home, 2 Heated Pools, Ping Pong Tables Steps to Beach!
Bedrooms:
6
Bathrooms:
8
Sleeps:
24
Welcome to The Abalone, a gorgeous vacation rental duplex located on the Southern end of Siesta Key. This spacious and a ...
From $1571 per night (USD)
VRBO
From $488 per night (USD)
Expedia
Peacock Villa | Spacious Outdoor Area, Cabana Room, Heated Pool, & Steps to Siesta Key Beach!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
🏖️ Peacock Villa | Heated Pool, Steps to Siesta Beach 💖 Why You'll Love This Home Step into coastal elegance across t ...
From $488 per night (USD)
Expedia
From $750 per night (USD)
VRBO
Casa Coquina | Pet Friendly, Ping Pong Table, Private Heated Pool, Steps to Beach!
Bedrooms:
3
Bathrooms:
4
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 $750 per night (USD)
VRBO
From $1548 per night (USD)
Expedia
The Nautilus | Luxury Pet Friendly Home, 2 Heated Pools, Ping Pong Tables Steps to Beach!
Bedrooms:
6
Bathrooms:
8
Sleeps:
24
"Welcome to the Nautilus, your luxurious tropical oasis on the Southern end of Siesta Key. This stunning beach vacation ...
From $1548 per night (USD)
Expedia
From $504 per night (USD)
VRBO
Casita Sun Star | Pet Friendly Home on Siesta Key, Heated Pool, Walk to Beach & South Village!
Bedrooms:
3
Bathrooms:
3
Sleeps:
10
Escape to Casita Sun Star, a magnificent vacation rental duplex retreat that offers nothing but luxury and relaxation. T ...
From $504 per night (USD)
VRBO
From $1056 per night (USD)
Expedia
Casa De Mariposa | Private Heated Pool, Ping Pong, & Steps to Siesta Key Beach!
Bedrooms:
6
Bathrooms:
6
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 $1056 per night (USD)
Expedia
From $712 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 $712 per night (USD)
VRBO
From $729 per night (USD)
Expedia
Villa De Paradisio | Waterfront Home w/ Private Pool, Fishing Dock, Close to Beach & Village!
Bedrooms:
2
Bathrooms:
4
Sleeps:
12
Experience the pinnacle of waterfront luxury at Villa De Paradisio, a stunning Siesta Key rental home nestled along the ...
From $729 per night (USD)
Expedia
From $294 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 $294 per night (USD)
VRBO
From $819 per night (USD)
Expedia
Casa Mahalo | Pet Friendly, Ping Pong Table, Private Heated Pool, Steps to Beach!
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
"🌺 Casa Mahalo | Island Bliss in the Heart of Siesta Key Welcome to Casa Mahalo, your serene island escape perched on t ...
From $819 per night (USD)
Expedia
From $335 per night (USD)
VRBO
Sandy Cabana | Pet Friendly Home on Siesta Key w/ Heated Pool, Short Walk to Beach!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Fully Remodeled Interior – Perfectly Prepared for Your Stay! Welcome to Sandy Cabana, a peaceful retreat tucked ...
From $335 per night (USD)
VRBO
From $1775 per night (USD)
Expedia
The Big Kahuna | SK Village, Pet Friendly, 2 Heated Pools, Elevator, Ping Pong Tables Steps to Beach
Bedrooms:
6
Bathrooms:
8
Sleeps:
24
🌞 The Big Kahuna | Siesta Key's Ultimate Beach Retreat Welcome to The Big Kahuna, your private, two-in-one beach haven ...
From $1775 per night (USD)
Expedia
From $566 per night (USD)
VRBO
🌴 Serenity Cottage | Multilevel Home on Siesta Key w/ Private Pool & Spa, Short Walk to Beach!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
🌴 Serenity Cottage | Heated Pool & Spa + 2‑min Walk to Crescent Beach 💖 Why You'll Love This Home Sunlight fills ever ...
From $566 per night (USD)
VRBO
From $1586 per night (USD)
Expedia
The Conch | Luxury Pet Friendly Home, 2 Heated Pools, Ping Pong Tables Steps to Beach!
Bedrooms:
6
Bathrooms:
8
Sleeps:
26
Welcome to The Conch: Your Ultimate Luxury Retreat on the Southern End of Siesta Key Discover The Conch, an extraordina ...
From $1586 per night (USD)
Expedia
From $762 per night (USD)
VRBO
Casa Stolida | Pet Friendly 🐶 Ping Pong Table, Private Heated Pool, Steps to Beach!
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Welcome to Casa Stolida, your luxurious tropical oasis on the Southern end of Siesta Key. This stunning beach vacation r ...
From $762 per night (USD)
VRBO
From $467 per night (USD)
Expedia
Casita Morning Star | Pet Friendly Home on Siesta Key, Heated Pool, Walk to Beach & South Village!
Bedrooms:
3
Bathrooms:
3
Sleeps:
10
Escape to Casita Morning Star, a magnificent vacation rental duplex retreat that offers nothing but luxury and relaxatio ...
From $467 per night (USD)
Expedia
From $542 per night (USD)
VRBO
Monarch Villa | Ocean Views, Cabana Room, Heated Pool, & Steps to Siesta Key Beach!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Welcome to Monarch Villa – Your Ideal Siesta Key Getaway Discover the perfect vacation retreat at Monarch Villa, an exq ...
From $542 per night (USD)
VRBO
From $714 per night (USD)
Expedia
Topsail Cottage | Luxury Home on Siesta Key w/ Heated Pool & Rooftop View of Gulf, Walk to Beach!
Bedrooms:
4
Bathrooms:
4
Sleeps:
12
Welcome to Topsail Cottage, a luxurious condo located on the southern end of Siesta Key. This exquisite 4-bedroom, 4-bat ...
From $714 per night (USD)
Expedia
From $1149 per night (USD)
VRBO
AMAZING 4 level SIESTA KEY home on large water with dock, crows nest, spa/pool
Bedrooms:
6
Bathrooms:
5
Sleeps:
10
Indulge in unbeatable waterfront living in this breathtaking Siesta Key vacation rental, nestled on the serene waters of ...
From $1149 per night (USD)
VRBO
From $662 per night (USD)
Expedia
Beachfront Home on Gulf of Mexico w/ Indoor Pool
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Pack your bags for a lavish getaway and stay at this chic oceanfront vacation rental in Englewood! Resting on a stunning ...
From $662 per night (USD)
Expedia
From $220 per night (USD)
VRBO
2 Bedroom 2 Bath home near Siesta Key Beach
Bedrooms:
2
Bathrooms:
2
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 $220 per night (USD)
VRBO
From $68 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 $68 per night (USD)
Expedia
From $532 per night (USD)
VRBO
Crystal Sands Tower Unit 903 - Beachfront
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Breathtaking, unobstructed, North to South, panoramic views of the Gulf of Mexico on renowned Crescent Beach; located o ...
From $532 per night (USD)
VRBO
From $433 per night (USD)
Expedia
Crystal Sands Tower Unit 1206 - Beachfront
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Penthouse Condo - Direct Beachfront -Million Dollar View This condo is in the most requested part of the Crystal Sands c ...
From $433 per night (USD)
Expedia
Click For Pricing
VRBO
Spectacular penthouse view over downtown Sarasota plus private beach access
Bedrooms:
2
Bathrooms:
2
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 $572 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 $572 per night (USD)
Expedia
From $245 per night (USD)
Expedia
VILLA DEL SOL 🌞💥🥂🌴🌴🌴🌴🍸🍸
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to Villa Del Sol, our sunny piece of paradise. From the time you arrive at the Villa, you will feel the sunshin ...
From $245 per night (USD)
Expedia
From $748 per night (USD)
Expedia
Beautiful West of The Trail Home
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Exquisite West of Trail home in Granada is a quiet, private neighborhood with easy access to all amenities. 4 Bedrooms 3 ...
From $748 per night (USD)
Expedia
From $440 per night (USD)
VRBO
Luxury Beach Condo on Crescent Beach #1 Beach in USA
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Discover your dream vacation rentals at Crescent Siesta Key - Prime Location: Situated on the pristine Crescent Beach, ...
From $440 per night (USD)
VRBO
From $295 per night (USD)
Expedia
Private beach getaway near point of rocks
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Beautiful 2nd-floor family-friendly beachside condo. Located on the world-famous crescent beach. 1 private parking space ...
From $295 per night (USD)
Expedia
From $218 per night (USD)
VRBO
Walk to Beach: Resort-Style Siesta Key Condo!
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
2 Heated Community Outdoor Pools | Large Sunroom w/ Desk & Dining Area | 7 Mi to Downtown Sarasota | 1,600 Sq Ft Have f ...
From $218 per night (USD)
VRBO
From $394 per night (USD)
Expedia
Family getaway 5 miles to Siesta Beach. Heated private Pool, bicycles.Sleep 10.
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Welcome to our Blue Beach House! Look no further, you have found the ideal rental for relaxing in the Florida sun! This ...
From $394 per night (USD)
Expedia
From $338 per night (USD)
VRBO
'Casa Bella' Florida Getaway w/Heated Spa & Grill
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Treat yourself to “Casa Bella” on your next trip to Florida’s beautiful west coast. A private and relaxing home with ple ...
From $338 per night (USD)
VRBO
Click For Pricing
Expedia
Villa Las Flores | Pet Friendly Home in Sarasota w/ Private Heated Pool & Screened-In Porch
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Villa Las Flores: Your Ideal Getaway in Sarasota Welcome to Villa Las Flores, a stunning duplex retreat offering the pe ...
Click For Pricing
Expedia

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