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From $573 per night (USD)
VRBO
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 $573 per night (USD)
VRBO
From $666 per night (USD)
Expedia
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 $666 per night (USD)
Expedia
From $200 per night (USD)
VRBO
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)
VRBO
From $229 per night (USD)
Expedia
14th floor condo heart of city ,overlooking bay .Available 3months or yearly !
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
It’s a beautiful 2 BR, 1 Bath corner unit with 270 degree view of the bay as well as city with one allocated parking o ...
From $229 per night (USD)
Expedia
From $358 per night (USD)
VRBO
Fall Into Paradise 7 Night Stay
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Looking for a great deal? Discounts are automatically applied based on your length of stay! No need for promo codes or r ...
From $358 per night (USD)
VRBO
From $193 per night (USD)
Expedia
Quaint Historic Apartment in Walkable Downtown #5
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
My historic building was built in the 1950's and has clean character and ambiance. Walking distance to Whole Foods/Publi ...
From $193 per night (USD)
Expedia
From $253 per night (USD)
VRBO
Studio Apartment, Safe & Walkable area, Pet Friendly
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Super cute, secure and private in downtown Sarasota. Queen sized bed and sofa with private bathroom/shower. Located abov ...
From $253 per night (USD)
VRBO
From $202 per night (USD)
VRBO
2 Bed w/ Private Pool on Canal/Cul-de-sac, minutes from the Beach, Dog friendly
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This home is bright, open, airy, and clean - the perfect place to relax and unwind. The location is just 2.5 miles from ...
From $202 per night (USD)
VRBO
From $1026 per night (USD)
VRBO
Isla Amor | Escape to a Luxury Waterfront Home with Heated Pool & Stunning Views in Siesta Key
Bedrooms:
3
Bathrooms:
5
Sleeps:
11
🌴 Isla Amor | Waterfront Oasis + 0.3 Miles to Siesta Key Beach 💖 Why You'll Love This Home Imagine waking up to serene ...
From $1026 per night (USD)
VRBO
From $277 per night (USD)
Expedia
Entire Standalone Lido Beach Villa, 1.2k sf, 1 block to the beach
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Welcome to our cute, spacious, sun filled and newly renovated Beach Villa. A Happy place for sandy feet, friends, and fa ...
From $277 per night (USD)
Expedia
$\Discover Your Coastal Oasis in Longboat Key, FL\ and St. Armands Area$
From $332 per night (USD)
VRBO
\"Discover Your Coastal Oasis in Longboat Key, FL\" and St. Armands Area
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Stunning one bedroom one bath unit with just a short walk to Longboat Key Beach(Across the Street). Come enjoy beautiful ...
From $332 per night (USD)
VRBO
From $137 per night (USD)
Expedia
Waterfront Villa Manatee on Warm Mineral Springs *Pool *Deck
Bedrooms:
2
Bathrooms:
2
Sleeps:
3
Very private, peaceful and quiet natural setting. Relax while listening to singing birds or watch the wild-life includin ...
From $137 per night (USD)
Expedia
From $339 per night (USD)
VRBO
Perfect Local In Village,1 1/2 Block From #1 Beach In USA, Pool, Wifi, Sun & Fun
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Happy Clam has just undergone a significant makeover and upgrade. It is better than ever! Absolutely, amazing condo i ...
From $339 per night (USD)
VRBO
From $153 per night (USD)
Expedia
Siesta Key 2 Bedroom Condo
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
Perfect little condo on siesta key, home of the #1 rated beach in the USA. Just minutes from the beaches and great rest ...
From $153 per night (USD)
Expedia
From $141 per night (USD)
VRBO
3-bedroom vacation cottage, 2 min drive to Nokomis Beach/ Gulf of Mexico beaches
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
Our remodeled and chic beach cottage is close to Casey Key Public Beach (3/4 of a mile), 9 minutes from Venice Beach. O ...
From $141 per night (USD)
VRBO
From $535 per night (USD)
Expedia
🏝Private Gated Home w/ heated pool - a 1 minute walk to St Armands Circle🏖
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Premier local manager, Destination Paradise welcomes you to “The President”… a cozy 3 bedroom 3 bath vacation home with ...
From $535 per night (USD)
Expedia
From $246 per night (USD)
VRBO
Completely remodeled Siesta Key 2 bedroom 1 bath Condo
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
This 2 Bedroom, One Bath Condo is just steps to the white, powered sugar sand of Siesta Key. We have easy access to Sies ...
From $246 per night (USD)
VRBO
From $484 per night (USD)
Expedia
Gertrude's Siesta | Private Patios, Beach & Village, 100 steps to Best Views on Siesta Key!
Bedrooms:
3
Bathrooms:
3
Sleeps:
10
Casa Tranquilla Spacious luxury home, 100% private, just 100ft from best views on Siesta Key. Impeccable 2025 remodel a ...
From $484 per night (USD)
Expedia
From $274 per night (USD)
VRBO
Siesta Key # Beach Oasis with special summer rates!!!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Now with private Wifi. This One Bedroom, One Bath condo is just steps to the white, powdered-sugar sand of Siesta Key. H ...
From $274 per night (USD)
VRBO
Click For Pricing
Expedia
Lido Beach Corner of Beach and St. Armand Circle B
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Perfect Beach Location. Right across from Lido Beach and immediatly next to St. Armands Circle. Walk to the many resta ...
Click For Pricing
Expedia
From $287 per night (USD)
VRBO
Top Rated Villa For Rent! Short Walk To Beach. Swimming Pool. Family-Friendly
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Vacation rental home in Englewood / South Venice, Florida. The house is literally a short walk from the beach. It was co ...
From $287 per night (USD)
VRBO
From $366 per night (USD)
VRBO
Walk to Lido Beach, Walk to Armand Cir with Dining & Shopping, WiFi, Xfinity, 2TV's, Heated Pool/Spa
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Looking for a great deal? Discounts are automatically applied based on your length of stay! No need for promo codes or r ...
From $366 per night (USD)
VRBO
From $243 per night (USD)
VRBO
Lido Beach and St. Armand's Circle at your Footsteps.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Sarasota Certificate of Registration # VR22-00027 Minimum 7 night stay Beautiful, roomy, sunny 2BR, 2 BA old style Flori ...
From $243 per night (USD)
VRBO
From $160 per night (USD)
Expedia
Newly renovated only minutes away from the beach!!
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
This beautiful and completely remodeled cottage retreat has all the comfort you will need for your next vacation! Fully ...
From $160 per night (USD)
Expedia
$Lido Beach Gulf View Condo w/ pool. Right across from beach! !\nOFF SEASON RATES$
From $156 per night (USD)
VRBO
Lido Beach Gulf View Condo w/ pool. Right across from beach! !\nOFF SEASON RATES
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Panoramic ocean View . 1bd, 1bth located immediately across for the beach. Right in the middle of Lido Beach. Close t ...
From $156 per night (USD)
VRBO
From $715 per night (USD)
Expedia
Casa Leone | Pet Friendly 🐶 on Siesta Key w/ Private Heated Pool, Golf Cart, & Putting Green!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Unparalleled Luxury at Casa Leone, Siesta Key's Hidden Gem Welcome to Casa Leone, your ultimate luxury getaway on Siesta ...
From $715 per night (USD)
Expedia
From $520 per night (USD)
VRBO
3 bedroom/2 bath in a quiet neighborhood. Large backyard with privacy fence.
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
3 bedrooms, 2 bathrooms, possible forth bed. Closed lanai, fenced backyard, pet's welcome. 1 car garage, laundry room, B ...
From $520 per night (USD)
VRBO
From $141 per night (USD)
VRBO
Newly Decorated with Pool Views! Convenient Access-no stairs!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Lots of room for you and your guests. New carpeting in the bedrooms, fresh paint, plantation shutters, beautiful tile fl ...
From $141 per night (USD)
VRBO
From $264 per night (USD)
VRBO
Downtown,Italian Villa For Two,Resort Style.5 minutes to Siesta-Lido.
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Please Read the entire descriptions and additional information about our propriety. A spacious space to relax for two. ...
From $264 per night (USD)
VRBO
From $224 per night (USD)
Expedia
Water Front on Turtle Lagoon. Minutes from Turtle Beach & Siesta Key Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
*** UPDATE January 2025 - We recently did a major update to our property. We addressed all issues from our previous gu ...
From $224 per night (USD)
Expedia
From $497 per night (USD)
VRBO
Steps to Siesta Key Beach / Charming 2-Bedr + den apartment with Patio & Pool
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Just Steps from Siesta Key Beach – Charming 2-Bedroom Apartment with Patios & Pool Only 60 steps from the stunning Sies ...
From $497 per night (USD)
VRBO
From $447 per night (USD)
Expedia
Siesta Key Red Door House 3 Miles from the Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This is a cozy four bedroom house. The smaller 4th bedroom can be used as an office. We offer free WiFi, free guest park ...
From $447 per night (USD)
Expedia
From $289 per night (USD)
VRBO
Siesta Key Bungalows: Coquina Bungalows
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This beautiful courtyard bungalow has a queen bed, sleeper sofa & full kitchen with cable TV. This property is close t ...
From $289 per night (USD)
VRBO
Click For Pricing
Expedia
Beachfront Resort Style Living - Siesta Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
**NEWLY REMODELED KITCHEN -- UPDATED FLOORS AND BATHROOMS** Come enjoy luxurious resort style living in this beautiful t ...
Click For Pricing
Expedia
From $150 per night (USD)
VRBO
Newly renovated cozy and modern 2 bed. appartment
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 $150 per night (USD)
VRBO
From $433 per night (USD)
Expedia
Island House Beach Resort 18S
Bedrooms:
2
Bathrooms:
1
Sleeps:
4
This beautifully appointed 1 bedroom, 2 bathroom features a primary ensuite with a king bed and a sofa sleeper. The unit ...
From $433 per night (USD)
Expedia
From $277 per night (USD)
VRBO
Cozy cottage on Casey Key
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Beautifully decorated 1 bedroom 1 bath bay side condo with private beach access. Full kitchen and dining bar with barsto ...
From $277 per night (USD)
VRBO
From $416 per night (USD)
Expedia
The Beach Club at Siesta Key #106A Resort by RVA
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
RVA offers beautiful turquoise waters and quartz-crystal white sands, which have been officially ranked as the “finest, ...
From $416 per night (USD)
Expedia
From $404 per night (USD)
VRBO
Turquoise Water & Soft White Sand - The Beach Club at Siesta Key #104A by RVA
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
RVA offers beautiful turquoise waters and quartz-crystal white sands, which have been officially ranked as the “finest, ...
From $404 per night (USD)
VRBO
From $374 per night (USD)
Expedia
2BR Cook, Relax, Walk to Beach at The Beach Club Siesta Key #101E by RVA
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
RVA offers beautiful turquoise waters and quartz-crystal white sands, which have been officially ranked as the “finest, ...
From $374 per night (USD)
Expedia
From $443 per night (USD)
VRBO
Bright & Modern ~ Heated Pool ~ Gated Beach ~ Pkg!
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Experience the modern design and relaxing comfort of this newly renovated 2BR 2Bath quadplex unit, just a few mins from ...
From $443 per night (USD)
VRBO
From $420 per night (USD)
Expedia
Blue Seas & White Sand 2BR-The Beach Club at Siesta Key #200C Resort by RVA
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
RVA offers beautiful turquoise waters and quartz-crystal white sands, which have been officially ranked as the “finest, ...
From $420 per night (USD)
Expedia
From $315 per night (USD)
VRBO
Steps to Siesta Key beach, restaurants and shops!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Overlooking the large, heated pool and just a few steps to the famous white sands of Siesta Key Beach, Unit 410 is an is ...
From $315 per night (USD)
VRBO
From $645 per night (USD)
Expedia
Newly Renovated Large 4BR w/ Pool - Walk to Gated beach
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Newly renovated gated beach access apartment with a pool. This is a four bedroom and two bath apartment that makes up on ...
From $645 per night (USD)
Expedia
From $329 per night (USD)
VRBO
On Siesta Key Beach - no streets to cross! Large, heated pool.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
You don’t have to cross any streets to get to Siesta Key Beach from this beautiful two-bedroom, two-bath condo! This new ...
From $329 per night (USD)
VRBO
From $482 per night (USD)
Expedia
Beachfront Luxury Condo. Best View on Siesta Key Beach - no streets to cross!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Make your next vacation one to remember forever by booking a stay in the Sea Shell Penthouse Condo. This beachfront cond ...
From $482 per night (USD)
Expedia
From $266 per night (USD)
VRBO
Island Paradise: House on Longboat Key by RVA
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
RVA features a relaxing, serene home beautifully furnished and ready for you to enjoy Longboat Key's sunshine. This home ...
From $266 per night (USD)
VRBO
From $440 per night (USD)
Expedia
2-BR Suite Close to Beach w Trolley-The Beach Club at Siesta Key #204B by RVA
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
RVA offers beautiful turquoise waters and quartz-crystal white sands, which have been officially ranked as the “finest, ...
From $440 per night (USD)
Expedia
From $478 per night (USD)
VRBO
Fresh. Heated Pool.Minutes to Siesta Beach.Office
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Summary: Spice Your Life With Color, Beauty & Style! Welcome to “Coral Latitude “ the oasis of comfort and style with to ...
From $478 per night (USD)
VRBO
From $371 per night (USD)
Expedia
St. Armands oasis with saltwater pool - walk to beach & shops
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Anything Is Possible Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
From $371 per night (USD)
Expedia
From $473 per night (USD)
VRBO
Luxe home with pool & alfresco living - amazing walkable location
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Organic Fun Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
From $473 per night (USD)
VRBO
From $602 per night (USD)
Expedia
Huge Home with Pool, Home Office, & Sunroom | Walk to Lido Beach
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
You Only Live Once Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $602 per night (USD)
Expedia
From $953 per night (USD)
VRBO
Slice of Beach Paradise | Private Wraparound Balcony with Amazing Gulf Views
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Beach Road Condo Unit 2 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $953 per night (USD)
VRBO
From $306 per night (USD)
Expedia
Palm Bay Club Unit 311 with pools & hot tub - walk 1,500 feet to beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
The Palm Bay Club Unit 311 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply en ...
From $306 per night (USD)
Expedia
$First Lido - 3rd floor unit\nNOTE: DUE TO HURRICANES, ELEVATOR IS UNDER REPAIRS$
From $407 per night (USD)
VRBO
First Lido - 3rd floor unit\nNOTE: DUE TO HURRICANES, ELEVATOR IS UNDER REPAIRS
Bedrooms:
2
Bathrooms:
1
Sleeps:
4
Beach front - Full view of the Gulf of Mexico. Fully furnished and equiped. Includes Long Distance phone service within ...
From $407 per night (USD)
VRBO
From $517 per night (USD)
Expedia
Coral Breeze | Pet Friendly Home, Heated Pool & Spa, Minutes to Village and Siesta Beach!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
🌴 Coral Breeze | Private Pool + Walk to Siesta Key Village 💖 Why You'll Love This Home Sunshine, swaying palms, and ...
From $517 per night (USD)
Expedia
From $411 per night (USD)
VRBO
Spacious 2BR Close to World-Famous Sand Beach Club at Siesta Key #102A by RVA
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The Beach Club at Siesta Key by RVA Resort Vacations – Your Coastal Escape Awaits Discover the breathtaking beauty of ...
From $411 per night (USD)
VRBO
From $446 per night (USD)
Expedia
Tropical Waters & Magical Sunsets-The Beach Club at Siesta Key #106B by RVA
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
RVA offers beautiful turquoise waters and quartz-crystal white sands, which have been officially ranked as the “finest, ...
From $446 per night (USD)
Expedia
From $277 per night (USD)
VRBO
Beautiful newly decorated and furnished private home. Fits any personality!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Spacious home. Large open concept with lots of sunlight. Split home so master bedroom on other side with private bath. W ...
From $277 per night (USD)
VRBO
From $184 per night (USD)
Expedia
Updated Spacious. 5 Min to Manasota Beach. Loaded w/amenities. Pets Welcome!
Bedrooms:
2
Bathrooms:
3
Sleeps:
12
Thank you for taking a moment to view one of out vacation home brough to you by Sandy Flamingo Vacations. This home is ...
From $184 per night (USD)
Expedia
Click For Pricing
VRBO
Cute Property in Sarasota Fl close to beach, amenities like pools
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This is a great 1 bedroom 1 Bathroom Place. all furnished with all the comforts of home.It does sleep 4 the main Bedroom ...
Click For Pricing
VRBO
From $1090 per night (USD)
Expedia
Gertrude's Siesta | 4-min Walk to Beach & Village, Tropical & 100% Private!
Bedrooms:
4
Bathrooms:
6
Sleeps:
22
Casa Van Lopik 100% Private 6BR duplex in the Siesta Key Village, 4-min walk to best beaches shopping dining and enterta ...
From $1090 per night (USD)
Expedia
From $692 per night (USD)
VRBO
Gertrudes Siesta Village Properties - short walk to Siesta's best beaches!
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Gertrude's Village Properties Two properties in the top location on the island with 4 patios and private gate into world ...
From $692 per night (USD)
VRBO
From $368 per night (USD)
Expedia
Stunning Gulf Views From Horizons West #704, a 2B, 2B on Siesta Key
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Located in the centre of the high rise on the 7th floor, the views from the lanai are directly to the garden, pool, the ...
From $368 per night (USD)
Expedia
From $405 per night (USD)
VRBO
Pristine Gulf Waters & Location-The Beach Club at Siesta Key #108D by RVA
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
RVA offers beautiful turquoise waters and quartz-crystal white sands, which have been officially ranked as the “finest, ...
From $405 per night (USD)
VRBO
From $224 per night (USD)
Expedia
Amazing Villa with Extra Large Heated Pool ! 50% off Regular Rates!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
If you are looking for a luxurious and serene holiday in the sun, then look no further. Our spacious and beautiful Flor ...
From $224 per night (USD)
Expedia
From $181 per night (USD)
VRBO
Sleeping Studio, Secure & Cute Downtown between Siesta & Lido Beaches
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This is a small room with cuteness and amenities, poster bed with space to store underneath, coffee maker/small refriger ...
From $181 per night (USD)
VRBO
From $387 per night (USD)
Expedia
The Casa Coco | Garden : Modern and relaxing home with heated pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
If you see a gap in our calendar you are interested in send us an inquiry. If your dates are not available Check our ot ...
From $387 per night (USD)
Expedia
From $295 per night (USD)
VRBO
Sunny Cottage🌴half mile to Downtown-near famous beaches
Bedrooms:
1
Bathrooms:
4
Sleeps:
8
Relaxing and charming 3 bedrooms cottage half mile to Main steet, Downtown, parks, restaurants, art galleries,boutiques ...
From $295 per night (USD)
VRBO
From $613 per night (USD)
Expedia
Breathtaking Turquoise Gulf Water-The Beach Club at Siesta Key #104D by RVA
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
RVA offers beautiful turquoise waters and quartz-crystal white sands, which have been officially ranked as the “finest, ...
From $613 per night (USD)
Expedia
From $4175 per night (USD)
VRBO
Rare private beachfront estate on Gulf of Mexico.
Bedrooms:
5
Bathrooms:
5
Sleeps:
8
Wake up in the morning and go for a walk along the beautiful sandy beach. The beach is incredible. Very rare and private ...
From $4175 per night (USD)
VRBO
From $220 per night (USD)
Expedia
Harbor Towers Gulf Facing 1/1 Fully Upgraded Condo!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Stunning Siesta Key sunsets from this freshly upgraded 1/1 condo! This condo is located at Harbor Towers Yacht & Racque ...
From $220 per night (USD)
Expedia
From $388 per night (USD)
VRBO
Beachplace 7-404 Condo by RVA
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
RVA presents a delightful two-bedroom, two-bathroom unit at Beachplace, featuring a king-sized master bedroom and two tw ...
From $388 per night (USD)
VRBO
From $362 per night (USD)
Expedia
Coastal Tropical Oasis With Salt Water Pool
Bedrooms:
3
Bathrooms:
4
Sleeps:
7
Our home is the perfect spot for a getaway with friends, relaxing family vacation Our goal is for our guests to feel lik ...
From $362 per night (USD)
Expedia
From $260 per night (USD)
VRBO
Adorable Beach Retreat
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
This beautiful Venice Island Home is less that 1 mile to Venice Beach. Just think you can have the beach life this wint ...
From $260 per night (USD)
VRBO
From $571 per night (USD)
Expedia
At Sun Sea Terrace | Luxury Siesta Key Condo w/ Heated Pool, Short Walk to Beach and Village!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
🌴 At Sun Sea Terrace | Rooftop Views + Steps to Siesta Beach & Village 💖 Why You'll Love This Home Start your morning ...
From $571 per night (USD)
Expedia
From $768 per night (USD)
VRBO
Hidden Treasure | Located on Siesta Key w/ Private Heated Pool/Hot Tub & Spacious Outdoor Area
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Escape to Siesta Key's Hidden Treasure – A Peaceful, Private Island Retreat Welcome to Siesta Key's Hidden Treasure, a ...
From $768 per night (USD)
VRBO
From $308 per night (USD)
Expedia
Location! Location! Location! Steps to Siesta Key Beach and many shops!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Bright and inviting, this 2 bedroom, 2 bath condo has to be experienced to be believed! Located just steps from the famo ...
From $308 per night (USD)
Expedia
From $286 per night (USD)
VRBO
Heated Pool in Luxurious home, 3 minutes to beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
High End Spacious Home in the best laid back part of Florida's Gulf coast. Right on the border between Venice and Englew ...
From $286 per night (USD)
VRBO
From $243 per night (USD)
Expedia
Beutiful updated Condo Siesta Key
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
This unit has private WIFI and is appointed in cheerful clean modern decor and the patio opens just steps to the pool. T ...
From $243 per night (USD)
Expedia
From $165 per night (USD)
VRBO
Luxury motorhome from the Monoco dynasty
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This is a luxury class A motor home situated on the banks of beautiful Phillippi Creek in Sarasota Florida, this is stat ...
From $165 per night (USD)
VRBO
From $160 per night (USD)
Expedia
*** Downtown Bungalow ***Beaches / Restaurants / Cafes***Just Minutes away!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This charming cottage is the perfect place for your stay in downtown Sarasota. The space: This two bedroom home has ...
From $160 per night (USD)
Expedia
From $359 per night (USD)
VRBO
Best location on Siesta Key/Crescent Beach - just steps to the water!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This beautiful two-bedroom condo is located just steps from the world-famous white sands of Siesta Key Beach. That mean ...
From $359 per night (USD)
VRBO
From $1791 per night (USD)
Expedia
The Hummingbird | Located in Siesta Key Village w/ Private Pool, Walk to Beach!
Bedrooms:
6
Bathrooms:
6
Sleeps:
20
🕊️ The Hummingbird | 6BR/6BA | Sleeps 20 | Private Heated Pool | Heart of Siesta Key Village 🌴 Why You'll Love This H ...
From $1791 per night (USD)
Expedia
From $202 per night (USD)
VRBO
Beach Vacation House - Minutes from the Beach and Hiking trails
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This beautiful renovated 2 bedroom 2 bath 1900 sq ft home is minutes from the beach and hiking trails. It has a huge out ...
From $202 per night (USD)
VRBO
$\Updated & Charming Pool Home 1 Mile from Siesta Key \$
From $486 per night (USD)
Expedia
\"Updated & Charming Pool Home 1 Mile from Siesta Key \"
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to our beautifully updated 3-bedroom, 2-bathroom single-family pool home, just 1 mile from the Siesta Key North ...
From $486 per night (USD)
Expedia
$\Safe & Clean\ Honeymoon Suite, - only 60 steps to the Siesta Key Public Beach -$
From $482 per night (USD)
VRBO
\"Safe & Clean\" Honeymoon Suite, - only 60 steps to the Siesta Key Public Beach -
Bedrooms:
2
Bathrooms:
1
Sleeps:
4
Only 60 steps to the beach. Entire apartment refurbished and updated incl. new flooring 2020. Spacious 1 bedroom / 2 f ...
From $482 per night (USD)
VRBO
From $217 per night (USD)
Expedia
2bed 2 bath sleeps 5 .. 3 smart TVs.. fully refurbished Very Close to the beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
RENOVATED 2025 2 BED, 2 BATH CONDO 1st floor parking right outside WI-FI and smart tvs ...
From $217 per night (USD)
Expedia
From $436 per night (USD)
VRBO
Manasota Key Dream Beach House
Bedrooms:
3
Bathrooms:
5
Sleeps:
14
Perfect Get-Away Beach Home for Families! Sleeps 12 to 14, Heated Pool & Spa. This beautiful 5 bedroom, 4 bathroom beac ...
From $436 per night (USD)
VRBO
From $133 per night (USD)
Expedia
Luxurious Living Steps to Lido Beach & Walking Distance to St. Armands Circle
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Freshly updated/painted condo with luxurious furnishings and steps to the Gulf of Mexico on exclusive Lido Key. This con ...
From $133 per night (USD)
Expedia
From $128 per night (USD)
VRBO
Amazing View - On Golf Course - Near Beaches, Shopping & Restaurants
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Highly sought after condo in Farmington Vistas. Newly furnished property perfect for extended vacation and/or leisure. ...
From $128 per night (USD)
VRBO
From $302 per night (USD)
Expedia
Stunning Fully Remodeled House with Heated Pool! 30%OFF
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
If you are looking to unwind in the sun, then look no further than our beautiful and traditionally furnished Floridian v ...
From $302 per night (USD)
Expedia
From $316 per night (USD)
VRBO
New Listing! Renovated End Unit, Pool/Bay Views, Heated Pool, Desk for Remote Work
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 $316 per night (USD)
VRBO
From $222 per night (USD)
Expedia
Walk to Nokomis Beach. Quality, Cleanliness, Affordable. SmartTV, Full Kitchen
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Seahorse Shores - 409 Shore Road - Two Bedroom Beach Villa Located 1/2 Mile From Nokomis Beach and Casey Key. Gas grill ...
From $222 per night (USD)
Expedia
From $989 per night (USD)
VRBO
Honeysuckle | Located in Siesta Key Village w/ Heated Pool, Walk to Beach!
Bedrooms:
3
Bathrooms:
3
Sleeps:
12
🌴 Honeysuckle | 3 King/Queen Bedrooms + Dual Kitchens | 0.2 Miles to Siesta Key Beach 💖 Why You'll Love This Home Hon ...
From $989 per night (USD)
VRBO
From $356 per night (USD)
Expedia
Siesta Key GULF SIDE~#100 - Peaceful Private Condo, 3 Pools, Jamaica Royale
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This 2 bedroom, 2 bath tropical garden condo was completely renovated in the spring of 2025 ~ thanks to the floods of 20 ...
From $356 per night (USD)
Expedia
From $549 per night (USD)
VRBO
Siesta Key Pool House 3 Miles from the Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
The house is located within 10 minutes drive from both downtown and Siesta Keys beach, and about 20 minutes drive from L ...
From $549 per night (USD)
VRBO
From $164 per night (USD)
Expedia
Siesta Key Beach IDEAL LOCATION BEACH, VILLAGE, HEATED POOL
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
2 week rental minimum from April through December. January, February March, are monthly rentals please select the first ...
From $164 per night (USD)
Expedia
From $386 per night (USD)
VRBO
The Casa Coco | Coronado: Updated home, Heated pool close to S. Venice beach.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
If you see a gap in our calendar you are interested in send us an inquiry. If your dates are not available Check our ot ...
From $386 per night (USD)
VRBO
From $231 per night (USD)
VRBO
Pet Friendly Longboat Key Condo - Steps from Beach !!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
The condo directly across the street from the public beach access. This is a very private part of Longboat and often y ...
From $231 per night (USD)
VRBO

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