Vacation Rentals By Owner In Sarasota, FL

Wake up to Gulf views at this beautifully appointed 2BR/2BA condo in the Beach Club on Siesta Key, just steps from the powdery white sands of award-winning Siesta Beach. Located in a stretch near the South Village, this coastal retreat offers walkable dining, easy trolley access, and the rare luxury beach experience with snorkeling at nearby Point of Rocks.brbrWhy You’ll Love Itbr• Gulf views from the bedroom—wake up to coastal sunshinebr• Beach access with no public access pointsbr• One-minute walk to Siesta Beach’s sugar-white sandbr• Walk to South Village shops, dining & island favoritesbr• Free Breeze Trolley access to the North Village & beyondbrbrSleeping Arrangementsbr• Primary Suite – Queen bed – ensuite with walk-in showerbr• Guest Bedroom – Queen bedbr• Living Area – Queen sofa sleeperbr• Sleeps up to 6 comfortablybrbrOutdoor Highlightsbr• Heated community pool & hot tubbr• Covered grilling station for easy island cookoutsbr• Shared front porch—perfect for morning coffee or evening breezesbr• Snorkeling & reef exploration at Point of Rocks nearbybrbrInterior Comfortsbr• Open living and dining layoutbr• TV in every roombr• Dining table seating for fourbr• In-unit washer & dryerbr• Bright, coastal décor throughoutbrbrKitchen & Diningbr• Fully equipped kitchenbr• Drip coffee maker + single-cup Keurigbr• Everything you need for beach-day breakfasts or sunset dinnersbrbrIncluded Home Essentialsbr• Beach chairs, umbrellas & beach towelsbr• Wi-Fi and smart TVsbr• Fresh linens, bath towels & starter suppliesbrbrNeighborhood Perksbr• Twelve restaurants within a half-milebr• South Village boutiques, cafés & nightlife nearbybr• Free Breeze Trolley for easy island exploringbr• Close to snorkeling, paddleboarding & sunset walksbrbrAccess & Parkingbr• Stairs required to enter the unitbr• Free onsite parking included for one vehicle brbrVacay Your Way on Siesta Key—book now with Gulf Coast Vacations and turn every beach day into a postcard moment.

2BR Beach Club – Beach, Heated Pool & Hot Tub

Sarasota, Florida, United States

Bed

Bath

Sleeps

$266.12

** This unit offers reservations with a 4-night minimum from April/11/2026 through December/11/26br and April/10/27 through December/10/27** Please contact our Office for assistance.brbrThis condo is situated in great viewing of the beach at La Siesta Condominiums. Unit 212 is located in one of Siesta Keys most popular relaxing getaway destinations. The newly renovated two (2) bedroom and two (2) bathroom is conveniently located across the street to the public beach access of the World famous powdery white sands of Siesta Key Beach. The prime location is short walking distance or quick ride on the Breeze trolley to the Siesta village, which is notably the heart of Siesta Key for family outings, adult nightlife, shopping and amazing restaurants for all to enjoy. This spacious 2B/2B unit is situated on the 2nd floor with access to an elevator, washers and dryers. The condo consists of an open floor plan of kitchen, living room, and dining room. This space is great for couples, families and friends to gather for a nice relaxing vacation getaway from the daily life grind. We want you to sit back and relax during your stay, whether it is a week or as long as you need to unwind.

Condo# 212 Renovated 2 bedroom 2 bath accross the street from beautiful Siesta Key Beach

Sarasota, Florida, United States

Bed

Bath

Sleeps

$175.95

Newly renovated charming house close to beaches, shops, restaurants and movie theaters. Queen size bed and a pull out sofa bed. Quiet area walking distance to restaurants and shops. Front yard is great for walking small dogs. Beach towels and beach chairs are supplied. Fully equipped kitchen. Supermarkets near by. Generous discount at one of the best restaurants in town located right down the street.

Centrally located near everything with bonus facilities!

Sarasota, Florida, United States

1

Bed

1

Bath

4

Sleeps

$559.78

Slow down and settle into the Sarasota lifestyle at this thoughtfully designed 2-bedroom retreat, tucked just close enough to downtown to walk to your favorite coffee shops and restaurants, yet far enough to feel calm and removed. From the moment you arrive, the home invites you to exhale; welcoming, stylish, and intentionally designed to feel like a true escape.brbrInside, the space is light-filled and serene, with soft pops of pink, clean lines, and warm textures that create an atmosphere of relaxed luxury. Mornings are meant for unhurried coffee at home, afternoons for beach days and exploring the city, and evenings for coming back to a place that feels quietly special. Every detail has been chosen to make the home feel elevated without ever feeling formal.brbrStep outside and the saltwater pool and outdoor space become a natural extension of the home, perfect for sun-soaked afternoons, refreshing dips, and slow evenings under the sky. It’s a space that encourages lingering, conversation, and the simple pleasure of doing nothing at all.brbrThe home features a spacious king bedroom, a cozy queen bedroom, and a fold-away twin on request, ideal for a fifth guest. Whether you’re traveling with friends, family, or as a couple wanting extra space, the layout offers flexibility while maintaining comfort and style. brbrA well-appointed bathroom with a walk-in shower and all the essentials, along with central heating and air conditioning, ensures an easy, comfortable stay in every season.brbrWhether you’re here to explore Sarasota’s beaches, dining, arts, and culture or simply to slow down and enjoy being present, this home offers a beautiful place to land at the end of each day. We’re always available for questions, local recommendations, or anything you need to make your stay effortless.brbrIf your dates aren’t available, feel free to message us! brDon't see your dates available feel free to message us! brCheck out all our bespoke stays at Elsewherewithme.com

Beach Life + Walk to Downtown, Heated Saltwater Pool + Large Yard

Sarasota, Florida, United States

Bed

Bath

Sleeps

$236.21

This is a wonderful one-bedroom house, perfect for your next getaway. It's located west of the trail, within walking distance to Starbucks and other stores and restaurants. It's located between the two bridges to Siesta Beach, also 5 minutes away from downtown and other attractions. Mid Century Gem.

Mid-Century Gem

Sarasota, Florida, United States

Bed

Bath

Sleeps

$208.26

Modern home has great room with cathedral ceiling and waterfall mural, large kitchen and master bedroom, includes extra sleeping space and 2 car garage. We built this house for our future retirement. It has extra features like a bay window with window seat, and a stone and dark wood motif. There is a sunny front yard and shaded private back yard.brWe are one and one half mile easy biking distance from Pinecraft.

Spacious 2 1/2 bed home.

Sarasota, Florida, United States

Bed

Bath

Sleeps

$541.48

Villa #6 is a 2 Bedroom 2 Bathroom Ground Floor Villa on Siesta Key, br2 minutes walk to the Public Beach Access #13,brA/C SystembrFull Kitchen with Granite Counter Tops, brStainless Steel Appliances,br65 Inch SMART TV in Living Room,brEach Bedroom has an Ensuite Bathroom,brLarge 2 Person Showers, brOverlooks Swimming Pool, brDaily and Weekly Rentals,brFree Parking by your front door,brFree Wifi,brNo pets,brGreat Location, Good Value.brBike Rack on site outside.brWalk to the beach, bars shops and Restaurants.brbrAll Villas are Ground Floor ,brShort Walk to Public Beach Access #13, brWe provide Chairs and Towels for the Public Beach , brEnsuite Bathrooms,brFull Kitchen,brSwimming Pool,brLaundry Room on site,brFree parking by your door,brFree WIFI,brDaily and Weekly RentalsbrGreat Location, Good Value.brBike Rack outside.brWalk to the beach, bars, shops and restaurants.brbrThis is a Vacation Rental, brSelf Check in , Key Pad Entrance. brThe Owner does not live here.brThis is a Family Owned and Operated Vacation Home,brThis 2 bedroom 2 Bathroom Villa is for Sole Use of your self and your Guests staying in the Villa.brPark directly outside your front door.brbrThe Swimming Pool is shared with other guests staying on site.brThe Laundry Room is shared with other guests stying on site.brThe Owners live close by and are available if Guests should need anything.brbrGreat area br2 minutes walk from your door to the beach access on Crescent beach Siesta key brA mix of vacation rentals and family owned homes and big fancy housesbrbrA short walk to the beach br2 car parking spaces by your door brNo car needed as everything is just minutes awaybrbrNo Pets..$250 Fee. brService Pets Welcome, please let us know in advance. brNo Smoking in Villas..$250 Fee. brWe are a Small Resort on Siesta Key offering 6 Villas on daily/weekly Rentals for Vacations close to the Beach.br- No smokingbr- No pets

Apartment

VILLA 6 ·Pool 1 King 1 Queen. Daily rentals

Sarasota, Florida, United States

Bed

Bath

Sleeps

$289.92

Welcome to your Sarasota Arts & Culture Retreat — a modern, beautifully furnished 1BR + private den condo located in one of Sarasota’s most sought-after neighborhoods. This 890 sq. ft. condo is ideal for couples, snowbirds, traveling professionals, and anyone visiting Sarasota for its world-class museums, theater, galleries, and waterfront beauty. Built in 2022 and thoughtfully designed with upscale Crate & Barrel furnishings, this is your serene home base in the heart of the city’s cultural district.brbrLocated within walking distance of the Ringling Museum, Asolo Repertory Theatre, The Bay Park, and just minutes from Van Wezel Performing Arts Hall and Downtown Sarasota, the condo blends exceptional convenience with quiet, boutique comfort. Whether you're here for a week of performances, a month-long professional assignment, or a peaceful couples’ getaway, this modern retreat has everything you need.brbrIdeal Layout for Couples + One Additional GuestbrbrThis condo features two private sleeping spaces, making it perfect for one couple and an additional adult guest.brbr• Primary Bedroom:br– King bedbr– High-end linensbr– Smart TVbr– En-suite access to full bathbrbr• Den / Second Sleeping Space:br– Queen bedbr– Compact, private room without windowsbr– Best suited for one adult guestbr– Ideal for a traveling companion, adult child, or visiting friendbr– Full bathroom located next to the den in the hall.brbrNote: This layout is intentionally designed for comfortable occupancy of up to 3 adults, not two couples.brbr- Modern Design & Stylish Comfort:brbrEvery detail has been chosen to create a relaxing, contemporary environment:brbr2022 construction with quiet, efficient designbrbrCrate & Barrel furnishings throughoutbrbrBright open living area with comfortable seatingbrbrSmart TV with streaming appsbrbrBalcony with views of the Sarasota Bay and beautiful sunsets.brbrPlenty of storage for longer staysbrbrFast WiFi suitable for remote workbrbrWhether you're curling up with a book, streaming a show, or unwinding after a day of exploration, this space provides comfort and tranquility.brbr- Fully Equipped Kitchen:brbrIdeal for longer stays and guests who enjoy preparing meals:brbrStainless steel appliancesbrbrFull-size refrigeratorbrbrOven, stove, microwave, dishwasherbrbrKeurig + traditional coffee makerbrbrCookware, dinnerware, and essentialsbrbrEnjoy quiet mornings, a cozy dinner at home, or a glass of wine before catching a show.brbr- Work-Friendly Space:brbrPerfect for business travelers or remote workers:brbrReliable high-speed WiFibrbrComfortable workspacebrbrPeaceful atmosphere for productivitybrbrClose proximity to Sarasota Memorial, New College, and Ringling CollegebrbrTraveling nurses and remote professionals particularly love this location.brbr-Boutique Building Amenities: brbrThe Strand is a quiet, modern community with upscale features:brbrOutdoor poolbrbrHot tubbrbrFitness centerbrbrWaterfront boardwalkbrbrGrilling area + outdoor fire pitbrbrParking garagebrbrElevator accessbrbrBeautiful landscaping and relaxing atmospherebrbrEnjoy all the conveniences of a resort while staying in a peaceful, residential environment.brbr- Unmatched Arts & Culture Location:brbrStep outside and explore Sarasota’s world-class cultural attractions:brbr• The Ringling Museum of Art — short drivebr• Asolo Repertory Theatre — short drivebr• Sarasota Balletbr• Van Wezel Performing Arts Hallbr• The Bay Park waterfront trails & eventsbr• Ringling College galleries & eventsbr• Downtown Sarasota dining, live music & shopsbrbrThis is the perfect home for culture lovers, festival-goers, and guests attending performances or special events.brbr- Beautiful Beaches — A Short Drive Away:brbrLido Beach – just 10 minutesbrbrLongboat Key – 12 minutesbrbrSiesta Key Beach – about 20 minutesbrbrAnna Maria Island – ~30 minutesbrbrExperience the best of both worlds — arts, culture, and waterfront tranquility.brbr- Nearby Shopping, Dining & Essentials:brbrYou’re surrounded by some of Sarasota’s best destinations for dining, strolling, and convenient essentials:brbrSt. Armands Circle – boutique shops, cafés, cocktails, and unique restaurants in a charming, walkable atmospherebrbrUniversity Town Center (UTC) – modern dining, upscale retail, Whole Foods, Target, and everyday essentialsbrbrDowntown Sarasota – galleries, theaters, wine bars, rooftop lounges, and waterfront diningbrbrThe Rosemary District – trendy cafés, bakeries, coffee shops, and creative local restaurantsbrbrMarina Jack & Bayfront Park – waterfront walks, sunset views, boating charters, and elegant marina-side diningbrbrNearby Groceries – Publix, Whole Foods, and Fresh Market are all a short drive awaybrbrEverything you need — from boutique shopping to fine dining to daily essentials — is just minutes from your door.brbr- Pets Welcome (With Approval):brbrWe allow pets on a case-by-case basis. Please inquire before booking.brbr- Perfect For:brbrArts & culture tripsbrbrCouples’ getawaysbrbrTraveling nursesbrbrSnowbirdsbrbrProfessors/academicsbrbrBusiness travelersbrbrLong-stay guestsbrbrVisitors attending Ringling/Van Wezel eventsbrbrGuests love the combination of modern design, unbeatable location, walkability, and quiet atmosphere.brbr*Your Sarasota Retreat Awaits* -brbrIf you’re looking for a modern, peaceful, beautifully furnished home base close to Sarasota’s cultural treasures and waterfront beauty, this condo offers everything you need for a memorable stay.brBook your getaway today and experience Sarasota like a local — with arts, nature, dining, and entertainment at your doorstep.

Modern Arts District Retreat • Walk to The Bay & Van Wezel • Near Ringling

Sarasota, Florida, United States

Bed

Bath

Sleeps

$353.85

Island House Beach Resort | Lanai | Brand New Unit | Trolley Stop On-SitebrbrBring your flip-flops and enjoy island vibes from this 2-bed, 2-bath villa in Sarasota. The vacation rental has a prime Siesta Key location — step outside and relax on powder-white sands with private access to one of America’s top beaches. Roll down to Siesta Village for bites, bars, and shopping. In the evenings, have sunset cocktails on the patio and recharge in serenity for the next coastal adventure.brbr-- THE PROPERTY --brbrSLEEPING ARRANGEMENTSbr- Bedroom 1: 1 king bedbr- Bedroom 2: 2 twin bedsbr- Living Room: 1 queen sleeper sofabrbrCOMMUNITY AMENITIESbr- Heated outdoor poolbr- Game room w/ ping-pong, pool, air hockey & foosballbr- Shuffleboard, 2 gas grillsbr- Private beach, beach chairs, beach showerbrbrINDOOR LIVINGbr- Smart TV, board gamesbr- Dining tablebr- Washer & dryerbrbrOUTDOOR LIVINGbr- Lanai, outdoor seatingbr- Outdoor shower br- Grilling tools, beach towelsbrbrKITCHENbr- Dishwasher, refrigerator, stove/oven, microwavebr- Drip coffee maker, coffee filters, toasterbr- Cooking basics, dishware & flatware, starter trash bags & paper towelsbrbrGENERALbr- Central heating & A/Cbr- Towels & linensbr- Hair dryerbr- Free WiFibr- Keyless entrybrbrFAQbr- Quiet hours (10:00 PM-7:00 AM)brbrACCESSIBILITYbr- Single-story villa, 1 step to enterbrbrPARKINGbr- Carport (1 vehicle)br- Driveway (1 vehicle)br- No street parkingbrbr-- THE LOCATION --brbr- Walking distance to Crescent Beachbr- Nearby: parasailing, golf cart rentals, boat rentals & intercoastal fishingbr- 77 Siesta Islander trolley stop on-site: service to beaches & the villagebr- 2 miles to Siesta Key Village: bars, restaurants, shopsbr- 11 miles to The John and Mable Ringling Museum of Artbr- 7 miles to Marie Selby Botanical Gardens Downtown Sarasotabr- 11 miles to Sarasota Bradenton International Airportbrbr-- 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- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- Please observe quiet hours from 10:00 PM to 7:00 AMbrbrADDITIONAL INFORMATIONbr- This single-story villa requires 1 step to enter

Villa

Private Beach Retreat on Siesta Key! Bright Villa

Sarasota, Florida, United States

Bed

Bath

6

Sleeps

$339.0

brbrHuge, beautiful space overlooking the blue waters of the Golf of Mexico. This is a 2 bedroom 2 bath penthouse apartment with full-kitchen, living room, dining room with everything included. All cooking utensils, 2 color TV, very modern, clean and beautiful. There is a balcony off the kitchen for outdoor dining or to view the magnificent sunsets. brbrThe beach is only steps away and the white sand is world famous because it never gets hot! There is snorkeling in the sea or rental of fishing gear or boats and para-sailing is all near by. Short stroll to the village where there many great restaurants, bike rental places, shops and tiki hut for drinks and music. The white sand of Siesta Key are famous for sand castle building and shelling...The sand never gets hot. there are beach chairs at the pool and a barbeque. Game room extra funbrbrNo car is necessary to live everything is so close. brbrYou are living on a world famous barrier island. There is a huge swimming pool and barbeques and a game room. brbrThe resort is called Calini Resort and can be looked up by that name for more information and pictures. The rent is $300 a night and $2100 for the week. all included. A motel room would cost the same if there is one available for this busy week. Available for Labor day week!brbrThe days are long and the water is the best time to be on Siesta Key.

FABULOUS APARTMENT ON WORLD RENOWNED SIESTA KEY BEACH. SLEEPS 6

Sarasota, Florida, United States

Bed

Bath

6

Sleeps

$178.91

A year-round haven awaits when you choose this sunlit condo for your vacation. Take in fabulous views of the golf course and lake from your tranquil screened porch, which offers a cushioned sitting area. This snowbird-friendly getaway features two living areas, two dining areas, and a full kitchen.brbrSchedule a tee time at the on-site golf course or enjoy the use of shared amenities, which include a pool, hot tub, or tennis courts. Amazing perks include free WiFi, central air-conditioning, a washer/dryer, and private garage parking. For blissful days of fun in the sun, drive just over 6 miles to miles of beautiful white-sand beaches. Other nearby attractions include Oscar Scherer State Park and the Marie Selby Botanical Gardens' Historic Spanish Point.brbrNearby Services and Dining OptionsbrMultiple amazing dining options within 10 miles. Gas station within 3 miles. Multiple supermarkets within 3 miles.brbrPlaces to Visit During Your StaybrbrAttraction Distance From HomebrSiesta Key Watersports 5.5 MilesbrMarie Selby Botanical Gardens Downtown Sarasota Campus 10.6 MilesbrBayfront Park 10.9 MilesbrBig Cat Habitat Gulf Coast Sanctuary 11.5 MilesbrMote Marine Laboratory & Aquarium 15.2 MilesbrPelican Pointe Golf And Country Club 13.7 MilesbrVan Wezel Performing Arts Hall 12.2 MilesbrThings to KnowbrFree WiFibrFree live and streaming TV servicebrCentral ACbrFull kitchenbrSnowbird friendlybrbr*Golf and Social Transfer Membership is available for a monthly fee paid directly to the county club. This fee includes access to the newly redesigned 18 hole stadium style golf course, dining at the club, fitness center, club pool and hot tub, clay tennis courts, and bocce. brbrNo pets are allowed at this vacation rental at any time.brThis rental is located on floor 2 (no elevator).brParking notes: Unit comes with one garage stall and one unassigned spot. brYou must be 21 years or older to rent this property.

Golf oasis, 10 minutes from gulf beaches - Sarasota, FL

Sarasota, Florida, United States

Bed

Bath

Sleeps

$623.11

Avanti Villa | Rooftop Deck, Walk to Siesta Key Beach & Village, Canal Accessbrbr Why You'll Love This HomebrAvanti Villa is a well-located Siesta Key retreat just a short walk to both Siesta Key Beach and Siesta Key Village. This three-bedroom duplex unit is designed for easy island living, combining walkability with comfortable indoor and outdoor spaces.The private rooftop deck creates a standout feature of the home, offering open views and a dedicated space to unwind throughout the day. Inside, the open-concept layout provides room to gather, while the elevator adds convenience across all levels. Located near the Grand Canal, the home includes access to a dock for kayaking, offering a simple way to get out on the water while still being close to the beach and village.brbr ‍ ‍ Perfect ForbrFamilies or small groups looking for a walkable Siesta Key stay, flexible sleeping arrangements, and access to both the beach and village.brbr ️ Imagine ThisbrStart your morning with a short walk to Siesta Key Beach, where the day begins with time on the sand and in the water. On the way back, stop in the village for coffee or breakfast before returning home to relax. Spend the afternoon enjoying time together in the open living space or head up to the rooftop deck for a quiet break. If you're looking to get out on the water, take advantage of the nearby canal access and launch a kayak from the dock. As evening sets in, walk to Siesta Key Village for dinner and live music, or stay in and gather on the rooftop as the sky changes color.brbr Where You'll Sleepbr• Bedroom 1 – Second Floor: King Bed and Twin Daybedbr• Bedroom 2 – Third Floor: King Bed, Ensuite Bathbr• Bedroom 3 – Third Floor: Two Twin Bedsbr• Common Area – First Floor: Queen Sleeper Sofabrbr Explore the Areabr• 0.6 Miles to Siesta Key Beach – Quick Walk to Sand and Gulf Watersbr• 0.5 Miles to Siesta Key Village – Dining, Shops, and Entertainmentbr• 6.5 Miles to Downtown Sarasota – Bayfront Parks, Arts, and Restaurantsbr• Nearby Grand Canal Access – Launch a Kayak from the Dockbrbr⌛Don't WaitbrYour reservation includes peace of mind with our CottageClean™ program, featuring a six-hour deep clean and a detailed 35-point inspection prior to arrival.brbr Need to KnowbrThis home is part of a duplex and may share a dividing wall, floor, ceiling, or exterior areas with another unit. Guests will have access to a private backyard area and the left side of the building. Please contact us if you have any questions about the layout. Starter packs of kitchen and toiletry essentials are provided for your first couple of nights. Free high-speed WiFi is included. This home is equipped with an elevator for convenience.

Avanti Villa | Rooftop Deck, Walk to Siesta Key Beach & Village, Canal Access

Sarasota, Florida, United States

Bed

Bath

Sleeps

$262.11

BNB Breeze Presents: Cannonball Cottage!brWelcome to Cannonball Cottage, a stunning vacation home nestled in the heart of Sarasota, Florida. This beautiful property offers a perfect blend of comfort and style, making it an ideal retreat for families or groups looking to unwind and enjoy the sunny Florida lifestyle. Explore the nearby beaches, botanical gardens, and marinas, or indulge in shopping and dining options just a short drive away.br- Private Heated Pool - heated at NO extra cost from Nov 21 - April 1stbr- Gas Grillbr- Wi-Fibr- Infinity Gaming Table br- Outdoor Gamesbr- Private Fenced-In Backyardbr- Beach Supplies br- 2 E-Bikes includedbr- Very large lot, which means huge back yard :)brbrExperience this beautiful home nestled in the heart of Sarasota, FL. Step outside to discover your own private oasis! Cannonball Cottage features three comfy bedrooms, accommodating up to seven guests. Inside, the cottage is designed for comfort and convenience. The fully equipped kitchen features modern appliances, and the open living area is perfect for gathering, complete with a smart TV for entertainment and comfortable seating. Challenge your family and friends on the Infinity gaming table in the reading nook. The vibrant mural adds a playful touch to the ambiance, making it a perfect backdrop for memorable vacation photos. Don't miss out on the chance to experience this charming home in Sarasota.brbrWe know, contracts aren't the most exciting part of your getaway, but to keep our home safe, we'll need you to sign a quick rental agreement upon booking (this will be sent to you, after you book) — then it's all fun from there! You can see what the contract looks like in the House Rules section. Note, check in details will not be sent until that contract has been signed. brbrTHE INTERIOR SPACEbr• Wi-Fibr• Laundry Room w/ Washer + Dryer (Detergent Provided)br• Sitting Areas w/ Plush Furniture br• Single-Level Home br• Our home is stocked with clean and sustainable products and toiletries to give you and your loved ones a toxin-free stay! brbrKITCHEN + DINING AREAbr• Fully-Equipped Kitchen w/ Cooking + Baking Essentials (No Food)br• Coffee Maker! br• Beautiful Dining Tablebr• Spacious Countertops br• Stove + Ovenbr• Fridge + Freezerbr• Microwavebr• Dishwasher (Detergent Provided)br• Kitchen Knife Block Setbr• Dishesbr• Silverwarebr• Glasses brbrLIVING ROOMbr• Smart TVbr• Large Comfortable Sofabr• Reading Nook w/ infinity Gaming Table br• Throw Pillows + Blankets brbrTHE SLEEPING ARRANGEMENTS | 3 Bedrooms br• Bedroom 1: King Bed w/ Attached Bathroombr• Bedroom 2: Queen Bedbr• Bedroom 3: Queen BedbrExtra room: Twin BedbrbrBATHROOMS | 2br• Bathroom 1: Full Bath: Standing Shower (located in bedroom 1)br• Bathroom 2: Full Bath: Shower/tub Combo (located in the hall) brbrThe highlight of this home is the inviting private pool, surrounded by a beautifully landscaped yard. Enjoy outdoor dining with the grill and patio area, or challenge your friends and family to fun outdoor games. Including Corn Hole and Giant Jenga, this home makes your vacation relaxing and fun. brbrTHE OUTDOOR SPACEbr• Private Pool! (See below for heat details.)br• Gas Grillbr• Corn Holebr• Giant Jengabr• Sun Deck w/ outdoor diningbr• Stunning landscape lightingbr• Private Green back yardbr• Parking Space for up to 4 Vehicles in the Driveway!br• 2 E-Bikes, please note that you are responsible for any damages or incidentals that could occur by using the bikes. They are stored in the garage. brbrDon't miss out on the chance to experience this charming home in Sarasota. Book your stay at Cannonball Cottage today and create unforgettable memories!brbrNAVIGATING THE AREAbrThe Bay Runner is a new, open-air trolley that provides complimentary service seven days a week, until midnight, with multiple stops along the way between Lido Key, St. Armands Circle, and downtown Sarasota!brbrSEE HOW WE ARE GOING GREEN!brWe love the environment, and are doing everything that we can to minimize our carbon footprint. Sarasota has been voted one of the cleanest and greenest cities in the US! Here are a few ways that we are loving on the beautiful Florida environment, and welcoming you to join us!br• This stay is central to beaches, restaurants, and shops! We encourage you to use our loved public transportation system to make traveling easy, and eco-friendly!br• We use high-quality, sustainable mattresses and linens.br• All of our toiletries are eco-friendly, clean products that come with reusable dispenser bags to eliminate waste.br• We use LED lighting throughout the home to minimize electricity usage. • Thanks to the natural Florida sunshine, you can soak in the sun that floods this home through all of the large windows, without using excessive home lightning during the day!br• Our home is in a great location for Instacart! Make grocery shopping for the family easy while saving on gas!brbrHere are a few of our favorite local attractions:brbrNEARBY AIRPORTS:br1. Sarasota Airport (SRQ)br2. Tampa International Airport (TPA)br3. St Pete/Clearwater Airport (PIE)brbrLOCAL ATTRACTIONSbr1. Pompana Park for Pickleball Courts!br2. Legacy Trailbr3. Siesta Key Beachbr4. Lido Key Beachbr5. Downtown Sarasotabr6. St Armands Circlebr7. AquariumbrbrGOLFbr1. The Meadowsbr2. University Park Country Clubbr3. Tatum Ridgebr4. The Founders Club (Private Club)br5. Longboat Key (Private Club)br6. The Ritz (Private Club)br7. IMG Academy Golf Clubbr8. Esplanade Golfbr9. WaterleafbrbrRESTAURANTSbr1. The Shore: Trendy waterfront restaurant with amazing seafood!br2. Connors: High-end restaurant without the high price tag!br3. Grillsmith: If you go here, you MUST get the plank grilled salmon!br4. Dry Dock: Waterfront Seafoodbr5. The Fish Camp: Wonderful seafood, but often very busy!br6. Baker + Wife: You will just love this fantastic restaurant.br7. Riverhouse Reef + Grill: Further away in Bradenton, but fantastic!br8. Der Dutchman: Fantastic home-cooked meals just down the road from you!br9. Summer Tap Juice Bar: The BEST A ai bowl in town!brbrCOFFEEbr1. Breaking Wave Coffeebr2. Perq: Do not expect syrups, just great coffee :)br3. Project Coffee (2 Locations)br4. Out About Coffee (O A)br5. Postal 98 CafebrbrGROCERYbr1. Detwilers Farm Markets: The best place to buy organic fruits and vegetables!br2. Publixbr3. Trader Joesbr4. Whole Foodsbr5. Fresh Marketbr6. Walmart GrocerybrbrADDITIONAL AMENITIES:brLinens for each BedbrTowels and WashclothsbrRoll of Paper TowelsbrBottle of Dish SoapbrTrash BagsbrCoffeebrLaundry Detergentbr2 Rolls of toilet paper, per bathroombrBath essentials - Body soap, shampoo conditionerbr*Please be prepared to bring any additional supplies that you will need during your stay.brbrPlease Note:br1. Upon booking, each guest will receive a guest rental agreement. This must be signed before the Guide Book (which includes access instructions for the property) is sent.brbr2. Pet Policy: **This property is NOT pet friendly. Please note, if we find evidence of an unauthorized pet in the home, we will ask for it to be removed immediately and guests will be charged a $400 non-refundable fine. This is also grounds for immediate removal of the guests from the home.brbr3. No Smoking: If any signs of smoking are documented, the renter agrees to pay a $200.00 / per day.brbr4. Quiet hours for the property are between 10:00 PM and 8:00 AM. Please keep the noise levels down over this time.brbr5. There are NO LONG CHECK-OUT INSTRUCTIONS! We want for you to be able to fully enjoy every minute of your stay at Cannonball Cottage!brbr6. This property is equipped with pool heat. Heat is turned on from November 21st through April 1st and is included with your stay at no extra costs. The FL sunshine does an incredible job at warming the pool for stays outside of these dates. Any request for pool heat outside of these dates will be considered individually and will incur an extra fee. brbr7. We offer complimentary 24/7 communication to ensure that your stay exceeds your expectations! Please feel free to reach out to us day or night, and we will provide you with a swift response. brbrCity of Sarasota Vacation Rental License #26-VR-000043.

Cannonball Cottage | Private Heated Pool + Outdoor Oasis

Sarasota, Florida, United States

Bed

Bath

Sleeps

$248.48

Hemingway Hideaway | Beachy Cottage Near Siesta Key with Hot Tub and Fire Pitbrbr Why You'll Love This HomebrHemingway Hideaway is a bright, beachy cottage near Siesta Key with a private hot tub, outdoor deck with dining table, grill, and fire pit—perfect for cooking, sunset cocktails, and evening gatherings.brbrLight-filled rooms, casual comforts, and easy flow make it effortless to relax after beach days or exploring Sarasota.brbr ‍ ‍ Perfect ForbrCouples, families, friends, snowbirds, and remote workers seeking sunny Florida beaches, outdoor fun, and relaxed coastal living.brbr ️ Imagine ThisbrWake to soft breezes and sunlight spilling into the rooms. Enjoy morning coffee on the deck, plan a beach day at Siesta Key, and return to rinse off your sandy toes.brbrFire up the grill for an alfresco dinner, then gather around the fire pit under starlit skies. End the evening soaking in your private hot tub, feeling the tension melt away, while the gentle Florida night unfolds around you.brbr Where You'll Sleepbr• Bedroom 1: Queen Bed, Hall Bath With Shower, TVbr• Bedroom 2: Queen Bed, Hall Bath With Showerbr• Living Area: Murphy Cabinet Bedbrbr Explore the Areabr• 3.9 Miles to Siesta Key Beach (Access 5) – World-Famous Quartz Sand, Swimming, and Unforgettable Sunsetsbr• 4.4 Miles to Siesta Key Village – Local Shops, Casual Dining, Ice Cream, and Live Musicbr• 6.8 Miles to Turtle Beach – Quieter Shoreline, Picnic Tables, and Kayaking Accessbr• 2.6 Miles to Downtown Sarasota – Arts Scene, Waterfront Parks, Restaurants, and Boutiquesbrbr⌛ Don't wait— This home books fast. Your reservation includes peace of mind with enhanced cleaning protocols and a welcoming Sarasota stay near Siesta Key.brbr Need to Know: Starter packs of kitchen and toiletry essentials provided for a seamless first couple of nights. A security camera is located by the front door overlooking the front door, front sidewalk, and driveway.

Coastal Cottage Escape Near Siesta Key Beach with Hot Tub

Sarasota, Florida, United States

Bed

Bath

Sleeps

$449.68

Reflecting a desire for inner peace, unconventional living, and artistic expression, Maison Bohème is styled in Nomad Modern design, blending global travel finds with clean, functional minimalism. Natural textures like jute, rattan, and wood pair with earthy neutrals and rich color accents, handcrafted details, and adaptable furnishings to create a serene, worldly space that feels both lived-in and effortlessly modern.brbrCharming and exceptionally private, this Florida oasis offers an intimate retreat in the heart of the sought-after Indian Beach–Sapphire Shores Bayfront neighborhood—just a short Uber or drive to art-centric Sarasota’s magnetic downtown, known for fine dining, boutique shopping, and its vibrant arts district. The Ringling Museum of Art, Asolo Repertory Theater, Sarasota Ballet, Sarasota Jungle Gardens, and the Sarasota Bay and Sarasota's famous white sandy beaches are just minutes away. A spacious living and dining area welcomes you with an open, comfortable flow, while the split-bedroom layout provides privacy for both residents and guests. The kitchen and bathroom feature brand-new cabinetry with granite countertops, along with all-new kitchen appliances for a truly move-in-ready experience. A cozy Florida room is perfect for morning coffee, reading, or quiet afternoons.brbrThe outdoor space is a true highlight, featuring a resort-style dipping pool with waterfall, grotto, and screened lanai for year-round enjoyment. Surrounded by a private, low-maintenance tropical landscape, the backyard offers three distinct seating areas—ideal for relaxing, entertaining, or escaping into your own secluded paradise.

Maison Bohème - Adults Only With Pool

Sarasota, Florida, United States

Bed

Bath

Sleeps

$208.61

Discover your Sarasota oasis! This fully renovated, private pool home is perfect for families. Features a chef's kitchen, luxury bathrooms, a retro arcade console, and a dedicated workspace. Enjoy your private, heated pool in a fully-fenced yard. Perfectly located just a short walk from the Legacy Trail and vibrant downtown Sarasota, and a quick drive to world-class beaches like Siesta Key. Comfortably accommodates families and groups seeking a stylish getaway.brbrOutside:brStunning, heated poolbrFully-fenced backyard and side yard for both privacy and safetybrCharbroil Bistro GrillbrSunny backyard and pool area with chaise loungesbrSix-person outside dining tablebrTropical plantingsbrOff-street parking for up to three vehiclesbrCovered carportbrbrClose to:brTennis and pickleball courtsbrWorld-class golfingbrBeaches: Siesta Key, Lido Key, and Longboat Key, all with powdery white sand and warm, clear waterbrMarie Selby Botanical GardensbrDowntown Sarasota, with lively nightlife, bars, cafes, and restaurantsbrLegacy Trail for walking, jogging, and bikingbrPayne Park -- spectacular playground, skate park, and walking trailsbrIce cream and doughnut shops for the kiddos :)brGrocery Stores -- Short drives to Whole Foods, Trader Joe's, Publix, Aldi, and more!brArlington Park -- Olympic-size swimming pool (50m/25yards)brBoat and jet-ski rentalsbrbrLiving & Entertainment:br Unwind on a plush couch in the main living area.br Enjoy movies on the 55 Smart TV.br Challenge friends and family on the retro gaming table with classics like Ms. Pac-Man and Galaga.brbrKitchen & Dining:br A modern, fully-equipped chef's kitchen with Carrara quartz countertops and an induction cooktop.br Elegant dining room with lovely views of the private pool.br Family-friendly amenities include a high chair, a crib, and kid-safe cups, plates, and utensils.brbrBedrooms & Bathrooms:br Private master suite with direct access to the pool area.br Luxurious master bathroom with a walk-in waterfall shower.br A gorgeous second bathroom featuring a generous soaking tub for ultimate relaxation.brbrWorkspace:br A dedicated workspace is available for those needing to mix work with pleasure.brbrOutdoor Oasis:br Your own private, heated pool in a tropical setting.br Fully-fenced backyard for complete privacy and safety.br Soak up the Florida sun on comfortable chaise lounges.br Enjoy meals al fresco with a Charbroil Bistro Grill and outdoor dining table.brbrSarasota Short Term Rental Certificate: 25-VR-000049

Peaceful Oasis with Pool near Downtown and Beaches

Sarasota, Florida, United States

Bed

Bath

Sleeps

$127.57

Bright and inviting 1BR/1BA cottage in peaceful Pinecraft, Sarasota’s Amish village. Now under new ownership with exciting upgrades and improved amenities on the way. Sleeps 4 with queen bed + futon. Features a compact kitchen with fridge, microwave, kitchenware, coffee maker, and essentials. Walk to Amish restaurants, produce markets, ice cream shops, and more. Just minutes to world-class beaches and downtown Sarasota.brbr Welcome to Your Stay Near Sarasota`s Amish HeartbrbrStep into Casa Orange – a cozy and cheerful 1BR/1BA cottage located in the heart of Sarasota’s Amish and Mennonite community of Pinecraft. Now under new ownership, this home is entering an exciting refresh phase with planned upgrades, improved amenities, and elevated guest comforts — all designed to create a more memorable experience for travelers.brbrWith its walkable location, peaceful surroundings, and central proximity to Gulf beaches and downtown Sarasota, Casa Orange is ideal for couples, solo travelers, or small families seeking a relaxing escape with local flavor.brbr✨ The SpacebrbrCasa Orange balances comfort and simplicity in a compact, efficient layout:brbr1 Bedroom: Queen bed with fresh, hotel-style linensbrbrLiving Area: Sofa or futon for additional guest(s)brbrKitchen: Includes a refrigerator, microwave, stove/oven and counter space for light meal prepbrbrFully Stocked: Cookware, dinnerware, coffee maker, hair dryer, and ironbrbrStarter Supplies: Paper towels, dish soap, sponge, trash bags, and toilet paper provided for your first few daysbrbrGuests also have access to shared on-site laundry, two private entrances, and driveway parking for one vehicle, with street parking available for additional cars.brbr Multi-Unit PropertybrbrCasa Orange is one of four private 1–2 bedroom cottages at this address (alongside Casa Grapefruit, Casa Lemon, and Casa Lime), each with its own entrance. Outdoor areas and laundry are shared, making it ideal for families or friend groups looking to rent multiple units while enjoying their own space.brbr Personalized Hosting ExperiencebrbrYou`ll be supported by a local co-host (that`s me, Jennifer!) who’s here to answer questions, provide real-time recommendations, and make sure your stay goes smoothly — whether it’s helping you find the best beach access, farmer’s market, or local cafe.brbr Location HighlightsbrbrLocated in the beloved neighborhood of Pinecraft, you`re walking distance to:brbrYoder’s Restaurant & Amish Village shopsbrbrProduce markets, bakeries, and hand-churned ice creambrbrPinecraft Park & shaded walking trailsbrbrAnd just minutes from:brbrSiesta Key Beach – ~15 minbrbrLido Key & St. Armands Circle – ~15 minbrbrDowntown Sarasota – ~10 minbrbrThe Ringling Museum – ~15 minbrbrMarie Selby Botanical Gardens – ~12 minbrbrCasa Orange offers a warm, thoughtful, and well-placed retreat in Pinecraft — the perfect balance of village charm and Sarasota access. We look forward to hosting you!brbrCasa Orange is a ground-level stand alone cottage with its own private entrance. Guests have access to the property and their unit. They may park one vehicle in the shared driveway; please be sure not to block entrances, as cars may need to be moved to allow access for others. Additional vehicles may be parked on the street, where there is ample free parking.brbrThis home is proudly co-hosted by HomeIngo, founded by Jennifer, a Sarasota local with 18+ years in the area and 6 years of hosting experience. Guests enjoy personalized support, and insider tips. Jennifer and her team are nearby and happy to help ensure your stay is seamless, comfortable, and unforgettable.brbrNeighborhood VibebrbrCasa Orange is nestled in the heart of Pinecraft, Sarasota’s historic Amish and Mennonite community. Guests love strolling to local restaurants, produce markets, pizza shops, and ice cream parlors. The neighborhood is peaceful and family-friendly — the perfect place to unwind. While we want all guests to enjoy their stay, this is not a party house. Please keep noise low and respect the community’s quiet nature.brSarasota enforces towing for cars that block driveways or mailboxes. We kindly ask that all guests park with courtesy so everyone — including neighbors — can come and go easily. Guests also have access to shared on-site laundry facilities.brbrPlease do not block walkways or other units with bicycles. brbrSmoking is not allowed in any of the units. Smell or other evidence will incur a $500 fee.

Apartment

Charming 1BR • Pinecraft Vibes, Beach Nearby

Sarasota, Florida, United States

1

Bath

4

Sleeps

$207.11

Discover this lakefront 2/2 condo in a beautifully kept gated community! It’s PERFECTLY located in Sarasota — Easy and quick access to interstate, walking distance to multiple shopping centers, and less than 5 miles away from Siesta Key Beach. Downtown and gulf gate are even closer! If you feel like checking out America’s newest mall - UTC is only 15 minutes away. This “Tommy Bahama” furnished condo has 2 master bedrooms with walk-in closets and 2 full bathrooms. The bedrooms feature brand new sleep number mattresses (1 king bed and 1 queen bed total) and en-suite bathrooms fully equipped with a garden tub/shower, hair dryer, linens, towels, and toiletries to ensure a cozy coastal stay. This fully updated unit is in a gated community and comes with many wonderful amenities like Fiber Optic (ultra fast) WiFi, stocked coffee station, resort style Heated pool, hot tub, AC, club house (full kitchen as well as a pool table and poker table), a fitness center, and much more! You don’t even have to leave the property to feel like you’re on vacation!brbrWe are hosts that live in Sarasota so we would be able to provide travel tips, restock depleted things, or quickly resolve any unforeseen issues. brbrWe also have high chair, pack n play, baby and toddler toys, etc that we can supply upon request.brbrWe look forward to hosting you in our sunny home.

2/2 Condo in Sarasota w/ heated pool, gym, lake view, fiber WiFi. < 5 mi beach!

Sarasota, Florida, United States

Bed

Bath

Sleeps

$284.84