
Sarasota Area Rentals
- From $232 per night (USD)
VRBO
Very clean 3 bedroom, 2 bath. Easy walk to Siesta Key Beach & Restaurants.
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
This home is 1/2 mile from Siesta Key Beach. It is furnished with quality. Your stay includes super-fast WiFi, a washer/ ...
From $232 per night (USD)VRBO
- From $430 per night (USD)
Expedia
Ventana Rosa | Beautiful Sarasota Home Near Siesta Key w/ Private Pool & Large Outdoor Space
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
🌴 Ventana Rosa | Heated Pool + Lush Tropical Outdoor Living 💖 Why You'll Love This Home Wrapped in tropical foliage a ...
From $430 per night (USD)Expedia
- From $132 per night (USD)
VRBO
amazing apartment on the beach. With warm pool .
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
On the landscaped side of the complex, you will hear a calming waterfall right from your tropical patio! The apartment ...
From $132 per night (USD)VRBO
- From $406 per night (USD)
VRBO
“Casa Concord: 3BR-2BA Home with Private SaltH20 Pool, 2 Miles from Siesta Key”
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Just 2 miles to Crescent Beach, Siesta Key, 3.9 miles to Siesta Key Beach! Ranked the #1 Beach in America and the World, ...
From $406 per night (USD)VRBO
- From $305 per night (USD)
VRBO
Beachfront Condo - 2-Bedroom - Luxury - Directly on Crescent Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
CRESCENT ARMS - Siesta Key Beachfront Vacation Condos on Crescent Beach (Two Bedroom Beachfront Unit for Rent) Located ...
From $305 per night (USD)VRBO
- From $265 per night (USD)
Expedia
Relax`n - Beautiful newer South Venice home with pool and spa
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Beautiful newer South Venice pool home in immaculate condition. Open plan with gleaming tiled floors throughout, high ce ...
From $265 per night (USD)Expedia
- From $441 per night (USD)
VRBO
Beautiful 2025 renovated - 550 Sq Ft Patio - across street from beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Long term rental available from May 1 - Dec 15th - please contact for details UV OZONE Sanitized between each guest. ...
From $441 per night (USD)VRBO
- From $329 per night (USD)
Expedia
Longboat Key Escape–2BR Beachplace Condo Near the Ocean Unit 5-301 by RVA
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
RVA proudly presents an exquisite two-bedroom, two-bathroom residence nestled in building 5, offering unparalleled Gulf ...
From $329 per night (USD)Expedia
- From $365 per night (USD)
VRBO
Venice Pool Home- Breezy Inn
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
3BR Heated Pool Home Minutes from the Gulf! Get ready to unwind in paradise! This newly remodeled 3-bedroom, 2-bath heat ...
From $365 per night (USD)VRBO
- From $175 per night (USD)
Expedia
Hotel Studio (Ground Level) - Unit C
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Experience Escape’s brand new luxury villas including one bedroom hotel units, two bed two bath and three bed three bath ...
From $175 per night (USD)Expedia
- From $196 per night (USD)
VRBO
Hotel Studio (Ground Level) - Unit B
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Experience Escape’s brand new luxury villas including one bedroom hotel units, two bed two bath and three bed three bath ...
From $196 per night (USD)VRBO
- From $215 per night (USD)
Expedia
Escape Casey Key Hotel & Marina - 1 Bed 1 Bath K Bed Villa 4b
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Experience Escape’s brand new luxury villas including one bedroom hotel units, two bed two bath and three bed three bath ...
From $215 per night (USD)Expedia
- From $306 per night (USD)
VRBO
2 Bedroom/1 Bath Villa (Ground Level) - Unit 5
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Experience Escape’s brand new luxury villas including one bedroom hotel units, two bed two bath and three bed three bath ...
From $306 per night (USD)VRBO
- From $400 per night (USD)
Expedia
2 Bedroom/2 Bath Villa (Ground Level) - Unit 4/A
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Experience Escape’s brand new luxury villas including one bedroom hotel units, two bed two bath and three bed three bath ...
From $400 per night (USD)Expedia
- From $242 per night (USD)
VRBO
1 Bedroom/1 Bath Villa Ground Level - Unit 9
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Experience Escape’s brand new luxury villas including one bedroom hotel units, two bed two bath and three bed three bath ...
From $242 per night (USD)VRBO
- From $392 per night (USD)
Expedia
3 Bedroom/3 Bath Townhouse - Unit 2
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Experience Escape’s brand new luxury villas including one bedroom hotel units, two bed two bath and three bed three bath ...
From $392 per night (USD)Expedia
- From $175 per night (USD)
VRBO
Hotel Studio (Ground Level) - Unit A
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Experience Escape’s brand new luxury villas including one bedroom hotel units, two bed two bath and three bed three bath ...
From $175 per night (USD)VRBO
- From $487 per night (USD)
Expedia
3 Bedroom/3 Bath Townhouse - Unit 3
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Experience Escape’s brand new luxury villas including one bedroom hotel units, two bed two bath and three bed three bath ...
From $487 per night (USD)Expedia
- From $400 per night (USD)
VRBO
2 Bedroom/2 Bath Villa (Ground Level) - Unit 7
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Experience Escape’s brand new luxury villas including one bedroom hotel units, two bed two bath and three bed three bath ...
From $400 per night (USD)VRBO
- From $381 per night (USD)
Expedia
2 Bedroom/1 Bath Villa (Ground Level) - Unit 13
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Experience Escape’s brand new luxury villas including one bedroom hotel units, two bed two bath and three bed three bath ...
From $381 per night (USD)Expedia
- From $380 per night (USD)
VRBO
2 Bedroom/2 Bath Villa (Second Level) - Unit 6
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Experience Escape’s brand new luxury villas including one bedroom hotel units, two bed two bath and three bed three bath ...
From $380 per night (USD)VRBO
- From $330 per night (USD)
Expedia
ADA Compliance - 1 Bedroom/1 Bath Villa (Ground Level) - Unit 8
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Experience Escape’s brand new luxury villas including one bedroom hotel units, two bed two bath and three bed three bath ...
From $330 per night (USD)Expedia
- From $477 per night (USD)
VRBO
2 Bedroom/2 Bath Villa (Second Level) - Unit 10
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Experience Escape’s brand new luxury villas including one bedroom hotel units, two bed two bath and three bed three bath ...
From $477 per night (USD)VRBO
- From $380 per night (USD)
Expedia
2 Bedroom/1 Bath Villa (Ground Level) - Unit 12
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Experience Escape’s brand new luxury villas including one bedroom hotel units, two bed two bath and three bed three bath ...
From $380 per night (USD)Expedia
- From $428 per night (USD)
VRBO
2 Bedroom/2 Bath Villa (Ground Level) - Unit 9/C
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Experience Escape’s brand new luxury villas including one bedroom hotel units, two bed two bath and three bed three bath ...
From $428 per night (USD)VRBO
- From $610 per night (USD)
Expedia
3 Bedroom/2 Bath Villa (Ground Level) - Unit 5/B
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Experience Escape’s brand new luxury villas including one bedroom hotel units, two bed two bath and three bed three bath ...
From $610 per night (USD)Expedia
- Click For Pricing
VRBO
Casa Bella Vita | Luxury Home w/ Heated Pool, Ping Pong Table, & Walking Distance to Crescent Beach!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Welcome to Casa Bella Vita – Your Ultimate Siesta Key Escape! Discover the charm and elegance of Casa Bella Vita, a stu ...
Click For PricingVRBO
- From $392 per night (USD)
Expedia
Escape Casey Key Hotel & Marina - Deluxe 3 Bedroom 3 Bath Villa 2 K 1 Q 1
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Experience Escape’s brand new luxury villas including one bedroom hotel units, two bed two bath and three bed three bath ...
From $392 per night (USD)Expedia
- From $474 per night (USD)
VRBO
Coastal 3BR Villa – Lil’ Nauti with Pool & Waterfront Access
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
*Fully Renovated as of February 2025* Your own private Siesta Key villa that's a little bit tropical, a little bit salt ...
From $474 per night (USD)VRBO
- From $193 per night (USD)
Expedia
Beautiful Venice Beach Condo
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
Prime location one block from the beach with a marina, dining, and lounge nearby. Two minute walk to three different bea ...
From $193 per night (USD)Expedia
- From $301 per night (USD)
VRBO
Drift Inn B, Heated Pool, Beach and Amenities, 2-3 min walk
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Cottage style 2 bedroom 1 bath condo in Siesta Key is just a 2-3 min walk to the Pool, Beach, Restaurants and shops. ((A ...
From $301 per night (USD)VRBO
- From $307 per night (USD)
Expedia
Condo# 314 Siesta Key 3rd Flr 2b/2b unit; Open kitchen; newly renovated master shower
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
This Two Bedroom, Two Bath condo is just steps to the white, powdered-sugar sand of Siesta Key. Here at La Siesta Condom ...
From $307 per night (USD)Expedia
- From $311 per night (USD)
VRBO
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Cottage style 2 bedroom 1 bath condo in Siesta Key is just a 2-3 min walk to the Pool, Beach, Restaurants and shops. (Al ...
From $311 per night (USD)VRBO
- From $143 per night (USD)
Expedia
Paradise! Gulf beach, On bay, bike, fish, kayak, relax, shop, swim, tennis.....
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Beautiful condo located on 2nd floor. End unit overlooking beautiful tropical plants and offering natural light ! Turn ...
From $143 per night (USD)Expedia
- From $482 per night (USD)
VRBO
Contemporary, Downtown location, Pool, Spa & Sauna, very close to Beaches
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Gorgeous courtyard pool home features high end quality construction throughout with high end upgrades, open split floor ...
From $482 per night (USD)VRBO
- From $291 per night (USD)
Expedia
Beachplace Living – Walk to Beach, Swim, Play & Unwind #11-303 Condo by RVA
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
RVA offers this comfortably appointed two-bedroom, two-bathroom condominium in the desirable gated community of Beachpla ...
From $291 per night (USD)Expedia
- From $312 per night (USD)
VRBO
Paradise Found-heated pool & spa-bikes, game room-close to beach & Legacy Trail
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Paradise awaits at this charming 3-bedroom vacation home in the heart of South Venice. Nestled just minutes from the bea ...
From $312 per night (USD)VRBO
- From $678 per night (USD)
Expedia
Large Siesta Key Home On Water With Pool/Spa
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Welcome to “Siesta Retreat”… a grand 5 bedroom 4 bath vacation home right on the canal with an awesome pool and hot tub ...
From $678 per night (USD)Expedia
- From $428 per night (USD)
VRBO
Palm Bay Club!!! RESORT STYLE LIVING ON SIESTA KEY!!! Beach to Bay!!!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Walk onto the Famous Siesta Key beach, voted #1 beach in the US, with the worlds whitest and softest sand. This complex ...
From $428 per night (USD)VRBO
- From $202 per night (USD)
Expedia
Wonderful Home with Heated Pool near Beaches and Shamrock Park free wifi
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Located a block from Shamrock Park and close to 4 different beaches, you'll enjoy this completely updated 2/2/1 heated p ...
From $202 per night (USD)Expedia
- From $197 per night (USD)
VRBO
Private 2 Bedroom 1 bathroom house. private pool and SPA. Close to beaches
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Located just 10 minutes away from Nokomis beach at Casey Key, and 5 minutes to the Oscar Scherer State Park. You have e ...
From $197 per night (USD)VRBO
- From $378 per night (USD)
Expedia
Spacious 2BR Sarasota Executive Suite – Suited for Business, Medical Stay, Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
The Property Welcome to one of the most exciting vacation rental properties in Sarasota. The Southside Village Executive ...
From $378 per night (USD)Expedia
- From $299 per night (USD)
VRBO
Condo# 206 View Siesta Key Beach from balcony! LOCATION!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Enjoy the beach for the 4th!...Week ending July 6th 20% off rental rate. LOCATION, LOCATION, LOCATION! Spacious, updat ...
From $299 per night (USD)VRBO
- From $182 per night (USD)
Expedia
Kingston Arms Paradise!\n Saint Armands Circle & Lido Beach! Fully Equipped!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Kingston Arms Condominium, an exquisite retreat located on vibrant Saint Armands Circle in Sarasota, Florida. ...
From $182 per night (USD)Expedia
- From $333 per night (USD)
VRBO
3 Palms Inn- 2/3 bedroom heated pool house!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
We are also the hosts for VRBO listing #1718910. We are experience host with great reviews. We have decided to add anoth ...
From $333 per night (USD)VRBO
- From $449 per night (USD)
VRBO
Luxury and elegance in Venice
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to your luxurious, cozy, and relaxing, three bedroom, two bathroom, fully heated pool home in beautiful Venice, ...
From $449 per night (USD)VRBO
- From $749 per night (USD)
VRBO
Gertrude's Siesta | 4-min Walk to Beach & Village with Tiki-Bar, Balcony, Tropical Patio!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 12
Casa Van Lopik Large 3BR home in the Siesta Key Village, 4-min walk to best beaches shopping dining and entertainment on ...
From $749 per night (USD)VRBO
- From $329 per night (USD)
Expedia
Anchorage 310
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
We invite you to stay in our spacious 1,250 square foot 2 bedroom 2 bathroom condominium at The Anchorage Yacht and Tenn ...
From $329 per night (USD)Expedia
- From $385 per night (USD)
VRBO
Walk to Siesta Key Beach & Village | Private Patio | Prime Location!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The Village Studio Top location on the island! Apartment with full kitchen, private patio, quiet gated courtyard, in wo ...
From $385 per night (USD)VRBO
- From $282 per night (USD)
Expedia
☆ KING Bed in Master • 1st Floor • Heated Pool • ¼ mile walk to Siesta Key ☆
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Escape to the sugary sands of Siesta Key, just one-quarter mile from this well-appointed and stylish vacation condo! It ...
From $282 per night (USD)Expedia
- Click For Pricing
VRBO
Sunsets at Gulf of Mexico
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Location, location, location 1 block to the beach, 3 blocks to restaurants and shopping Venice inlet, Sharkey's at the p ...
Click For PricingVRBO
- From $613 per night (USD)
Expedia
Gertrude's Siesta | 4-min Walk to Beach & Village with Tiki-Bar, Balcony, Tropical Patio!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 12
Casa Van Lopik Large 3BR home in the Siesta Key Village, 4-min walk to best beaches shopping dining and entertainment on ...
From $613 per night (USD)Expedia
- From $229 per night (USD)
VRBO
2-3 bedroom pool home just 5 minutes to Beach. Bicycles & beach gear included!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
“Pool Villa by the Beach” located in South Venice - a recently remodeled home that's less than 2 miles to the famous Ma ...
From $229 per night (USD)VRBO
- From $270 per night (USD)
Expedia
Siesta Key 2 BR 1BA less than 1000 ft from Beach-“GEM”-Barefoot Bungalows
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
“GEM” at Barefoot Bungalows is a 2 bedroom, 1 bath, fully furnished villa just minute walk to the beach! This 1945 Tripl ...
From $270 per night (USD)Expedia
- From $276 per night (USD)
VRBO
Beautiful Villa in Private Resort-Style Community
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This spacious 2-bed/2-bath corner villa has 1,350 sq. ft. of fully tiled living space, attached garage and screened-in l ...
From $276 per night (USD)VRBO
- From $292 per night (USD)
Expedia
Ground-Level Condo | Beach Access, Pool & Canal Views | Walk to Everything
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy automatic discounts based on your stay length, no codes needed, and the price you see already includes your saving ...
From $292 per night (USD)Expedia
- From $180 per night (USD)
VRBO
Tiny House Margarita - Sleeps 6
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: This Tiny House began its life in our home state of Pennsylvania. Originally, it was meant to be a vacation hom ...
From $180 per night (USD)VRBO
- Click For Pricing
Expedia
Castel Del Mare Condo for rent
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Sarasota vacation condo is located in Castel Del Mare Condominum Complex, on the intercoastal waterway between Sarasota ...
Click For PricingExpedia
- From $175 per night (USD)
VRBO
Cozy Home away from Home - Central to Warm Mineral Springs and Englewood Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Private house, with Florida charm. Less than 15 min to Warm Mineral Springs 5 miles to Englewood Beach. Private back ya ...
From $175 per night (USD)VRBO
- From $2187 per night (USD)
Expedia
Just remodeled, professionally decorated bright and airy!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Oceanfront CLEAN condo on BEACH! Total remodel and professionally Decorated with a coastal vibe. New shiplap, new mirro ...
From $2187 per night (USD)Expedia
- From $379 per night (USD)
VRBO
Newly Renovated - 2BR Beachfront Condo by FVC
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
NEWLY RENOVATED!! A beachfront condominium managed by Florida Vacation Connection is located on the world-renowned Long ...
From $379 per night (USD)VRBO
- From $294 per night (USD)
Expedia
Beachview 2 BR / 2 BA Beachplace condo by FVC
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Beachplace 5-402 | Pond & Beach Views | Florida Vacation Connection Welcome to Beachplace 5-402, your serene getaway on ...
From $294 per night (USD)Expedia
- From $227 per night (USD)
VRBO
Warm and Inviting pet-friendly 2BR/2BA in Idyllic Bay Front Neighborhood
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Beautiful late 70's home with primary bedroom suite and bath, and guest bedroom with adjacent bathroom. Large fenced ya ...
From $227 per night (USD)VRBO
- Click For Pricing
Expedia
Siesta Key Old Florida Estate
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Magical, with in a Tree filled almost 2 acres on the bay sits Your Retreat, Your paradise includes a 3 bedroom 2 bath o ...
Click For PricingExpedia
- Click For Pricing
VRBO
NEW! Nokomis Seasonal Rental Jan-Mar
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
JUST LISTED! Mothly Rentals. Currently Available May-Oct Amazing Private 1000 Sq.Ft, One Bedroom Apartment . 1 Mile ...
Click For PricingVRBO
- From $1789 per night (USD)
Expedia
Perfect Location. Roof Top Deck. Gulf Views. Heated Pool/Spa w/ Rain Curtain
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 18
Blue Paradise by Siesta Key Luxury Rental Properties Home in Siesta Key, Florida Welcome to Blue Paradise - a six-bed ...
From $1789 per night (USD)Expedia
- From $342 per night (USD)
VRBO
Perfect 2 Bedroom Apartment on The Anchorage, Siesta Key Apartment 1020
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
5 Star Villa Holidays is proud to present Siesta Key Apartment 1020. A stones throw from the Siesta Key bea ...
From $342 per night (USD)VRBO
- From $500 per night (USD)
Expedia
Perfect 3 Bedroom Apartment on The Anchorage, Siesta Key Apartment 1010
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
5 Star Villa Holidays is proud to present Siesta Key Apartment 1010. Make Siesta Key your summer destinatio ...
From $500 per night (USD)Expedia
- From $328 per night (USD)
VRBO
Perfect 2 Bedroom Apartment on The Anchorage, Siesta Key Apartment 1014
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
5 Star Villa Holidays is proud to present Siesta Key Apartment 1014. Your dream vacation awaits you inside t ...
From $328 per night (USD)VRBO
- From $352 per night (USD)
Expedia
Rent the Perfect 2 Bedroom Apartment on The Anchorage, Siesta Key Apartment 1031
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
5 Star Villa Holidays is proud to present Siesta Key Apartment 1031. Let adventure take the front seat as yo ...
From $352 per night (USD)Expedia
- From $526 per night (USD)
VRBO
Rent the Perfect 3 Bedroom Apartment on The Anchorage, Siesta Key Apartment 1022
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
5 Star Villa Holidays is proud to present Siesta Key Apartment 1022. Your dreams of a luxurious vacation hav ...
From $526 per night (USD)VRBO
- From $329 per night (USD)
Expedia
Beautiful Apartment with first class amenities on The Anchorage, Siesta Key Apartment 1006
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
5 Star Villa Holidays is proud to present Siesta Key Apartment 1006. Welcome to this 2 bedroom 2 bathroom va ...
From $329 per night (USD)Expedia
- From $387 per night (USD)
VRBO
Luxury Contemporary Style Apartment on The Anchorage, Siesta Key Apartment 1001
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
5 Star Villa Holidays is proud to present Siesta Key Apartment 1001. Setting your travel sights on scenic Sie ...
From $387 per night (USD)VRBO
- From $323 per night (USD)
Expedia
Rent the Perfect 2 Bedroom Condo on The Anchorage, Siesta Key Condo 1002
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
5 Star Villa Holidays is proud to present Siesta Key Condo 1002. If you’re the type of traveler that can’t w ...
From $323 per night (USD)Expedia
- From $355 per night (USD)
VRBO
Perfect 2 Bedroom Apartment on The Anchorage, Siesta Key Apartment 1025
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
5 Star Villa Holidays is proud to present Siesta Key Apartment 1025. Your vacation begins as soon as you ste ...
From $355 per night (USD)VRBO
- From $348 per night (USD)
Expedia
Luxury Private Condo on The Anchorage, Siesta Key Condo 1024
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
5 Star Villa Holidays is proud to present Siesta Key Condo 1024. In quaint Siesta Key you’ll find gorgeous b ...
From $348 per night (USD)Expedia
- From $399 per night (USD)
VRBO
Rent the Perfect 2 Bedroom Apartment on The Anchorage, Siesta Key Apartment 1016
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
5 Star Villa Holidays is proud to present Siesta Key Apartment 1016. Warm natural light fills this home maki ...
From $399 per night (USD)VRBO
- From $330 per night (USD)
Expedia
Luxury 5 Star Apartment on The Anchorage, Siesta Key Apartment 1018
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
5 Star Villa Holidays is proud to present Siesta Key Apartment 1018. Bask in the ambiance of a true home whe ...
From $330 per night (USD)Expedia
- From $320 per night (USD)
VRBO
Beautiful Apartment with first class amenities on The Anchorage, Siesta Key Apartment 1019
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
5 Star Villa Holidays is proud to present Siesta Key Apartment 1019. Welcome to this pristine 2 bedroom, 2 b ...
From $320 per night (USD)VRBO
- From $315 per night (USD)
Expedia
Rent this Luxury 5 Star Apartment on The Anchorage, Siesta Key Apartment 1008
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
5 Star Villa Holidays is proud to present Siesta Key Apartment 1008. Bright colors and warm neutrals fill th ...
From $315 per night (USD)Expedia
- From $340 per night (USD)
VRBO
Rent the Perfect 2 Bedroom Apartment on The Anchorage, Siesta Key Apartment 1009
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
5 Star Villa Holidays is proud to present Siesta Key Apartment 1009. Just steps from the water and minutes f ...
From $340 per night (USD)VRBO
- From $337 per night (USD)
Expedia
Siesta Sol Bungalow, Relax by Siesta Key Beach 6 min drive in Gulf Gate Estates
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Siesta Sol Bungalow | Mid-Century Modern Retreat Near Beaches, Dining, and Entertainment Welcome to Siesta Sol Bungalow ...
From $337 per night (USD)Expedia
- From $318 per night (USD)
VRBO
Longboat Key Escape–Resort Pool + Ocean: Beachplace Condo # 7-102 by RVA
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Beachplace 7-102, a nicely decorated two-bedroom, two-bath unit at Beachplace that includes direct, private w ...
From $318 per night (USD)VRBO
- From $1212 per night (USD)
Expedia
Private Gated Home in Siesta Village, Heated Pool & Pool Table - The Hideaway
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 10
The Hideaway by Siesta Key Luxury Rental Properties Home in Siesta Key, Florida Siesta Key Luxury Rental Properties ...
From $1212 per night (USD)Expedia
- From $121 per night (USD)
VRBO
Lovely apartment 5 minutes to the beach, restaurants, shopping and services
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
<p>Close to sailing, windsurfing, and more, this pet-friendly apartment brings it all within reach. With the property's ...
From $121 per night (USD)VRBO
- From $121 per night (USD)
Expedia
Amazing Renovated Studio in Sarasota!!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
1 bed room, 1 bathroom, private entrance, wifi access, beautiful pool view, very close to restaurants and shopping cente ...
From $121 per night (USD)Expedia
- From $375 per night (USD)
VRBO
Waterfront/Pool mins to Siesta Key Beach- bikes/kayaks/SUPs incl-paddle to beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
WATERFRONT PROPERTY - View the Gulf in our waterside rocking chairs and lanai!! Everything you need for a vacation or sh ...
From $375 per night (USD)VRBO
- From $190 per night (USD)
Expedia
Cute home, close to beaches. Fishing equipment, golf clubs, bicycles supplied.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
This large & spacious home is a great base for visiting the Venice area. Formal living room & dining room plus family ro ...
From $190 per night (USD)Expedia
- From $174 per night (USD)
VRBO
Beautiful renovated 4th floor Condo across the street from Lido beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Beautiful 2 bedroom 4th floor condo located on Lido Key (Sarasota). Enjoy beautiful walks, the beach and the nice pool/h ...
From $174 per night (USD)VRBO
- From $386 per night (USD)
Expedia
The Palm Bay club Siesta Key Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to The Palm Bay Club on Siesta Key Beach Enjoy sunrise to sunset from our great resort that has private bay to b ...
From $386 per night (USD)Expedia
- From $1010 per night (USD)
VRBO
Crystal Sands Tower Unit 1109 - Beachfront
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Unique... Highly desirable 4 bedroom unit in Crystal Sands on Siesta Key. Very rare 4 bedroom beachfront condo with a d ...
From $1010 per night (USD)VRBO
- From $672 per night (USD)
Expedia
Endless Views | Walking Distance To Siesta Key Beach + Village w/ Rooftop Panoramic Views!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
🌴 Endless Views | Rooftop Balcony + 3-Min Walk to Siesta Key Beach 💖 Why You'll Love This Home Wake up to sweeping co ...
From $672 per night (USD)Expedia
- From $194 per night (USD)
VRBO
Updated,Sunny Cottage🌴near famous beaches🏝half mile to Downtown
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
Relaxing and charming 3 bedrooms, 2 bathrooms cottage walking distance /half mile/ to Main steet, Downtown, parks, resta ...
From $194 per night (USD)VRBO
- From $240 per night (USD)
VRBO
Grand Villa with Pool in Venice, FL
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Dramatic two-story Tuscan-style villa in the heart of South Venice. You'll love the tall ceilings, stained glass window ...
From $240 per night (USD)VRBO
- From $996 per night (USD)
VRBO
Eclectic Sarasota Spiritual Oasis - Pool, BBQ, Firepit & Short Walk to the Bay
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to the Bohemian Bungalow! Spiritual Oasis! This is the perfect location for those who have a flair for the heal ...
From $996 per night (USD)VRBO
- From $465 per night (USD)
Expedia
Beachfront Condo at Siesta Breakers | Gulf Views | 2nd Floor | Renovated | Tennis & Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy automatic discounts based on your stay length, no codes needed, and the price you see already includes your saving ...
From $465 per night (USD)Expedia
- From $1560 per night (USD)
VRBO
Heated Pool & Spa, Rooftop Deck for sunsets, Luxury Home for all ages!
- Bedrooms:
- 8
- Bathrooms:
- 8
- Sleeps:
- 24
Point Break by Siesta Key Luxury Rental Properties Home in Siesta Key, Florida Siesta Key Luxury Rental Properties - Th ...
From $1560 per night (USD)VRBO
- From $611 per night (USD)
Expedia
Private Gulf Beach-4 BRs- Luxury Cottage, Pet Friendly-Kayaks & SUPs-Grill
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 9
Charming Private Beach in one of the last remaining “Old Florida” regions of the Gulf Coast on North Manasota Key at th ...
From $611 per night (USD)Expedia
- From $642 per night (USD)
VRBO
Bali Hai House | Charming Siesta Key Waterfront Home with Heated Pool, Patio & Easy Beach Access!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Escape to Bali Hai House – A Stunning Waterfront Retreat on Siesta Key Discover your own slice of paradise at Bali Hai ...
From $642 per night (USD)VRBO
- From $200 per night (USD)
Expedia
Lido Beach Ocean View/POOL Sarasota Beachfront OFF SEASON RATES
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Lido Beach Spectacular Ocean View. St. Armands Circle. Close to many shops, resTaurants and entertainment. Deluxe unit ...
From $200 per night (USD)Expedia




































































































