Vacation Rentals By Owner In Siesta Key, FL

The Anchorage Resort on Siesta Key - includes resort amenity access!brbrOur 2 bedroom, 2 bathroom, private vacation condo is a great option for anyone wanting a home base to enjoy the best of all that Siesta Key has to offer.br* Anchorage Resort Condo br* 2 bedrooms / 2 bathroomsbr* Spacious Balcony overlooking Southern Siesta Keybr* Fifth Floor Condo overlooks the canal and Southern Siesta Keybr* Fully equipped Kitchen with seating for 4 at the dining tablebr* Beach Supplies include- Beach Cart, Chairs, Umbrella, Cooler, Raft/Float Items, Beach Towelsbr* Community Pool- Largest pool on the Key!br* Gated Communitybr* Siesta Key Trolley- free pickup in front of the resort entrancebr* Private Beach access to Crescent Beach across the streetbr* Sofa Bed & Queen Air Mattressbr* Pack n Playbr* Xbox Game Systembr* Elevator in buildingbr* 25-year minimum age to rent restrictionbrbrBEDROOMS (Fifth Floor Condo)brBedroom 1: One King Bed (Ensuite Bathroom) / Balcony Access / 42 TV / Pack N PlaybrBedroom 2: Two Queen Beds / Balcony Access / 32 Smart TV / XboxbrbrPool Information:br- Community Poolbr- Heated brbrResort Parking Rules:brThe resort allows a maximum of 2 cars.brVehicles must be registered with the front office during office hoursbrbrHOA Rules:brLead guest must be age 25 or older. ID is checked upon registration at the resort.brNo petsbrJanuary 1- April 16 Rentals are 7-nights beginning and ending on Saturday onlybrbr brThe Anchorage Resort Amenity Access Included with Rental:br* Olympic-Size poolbr* 3 Lighted Tennis/Pickleball Courtsbr* Shuffleboardbr* Community BBQ areabr* Individual Picnic areas along the Canal/Intracoastal Waterwaybr* Exercise Roombr* Bike & Kayak Racks (subject to availability)br* Boat Dock/Seawallbr* Coin-Operated Washer/Dryer on Each Floorbr brDistances from Resort to Shopping & Attractions:br* Daiquiri Deck South Siesta Key- 5-minute walk across the streetbr* Crescent Beach Private Beach Access- 7-minute walk across the streetbr* Toasted Mango Cafe - 9-minute walkbr* Siesta Key Watersports - .6 milebr* Siesta Key Village- 2.7 (trolley stop)br* Publix at Sarasota Pavilion- 1.4 milesbr* Marie Selby Botanical Gardens - 6 milesbr* Sarasota Bradenton Airport (SRQ) - 11 milesbr brWhy Choose this Rental br- Professionally managed to serve all your needsbr- Management company has over 26 years of experience hosting well over 200,000 familiesbr- Go straight to your rental with online email check-inbr- 24/7 on-call maintenancebr- Free On-Site Parkingbr- Smoke-free and pet-free for your comfortbr- Towels and linens are providedbr- Complimentary WiFibr brOur Starter Welcome packet supplies:br- 2 rolls toilet paper per bathroombr- 1 hotel-size bar soap per bathroombr- 1 hotel-size shampoo/conditioner per full bathroombr- 1 roll paper towelbr- 2 packet dishwasher detergentbr- Size 13-gallon Trash bagsbrAny supplies beyond this are up to the guest to replenish, we do not restock these items. brNo salt/pepper or cleaning supplies are stocked due to safety issues. brThis is an industry-standard practice.br brFOR GUESTS WHO BOOK 30 NIGHTS OR LONGER STAYS: (this does not apply if you are staying less than 30 nights)brWe will collect a $1,500 deposit.brBalance is due 60 days prior to arrivalbrIf canceled 90 days or more before arrival, we keep with us $250.00. $1,250.00 will be refunded.brIf canceled between 61 and 89 days prior to arrival, we keep with us the $1,500.00 deposit.brNo cancellation or modification 60 days or less prior to arrival.

Anchorage Resort 5th Floor 2 bedroom condo with Beach Access

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$433.35

Kick back and relax in this calm, stylish 3-bedroom, 4-full bathroom canal-front home, perfect for families or couples seeking a tranquil getaway. Just a short 5-minute walk away, you`ll find the vibrant Siesta Key Village, offering a variety of shops, restaurants, and entertainment. And, of course, you`re just minutes from Siesta Key Beach, consistently ranked as the #1 beach in the US! brBook your dream vacation today and experience the best of Siesta Key!`

Pineapple on Siesta Key

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$539.04

Take it easy at this mid-century modern peaceful Siesta Key Beach family & pet friendly getaway. 3 BD, 2 BA’s & 2 outdoor showers to wash off the sand after beach fun. Don’t forget to bring Fido! Hang out by the fire pit in the evenings while you grill out taking in the ocean air with a sky full of stars after an amazing day at America’s #1 beach. Enjoy the beach cruisers for morning coffee runs, sunset rides, live music, ice cream, shops or any of the amazing restaurants in Siesta Key village.brbrA very quiet, peaceful, relaxing family neighborhood across the street from the grand canal.brThe county picks up recycling and trash, Monday morning. There is one 96 gallon container for each for your use while staying. Please make sure each is positioned in front of the house on the sidewalk Wednesday evenings after dark.

Zach’s Siesta Key Beach House|Pet Friendly| #1 Beach in USA

Siesta Key, Florida, United States

2

Bath

6

Sleeps

Exceptional(2)

$263.66

Enjoy ocean front living at this gorgeous condo with private beach. Warm island-inspired colors and custom furnishings. Most every room has full ocean views with amazing sunsets.br26' private lanai, new interior floors, new leather furniture, new flat screen TV's, unbelievably comfortable beds and luxury linens, and 10/10 walking score! Walk to Siesta Key Village shops and restaurantsbrWhispering Sands is 55 plus complex , at least 1 renter must be 55.brbrThe spacebrLovely 2 bedroom 2 bathroom condo in 55 plus complex with private beach, 2 luxury pools, fitness center, recreation room, library , community room, tiki bar area with bbq , shuffle board and kayaks.brGuest accessbrFully secure complex with fob entry to all buildings and Keypad entry to condo.brOther things to notebrThe condo is beachfront with private beach access

Sunset Paradise Condo on private beach.

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$292.53

The Anchorage Resort on Siesta Key - includes resort amenity access!brbrOur 2 bedroom, 2 bathroom, private vacation condo is a great option for anyone wanting a home base to enjoy the best of all that Siesta Key has to offer.brbrAnchorage Resort Condo br* 2 bedrooms / 2 bathroomsbr* Sixth Floor Condo with balcony overlooks Southern Siesta Keybr* Fully equipped Kitchen with seating for 4 at the dining tablebr* Beach Supplies include- Chairs, Beach Cart, Umbrella, Cooler, Raft/Float Items, Beach Towelsbr* Community Pool- Largest pool on the Key!br* Gated Communitybr* Siesta Key Trolley- free pickup in front of the resort entrancebr* Private Beach access to Crescent Beach across the streetbr* 25-year minimum age to rent restrictionbrbrBEDROOMS (Sixth Floor Condo)brBedroom 1: One King Bedroom (Ensuite Bathroom) / Balcony AccessbrBedroom 2: Two Queen Bedroom / Balcony AccessbrbrThe Anchorage Resort Amenity Access Included with Rental:br* Olympic-Size Poolbr* 3 Lighted Tennis / Pickleball Courtsbr* Shuffleboardbr* Community BBQ areabr* Individual Picnic areas along the Canal/Intracoastal Waterwaybr* Exercise Roombr* Bike & Kayak Racks (subject to availability)br* Boat Dock/Seawallbr* Coin-Operated Washer/Dryer on Each FloorbrbrPool Information:br- Community Poolbr- Heated brbrResort Parking Rules:brThe resort allows a maximum of 2 cars.brVehicles must be registered with the front office during office hoursbrbrHOA Rules:brLead guest must be age 25 or older. ID is checked upon registration at the resort.brNo petsbrJanuary 1- April 16 Rentals are 7-nights beginning and ending on Saturday onlybrbr brDistances from Resort to Shopping & Attractions:br* Daiquiri Deck South Siesta Key- 5-minute walk across the streetbr* Crescent Beach Private Beach Access- 7-minute walk across the streetbr* Toasted Mango Cafe - 9-minute walkbr* Siesta Key Watersports - .6 milebr* Siesta Key Village- 2.7 (trolley stop)br* Publix at Sarasota Pavilion- 1.4 milesbr* Marie Selby Botanical Gardens - 6 milesbr* Sarasota Bradenton Airport (SRQ) - 11 milesbr brWhy Choose this Rental br- Professionally managed to serve all your needsbr- Management company has over 26 years of experience hosting well over 200,000 familiesbr- Go straight to your rental with online email check-inbr- 24/7 on-call maintenancebr- Free On-Site Parkingbr- Smoke-free and pet-free for your comfortbr- Towels and linens are providedbr- Complimentary WiFibr brOur Starter Welcome packet supplies:br- 2 rolls toilet paper per bathroombr- 1 hotel-size bar soap per bathroombr- 1 hotel-size shampoo/conditioner per full bathroombr- 1 roll paper towelbr- 2 packet dishwasher detergentbr- Size 13-gallon Trash bagsbrAny supplies beyond this are up to the guest to replenish, we do not restock these items. brNo salt/pepper or cleaning supplies are stocked due to safety issues. brThis is an industry-standard practice.br brFOR GUESTS WHO BOOK 30 NIGHTS OR LONGER STAYS: (this does not apply if you are staying less than 30 nights)brWe will collect a $1,500 deposit.brBalance is due 60 days prior to arrivalbrIf canceled 90 days or more before arrival, we keep with us $250.00. $1,250.00 will be refunded.brIf canceled between 61 and 89 days prior to arrival, we keep with us the $1,500.00 deposit.brNo cancellation or modification 60 days or less prior to arrival.

Anchorage Resort Siesta Key 6th Floor 2 bedroom Condo Beach Access

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$309.14

The Anchorage Resort on Siesta Key - includes resort amenity access!brbrOur 2 bedroom, 2 bathroom, private vacation condo is a great option for anyone wanting a home base to enjoy the best of all that Siesta Key has to offer.brbr* Anchorage Resort Condo br* 2 bedrooms / 2 bathroomsbr* Seventh Floor Condo with balcony overlooks Southern Siesta Keybr* Fully equipped Kitchen with seating for 4 at the dining tablebr* Beach Supplies include- Chairs, Beach Cart, Umbrella, Cooler, Beach Towelsbr* Community Saltwater Pool- Largest pool on the Key!br* Gated Communitybr* Siesta Key Trolley- free pickup in front of the resort entrancebr* Private Beach access to Crescent Beach across the streetbr* 25-year minimum age to rent restrictionbrbrBEDROOMS (Seventh Floor Condo)brBedroom 1: One King Bedroom (Ensuite Bathroom) / Balcony Access / 43 Smart TVbrBedroom 2: Two Queen Bedroom / Balcony Access / 32 TVbrbrThe Anchorage Resort Amenity Access Included with Rental:br* Olympic-Size Saltwater poolbr* 3 Lighted Tennis Courts- Can turn into Pickleball courts br* Shuffleboardbr* Community BBQ areabr* Individual Picnic areas along the Canal/Intracoastal Waterwaybr* Exercise Roombr* Bike Racks (subject to availability)br* Boat Dock/Seawallbr* Coin-Operated Washer/Dryer on Each FloorbrbrPool Information:br- Community Poolbr- Saltwaterbr- Heated in winter monthsbrbrResort Parking Rules:brThe resort allows a maximum of 2 cars.brVehicles must be registered with the front office during office hoursbrbrHOA Rules:brLead guest must be age 25 or older. ID is checked upon registration at the resort.brNo petsbrJanuary 1- April 16 Rentals are 7-nights beginning and ending on Saturday onlybr br brDistances from Resort to Shopping & Attractions:br* Daiquiri Deck South Siesta Key- 5-minute walk across the streetbr* Crescent Beach Private Beach Access- 7-minute walk across the streetbr* Toasted Mango Cafe - 9-minute walkbr* Siesta Key Watersports - .6 milebr* Siesta Key Village- 2.7 (trolley stop)br* Publix at Sarasota Pavilion- 1.4 milesbr* Marie Selby Botanical Gardens - 6 milesbr* Sarasota Bradenton Airport (SRQ) - 11 milesbr brWhy Choose this Rental br- Professionally managed to serve all your needsbr- Management company has over 26 years of experience hosting well over 200,000 familiesbr- Go straight to your rental with online email check-inbr- 24/7 on-call maintenancebr- Free On-Site Parkingbr- Smoke-free and pet-free for your comfortbr- Towels and linens are providedbr- Complimentary WiFibr brOur Starter Welcome packet supplies:br- 2 rolls toilet paper per bathroombr- 1 hotel-size bar soap per bathroombr- 1 hotel-size shampoo/conditioner per full bathroombr- 1 roll paper towelbr- 2 packet dishwasher detergentbr- Size 13-gallon Trash bagsbrAny supplies beyond this are up to the guest to replenish, we do not restock these items. brNo salt/pepper or cleaning supplies are stocked due to safety issues. brThis is an industry-standard practice.br brFOR GUESTS WHO BOOK 30 NIGHTS OR LONGER STAYS: (this does not apply if you are staying less than 30 nights)brWe will collect a $1,500 deposit.brBalance is due 60 days prior to arrivalbrIf canceled 90 days or more before arrival, we keep with us $250.00. $1,250.00 will be refunded.brIf canceled between 61 and 89 days prior to arrival, we keep with us the $1,500.00 deposit.brNo cancellation or modification 60 days or less prior to arrival.

Anchorage Resort 7th Fl 2 Bedroom Condo with Beach Access

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$261.07

This new vacation rental is the 'Calm of Siesta', as you enter with a full view of the Gulf of Mexico and Siesta Key Beach. The property has just been newly transformed to accommodate our guests best welcome to Siesta. The property is equipped with a full service/ stocked kitchen, for all your cooking and bar needs. There is a granite island in the center that seats 4, with lots of other counter space if needed. The living room is furnished with a full size couch, love seat, Vintage Wine Bar with supplies, HD Television /cable and internet. Pass through here to the 'Main Attraction Room', the enclosed Lanai, overlooking the Gulf. The Lanai is enclosed with large Bay Windows to relax and watch the sunset and watch for Dolphins! The master bedroom is furnished with a King size Italian lacquer Bedroom set with plenty of drawer space. The full size master bath is surrounded by travertine tile, equipped with enclosed shower and plenty of cabinet space. The Guest Room is furnished with a queen size wicker bed , two dressers, and a tv. Both bedrooms have large walk in closets. The second bath is a travertine tiled, full size with shower enclosure and is adjacent to the guest room. Just outside the front door there is a storage closet equipped with 4 beach chairs, beach towels, beach toys for the little ones, umbrellas you can rent at beach concession and they put them in the ground for you or you can purchase. There is outdoor seating with a garden water fountain to sit or take a 'Siesta', if you prefer. The property has a carport and guest parking space right behind building. Additional parking would be subject for approval..

Siesta Key's PREMIER LOCATION with amazing beach view!

SIESTA KEY, Florida, United States

Bed

Bath

Sleeps

$869.11

️ Villa Castile | Private Heated Pool + Walk to Beach & Villagebrbr Why You'll Love This HomebrPicture yourself gathered poolside in your sunlit courtyard, the warmth of the heated pool inviting you to pause time. Just steps from Siesta Key Village and a short stroll to world‑famous Siesta Key Beach, Villa Castile blends sophisticated comfort with laid‑back island energy.brbr ‍ ‍ Perfect ForbrFamilies, multi‑family groups, or friends looking for space, privacy, and proximity—all with a touch of pet‑friendly flair.brbr ️ Imagine ThisbrYou awaken in the elegant king suite and sip morning coffee as dappled sunlight filters through courtyard greenery. Up for a beach day Grab chairs, towels, a caddy—and you're on the soft, white sand in under 10 minutes. Evening arrives and the screened lanai sets the stage for hearty grilled fare, laughter, and good wine. Later, you sink into plush sofas or cozy up by the fireplace—staying connected, relaxed, and utterly in the moment.brbr Where You'll Sleepbr• Bedroom 1: King Bed, ensuite bathroom, main floor, TVbr• Bedroom 2: King Bed, shared hall bath, second floor, TVbr• Bedroom 3: Two Queen Beds, ensuite bath, top floor, TVbrbr Explore the Areabr• 0.3 miles to Siesta Key Village – shops, restaurants, and lively island charmbr• 0.3 miles to Siesta Key Beach – powder‑white sand, turquoise surfbr• Walkable, vibrant, and deeply coastal—everything you need is right around the cornerbrbr⌛ Don't Wait - Homes this close to the beach with private heated pools book fast. Enjoy peace of mind with our CottageClean™ Program — a 6‑hour deep clean plus rigorous 35‑point inspection to welcome you into what feels like a brand‑new vacation home.brbr Need to Know - This home is part of a duplex — you'll have access only to the right‑side unit, including a private fenced backyard and heated pool. Pool jets are not usable by guests. The pool is heated November 15 – April 15. This unit has stairs, Contact us for questions about stairs, shared spaces, or pet policies.

Villa Castile | Pet Friendly Home on Siesta Key w/ Private Heated Pool, Walk to Beach & Village!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$516.3

New pool and spa/hot tub just completed! Pool has tanning ledge with chase loungers. Now, additional seating area by canal and landscaping. brbrPrime location! Fresh & luxurious ambiance in this newly renovated canal-front home. In the heart of the Village and an easy 6-minute walk to the beach. brbrUpon entering the home the striking panoramic views of the lush and secluded backyard grasp your attention. Imagine lush grass with plenty of space to play cornhole, chase the kids around, or have a great backyard BBQ on the Weber charcoal grill. All this seclusion just footsteps from the heart of the Village of Siesta Key. brbrBeach Day Everything you need (beach cart, chairs, bag, towels, cooler) is stocked. brbrVeg-out Day Enjoy the rocking chairs under the covered front porch or bask in the sun on the outdoor furniture on the back patio. If A/C is your thing, all 3 bedrooms plus the living room have WIFI connected televisions to watch your favorite channels. brbrFoodie Dozens of restaurants within walking distance will satisfy any appetite.brbrBuilt in the 1950's as a mid-century modern Florida home, a complete makeover offers you the latest technology including Ultrafast WIFI, Xfinity cable, Assure Smartlock and for added security there are outdoor Google Nest Cameras. brbrAll-new, high-end quartz counters, stainless appliances, stylish leather chairs, Keurig, and gourmet pots and pans. Rolling bar cart and utensils are a great way to display your favorite spirits and celebrate the Siesta Key lifestyle. brbrAll-new appliances: Full-size washer and dryer, dishwasher, microwave, stove, side-by-side refrigerator with ice maker. Other appliances include blender, hand held mixer, and toaster. brbr--Sleeping Accomodations --brMaster Bedroom: Enjoy beautiful views of the green grass backyard, includes a king bed and en suite bathroom with marble accents, lots of dresser space, large closet with hangers, hair dryer, towels, and new smart television.brGuest Bedroom #1: Includes a queen bed with an extra-large dresser and closet with hangers as well as smart television. Located next to a full bathroom with shower/bath combination, hairdryer, and towels. brGuest Room #2: A cozy, private, 3rd room includes bunk beds, a desk for remote work or school and a 42 WIFI connected Samsung TV. Bonus space a bunk bed with two twin mattresses. Both bunks have task lamps and USB plugs for those important electronics. Also, it has a desk and tv. brSofa-sleeper in living room: Folds out to a queen Serta mattressbrbrAll bedrooms include high quality sheets. Extra sheets and blankets are available to meet all comfort needs. brbr--Miscellaneous--brThe house is treated quarterly for mosquitos and bugs to ensure your stay is as comfortable as possible. There is weekly lawn maintenance. brbrAdditional information is available from owner. Monthly rentals are for December through April. Contact owner for 14 day rentals from May through November. brbr brbr

Amazing Pool & Spa! Luxury Canal Home in Siesta Key Village! Walk Everywhere

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$468.53

Tucked away on a low traffic corner lot behind South Siesta Key Village, this newly renovated 2-bedroom, 2-bath property offers the perfect blend of comfort and convenience. brbrWhether you're vacationing or working remotely, this private pool home with central HVAC is your gateway to everything Sarasota has to offer. brbr Features include: br• Secure garage and gated privacy fencebr• Sparkling private pool and expansive entertainment deckbr• Beachcomber bikes and beach chairs provided at no additional costbr• Smart TVs and Ceiling Fans throughout br• Just a 10 or 15 minute stroll to the powdery sands of world-famous Siesta Key BeachbrbrLocation Highlights --- Soak up beach vibes, explore vibrant local culture, and enjoy effortless access to the charm, relaxation, and adventure of Sarasota’s Siesta Key Restaurants, shops, entertainment, recreational rentals and groceries are all within walking or biking distance. Call for house pickup, hop on one of the free tip-based ride shares, or take the complimentary trolley to explore Siesta Key, North Siesta, and Crescent Beaches with ease.brbrReady to roam beyond the Key brbr• Zoom! You're 10 minutes or less from Southside Village, Sarasota Memorial Hospital, or catching a flick at CineBistrobr• Feeling artsy Downtown Sarasota’s galleries, marinas, local flavors and nightlife are just 15 minutes away.br• Retail therapy St. Armands Circle and UTC are within a 30-40 minute joyride.br• Island vibes calling Anna Maria Island is just 45 minutes of scenic cruising.br• Theme park thrill-seeker Tampa and Orlando’s world-famous parks are 1–2 hours away—easy day trip material.br• Jet-setter friendly: br SRQ (Sarasota) – 30 minbr PGD (Punta Gorda) – 50 minbr TPA (Tampa) – 75 minbr RSW (Ft. Myers) – 90 min

Coastal Comfort Meets Florida Fun – Your Siesta Key Escape Awaits!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$662.01

Spend your vacation relaxing in this lovely 3-bedroom, 2-bathroom townhome. On the ground level, you will find parking for up to 2 cars. The second level hosts a spacious living room, dining, and kitchen areas. The kitchen offers plenty of storage and stainless countertops. The living room offers space for the entire family to relax with large windows looking out towards the beach. On this floor, you will also find a powder room and the first of two balconies for enjoying the fresh island breeze and ocean view. The 3 bedrooms, 2 full bathrooms, and second balcony are located on the third level. Located within walking distance to Siesta Key Village, this home is adjacent to beach access #10 – perfect for taking a trip down to Siesta Beach or enjoying a stunning view! br*This property is stairs only; all guests must have the ability to use stairs.brbrBedroom 1 – KingbrBedroom 2 – Twin over Queen Bunk BedbrBedroom 3 – King and Twin Bunk BedbrbrAdded Amenities Included in Your Stay:brComplimentary Bicycles Rentals,brOne Complimentary Parking Space,brWifi,brBeach Chairs,brBeach Towels,brBeach Wagon,brBeach Cooler,brPartner Property Pool/Hot tub Access,brAccess to Siesta Beach Pickleball Courts,brSiesta Key Trolly - Free-Rides Around Siesta Key,brA 7-day week, Beachside Management office for your convenience and guest needs!brbr*Minimum Age to Book: 25 br*To book a beachside managed Property Between February 1st and April 15th, the booker must be 27 years old or older. br*Security authorization Hold taken upon check-in. Amount: $1,000

Stunning 3 Bedroom Steps from Siesta Key Beach Access!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$348.17

Sea Foam | Bright Ground-Floor Escape 400 Ft to Beachbrbr Why You'll Love This HomebrCharming, sunlit, and nestled on the lower right corner of a peaceful Siesta Key property, Sea Foam brings casual island comfort just steps from both the beach and Siesta Key Village—no driving required.brbr ‍ ‍ Perfect ForbrBest suited for couples, small families, or solo travelers seeking a cheerful and walkable beach base with pet-friendly perks.brbr ️ Imagine ThisbrAfter a beachside breakfast in the Village, spend your day lounging in the sand—just 400 feet from your door. Return home to rinse off, sip something cold, and unwind on one of the chaise lounges or fire up the grill for dinner. With bright interiors, cozy touches, and easy beach access, Sea Foam feels like the relaxing home base your vacation needs.brbr Where You'll Sleepbr• Bedroom 1: King Bed, Ensuite Bath, Ground Floor (Lower Right Unit), TVbr• Living Area: Modular Sleeper Sofa, Open Layout, TVbrbr Explore the Areabr• 0.1 miles to Siesta Key Beachbr• 0.1 miles to Siesta Key Village – Walk to Dining, Nightlife, and Cafesbr• Casual, Pedestrian-Friendly Island Energybr• Access to Paddle Board Rentals, Boutiques, and Sunset Walksbrbr⌛ Don't Wait—This Home Books FastbrSea Foam offers walk-to-everything simplicity in a peaceful beach setting. Your reservation includes a 6-hour deep clean and 35-point inspection. One small dog (up to 25 lbs) is welcome with an additional pet fee.brbr Need to Know: Starter packs of kitchen and toiletry essentials provided for a seamless first couple of nights. One designated parking space available. Free High-Speed WiFi in the unit. Shared on-site laundry available. One dog allowed (max 25 lbs) with a pet fee. Your listing is part of a multi unit complex and is a distinct unit—with its own private entrance, kitchen, and living areas—with no interior connection. As a multi-unit complex, it could share a dividing wall, floor, ceiling, outdoor space, and/or amenities with another unit(s). Contact us directly for more information regarding any shared space for this vacation home.

Sea Foam - Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$363.63

Sea Escape | Central Ground-Floor Retreat 400 Ft to Beachbrbr Why You'll Love This HomebrWith a central location on the lower level and an effortless walk to Siesta Key Beach, Sea Escape offers comfort, walkability, and a laid-back, beach-town lifestyle—just steps from shops, restaurants, and the shore.brbr ‍ ‍ Perfect ForbrIdeal for couples or small families looking for a cozy, centrally located retreat with outdoor amenities and pet-friendly options.brbr ️ Imagine ThisbrWake up slow, grab your beach gear, and stroll just 400 feet to sugar-white sands. Spend the day soaking up the sun or exploring the nearby boutiques and bistros of Siesta Key Village. As the day winds down, grill your favorites on the patio while your dog lounges nearby. With shared chaise loungers, tables and no stairs to climb, Sea Escape offers vacation ease from start to finish.brbr Where You'll Sleepbr• Bedroom 1: King Bed, Ensuite Bath, Ground Floor (Lower Middle Unit), TVbr• Living Area: Modular Sleeper Sofa, Open Layout, TVbrbr Explore the Areabr• 0.1 miles to Siesta Key Beach (400 feet)br• 0.1 miles to Siesta Key Village – Walk to Restaurants, Bars, and Marketsbr• Laid-back Coastal Charm and Pedestrian-Friendly Energybr• Bike Rentals, Live Music, Coffee Shops all Within Blocksbrbr⌛ Don't Wait—This Home Books Fast! brSea Escape is a cozy, pet-friendly retreat in one of the most walkable parts of Siesta Key. Your stay includes a 6-hour deep clean and 35-point inspection. One small dog (under 25 lbs) is welcome with a pet fee.brbr Need to Know: Starter packs of kitchen and toiletry essentials provided for a seamless first couple of nights. One designated parking space available. Free High-Speed WiFi in the unit. Shared on-site laundry available. One dog allowed (max 25 lbs) with a pet fee. Your listing is part of a multi unit complex and is a distinct unit—with its own private entrance, kitchen, and living areas—with no interior connection. As a multi-unit complex, it could share a dividing wall, floor, ceiling, outdoor space, and/or amenities with another unit(s). Contact us directly for more information regarding any shared space for this vacation home.

Sea Escape - Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$346.14

Sea Dream | Ground Floor Gem 400 Ft to Beach + Dog Friendlybrbr Why You'll Love This HomebrNestled on the quiet lower level, Sea Dream offers laid-back ease, shaded comfort, and unbeatable walkability—just 400 feet to the award-winning sands of Siesta Key Beach and steps to the energy of Siesta Key Village.brbr ‍ ‍ Perfect ForbrPerfect for couples, small families, or beach-loving friends who want convenient ground-floor access, shared outdoor space, and proximity to everything.brbr ️ Imagine ThisbrStep outside your front door and into the sunshine. Mornings are best with coffee on a chaise lounge or a lazy walk to the beach. After catching waves and grabbing lunch in the Village, unwind in the shaded patio with a cold drink. Sea Dream is the kind of place that invites you to slow down and savor every moment— relaxed, and fully in vacation mode.brbr Where You'll Sleepbr• Bedroom 1: King Bed, Ensuite Bath, Ground Floor (Lower Left Unit), TVbr• Living Area: Modular Sleeper Sofa, Open Floor Plan, TVbrbr Explore the Areabr• 0.1 miles to Siesta Key Beach (400 feet)br• 0.1 miles to Siesta Key Village – Less than a 2-minute Walk to Restaurants, Shops, and Barsbr• Vibrant, Walkable Beach Town Energybr• Steps to Ice Cream, Bike Rentals, and Boutiquesbrbr⌛ Don't Wait—This Home Books FastbrSea Dream offers pet-friendly flexibility and all the comforts of home, just moments from the shoreline. Your stay includes a 6-hour deep clean and 35-point inspection. One dog under 25 lbs is welcome (pet fee applies).brbr Need to Know: Starter packs of kitchen and toiletry essentials provided for a seamless first couple of nights. One designated parking space available. Free High-Speed WiFi in the unit. Shared on-site laundry available. One dog allowed (max 25 lbs) with a pet fee. Your listing is part of a multi unit complex and is a distinct unit—with its own private entrance, kitchen, and living areas—with no interior connection. As a multi-unit complex, it could share a dividing wall, floor, ceiling, outdoor space, and/or amenities with another unit(s). Contact us directly for more information regarding any shared space for this vacation home.

Sea Dream - Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$359.61

Sea Coast | Steps to Siesta Beach + Dog Friendly + Top Floorbrbr Why You'll Love This HomebrWith its elevated corner perch and walk-to-everything access, Sea Coast brings bright beach energy and quiet coastal comfort together in perfect balance. It's the kind of place where mornings start slow, and evenings melt into palm-shaded serenity—just 400 feet from the sugar sands of Siesta Key Beach.brbr ‍ ‍ Perfect ForbrIdeal for couples, solo travelers, or small families seeking a stylish beach retreat with pet-friendly flexibility.brbr ️ Imagine ThisbrSip coffee as soft sunlight streams into your top-floor corner unit. Grab the beach caddy and head out for a morning of surf and sun, then treat yourself to lunch at a Village café just around the corner. After a laid-back afternoon nap, unwind with a book on a chaise lounge or fire up the shared grill. Whether you're soaking in local flavor or enjoying the cozy calm of your private space, Sea Coast lets you move at your own vacation pace.brbr Where You'll Sleepbr• Bedroom 1: King Bed, Ensuite Bath, Second Floor (Top Right Unit), TVbr• Living Area: Modular Sleeper Sofa, Open Concept Layout, TVbrbr Explore the Areabr• 0.1 miles to Siesta Key Beach (400 feet)br• 0.1 miles to Siesta Key Village – Quick Walk to Shops, Restaurants, and Nightlifebr• Corner Unit in a Lively, Walkable Beach Districtbr• Steps to Bike Rentals, Coffee Shops, and Coastal Trailsbrbr⌛ Don't Wait—This Home Books FastbrSea Coast offers the freedom of your own private, pet-friendly unit within a boutique-style beach compound. Book with confidence knowing a 6-hour deep clean and 35-point inspection before each stay. One dog up to 25 lbs welcome (pet fee applies).brbr Need to Know: Starter packs of kitchen and toiletry essentials provided for a seamless first couple of nights. One designated parking space available. Free High-Speed WiFi in the unit. Shared on-site laundry available. One dog allowed (max 25 lbs) with a pet fee. If any guest has difficulty with stairs, please contact us for alternative accommodations. Your listing is part of a multi unit complex and is a distinct unit—with its own private entrance, kitchen, and living areas—with no interior connection. As a multi-unit complex, it could share a dividing wall, floor, ceiling, outdoor space, and/or amenities with another unit(s). Contact us directly for more information regarding any shared space for this vacation home.

Sea Coast - Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$918.17

Imagine waking up in your own private coastal retreat. At Shore Thing, island serenity meets modern luxury—your dream Siesta Key escape begins here.brbrWelcome to Shore Thing—your private slice of paradise in the heart of Siesta Key. This newly renovated home was thoughtfully curated for your comfort where upscale comfort meets laid-back beach living, Your just a 5-minute drive to the world-famous Siesta Key Beach.brbrAs you step into the backyard, prepare to be transported. A sprawling resort-style pool shimmers under the Florida sun, bordered by lush tropical landscaping and swaying palms. Whether you're floating in the crystal-clear water, enjoying the soothing spillover hot tub, or sipping cocktails by the fire pit, this outdoor oasis was designed for unforgettable moments.brbrEvenings are best spent under the stars, sharing laughter around the propane fire feature or enjoying a sunset dinner on the covered patio. The backyard seamlessly connects to the interior, offering a true indoor-outdoor living experience.brbrInside, Shore Thing offers the ideal layout for families or groups traveling together:br• Three private master suites, each with spa-inspired en-suite bathrooms and direct access to the outdoor area.br• A fourth bedroom with a private lounge area behind sliding glass doors—perfect for quiet reading or morning yoga.br• A fifth bedroom with a twin-over-full bunk setup—ideal for kids or teens.brbrAt the heart of the home is a chef-ready kitchen with modern appliances and everything you need to cook, dine, and entertain. Start your day with coffee from either the classic drip machine or Keurig, then enjoy a breezy breakfast outdoors as the palms rustle overhead.brbrEach bedroom—aside from the bunk room—is equipped with a large Smart TV, making it easy to unwind after beach days or poolside lounging.brbrExplore the charm of Siesta Key Village, just minutes away, where you'll find boutique shops, waterfront dining, and lively coastal nightlife. Whether you seek adventure, relaxation, or quality time with loved ones, Shore Thing delivers the full island experience.brDon't miss your chance to stay at one of Siesta Key's most captivating private homes. Book your stay at Shore Thing today and create lasting memories in your own tropical paradise—steps from the beach and a world away from ordinary.brShore Thing Siesta Key | 5BR home w/ pool, hot tub & fire pit. Book your luxury island escape today!brbrShore Thing can accommodate up to 10 guest with a bedding configuration as follows:brBedroom #1: Queen Bed (1) sleeps 2brBedroom #2: King Bed (1) sleeps 2brBedroom #3: King Bed (1) sleeps 2brBedroom #4: Queen Bed (1) sleeps 2brBedroom #5: Twin bed (1) and a Full Bed (1) sleeps 3brbrWe 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: The Spa is heated from November 15th to April 15th. This property is registered as a vacation rental within the City of Sarasota with the Registration Number VR25-00056. Due to the City of Sarasota vacation rental code, this property can only be rented once during a seven (7) day period and has a maximum occupancy of 10 guests.

Shore Thing | Luxe Pool Oasis, Hot Tub, Siesta Key Beach

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$390.21

Enjoy automatic discounts based on your stay length, no codes needed, and the price you see already includes your savingsbrbrWelcome to Siesta Bayside with Bay/Dock Views! brbr brbrWelcome to your perfect getaway in Siesta Bayside on the Bay, a beautiful 3-bedroom, 2-bathroom townhome offering stunning bay views and a short walk to Siesta Key Beach via private access. This updated, two-story residence features modern decor and resort-style amenities, making it ideal for a luxurious beach vacation. brbr brbrLOCATION HIGHLIGHTS: brbr- Just a 5-minute drive to Siesta Key Village with dining, shopping, and nightlife brbr- Nearby intracoastal bay access for fishing and boating brbr- Free shuttle service available to explore the area without driving brbr- Private beach access across the road brbr- Two heated community pools, Tennis courts brbr- Down the street from public beach brbr brbrPROPERTY FEATURES: brbr- 3 Bedroom/ 2 bathroom townhouse condo (2185 sq ft) brbr- Second-story unit accessible by stairs (no elevators) brbr- Dock/water views brbr- Keyless entry and self check in brbr- Dedicated WIFI and cable brbr- Central A/C with ceiling fans brbr- Parking in the driveway brbr- Private washer and dryer brbr brbrLIVING ROOM: brbr- Comfortable seating with bay views brbr- Big screen smart TV with cable brbr- Access to private balcony for enjoying fresh bay breezes brbr brbrKITCHEN AND DINING: brbr- Large stainless steel kitchen with solid stone countertops brbr- Breakfast bar and dining table for 6 brbr- Fully equipped with cookware, dishes, and essentials brbr brbrBEDROOMS AND BATHROOMS: brbr- Master Bedroom (upstairs): King bed, Smart TV, walk-in closet, ensuite bathrooms, access to enclosed balcony, view of the water brbr- Guest Bedroom 1 (downstairs): King bed, Smart TV with cable, walk-in closet brbr- Guest Bedroom 2 (downstairs): Two twin beds, walk-in closet, smart TV with streaming capabilities brbr- Master bathroom (upstairs): renovated, corner to corner vanity, walk-in shower with rain showerhead brbr- Guest bathroom (downstairs): tub/shower combo brbr brbrEXTRA PERKS: brbr- Complimentary beach items: a couple of beach chairs, a beach umbrella, and beach towels brbr brbrLOCAL FAVORITES: brbr- South end: - Clayton’s Grill, Miguel’s, Captain Curt’s, Anna’s Deli, Orange Octopus, Crescent Beach Grocery brbr- Village: Daquiri Deck, Siesta Key Oyster Bar, Another Broken Egg, Old Salty Dog, Siesta Market, Beach Club, Big Tiki Lounge brbr brbrIMPORTANT INFO: brbr- Other than the beach access, no gulf side amenities (including their pool) are not available brbr- Garage is accessed weekly by staff to remove garbage brbr- Parking restrictions: no boats, motorcycle, trailers, jet skis, oversized or commercial vehicles allowed. brbr- Golf carts are allowed but must be stored in the garage or driveway brbr- Parking passes and onsite check in required brbr brbrFROM SUNRISE ON THE BAY TO SUNSETS ON THE GULF, YOUR PERFECT DAY AWAITS!brbrThis property does not allow Emotional Support Animals in addition to their no pet policy.brbrIMPORTANT: The min age to rent is 25 years old. No parties, large gatherings. Please reach out if you have any questions.brbrParking passes: 1 parking pass is provided. There is a fee for extra parking passes.

Beautiful Condo, Waterfront, Dock Views, Walk to Private Beach, Heated Pools, Tennis, Pickleball

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$264.34

Enjoy this fully renovated condo in beautiful Siesta Key with views of the Gulf of Mexico! The Harbor Towers Yacht & Racquet Club! Relax in multiple pools and marina on the bay side. There is a beautiful view of the Gulf of Mexico from the balcony. The condo has been completely renovated throughout the space. The building has recently been updated with hurricane windows and doors and a new exterior.

Enjoy the crystal white sands of Siesta Key!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$307.99