Vacation Rentals By Owner In Sarasota, FL

$236.86

Meadows Villa -Now can rent in 2025-2026!

Sarasota, Florida, United States

Welcome to a breathtaking villa that seamlessly blends elegance and sophistication from the moment you walk through the door. This recently renovated home reflects the highest standards of craftsmanship, with every detail carefully curated by a talented interior designer. The kitchen is a masterpiece, featuring sleek new grey cabinets that not only enhance the villa's modern aesthetic but also offer ample storage for all your gourmet cooking needs. Equipped with top-of-the-line appliances, this kitchen ensures that every culinary experience is exceptional. The villa's indoor and outdoor dining areas provide the perfect settings for unforgettable gatherings with family and friends. The spacious living room opens up to stunning views of the lake, where you can relax and take in the tranquil beauty of the surrounding wildlife. The large primary suite is a true retreat, featuring a beautifully renovated bathroom with a double vanity and plenty of storage. The second suite is equally impressive, with a fully updated bathroom and a generously sized bedroom that easily accommodates a king-sized bed. Moving into this villa is effortless. You're ready to enjoy your new home. LOCATION: Nestled in one of Sarasota's most popular and sought-after communities, The Meadows is ideally located just east of downtown Sarasota, near I-75. This vibrant community offers an array of amenities, including golf, tennis, racquetball, and biking, all set within a meticulously maintained and environmentally rich resort-style atmosphere. The Meadows is also conveniently close to some of Sarasota's most upscale shopping and dining destinations. The community boasts over 80 stocked lakes, pristine waterways, and nature preserves, along with approximately 17 miles of roads, 14 miles of sidewalks and bike trails, and a 1.7-mile fitness trail.

2

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2

Bath

4

Sleeps

$313.58

/ Nightly

Condo

Charming Poolhouse · 1BR · Close to Siesta

Sarasota, Florida, United States

Modern, peaceful apartment in a three-unit property, featuring a shared, year-round heated pool and fenced backyard, used exclusively by the three guest units.brSiesta Key Beach is about a 4-minute drive, while the setting remains quiet and relaxing.brbr• Pet-friendly – flat $10 pet fee per reservation, regardless of number of petsbr• shared heated pool (only for the 3 on-site units)br• shared fenced backyardbr• large shared gas BBQ grillbrbr• KING bed in the bedroombr• Sofa in the living room (sleeping space)br• Smart TV in the bedroombr• Smart TV in the living roombr• Fast Wi-Fibrbr• Fully equipped kitchenbr• Shared washer & dryer on sitebrbr• Shared pool (used by the 3 apartments only)br• Shared fenced backyardbrbr• Pet-friendly – $10 per reservation (any number of pets)br• Free parkingbr• Beach chairs, towels & umbrellabr• Contactless check-in & check-out

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$1026.41

/ Nightly

Private Vacation Home

Waterfront Estate over an acre on the water with Large Heated Pool

Sarasota, Florida, United States

LaVida Vacations hosts this amazing hideaway is walking distance to restaurants and shopping as well as Starbucks yet hidden in the woods and on the water. This place sleeps 14 and 5 suites with 4 private bathrooms and two rooms on the opposite ends of the house with their own entrances for added privacy connected by a huge covered lanai pool area with a huge TV, BBQ, dinning table and relaxing lounges to hang out. The firepit is amazing at night and the hammocks in the massive tree are the best! Siesta Key beach and Lido Beach are incredible beaches where you can take the beach wagon and chairs and sunbrella to the beach than come back to the HUGE heated pool. Did anyone say fishing We have the best place to fish on the dock in the backyard. Go look at any other listing each neighbor is a few feet away. Here you have total privacy. Kayaks and Paddle boards included and yes you can rent that amazing pontoon! Reach out with any questions

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$344.65

/ Nightly

Private Vacation Home

Charming 1940s Bungalow – 6 Mins to Beach + Private Pool Oasis!

Sarasota, Florida, United States

Siesta Sunset Bungalows – Private Beachside Oasis with Heated Pool & GazebobrWelcome to Siesta Sunset Bungalows, your secluded 1940s beach hideaway — just 6 blocks from the world-famous shores of Siesta Key Beach.brbrThis charming bungalow offers the ultimate coastal escape where serenity, sunsets, and the shore come together to create the perfect getaway.brbrTreat yourself and your loved ones to a peaceful, relaxing stay in a private tropical oasis designed for pure bliss.brbrLounge in luxury by the enormous 40-foot heated pool, completely surrounded by an 8-foot privacy fence and lush areca palms that create the atmosphere of a private resort.brbrThe outdoor space is thoughtfully designed for both relaxation and entertaining:brbrA covered gazebo with a plush semi-circular sofa and ottoman — perfect for morning coffee or sunset cocktailsbrbrA stylish wrought iron bar-height table with four chairs and a large umbrellabrbrEight chaise lounges with three sun umbrellas and side tables between every pair — ideal for tanning, reading, or simply unwinding under the sunbrbrA hammock for ultimate laid-back lounging beneath the swaying palmsbrbrWhen you're ready to explore, take a short stroll to the beach and experience the unforgettable sunsets that make Siesta Key famous.brbrWhether you’re swimming, sunbathing, sipping wine under the gazebo, or walking hand-in-hand along the shore, you’ll feel like you’ve found your own slice of paradise.brbrThis isn’t just a vacation — it’s the kind of place that stays with you.

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$115.99

/ Nightly

Private Vacation Home

Private Guesthouse w/ King Bed, Putting Green, Covered Patio

Sarasota, Florida, United States

Welcome to Le Paradise- a family friendly vacation house with an amazing king-sized bed, a beautiful lanai, and putting green for the golf enthusiasts. This guest house includes a super long private driveway and a personal lanai. The house is just a short 12 minutes drive to the world famous Siesta Key Beach, 11 minutes from Sarasota Downtown, and 15 minutes from St Armand Circle. brbrWelcome home!

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$150.13

/ Nightly

Condo

Quiet Downtown Sarasota Condo minutes from Siesta Key.

Sarasota, Florida, United States

Quiet condo complex with 2 parking spots. Unit is directly across from community pool. Siesta Key is minutes away via free trolly, a couple from blocks from downtown dining and nightlife. 15 minutes from Sarasota Airport. Cable, internet and utilities included. Unit is brand new and was completed renovated with new appliances furniture and linens

2

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2

Bath

4

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$219.53

/ Nightly

Apartment

Luxury Bayside Condo – Pool, Tennis & Marina

Sarasota, Florida, United States

Set on Siesta Key’s bayside in the gated Harbor Towers Yacht & Racquet Club, this 5th-floor condo offers stunning Gulf sunsets and full resort amenities. From heated pools and tennis courts to a private marina and tropical grilling patio, you’ll have the best of both worlds - bayside tranquility just minutes from world-famous Siesta Beach.brbrWhy You’ll Love Itbr• Gated bayside community with luxury resort amenitiesbr• West-facing condo with screened patio for sunset viewsbr• Walk or bike to #1-ranked Siesta Key Beach and VillagebrbrSleeping Arrangementsbr• Primary Suite – King bed, walk-in closet, ensuite with large shower & vanitybr• Guest Bedroom – Two twin beds, reach-in closet, adjacent bathroom with showerbrbrOutdoor Highlightsbr• Heated pool and children’s pool with tropical landscapingbr• Marina with boat slips, fishing pier & island gazebo for dolphin watchingbr• Expansive patio with grills, shaded tables, and lounge chairsbr• Three Har-Tru clay tennis courts for guests to enjoybrbrInterior Comfortsbr• Spacious living room with flat-screen TV, DVD player & cablebr• Dining area with seating for 4br• Private screened patio overlooking a waterfall and partial Gulf viewbr• Free high-speed Wi-Fi throughout the condobrbrKitchen & Diningbr• Fully stocked kitchen with dishwasher, stove/oven, microwave & refrigeratorbr• Coffee maker, tea kettle, toaster, blender & juicerbr• Complete cookware, dishes, utensils, and baking suppliesbrbrIncluded Home Essentialsbr• Air conditioning & heatingbr• Fresh linens, bath & beach towels providedbr• Hair dryers, iron & board, vacuum cleanerbr• Washer & dryer available on floorbr• Beach chairs, umbrellas & cooler includedbrbrNeighborhood Perksbr• Siesta Key Beach – quartz sand & turquoise Gulf watersbr• Siesta Village – shops, dining, and nightlife just minutes awaybr• Farmer’s Market every Sunday with live music & local goodsbr• Outdoor fun: kayaking, fishing charters & bikingbr• Dining favorites: Siesta Key Oyster Bar, Gilligan's & Captain Curt’sbrbrAccess & Parkingbr• Single-level condo on the 5th floor with elevator accessbr• Gated community with designated parking spacebr• Secure building entry with staffed lobbybrbrFrom tennis matches at sunrise to sunsets over the Gulf, Harbor Towers offers the ultimate Siesta Key escape. brbrBook now with Gulf Coast Vacations and Vacay Your Way on Florida’s Gulf Coast.

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$193.56

/ Nightly

Private Vacation Home

Discover Hacienda del Sol - Dog-Friendly, Downtown, Walkable Neighborhood

Sarasota, Florida, United States

SLEEPING ARRANGEMENTS brbr brbr3 BR / 3 BA / Sleeps 8 brbr brbrMaster bedroom - One King bed with en-suite bathroom (walk-in shower) and wall-mounted TV. brbrGuest bedroom 1 - One Queen bed with en-suite bathroom (walk-in shower). brbrGuest bedroom 2 - One queen bedroom with desk and access to the hallway bathroom (tub/shower combination) brbrLiving Room - Pull out queen sofa can accommodate 2 people brbr______________________________________________________________________________ brbr brbrAMENITIES brbr brbrOne small well behaved dog would be CONSIDERED with a paid pet fee of 200.00. Check with the property manager for approval before booking. NO CATS brbr brbrClose to Downtown Sarasota, beaches, shopping, nightlife. brbrTwo blocks from the Legacy Trail brbr5 minutes to Payne Park brbr6 minutes to Pompano Pickleball Courts (12 hard courts) brbrOutdoor patio with seating and ambient lighting. brbrBeach chairs, towels, a beach umbrella, and a cooler are provided for use during the stay. brbrOutdoor fire pit with seating in the fenced backyard. brbrDesk in the living room and guest room, perfect for those remote workers to get some work done. brbrPropane grill for outdoor cooking. brbrLarge spacious living room with wall-mounted TV and two leather couches (one with pull out queen bed) brbrFully stocked modern kitchen with everything you need to make meals at home. brbrA separate dining room with seating for eight opens to the kitchen and living area. brbr1 set of towels (1 bath, 1 hand, and 1 washcloth) are provided per person for the max number of people the home sleeps brbrLaundry room with full-size washer and dryer brbrHigh Speed WIFI included (600 MBPS) brbrNo Smoking in the home! brbr brbr_____________________________________________________________________________ brbr brbrFULL DESCRIPTION brbr brbrThis charming 1953 home is 5 minutes from the beautiful and Dog-Friendly, Ringling/Payne Park where you can spend a leisurely morning or afternoon on the walking paths enjoying the scenery, or an action-packed day of enjoying the Circus themed playground, disc golf, cycling, Tennis Center, Skate Park, Cafe in the Park and more! The home has been newly renovated and professionally decorated. This is an incredible location! We are TWO BLOCKS from The Legacy Trail, downtown, and parks so bring your bikes or favorite walking shoes and come enjoy the fantastic Florida weather. brbr brbrUpon entering the home you are greeted with a large dining area with seating for eight that is open to the kitchen and living room. The master bedroom has a king bed and ensuite bathroom. The second guest room has a queen bed and en-suite bathroom with a shower stall and the third bedroom has a queen bed, desk, and access to the hallway bathroom. The third bedroom also has double doors that lead out to the patio. All bedrooms have comfortable new sheets bedding and towels. The living room has two sofas with one that pulls out into a queen bed and a large wall-mounted TV. Double doors off the living room lead to the private deck and back yard that come alive at night with ambient lighting. The backyard also has a BBQ grill and firepit with seating for a relaxing evening after a long day at the beach or sightseeing. The host has even provided a few games and puzzles for families to enjoy. brbr brbrThis comfortable private home is located just minutes from downtown Sarasota where you will find many options for dining, shopping, and nightlife. Payne Park is within walking distance from the home and includes Bicycle Trails, Equipment/Facility Rental, Hiking Trails, Picnic Facilities, Playground, and a Restaurant In Park. No trip to Sarasota would be complete without going to one of the world-class white sand beaches nearby. Siesta Key Beach is 7 miles and Lido Beach is 5 miles from the home. Check out St Armand's Circle near Lido Beach for additional shopping and great restaurant choices. Flying into Sarasota/Bradenton airport is easy and convenient with direct flights from many cities and is only a 20 minutes drive from the home. brbrPLEASE NOTE- For extended stays of 60 days or more we require a mid-stay clean be done by our cleaners. A member of our team will reach out upon your booking to coordinate the fee and scheduling.

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$595.67

/ Nightly

Private Vacation Home

Lido, walk to Lido Beach/ St. Armands, HEATED POOL 3 BR home w/grill

Sarasota, Florida, United States

VR22-00146 - This home is a piece of paradise! One block to the beach, 5-minute walk to St. Armands!!brThis listing is a beautiful home, nestled on a little piece of paradise!brIt's just a stone's throw from Lido Beach. What else makes this property unique It has a completely separate “in-law” suite, 1 bedroom, 1 bathroom, which enables those traveling who wish a little more privacy yet to be part of the activities on the same property! This charming home has incredible internet, with 457 mbps download and 28 mbps upload. brA perfect place to relax, unwind & enjoy your private, mature lush surroundings. This charming home has hardwood flooring, crown moldings, & ceiling fans. The fully equipped kitchen has been outfitted with cherry cabinets, stainless appliances, and granite countertops, microwave oven. All living room furniture has been recently purchased including the 60” flat screen plasma television. There are 4 tvs total in this home. Cable TV/HBO and wireless internet are available for your enjoyment. brbrThree bedrooms in total on this property; one with a new king sized bed, the second with a queen sized bed, the third also with a queen sized bed. All have comfortable mattresses & quality pillows that will afford you a peaceful night's sleep, leaving you refreshed and ready for a great day. In addition to the 60 living room tv, there are three extra 32” wall mounted LCD TV’s. Both bathrooms, with decorator porcelain tiles throughout. Bath towels and bed linens are provided for your use. brbrA private pool, surrounded by brick pavers is on the property for your exclusive use. A private place to relax and enjoy a morning cup of coffee or an evening beverage with good company and personal conversation.brbrHouse, 3 Bedrooms, 2 Baths, 6 SleepsbrbrLido Beach is one of the most beautiful beaches, not only in Florida, but in the United States. The world famous sunsets off the shores of Lido Beach draw not only our visitors but local residents as well. All there to soak in one of natures most spectacular performances.brbrThe view is so surreal that it is not uncommon to see people clap their hands in the joy they receive from this experience. All of this is just a short stroll from this quaint, Lido home. Walk to beach is approx 3 minute walk, 0.2 miles. Walk to St. Armands is approx 8 minutes, 0.4 mile!!!

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$391.97

/ Nightly

Villa

Modern Villa steps away from the white sandy beach on upscale Lido Key, Sarasota

Sarasota, Florida, United States

Treat yourself to an unforgettable vacation at a luxury modern villa in the perfect location of Lido Beach. Walking distance from St Armands Circle, a sophisticated outdoor dining and shopping area with distinct European flair, iconic examples of mid-century modern architecture and the turquoise waters of the Gulf of Mexico. St Armand's has some of the best coastal and ethnic cuisine restaurants, live entertainment, high end fashion and jewelry boutiques, spas, art galleries, unique gift shops, kids arcade and many more. Lido Key is known for marrying cosmopolitan life with seaside paradise. Catch some rays or take a walk on the shore and put your toes in the soft white sand of Lido Beach. The Villa is two blocks from ted Sperling Park at South Lido Beach where you can take a private tour on a kayak or paddle board in the enchanting mangrove labyrinths something you will always remember. If you like to explore all the surrounding keys you should try the fastest supercharged jet ski in Tampa Bay. Please let us know and we can arrange that for you.

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Sleeps

$222.4

/ Nightly

Condo

Condo on Quiet Cul-De-Sac | Heated Pool/Spa | Tennis | Putting Green | Short Drive to Beach

Sarasota, Florida, United States

Enjoy automatic discounts based on your stay length, no codes needed, and the price you see already includes your savingsbrbrWelcome Yellow Pine Villa! brbr brbrRelax in a spacious, updated 2-bedroom villa just minutes from Siesta Key’s world-famous beaches. Nestled in a peaceful community surrounded by ponds, palms, and lush greenery, Yellow Pine Villa offers the perfect balance of resort-style amenities and a convenient Sarasota location. Crescent Beach Access #12 is only 3.7 miles away, and the heated community pool and spa are just steps from your door. brbr brbrLOCATION HIGHLIGHTS: brbr- Heated community pool and tennis courts brbr- Shuffleboard, practice putting green, and tanning deck brbr- Access to community clubhouse with billiards, library, and social room brbr- South side of Sarasota, just 3.7 miles to Siesta Key’s Crescent Beach brbr-0.4 miles to Sarasota Square and 0.8 miles to Costco brbr- 1.8 miles to Legacy Trail for walking or biking brbr brbrPROPERTY FEATURES: brbr- 2 Bedroom/ 2 bathroom villa (1353 sq ft) brbr- Attached garage brbr- Dedicated WIFI and cable brbr- Keyless entry, self check in brbr- Central A/C brbr- Private washer and dryer brbr brbrLIVING ROOM: brbr- Spacious, bright living area with big bay windows brbr- Screened lanai access with outdoor furniture brbr- Cable TV and comfortable seating brbr brbrKITCHEN AND DINING: brbr- Fully equipped kitchen with dishes and cookware brbr- Dining table seats 4 with a breakfast bar brbr- Additional small cafe style table in the kitchen, seat 4 brbr brbrBEDROOMS AND BATHROOMS: brbr- Master Suite: New king bed, ensuite bathroom, cable TV, private lanai access, walk in closet brbr- Guest Bedroom: Two new twin beds, Smart TV with cable brbr- Master ensuite bathroom: large separate vanity area, shower/tub combo brbr- Guest bathroom: large vanity mirror and walk- in shower brbr brbrEXTRA PERKS: brbr- Complimentary beach items: a couple of beach chairs, a beach umbrella, and beach towels brbr brbrLOCAL FAVORITES: brbr- Siesta Key Crescent Beach for sun, sand, and water activities brbr- Sarasota Square and nearby grocery stores for dining and shopping convenience brbr- Legacy Trail for walking, running, and cycling brbr brbrIMPORTANT INFO: brbr- Weekly rentals brbr- No pets or emotional support animals allowed (per HOA rules) brbr- No smoking or vaping inside the villa or on the lanai brbr- Parking limited to passenger vehicles only (no work trucks or pickups over 7,000 lbs) brbr brbrBOOK YOUR STAY TODAY AND EXPERIENCE THE SUN, SAND, AND SERENITY OF SARASOTA RIGHT AT YOUR DOORSTEP!brbrIMPORTANT: The min age to rent is 25 years old. No parties, large gatherings. Please reach out if you have any questions.

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$851.84

/ Nightly

Private Vacation Home

Coconut Cottage | Home on Lido Key w/ Private Heated Pool/Spa, Walk to Lido Beach & St. Armands!

Sarasota, Florida, United States

Coconut Cottage | Pool, Spa, Fire Table + Walk to Beach & St. Armandsbrbr Why You'll Love This Homebr A breezy walk from St. Armands Circle and Lido Key Beach, Coconut Cottage is a private island escape with a lush backyard, a pool and spa oasis, and relaxed coastal style—ideal for making every moment unforgettable.brbr ‍ ‍ Perfect Forbr Families, couples, or small groups looking for luxury, comfort, and walkability in one of Sarasota's most coveted neighborhoods.brbr ️ Imagine Thisbr Wake up and step out to your private lanai, where the fire table crackles beside an outdoor lounge with HDTV and heaters. Start your morning with a bike ride or a quick stroll to Lido Beach. Spend afternoons kayaking or playing ping pong in the shaded patio. Grill dinner outdoors, gather under the stars, or unwind in the spa as the day melts away.brbr Where You'll Sleepbr- Bedroom 1: King Bed, Ensuite Bath, TVbr- Bedroom 2: King Bed, Ensuite Bath, TVbr- Bedroom 3: Queen Bed, Shared Bath,TVbr- Bedroom 4: Queen Bed, Shared Bath,TVbr- Bonus: Twin Roll-Away Bed – easily movable for flexible sleeping optionsbrbr Explore the Areabr - 0.1 miles to St. Armands Circle – 2-minute walk to shopping, dining, and nightlifebr - 0.3 miles to Lido Key Beach – just a 6-minute walk to soft sand and Gulf wavesbr - Walkable, bike-friendly neighborhood with classic Lido charm and downtown Sarasota accessbrbr Need to Know: Starter packs of kitchen and toiletry essentials provided for a seamless arrival. Free high-speed WiFi throughout. Heated Pool & Spa from November 15–April 15. This property is registered as a vacation rental with the City of Sarasota with a Registration Number of VR22-00038. Due to City of Sarasota vacation rental code, this property must be rented once during a seven (7) day period and have a maximum occupancy of 9 guests.

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$290.46

/ Nightly

Private Vacation Home

Amore Suite Siesta Sunset Bungalows ! Private Jacuzzi 6 Min from the Siesta Key!

Sarasota, Florida, United States

Charming 1940s Beach Bungalow – Private Jacuzzi, Walk to Siesta Key!brbrWelcome to your own secluded beach hideaway — a beautifully restored 1940s bungalow just a 4-minute drive or short 6-block walk from the world-famous sands of Siesta Key Beach.brbrThis private studio is thoughtfully designed for comfort and relaxation, featuring:brbrA plush, cozy bed with high-end linensbrbrA fully equipped kitchen for all your cooking needsbrbrA private outdoor patio with your own exclusive jacuzzibrbrOptional access to a shared pool (only available if the main house is not occupied)brbrYou're just steps away from the beach, with local restaurants, bars, shops, and cafes all within walking distance.brbrWhether you’re planning a romantic getaway or a solo retreat, this tranquil space offers the perfect blend of charm, comfort, and location.

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$324.19

/ Nightly

Private Vacation Home

Located in Sarasota Springs. 15 mins to Siesta Key and 10 mins to downtown

Sarasota, Florida, United States

This Hidden Gem in Sarasota Springs has 3 bedrooms and 3 bathrooms and sleeps 6. Your family will be close to everything when you stay at this relaxing home away from home. All the amenities are provided for your comfort including a heated swim spa. You will be 15 mins from world class beaches at Siesta Key, 10 mins from iconic downtown Sarasota, and 300 yards from the beautiful Legacy Trail that spans 40 miles from Venice to Bradenton. We are within 1 hour from regional and international airports and 3 miles from Interstate 75.

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$131.87

/ Nightly

Condo

Sunny Sarasota Oasis w/ Private Screened Lanai

Sarasota, Florida, United States

Escape to the vibrant city of Sarasota, FL, with a stay at this charming 2-bedroom, 2-bath vacation rental. Nestled in a peaceful community, this property offers comfortable accommodations and access to a community pool. Explore the world-renowned Ringling Museum of Art, soak up the sun on Lido Key Beach, or indulge in shopping and dining at St. Armands Circle. Whether you're seeking relaxation or adventure, this Sarasota condo is the perfect home base for your Florida vacation.brbr-- THE PROPERTY --brbrGolf Course Views | 2 Heated Outdoor Pools | Free WiFibrbrBedroom 1: Queen Bed | Bedroom 2: Queen Murphy BedbrbrCOMMUNITY AMENITIES: Shuffleboard courts, laundry facilities (washer/dryer), golf course (w/ fee), tropical landscapingbrOUTDOOR LIVING: Screened-in lanai, patio furniture & dining area, golf course viewsbrINDOOR LIVING: Cable TV, dining table, ceiling fans, desk workspacebrKITCHEN: Fully equipped, microwave, drip coffee maker, toaster, Crock-Pot, spices, cooking basics, dishware/flatwarebrGENERAL: Central heating & air conditioning, linens, towels, complimentary toiletries, keyless entrybrFAQ: 1 step to access (1st-floor unit), mandatory HOA fee (included in cleaning fee amount), pool depth (3'-6') brPARKING: Reserved parking spot (1 vehicle), guest parking (first-come, first-served)brbr-- THE LOCATION --brbrSUN & SAND: Bayfront Park (8 miles), Lido Key Beach (11 miles), Sarasota Beach (13 miles), Siesta Beach (14 miles), Coquina Beach (17 miles)brFLORIDA FUN: Conservatory Park (1 mile), The John and Mable Ringling Museum of Art (5 miles), Sarasota Jungle Gardens (6 miles), Marie Selby Botanical Gardens (8 miles), Big Cat Habitat Gulf Coast Sanctuary (11 miles), Mote Marine Laboratory & Aquarium (12 miles)brHIT THE LINKS: Palm Aire Country Club (walking distance), Rolling Green Golf Club (4 miles), University Park Golf Club (4 miles), The Highlands Golf Course (6 miles), The Preserve Golf Club (7 miles), IMG Academy Golf Club (9 miles), Manatee County Golf Course (11 miles)brAIRPORT: Sarasota-Bradenton International Airport (5 miles)brbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- No pets allowedbr- No events, parties, or large gatheringsbr- Must be at least 25 years old to bookbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: Access to this 1st-floor unit requires 1 stepbr- NOTE: A mandatory HOA fee of $150 is included in the cleaning fee amountbr- NOTE: The owner will be in touch shortly after booking to get forms filled out for HOA. Guest cannot stay at the property until these forms are filled out and approved by HOA. They need to be filled out and sent back to the owner the same day of booking

2

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2

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4

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Select Dates for Price

Condo

Newest luxury condo mile from downtown Sarasota

Sarasota, Florida, United States

Welcome to Strand, newest luxury condos just mile from downtown. This 1 bedroom, 1 den/office with closet and 2 bathrooms unit provides luxury vinyl floors, stainless steel appliances, solid stone countertops but first and foremost great location and canal & Sarasota Bay views from private terrace. Large Kitchen/Living Room combo provides ample room for relax & gather and sleeper sofa offers great comfort during the day & night. Community offers Resort style Pool & Spa, Fitness center, Parking place.

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$493.13

/ Nightly

Private Vacation Home

Heated Pool + Game Room + Sleeps 12 +12 min Beach

Sarasota, Florida, United States

Welcome to Paradise Palms, your perfect Sarasota escape! This family- and pet-friendly home in the peaceful Whitfield neighborhood is just minutes from downtown, the airport, and white-sand beaches. Enjoy a heated pool, epic game room, lush outdoor space, and everything you need for a relaxing Florida getaway. Sleeps up to 12 guests, the ultimate spot for memory-making!brbrDiscover the perfect blend of comfort, fun, and relaxation at this spacious family getaway, just minutes from Lido Key Beach, downtown Sarasota, and Anna Maria Island.brbrDesigned with families and groups in mind, this 4-bedroom home sleeps up to 12 guests and offers great amenities including a heated pool, epic game room, and all the beach gear you’ll ever need.brbr➞ WHAT YOU’LL LOVE ABOUT THIS HOMEbrbr• Sleeps up to 12 guests – 4 bedrooms + sleeper sofabr• Heated pool for year-round enjoymentbr• Fully loaded game room for kids and adults alikebr• Pet-friendly (with approval) – your furry friends are welcomebr• Fully equipped kitchen & dining area perfect for family mealsbr• 2 full bathrooms with all essentials providedbr• Comfortable beds and cozy living spaces for everyonebr• FREE 400 Mbps Wi-Fi + Roku Smart TVs for streamingbr• Washer & dryer (detergent provided) for your conveniencebr• Private driveway fits up to 5 carsbr• Lush outdoor space with plenty of room to relax and rechargebrbr➞ LOCATIONbrbrLocated in the quiet Whitfield neighborhood of Sarasota, this home offers easy access to top attractions:brbr• Sarasota–Bradenton International Airport – 3 miles (7 min)br• Downtown Sarasota – 10 miles (18 min)br• Lido Key Beach – 12 miles (22 min)br• Siesta Key Beach – 22 miles (35 min)br• Anna Maria Island – 22 miles (35 min)br• IMG Academy – 11 miles (20 min)br• Bradenton Beach – 18 miles (30 min)brbrPeaceful, convenient, and perfect for exploring all Sarasota has to offer.brbr➞ WHERE YOU’LL SLEEPbrbrEach bedroom is designed for comfort and relaxation, with fresh linens, cozy furnishings, and Smart TVs.brPerfect for large families or multiple couples traveling together.brbr• Bedroom 1: King bed + Smart TVbr• Bedroom 2: Queen bed + Smart TVbr• Bedroom 3: Queen bedbr• Bedroom 4: Full-over-Full bunk + Twin trundle + Smart TVbr• Living Room: Queen-size sleeper sofabrbr➞ WHAT GUEST ARE SAYING ABOUT THIS PROPERTY:brbr“Perfect for our family! Spacious, clean, and the kids LOVED the game room.” – Conradbr“Quiet neighborhood, beautiful home, and amazing host.” – Lillybr“We really enjoyed the pool and relaxing outdoor area.” – Shaianbrbr➞ FULLY EQUIPPED KITCHENbrbr• Cook, dine, and connect in a spacious kitchen with:br• Stainless-steel appliancesbr• Granite countertopsbr• Seating for 12br• Cookware, utensils, and family-style dining essentialsbr• Complimentary coffee, filters, and creamerbrbr➞ OUTDOOR OASISbrbrYour own private backyard paradise includes:br• Heated enclosed pool (optional heating $30/per day)br• Lounge chairs and al fresco dining BBQ grillbr• String lights for cozy eveningsbr• Perfect for poolside fun and sunset dinners.brbr➞ ULTIMATE GAME ROOMbrbrFun for all ages in a detached garage-turned-game-haven:brbr• PlayStation 5 + 65” Smart TVbr• Pac-Man arcadebr• Pool table, ping pong, foosballbr• Popcorn machine for movie night vibesbrbr➞ PETS WELCOME (WITH APPROVAL)brbrWe love hosting pets!brbr• Pets are welcome with prior approval and a $175 pet feebr• Certain breeds may have restrictions per insurancebr• Please keep pets off the furniture and out of the poolbrbr➞ KID FRIENDLY COMFORTSbrbrWe’ve got the little ones covered:brbr• Pack ’n play & baby monitorbr• Stroller & highchairbr• Sippy cups & kids’ dinnerwarebr• Bunk beds for extra funbrbr➞ BEACH READY GEARbrbrNo need to pack your own! Included:brbr• Beach towelsbr• Chairs & umbrellasbr• Toys, cooler, and wagon for easy transportbrbr➞ HOUSE RULESbrbrWe love sharing our home, and we respect our neighbors. Please note:brbr• No parties or loud gatheringsbr• No smoking or drug use (incl. marijuana)br• Quiet hours: 10 PM – 7 AMbr• Max 5 cars in the driveway (no street parking or trailers)br• Rule violations = immediate eviction + $1000 finebr• Once a guest has checked in, we do not offer refunds for early checkout.brbrYour Sarasota Escape AwaitsbrbrWhether you’re here for beaches, family fun, or relaxation, Paradise Palms is your ideal home base. Space, style, and sunshine are everything you need for an unforgettable Florida getaway.brbr★☆ Book Your Sunshine Stay Today & Start Making Memories! ☆★

4

Bed

2

Bath

12

Sleeps

$260.95

/ Nightly

Condo

Coastal 1BR with Pool View Near Crescent Beach

Sarasota, Florida, United States

Summary:brbrThink white sand, Gulf breezes, and nowhere you have to be.brbrbrbrWelcome to your laid‑back home base near Crescent Beach. Tucked inside a well‑kept beachfront community, this cozy one‑bedroom condo is all about simple comforts, salty air, and stress‑free island days.brbrbrbrThe Space:brbrThe open‑concept layout keeps things light and relaxed, with the living space, dining area, and kitchen flowing together effortlessly. Cook up quick beach snacks, gather around the dining table, or unwind after a sun‑filled day. The bedroom features two queen‑size beds, making it a great fit for friends, couples, or a small family.brbrbrbrStep out onto your private balcony, deck, or patio, feel the Gulf breeze, and let island time take over. When you’re not at the beach, enjoy a refreshing swim in the community pool or squeeze in a quick workout at the fitness area.brbrSun, sand, and that classic Siesta Key vibe—coastal living made easy.brbrbrbrHeated community poolbrbrFitness room/equipmentbrbrPrivate balcony, deck, or patiobrbrWasher & dryerbrbrSmart TV & televisionbrbrWiFi/cable/internetbrbrLinens & bath towels providedbrbrHair dryerbrbrIron & ironing boardbrbrParking includedbrbrbrbrGuest Access:brbrGuests will have access to the entire unit, resort amenities, and Crescent Beach.brbrbrbrThe Neighborhood:brbrLocated on the sought‑after south end of Siesta Key, the Crescent Beach neighborhood is known for its laid‑back island vibe, stunning turquoise waters, and world‑famous powdery white sand that stays cool underfoot. Just steps from the beach and near Point of Rocks snorkeling, the area offers the perfect blend of natural beauty and convenience. Local shops, casual dining, and Siesta Key’s free trolley are close by, making it easy to explore while still enjoying a peaceful, uncrowded beach atmosphere.brbrbrbrGetting Around:brbrWe recommend a vehicle for the area.brbrbrbrOther Things to Note:brbrGuests must be 21+ to book and check in.brbrThis is a no‑pets, no‑smoking, no‑parties kind of stay. Thanks for helping us keep things relaxed for everyone.brbrA refundable authorization hold is placed at check‑in and released after checkout, following a quick inspection.brbrResort amenities are regularly maintained, though availability can’t always be guaranteed.brbrbrbrInteraction with Guests:brbrOn‑site office hours: Monday–Saturday, 9:00 AM–5:00 PM

Bed

Bath

Sleeps

$2564.82

/ Nightly

Private Vacation Home

Experience the Ultimate in Coastal Luxury at A Point of Paradise

Sarasota, Florida, United States

Experience the ultimate in coastal luxury at Point of Paradise, a stunning new retreat nestled on the peaceful southern end of Siesta Key. Designed to host up to 18 guests in style, this 8-bedroom haven combines sophisticated design with all the comforts of home. With each bedroom featuring a private ensuite, multiple living spaces, and breathtaking views, this property is the perfect setting for unforgettable gatherings with family and friends.brbr An Outdoor SanctuarybrStep outside and be captivated by the resort-style pool, a true centerpiece of this tropical oasis. Stretching along the western edge of the property, it features a plunge section with submerged seating, a Baja shelf crowned with a gentle fountain, and a whirlpool spa for ultimate relaxation. The pool is framed by a row of inviting chaise lounges, perfect for basking in the Florida sunshine. Around the back, enjoy the convenience of a triple charcoal grill for al fresco feasts and an outdoor shower to rinse off after a day of adventure.brIndoors, the game room awaits with a pool table and a ping pong/air hockey combo table, offering hours of entertainment for guests of all ages.brbr Second-Floor ElegancebrAscend to the second floor, where the home's 12-foot ceilings and expansive layout create a light and airy atmosphere. At the heart of this level is the open-concept living area, featuring a chef's dream kitchen equipped with state-of-the-art Bosch appliances, sleek finishes, and ample counter space. The spacious dining table invites lively meals, while the plush wrap-around sofa and large flat-screen TV make movie nights a delight.brStep out onto the multi-level deck to enjoy the fresh coastal breeze and tranquil views of the pool below. Surrounding this central space are four opulent King bedrooms, each offering a serene retreat, plus a convenient half-bath and a well-appointed laundry room for added comfort.brbr Third-Floor IndulgencebrThe third floor continues the luxurious experience with a cozy lounge area complete with a wet bar—the perfect spot for a quiet drink or casual conversation. This level includes three more King bedrooms, as well as a double twin bunk room, ideal for younger guests or group flexibility.brThe crown jewel of this home is the rooftop patio, accessible via a dramatic spiral staircase. From this elevated perch, marvel at the sweeping panoramic views, including the shimmering Gulf waters and Siesta Key's legendary sunsets. This rooftop escape is a magical setting for evening cocktails, morning yoga, or simply gazing at the stars.brbr Steps to Island BlissbrA Point of Paradise is just a short stroll from the island's pristine beaches, where soft, powdery sands meet the warm Gulf waves. Explore Siesta Key's charming villages, filled with unique shops, local eateries, and endless opportunities for adventure. From paddleboarding and kayaking to sunset cruises, there's something for everyone to enjoy.brbr✨ Why Visit Point of Paradise brThis remarkable home offers the best of both worlds: expansive gathering spaces to bring everyone together and private retreats for moments of quiet relaxation. Whether you're savoring meals by the pool, toasting the sunset on the rooftop patio, or unwinding in your luxurious ensuite, every detail has been designed to create an unforgettable stay.brBook your stay today and capture your very own Point of Paradise—where memories are made, and dreams come to life.brbrExclusive Amenities Include:br• Private Heated Plunge Pool, Baja Shelf and Whirlpoolbr• Pool Views on 2nd & 3rd Story Balconiesbr• Roof top patio with Gulf Viewsbr• Less Than 1 mile to Crescent Villagebr• Less Than a 2 Minute Walk to Crescent Beach & Point of Rocksbr• Just a Short Drive to Siesta Key Village & Siesta Key Beachbr• Ping Pong Table / Air Hockey Tablebr• Outdoor Lounge Areasbr• 8 Bedrooms, 8.5 Full Baths with Luxury Towels & Bed Linens provided, br• Spacious Balconies With Seating Areabr• Full Gourmet Kitchenbr• 2 Private Garages and Off Street Driveway Parking for 3 Carsbr• Washer/Dryer Laundry Rooms on 2nd and 3rd floorsbr• Free WiFi & HDTV'sbr• Regular & Keurig Coffee Makers, Dishwasher, 2 Washers & Dryers, and Kitchen Essentials Providedbr• Starter Pack of Toiletry Essentials Included - Shampoo, Conditioner, Hand / Face Soap, Body Lotion, & Makeup Wipesbr• Starter Pack of Home Essentials Included - Dish Soap, Dish Sponge, Dishwasher Tablets, Laundry Tablets, & Cleaning Wipesbr• Beach Towels, Chairs, Cooler, & Caddy Providedbr• Triple Charcoal Grillbr• Enhanced Cleaning Protocols Provided by our CottageClean Teambr• Island Shuttle Transportation AvailablebrbrbrA Point of Paradise can accommodate up to 18 guests with a bedding configuration as follows:brbrBedroom 1 – King (1) - Sleeps: 2brBedroom 2 – King (1) - Sleeps: 2brBedroom 3 – King (1) - Sleeps: 2brBedroom 4 – King (1) - Sleeps: 2brBedroom 5 – King (1) - Sleeps: 2brBedroom 6 – King (1) - Sleeps: 2brBedroom 7 - King (1) - Sleeps: 2brBedroom 8 – Two Twin Bunk Beds (4 twin beds) - Sleeps: 4brbrWe go above and beyond the industry standard for cleanings with our multi-tiered cleaning protocol within our CottageClean Program. After our six hour in-depth cleaning of your home, we complete a 35 point property inspection to ensure that you feel tremendously safe and happy with this amazing home. This allows you to vacation worry free regarding the cleanliness of your home and truly relax as soon as you arrive. Our goal is to have you feel like you are walking into a brand new vacation home that no one has ever stayed at before!brbrPLEASE NOTE: brThe pool is heated from November 15th to April 15th.brThis home has stairs. If any member of your party has difficulty with stairs, please contact us to discuss alternative accommodations.

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Select Dates for Price

Condo

NEW! Stunning Waterfront 1.5/2 at The Strand

Sarasota, Florida, United States

Welcome to The Strand, where luxury waterfront living meets convenience and comfort. brThis rental unit features one bedroom, one den and two FULL bathrooms. brbrEnjoy amenities such as a heated outdoor pool, spa, fitness center, kayak launch, two communal barbecues, elevator access, and secure community entry—all just a short drive from downtown Sarasota. brRelax on your balcony overlooking the serene Whitaker Bayou.brbrWe have taken great care to ensure that you have everything you need to feel at home during your stay.brbr★Living Area:brThe living area, located down the hallway, features a desk with a chair, a comfortable couch and ottoman, an armchair, and a smart TV for streaming (requires your own login credentials) equipped with Roku for free TV streaming. The space also provides direct access to the balcony through sliding glass doors. brbr★Kitchen:brThe kitchen features brand new appliances such as a stove, oven, microwave, fridge, dishwasher & disposal, toaster oven, and coffee machine.brIt has 4 bar stools to enjoy the breakfast bar.brA new sponge, dish soap, trash bags and dishwashing detergent to get you started are included.brbr★Dining:brThe breakfast bar areas have 4 total chairs. brbr★Master bedroom:brLocated on the left-hand side upon entering the condo, it includes a Queen-sized bed, a dresser with a smart-tv, a nightstand with lighting as well as access to the en-suite bathroom. Bedding & linens are included.brbr★Den:brConsidered a guest bedroom without a window, it features a comfortable convertible couch.brbr★Bathrooms:brThe master bath is connected to the bedroom. It features a large walk-in shower, sink and toilet, and a large walk-in closet.brWasher and Dryer are located in master bathroom.brThe 2nd bathroom features a bathtub with sink and toilet. brTowels, a blow dryer and essential soap products are included.brbr★Balcony:brThe balcony can be accessed through the large sliding doors in the living room and features 2 chairs and a small side table. brIt is the perfect location to enjoy the sunsets on the bay!brbr★Laundry:brThe washing and dryer machines are located in the master bathroom.brBasic detergents are supplied to start you off.brbr★Parking:brYou have one reserved spot inside the parking garage.brPlenty of uncovered guest parking available on a first-come first-serve basis.brbr★Outdoor:br2 bikes for your enjoyment brbr★Community amenities:brCommunal pool & Gym, please note that pool temperature may vary depending on outdoor conditions, and during colder weather, it may not always reach the desired setting. The pool is heated seasonally in accordance with Homeowners Association guidelines. Guests are kindly asked to follow all HOA pool rules, including posted hours of operation.brKayak Launchbr2x barbequesbrEV charging stationsbrSecure entrybrbr★Accessories:brBeach towelsbrbr★Miscellaneous:brSelf check-in starting 4 pm & self check-out by 10 am.brSecure community with MyEnvera gate system.brCar charging stations available.brIf you wish to receive mail, it must be sent to our Orquera Florida Investment office - Sarasota downtown.brbr★Location:brDowntown Sarasota – 5-10 min drivebrLido Beach - 15 min drivebrSiesta Key Beach - 25 min drivebrWicked Cantina Mexican Restaurant & Subway within walking distance.brNew Bay Park – 5 min drive/10 min walkbrThe Westin – 5 min drivebrThe Ritz – 5 min drivebrbr★Important Notes & Rules:br- This rental requires HOA approval, which includes submitting your email address, a copy of your driver’s license, current address, vehicle information, and a $150 fee (included in booking, fee subject to change). To begin the application, please promptly provide your email address. While we will apply on your behalf, we are not responsible for any delays in the process due to late submission of required information.br- For your safety, swimming is at your own risk, and children must be supervised at all times.br- No parties and no smoking on the premises.br- AC temperature should not be set below 70°F, and heating must not exceed 77°F.br- Please ensure doors and windows remain closed when the AC or heating is running.br- The residence is located on the canal without a fence. Children must be supervised at all times.br- If you need elevator assistance, please note that elevators may be temporarily disabled during severe weather. Stairwells are available as an alternative.brbr★Add-on:brTraveling with a little one We offer a Pack 'n Play for use during your stay for a one-time fee of $50. This includes clean, fitted sheets for your convenience. Just let us know in advance if you'd like to add this to your booking!brbr★Wildlife Awareness:brFlorida's diverse wildlife awaits responsibly; refrain from direct contact and adhere to safety guidelines. For more information, visit the Florida Fish and Wildlife Conservation Commission.brbrAre you traveling with family or friends We manage other units in The Strand, just ask us!brbrFind us on FB or IG: Orquera Florida InvestmentsbrbrYour unforgettable getaway awaits!

2

Bed

2

Bath

3

Sleeps

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