Vacation Condo Rentals By Owner In Siesta Key, FL

Bayside Escape | Water Views, Walk to Siesta Key Beach, Balcony & Community PoolbrbrWhy You'll Love This HomebrBayside Escape offers a comfortable Siesta Key retreat just 0.6 miles from Siesta Key Beach, with easy access to both the shoreline and nearby dining in Siesta Key Village. Positioned near the Intracoastal, this home features a private balcony with water views, creating a relaxed setting to start and end your day. In addition to beach access, guests can enjoy a community pool located nearby, offering another option for cooling off or spending time outdoors. With a private garage, beach gear provided, and convenient access to the free island trolley, getting around the island is simple and flexible.brbrPerfect ForbrFamilies, couples, or small groups looking for a well-located Siesta Key stay with water views, beach access, and convenient amenities.brbrImagine ThisbrStart your morning on the balcony with coffee as boats move along the Intracoastal. Grab the provided beach gear and head out for the short trip to Siesta Key Beach, where the day unfolds on the sand and in the water. After time at the beach, return home to relax or take a short walk to the community pool for an afternoon swim. Spend the rest of the day at your own pace, whether that's exploring the island using the free trolley or stopping by Siesta Key Village for a casual meal or shopping. As evening settles in, head back to the balcony to unwind or gather indoors for dinner before settling into your private sleeping spaces.brbrWhere You'll Sleepbr• Bedroom 1: King Bedbr• Bedroom 2: King Bedbr• Bedroom 3: Two Twin BedsbrbrAccommodates up to 6 guests.brbrExplore the Areabr• 0.6 Miles to Siesta Key Beach – Powdery White Sand and Gulf Swimmingbr• 1.7 Miles to Siesta Key Village – Dining, Shopping, and Entertainmentbr• 6.5 Miles to Downtown Sarasota – Bayfront Parks, Arts, and Restaurantsbr• Nearby Intracoastal Waterway – Scenic Views and Boating ActivitybrbrDon'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.brbrNeed to KnowbrThis is a multi-level unit and does not have elevator access. If you need assistance bringing large items upstairs, please let us know and our team will be happy to help.brStarter packs of kitchen and toiletry essentials are provided for your first couple of nights. Free high-speed WiFi is included.Please contact us directly for more information regarding any shared spaces associated with this property. The community pool is seasonally heated.

Bayside Escape | Water Views, Walk to Siesta Key Beach, Balcony & Community Pool

Siesta Key, Florida, United States

3

Bed

Bath

Sleeps

$288.37

Welcome to Siesta Key # 407brbrWe invite you to stay in our spacious 1,250 square foot 2 bedroom 2 bathroom condominium at The Anchorage Yacht and Tennis Club which is ideally situated across the street from the #1 rated Siesta Key Crescent Beach. The Anchorage Yacht and Tennis Club offers all the amenities of a resort and all the comforts of a private residential condominium/community in one convenient location.brbrAs you enter the condo, your eye is immediately drawn to the bright and cheery living space and wall of sliding glass doors that open up to the balcony. Southern exposurebathes the condo in sunshine through large sliding glass doors in each room. The sliding gass doors open to create an indoor/outdoor living space where you can relax with picturesque views of the Canal and Intercoastal Waterway. Prepare your favorite meals in the fully stocked kitchen connected to the living space. The large master suite boasts an ensuite bathroom with separate dressing area, walk-in closet and balcony access. The spacious guest bedroom also has a walk-in closet and balcony access. Complementary Wi-Fi is provided in the condo and through out The Anchorage complex.brbrThe Anchorage is known for its amenities which include private gated beach access (across the street), heated Olympic-sized pool, lighted tennis and shuffleboard courts, BBQ grills, exercise room and free boat docking. The Anchorage complex backs up to the Intercoastal Waterway with a serene park-like setting where you can grill, picnic, fish or just relax and watch the boats go by.brbrEvery imaginable beach vacation option can be found within walking distance of The Anchorage including restaurants (many with live entertainment), shops, a market, charter boats, rental of fishing equipment, jet ski, kayak/paddleboard, para-sailing and bike rentals. You can also hitch a free trolley ride to Siesta Key Village to explore other shopping, dining and entertainment options.brbrBook your stay today and experience the magic of the Anchorage Yacht and Tennis Club and Siesta Key!brbrAmenities Include:brbr- Coin operated washer dryer: Yesbrbr- TUB/SHOWER: Yesbrbr- Balcony: Yesbrbr- BBQ Grill: 2 GASbrbr- Beach Access: PRIVATEbrbr- Bed Size 1st/Master: KINGbrbr- Bed Size 2nd Rm: 2 QUEENSbrbr- Elevator: 2brbr- Exercise Facility: Yesbrbr- Floor No.: 4brbr- Internet Access: WIFIbrbr- Parking: Yesbrbr- Parking Space Type: UNCOVEREDbrbr- Electric Stove: Yesbrbr- View: Baybrbr- PICKLEBALL: Yesbrbr- Bay View: Yesbrbr- Tennis Courts: Yesbrbr- Pool: Yesbrbr

Anchorage 407

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$289.45

We invite you to stay in our spacious 1,250 square foot 2 bedroom 2 bathroom condominium at The Anchorage Yacht and Tennis Club which is ideally situated across the street from the #1 rated Siesta Key Crescent Beach. The Anchorage Yacht and Tennis Club offers all the amenities of a resort and all the comforts of a private residential condominium/community in one convenient location.brbrAbsolutely gorgeous views of the Gulf of Mexico from the balconies are just one of the many features ...you will enjoy staying in this vacation home. Sitting in the living areas of this home you are overlooking the sights of Siesta Key. The openness of the floor plan allows for entertaining, family dinners and a sense of togetherness. The sliding gass doors open to create an indoor/outdoor living space where you can relax with picturesque views of the Intercoastal Waterway and the Gulf of Mexico. Prepare your favorite meals in the fully stocked kitchen connected to the living space. The large master suite boasts an ensuite bathroom with separate dressing area, walk-in closet and balcony access. The spacious guest bedroom also has a walk-in closet and balcony access. Complementary Wi-Fi is provided in the condo and through out The Anchorage complex.brbrThe Anchorage is known for its amenities which include private gated beach access (across the street), heated Olympic-sized pool, lighted tennis and shuffleboard courts, BBQ grills, exercise room and free boat docking. The Anchorage complex backs up to the Intercoastal Waterway with a serene park-like setting where you can grill, picnic, fish or just relax and watch the boats go by.brbrEvery imaginable beach vacation option can be found within walking distance of The Anchorage including restaurants (many with live entertainment), shops, a market, charter boats, rental of fishing equipment, jet ski, kayak/paddleboard, para-sailing and bike rentals. You can also hitch a free trolley ride to Siesta Key Village to explore other shopping, dining and entertainment options.brbrBook your stay today and experience the magic of the Anchorage Yacht and Tennis Club and Siesta Key!brbrAmenities Include:brbr- Coin operated washer dryer: Yesbrbr- TUB/SHOWER: Yesbrbr- Balcony: Yesbrbr- BBQ Grill: 2 GASbrbr- Beach Access: PRIVATEbrbr- Bed Size 1st/Master: KINGbrbr- Bed Size 2nd Rm: 2 QUEEN BEDSbrbr- Bed Size 3rd Rm: Pack & Play Availablebrbr- Elevator: 2brbr- Exercise Facility: Yesbrbr- Floor No.: TILE KIT, CARPETbrbr- Walk in shower: Yesbrbr- Parking: Yesbrbr- Parking Space Type: CARPORT 41brbr- Electric Stove: Yesbrbr- View: ISLAND VIEWbrbr- PICKLEBALL: Yesbrbr- Island View: Yesbrbr- Tennis Courts: Yesbrbr- Pool: Yesbrbr

Anchorage 402

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$282.06

Designer decorated two bedrooms, two bathrooms 6th floor condo on the Gulf side steps away from America's #1 beach, Siesta Key Beach in Peppertree Bay. brbrThis lovely condo features a dining table with comfortable wicker chairs for six guests, a lovely sectional sofa, and a barrel chair in the living room for relaxing by the television or entertainment. Spacious lanai open to the living space with a fold-out sofa, game table, and a glass top table with chairs for morning coffee facing the intercoastal and sunrise. The master bedroom has a king-size bed with a large dresser and nightstands and an ensuite bathroom. The master bedroom sliding doors open onto the east-facing lanai. The guest room has a full-size bed with an ensuite bathroom. The guest bedroom also has a desk and has a view of the gulf. A fully equipped kitchen, three televisions (70, 55, and 40), high-speed internet, and wi-fi. brbrThe building offers secured entry, elevators, shopping carts for ease of transporting groceries to the unit, and a parking garage with an assigned parking spot conveniently located in front of the elevators. The storage locker assigned to the parking space has a beach wagon, four beach chairs, two umbrellas, four ocean noodles, and a 10 x 10 pop-up canopy for long days on the beach. brbrVisit beautiful Siesta Key Village restaurants and shops on the free shuttle bus which stops right in front of Peppertree Bay.brbrPeppertree Bay property has 24/7 security on-site. Shared spaces include two heated pools, tennis/pickleball courts, an exercise room with a sauna, two clubhouses, outdoor dining areas, community grills, and a beautiful private beach with chairs and chaise lounges. brbr**Peppertree Bay requires reservations for a minimum of 30 days. Ideally, we are looking for reservations of 2-6 months. Note that during the season months of January-March, reservations must begin and end at the end of the month.

1125-607 Peppertree Bay Condo-2BR / 2BA

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$326.73

brbrWelcome to this amazing 2 bedroom 2 bathroom condominium located at the Anchorage Yacht and Tennis Club in beautiful Siesta Key, Florida. Absolutely gorgeous views of the Gulf of Mexico and the sunset from the balconies in this vacation home are just one of the many features you will enjoy while staying here. This 8th floor unit is a perfect place to relax and rejuvenate!brbrThere is plenty of space for everyone to call theirs in this two bedroom unit. The master bedroom boasts a king bed, a walk-in closet and its own dressing area and bathroom while the guest bedroom has 2 full size beds with a connecting bathroom. Sitting in the living areas of this home you are overlooking the sights of Siesta Key. The sliding glass doors open to create an indoor/outdoor room that allows you to enjoy the breathtaking views and the warmth of Siesta Key. The kitchen here is fully stocked and allows you to make all your meals right in the comfort of your home spending more time gazing at the Gulf.brbrWhile you enjoy the breathtaking views, be sure to enjoy all the Anchorage Yacht and Tennis Club has to offer as well! A pool, tennis and pickleball courts, grilling area and a place to relax overlooking the intercoastal waterway and so much more await you. A short walk leads you to the Anchorage Yacht and Tennis Club's private access to the beach and the Gulf of Mexico. Restaurants and shopping abound within walking distance as well. brbrBook your stay today and experience the magic of the Anchorage Yacht and Tennis Club and Siesta Key!brbrAmenities Include:brbr- Coin operated washer dryer: Yesbrbr- TUB/SHOWER: Yesbrbr- Balcony: Yesbrbr- BBQ Grill: 2 GASbrbr- Beach Access: PRIVATEbrbr- Bed Size 1st/Master: KINGbrbr- Bed Size 2nd Rm: 2 QUEENSbrbr- Elevator: 2brbr- Exercise Facility: Yesbrbr- Floor No.: 8thbrbr- Internet Access: WIFIbrbr- Walk in shower: Yesbrbr- Parking: Carport/Coveredbrbr- Parking Space Type: 79brbr- Electric Stove: Yesbrbr- View: Gulfbrbr- PICKLEBALL: Yesbrbr- Gulf View: PARTIALbrbr- Island View: Island Viewbrbr- Tennis Courts: Yesbrbr- Pool: Yesbrbr

Anchorage 802

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$339.74

Stunning direct beach views of Siesta Key! This 3-bedroom condo at Gulf and Bay Club is the perfect place for that home away from home. Relax on your large balcony or sit on the beach voted #1 in the USA! The beautifully landscaped property has 3 pools, 6 tennis/pickleball courts, fitness center, dry saunas, and private beach access for you to relax and enjoy your time on your island getaway. Located centrally on the island, this property is perfect for experiencing the entire island. Travel to the south to the Crescent Village, or take a trip north to the Siesta Key village. Either direction you go, you’ll be surrounded by wonderful shops and restaurants, perfect for hours of endless fun. Just bring your sunscreen, bathing suit, flip-flops and have an unforgettable vacation!brbrBedroom 1: KingbrBedroom 2: 2 QueensbrBedroom 3: 2 TwinsbrbrAdded 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 Trolley - Free-Rides Around Siesta Key,brA 7-day week, Beachside Management office for your convenience and guest needs!brbr*Minimum Age to Book: 25br*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

3bed Beachview condo w/ 3 pools on Siesta!

Siesta Key, Florida, United States

3

Bed

Bath

8

Sleeps

$396.79

Welcome to your perfect Siesta Key escape at Harbor Towers Yacht & Racquet Club, a beloved bayside community offering resort-style amenities and an unbeatable location. brbrThis beautifully furnished condo is designed for comfort in an upscale complex with tennis, a fitness room, sauna, heated pool and hot tub. This bayside community has fishing, boating, kayaking and more. Ideal for couples, families, or friends looking to experience the very best of Siesta Key.brbrHarbor Towers Amenities Include:br*Heated bayside swimming pool and hot tub br*Tennis courtsbr*Fitness center and saunabr*Community room with full kitchen, piano and pool tablebr*Organized community activitiesbr*Gas grills for outdoor cooking with plenty of outdoor tables and chairsbr*Fishing pierbr*Bayside and poolside loungers, and a shaded gazebobrbrInside, the condo feels warm and welcoming with stylish coastal décor and thoughtful touches throughout. The living area features a large, plush sectional, perfect for movie nights, afternoon naps, or gathering after a day at the beach. Just off the main living space, the cozy sunroom invites you to unwind with a morning coffee or evening cocktail while soaking in the Florida sunshine. The bedrooms offer comfy beds dressed in high-end linens, ensuring restful nights after days filled with adventure.brbrThe fully equipped kitchen makes dining in easy, whether you’re preparing a quick breakfast before heading out or cooking a full meal to enjoy at home. With quality cookware, ample counter space, and all the essentials, it’s as functional as it is inviting. You’ll also find beach essentials provided, so your days on the sand are stress-free and fun.brbrAdditional Amenities br- 2 Minutes from Top-Rated Siesta Key Beachbr- Fully Stocked Kitchenbr- High-End Furnishingsbr- High-Quality Linens & Turkish Beach Towels br- Ensuite Bathroom with Plush Towels br- Private Screened-in Balcony br- High Speed Internetbr- Smart TVs and Streamingbr- Free TrolleybrbrStep outside the condo and discover everything that makes Harbor Towers so special. This vibrant waterfront community is known for its extensive amenities and friendly atmosphere, offering something for everyone.brbrOne of the biggest highlights is the location. Siesta Key and Crescent Beach are just 2-minutes away. Hop on the free Siesta Key trolley, which stops nearby and runs throughout the island, making it easy to explore multiple beach access points and spend time in Siesta Key Village with its charming shops, restaurants, and nightlife.brbrWhether you’re here to relax, explore, or do a little of both, this Harbor Towers condo offers the perfect home base for an unforgettable Siesta Key vacation.

Upscale Complex Near Beach and Bay with Tennis, Fitness Room, Pool, Hot Tub

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$433.83

Try a Siesta Key vacation rental that’s within walking distance to the beach and has pool access for a new type of effortless fun under the sun. This 2-bedroom, 1-bath condo complements your getaway desires with beach gear, lounge space, and a coveted location. Walk to dining and shops in Siesta Key Village or take a drive to Sarasota Jungle Gardens, where you can feed flamingos, check out alligators, and fully immerse yourself in the coastal terrain!brbr-- THE PROPERTY --brbrLaptop-Friendly Workspace | Central A/C | Beach Towels, Chairs, Cooler & CartbrbrBedroom 1: King Bed | Bedroom 2: King Bed | Living Room: Queen Sleeper Sofa | Additional Sleeping: Pack ‘n PlaybrbrOUTDOOR LIVING: (shared w/ 2 other units): Heated pool w/ patio seating, outdoor shower, beach chairs, umbrellas, toys & 2 cartsbrOUTDOOR LIVING: Deck, gas grill (propane provided)brINDOOR LIVING: 3 Smart TVs, booster seat, small safe, ceiling fansbrKITCHEN: Fridge, stove & oven, dishwasher, cooking basics, microwave, Keurig, trash bags, paper towelsbrGENERAL: Free WiFi, shared washer & dryer, iron & board, complimentary toiletries, hair dryer, towels & linens, hangersbrFAQ: Step-free access (via keyless entry on back patio), 1 exterior security camera (facing out)brPARKING: Gravel driveway (2 vehicles, tandem parked)brADDT’L ACCOMMODATIONS: Two additional properties are available on-site, both with separate nightly rates: a studio for 4 guests and a studio for 3 guests. If you would like to reserve multiple rentals, please inquire for more information prior to bookingbrbr-- THE LOCATION --brbrLOCAL BEACHES: Sarasota Beach (0.3 miles), Crescent Beach (2 miles), Bayfront Park (6 miles)brSTATE PARKS: Oscar Scherer State Park (11 miles), Myakka River State Park (17 miles)brEXPLORE THE AREA: Siesta Key Village (0.1 miles), Marie Selby Botanical Gardens (5 miles), Sarasota Jungle Gardens (9 miles), Mote Marine Laboratory & Aquarium (10 miles), The John and Mable Ringling Museum of Art (10 miles)brAIRPORT: Sarasota Bradenton International Airport (10 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 smoking br- No pets allowedbr- No events, parties, or large gatherings br- Must be at least 25 years old to bookbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: There are other bookable rentals on-site; other travelers may be present and share the driveway and some outdoor amenities br- NOTE: Your safety matters. This property features 1 exterior security camera located above the property sign, facing outward toward the driveway. It does not look into any interior spaces. The camera records video and sound continuously

Siesta Key Dream Inn Vacation Rental Near Village!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$419.33

Summary:brWe pay your AIRBNB service fees for you! brbrUpdated & inviting coastal getaway, located on the island of Siesta Key in a small resort called Solitude Suites on Siesta Key. brThe “Sunset Suite” has a living/dining/kitchenette area w/ 65” TV, a separate bedroom & a separate bathroom. Off the bedroom is a private open wood deck. Table & chairs allow you to enjoy the perfect view of a Siesta Key sunset. New shower in Dec 2023!br2 min drive or 10 min walk to beach!brEnjoy FREE Kayaks, SUPs & Tiki Huts!brbrThe Space:brUpdated in 2023, this unit is fresh and clean. It has new grey luxury vinyl plank floor throughout, freshly painted blue walls, new furniture, 65” TV, sleeper sofa in the living room and sleeps upto 4 people total. brbrKing sized bed in the spacious bedroom. Your own A/C unit to control. brBeautiful new walk in shower in the bathroom. brOpen wood patio with table and chairs right off the master bedroom. brSpacious, bright and new!brbrSmall cooler and Bluetooth speaker provided, as well as beach towels, foldable beach chairs and pool/beach toys. $100 fee if speaker & cooler are not returned upon departure.brbrCommunity laundry onsite (bring quarters) as well as free parking, a heated swimming pool, a fishing pier/boat dock, sun loungers, waterfall in pool, and a ping pong table under a tiki hut!brbrKitchenette w/ fridge, freezer, ice maker, microwave, drip coffee maker, keurig, toaster oven, blender, plates, silverware, glasses, Bluetooth speaker and mini cooler for the beach/pool.brbrGuest Access:brCoin operated laundry onsite. $2 in quarters per wash, $1 in quarters per dryer. brPool (shared with other units onsite).brWaterfront dock (shared).brFree open parking. 1 car per unit. brFree shared and unsecured Wi-Fi.brComplimentary use of kayaks.brID copy (Driving license or passport) of guest will be required. brAny 3rd party credit card fees will not be refunded in the event of a cancellation or modification.brbrThe Neighborhood:brWe are located on the island of Siesta Key. It’s amazing! We have an award winning beach, great places to eat, shop, play and relax.brJust a 10-12 min walk to the closest public beach access and village area. Free Siesta Key Breeze Trolley stops right outside our parking lot. Hop on and off and take a tour of Siesta Key for free! Also there are lots of free golf carts, and small buses that will drive you around. You can also rent bikes, golf carts, etc at nearby rental shops.brYou’re walking distance to coffee, mini donuts, ice cream, Tiki bars, daiquiri bars, restaurants, breakfast places, pizza, fresh seafood, boat tours & marina!brbrGetting Around:brThere are several free types of transport that run up and down the island. There is a Trolley stop right by our parking lot area in front of our resort, or you can call Frog Hop or Jonny’s Free Rides for a pick up. Just tip the driver!brbrOther Things to Note:brTuft & Needle mattress. So dreamy!brExterior Cameras onsite.brStairs onsite. This suite is up 1 flight of stairs. brAbsolutely no animals or smoking inside the unit allowed. $500 fine. brbrGeneral maintenance, pool maintenance, landscapers and cleaning crew are onsite periodically. Any 3rd party credit card fees will not be refunded in the event of a cancellation or modification.brbrInteraction with Guests:brAvailable by text or phone, no face to face interaction is necessary. Available if needed though during business hours 9-5.

Siesta Key 1/1 King bed “Sunset Suite” Pool Kayaks

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$396.19

Summary:brWelcome to the Solitude Suite Studio, on Siesta Key. brLocated in the Solitude Suites on Siesta Key, an adorable small waterfront resort! This is the perfect getaway for 2 people in 1 king bed. Ground floor. Steps to the shared heated pool, Tiki Hut & waterfront dock area. brUpdated in 2025! Featuring a 65” smart TV, your own A/C, a king sized bed, full bathroom w/shower, coastal decor, closet & kitchenette.brbrThe Space:brEverything inside the front door is private: your own bedroom, bathroom and living space. brbrHalf a mile to the closest public beach access & also walking distance to shops, restaurants, bars, marina, ice cream, etc.brbrThe bathroom features a step in shower and large vanity.brbrOutside your door is shared: the pool, the tiki huts, the parking lot, Wi-Fi, Bbq grills and the kayaks. You can even fish from the dock! Bring a pole! brbrBeach chairs, beach towels, small cooler and Bluetooth speaker are provided for your use. $100 fee charged if any of these items are not left in your unit upon departure. brbrCheck in time is guaranteed by 4pm, however we try really, really hard to get you in earlier than 4! brbrCheck out is 10am, however after you’re checked out, you're welcome to stay onsite and use the pool, etc until 3pm!brbrGuest Access:brRegistered guests are welcome to use the pool and kayaks at their own risk. There are multiple on the dock, along with paddles and life jackets. Please use at your own risk in the daylight. The closest public beach access is approx a 10 min walk away. brShared pool, shared boat dock, open parking for 1 vehicle and shared laundry area.brbrThe Neighborhood:brThe Siesta Key Breeze Free Island Trolley stops right outside our parking area. Download the app: siesta key breeze. Or call Two Tides, or Frog hop for free scheduled pick up! brYou can rent bikes, golf carts, and more fun toys close by.brbrGetting Around:brJonnys free rides, and Frog Hop also offer free rides around the island, just tip your driver! We have Uber and Lyft on the island too!brbrOther Things to Note:brID will be verified by host. This is a ground floor unit, in a resort, but there are steps around the resort and a step into the bathroom inside the studio. brCameras onsite. Quiet time after 10pm. brAbsolutely no smoking and no animals of any kind. $500 fee will be charged for bringing an animal onsite or smoking inside the studio.brbrGeneral maintenance, pool maintenance, landscapers and cleaning crew are onsite periodically.brbrInteraction with Guests:brAvailable by text or phone as needed 9-5. Self check in allows flexibility to check in anytime.

Solitude Suite Studio-Siesta Key-Waterfront Resort

Siesta Key, Florida, United States

Bed

Bath

Sleeps

Select Dates for Price

Community Amenities Access | Free WiFi | In-Unit Washer & DryerbrbrA relaxing escape awaits at this Siesta Key condo! This 3-bedroom, 3-bath vacation rental offers stunning views, a convenient location, and all the comforts of home. Looking to soak up the beautiful Florida sunshine Spend your days lounging by the community pool or venture out to the nearby beaches. After enjoying aquatic activities or nearby attractions, retreat inside to refuel with a delicious home-cooked meal!brbr-- THE PROPERTY --brbrSLEEPING ARRANGMENTSbr- Bedroom 1: 1 king bedbr- Bedroom 2: 1 queen bedbr- Bedroom 3: 1 queen bed, 2 twin bedsbrbrCOMMUNITY AMENITIESbr- 2 outdoor poolsbr- Marina w/ waterfront accessbr- Fitness center, business centerbr- Tennis courtsbr- Grilling patio, island gazebo brbrMAIN FEATURESbr- Smart TVs w/ cablebr- Dining tablesbrbrKITCHENbr- Refrigerator, microwave, stove/oven, dishwasherbr- Drip coffee maker, toasterbr- Cooking basics, dishware/flatwarebrbrGENERALbr- Free WiFibr- Central A/Cbr- Washer/dryer, hair dryerbr- Linens & towels, trash bags & paper towelsbrbrFAQbr- Quiet hours (10:00 PM-8:00 AM)brbrACCESSIBILITYbr- Single-story condo w/ step-free access via community elevatorbrbrPARKINGbr- Designated parking spot (1 vehicle)brbr-- THE LOCATION --brbr- Near pristine beaches, dining, shopping, and other family-friendly activitiesbr- 0.8 miles to Crescent Beach br- 0.9 miles to Siesta Key Beachbr- 2 miles to Sarasota Beachbr- 3 miles to Phillippi Estate Parkbr- 6 miles to TPC Prestancia, Village Green Golf Club & Marie Selby Botanical Gardensbr- 10 miles to Sarasota Jungle Gardensbr- 11 miles to Sarasota-Bradenton International Airport, 70 miles to Tampa 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- Must be at least 25 years old to bookbr- Please observe quiet hours from 10:00 PM to 8:00 AMbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbrbrADDITIONAL INFORMATIONbr- Please note there is currently ongoing construction/renovation in the condo complex. The condo unit itself is not under constructionbr- This single-story condo offers step-free entry via the community elevator

< 1 Mi to Siesta Key Beach: Condo w/ Pool

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$423.85

Indulge in the ultimate relaxation experience on Siesta Key with a stay at our inviting vacation rental. Professionally managed by Gulf Coast Vacation Rentals, nestled within this tranquil retreat is a spacious three-bedroom, two-bathroom condo, meticulously designed to provide you with the utmost comfort and convenience throughout your stay.brbrStep inside to discover a welcoming ambiance, where every detail has been thoughtfully curated to ensure a memorable getaway. The living spaces are adorned with coastal furnishings, offering a perfect blend of sophistication and comfort. Soft, inviting hues and tasteful decor create an atmosphere that is both relaxing and luxurious, making it easy to unwind and enjoy your vacation.brbrPrepare delectable meals in the fully-equipped kitchen, complete with all the appliances you could need and ample counter space. Whether you're making a quick breakfast before hitting the beach or cooking a gourmet dinner for your family, this kitchen has everything you need.brbrEnjoy the convenience of having a washer and dryer right at your fingertips, allowing you to pack light and make the most of your time in paradise. The in-unit laundry facilities mean you can refresh your clothes and towels whenever you need, ensuring you always feel fresh and comfortable.brbrAfter a day of exploration, retreat to the cozy bedrooms, where plush bedding promises a restful night's sleep. Each bedroom is designed with your comfort in mind, featuring high-quality mattresses, soft linens, and ample storage space for your belongings. The master suite includes a luxurious en-suite bathroom, while the additional bedrooms share a beautifully appointed second bathroom.brbrWake up feeling refreshed and rejuvenated, ready to seize the day's adventures. The serene environment of the condo ensures that you and your guests will have a peaceful night's sleep, setting the stage for wonderful days ahead.brbrVenture outdoors to soak up the warm Florida sunshine. The condo includes a private garage, providing convenient parking for your vehicle and additional storage for beach gear and bicycles. This makes it easy to come and go as you please, exploring all that Siesta Key has to offer.brbrStroll to the nearby beach access, where you'll discover Siesta Key's famed white sandy shores stretching along the Gulf of Mexico. Spend your days basking in the sun, building sandcastles, or taking refreshing dips in the crystal-clear waters.brbrThe community also offers a variety of resort-style amenities for your enjoyment. Take a dip in the sparkling swimming pool, challenge friends to a game of tennis or pickleball, or relax in the beautifully landscaped gardens. There are also BBQ grills and picnic areas available, perfect for a fun family cookout.brbrHouse Rules: No Motorcycles, golf carts, RVs, boats, or trailers allowed. No smoking. No burning candles inside of lodging. No parties. No Pets.

Spacious 3br Siesta Key condo with beach access - GBB 1305

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$253.05

This lovely, well-maintained, and upgraded condo, professionally managed by Gulf Coast Vacation Rentals in a gated community, offers the perfect blend of comfort and convenience. Situated on the ground floor, this unit features one spacious bedroom and an additional den, thoughtfully furnished as a small guest bedroom. The condo is turnkey furnished, including a washer and dryer, and comes with a private garage. Just a short 5-minute walk away, via deeded walking access across the street, you'll find yourself on the #1 beach in the U.S.A., Siesta Key!brbrEnjoy an array of amenities designed to enhance your lifestyle. You can choose to relax in one of the two sparkling pools or engage in a friendly match on one of the two tennis courts. The community also boasts an exercise room for your fitness needs, a clubhouse complete with a sauna, and two BBQ grills perfect for outdoor gatherings. Additionally, there are picnic areas and a fishing dock available for residents to enjoy.brbrCentrally located on Siesta Key, this condo offers proximity to the vibrant Village, where you can explore a variety of dining options, shopping venues, and convenience stores. Discover the charm of Siesta Key, known for its pristine blue waters and 8 miles of white powder sand beaches made of quartz.brbrThe community itself exudes an Old Key West style, set on 25 acres of lush land with cedar siding and many-angled roofs that evoke an Old Florida era. Here, quality of life is measured by the beauty, comfort, and serenity that surround youbrbrHouse Rules: No Motorcycles, golf carts, RVs, boats, or trailers allowed. No smoking. No burning candles inside of lodging. No parties. No Pets.

Charming Siesta Key condo with beach access - GBB 1204

Siesta Key, Florida, United States

1

Bed

1

Bath

4

Sleeps

$1060.32

SPACIOUS BEACHFRONT LUXURY WITH SWEEPING GULF VIEWS. Situated on the 5th floor, this beautifully designed 4-bedroom, 4.5-bath residence offers stunning, unobstructed views of the beach and Gulf from a private waterfront balcony and expansive floor-to-ceiling windows. The open floor plan includes a fully equipped chef’s kitchen with high-end appliances and all the essentials for entertaining or enjoying quiet nights in.brThe master bedroom features a king bed, large walk-in closet, and a spa-style bathroom with double vanities and a rain shower. Each of the three additional bedrooms includes a queen bed and private en-suite bathroom—one with a deep soaking tub. All showers are upgraded with luxurious overhead rain fixtures. Designed for comfort, privacy, and style, this beachfront retreat combines the ease of modern living with the serenity of Gulf-front views—perfect for families or groups looking to unwind in a high-end coastal setting.

Direct Gulf View - Residence 505

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$326.73

Welcome to The Anchorage unit 808 on beautiful Siesta Key. brbrWe invite you to stay in our spacious 1,250 square foot 2 bedroom 2 bathroom condominium at The Anchorage Yacht and Tennis Club which is ideally situated across the street from the #1 rated Siesta Key Crescent Beach. The Anchorage Yacht and Tennis Club offers all the amenities of a resort and all the comforts of a private residential condominium/community in one convenient location.brbrAs you enter the condo, your eye is immediately drawn to the bright and cheery living space and wall of sliding glass doors that open up to the balcony. Southern exposurebathes the condo in sunshine through large sliding glass doors in each room. The sliding gass doors open to create an indoor/outdoor living space where you can relax with picturesque views of the Intercoastal Waterway and the Gulf of Mexico. Prepare your favorite meals in the fully stocked kitchen connected to the living space. The large master suite boasts an ensuite bathroom with separate dressing area, walk-in closet and balcony access. The spacious guest bedroom also has a walk-in closet and balcony access. Complementary Wi-Fi is provided in the condo and through out The Anchorage complex.brbrThe Anchorage is known for its amenities which include private gated beach access (across the street), heated Olympic-sized pool, lighted tennis and shuffleboard courts, BBQ grills, exercise room and free boat docking. The Anchorage complex backs up to the Intercoastal Waterway with a serene park-like setting where you can grill, picnic, fish or just relax and watch the boats go by.brbrEvery imaginable beach vacation option can be found within walking distance of The Anchorage including restaurants (many with live entertainment), shops, a market, charter boats, rental of fishing equipment, jet ski, kayak/paddleboard, para-sailing and bike rentals. You can also hitch a free trolley ride to Siesta Key Village to explore other shopping, dining and entertainment options.brbrBook your stay today and experience the magic of the Anchorage Yacht and Tennis Club and Siesta Key!brbrAmenities Include:brbr- Coin operated washer dryer: Yesbrbr- TUB/SHOWER: Yesbrbr- Balcony: BAYbrbr- BBQ Grill: 3brbr- Beach Access: Privatebrbr- Bed Size 1st/Master: KINGbrbr- Bed Size 2nd Rm: 2 QUEENSbrbr- Elevator: 2brbr- Exercise Facility: Yesbrbr- Floor No.: L/R,KIT TILE,CARPETbrbr- Internet Access: Yesbrbr- Walk in shower: Yesbrbr- Parking: Yesbrbr- Parking Space Type: # 50brbr- Electric Stove: Yesbrbr- View: Canalbrbr- PICKLEBALL: Yesbrbr- Bay View: Yesbrbr- Tennis Courts: Yesbrbr- Pool: Yesbrbr

Anchorage 808

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$399.53

Beautiful siesta key Siesta Key, at this 2-bedroom condo. This awesome property features a king bed and a twin bed, perfect for a small group of guests. With WiFi, heating, AC, and a washing machine available, your stay will be both convenient and charming. A great place to call homebase while you're away. A short walk across the street is siesta Key Beach. There is a pool and tennis courts on site. A short distance from the village, which has all your restaurants shops and tiki bars. An upscale condo waiting for you in paradise.

Charming 2-bedroom condo with WiFi, AC, across the street from Siesta Key Beach

Siesta Key, Florida, United States

Bed

Bath

4

Sleeps

$586.04

This ocean front 7th floor (of an 8-story building) 2-bedroom, 2-bathroom condominium faces the Gulf of Mexico and the 400 foot (125 meter) wide, powder sugar white sands of Siesta Key. The unit has an enclosed porch that offers year-round comfort; long, exterior balconies; plus Gulf-facing picture windows in the dining room and living room.br br Step on to the balcony of 701 and you can see the entire 1.5 mile (2.4 kilometer) long Siesta Key beach panorama from north to south. The location is perfect for early morning beach walks, all-day-long people watching, or enjoying a cold beverage as the sun sets.br br The rooms are spacious and furnished for comfort. The open kitchen was completely remodeled in 2020, the bathrooms were updated and grey wood-like plank tile was installed in 2022. There is a king-sized bed and en suite bath with walk in shower in the primary bedroom and a queen bed in the second bedroom. The second bathroom has a bathtub. There are ceiling fans in all rooms, all walls are freshly and neutrally painted.br br Jamaica Royale has three swimming pools and the largest of them is a freeform swimming pool located steps away from Tower II, where this unit is located, and is easily seen from the front door of #701. Other Jamaica Royale guest amenities include two grill areas and two shuffleboard courts. Pets are not allowed.

Siesta Key Jamaica Royale 701 Panoramic Gulf Views!!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$279.67

Welcome to your dream coastal retreat at Gulf & Bay Bayside in Siesta Key, Florida! Professionally managed by Gulf Coast Vacation Rentals,, nestled within this exclusive waterfront community, this exquisite two-bedroom condo offers a perfect blend of luxurious living and breathtaking views.brbrAs you step into this meticulously designed residence, you are greeted by an open-concept living space adorned with tasteful coastal decor. The living area, bathed in natural light, invites you to unwind and relax with its comfortable furnishings, creating a seamless connection between indoor and outdoor living. Slide open the glass doors to reveal a private lanai overlooking the lush landscaping.brbrThe kitchen is a culinary haven, boasting modern appliances, sleek countertops, and ample storage space. Whether you're preparing a gourmet meal or enjoying a casual brunch, the kitchen is as functional as it is aesthetically pleasing.brbrThe two bedrooms are offering a tranquil oasis for rest and relaxation. The primary bedroom, complete with a spa-like ensuite bathroom, provides a sanctuary of comfort utilizing a king-size bed and large TV. The second bedroom has a full-size memory foam bed with a TV, offering privacy and comfort. The living room offers a very comfortable queen size memory foam sleeper sofa complete with the necessary linens.brbrIn order to enhance the quality of your stay and create lasting memories, amenities such as beach towels, chairs, umbrellas, a cooler, and a cart are all included for your convenience.brbrGulf & Bay Bayside ensures guests enjoy a resort-style lifestyle with an array of amenities, including a sparkling pool overlooking the bay, a fitness center, and meticulously landscaped grounds. Take a leisurely stroll through the community, enjoying the tropical flora and the proximity to Siesta Key's famous white sandy beaches.brbrHouse Rules: No Motorcycles, golf carts, RVs, boats, or trailers allowed. No smoking. No burning candles inside of lodging. No parties. No Pets.

Garden view Siesta Key condo Pickleball, 2 pools, beach access - GBB 1326

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$217.52

Midnight Cove II 823brbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrLocated within the amenity-rich Midnight Cove II oceanfront complex, this second-story harbor-view condo is sure to delight guests of all ages for your next visit to Siesta Key! brbrThe open and sunlit layout of this vacation rental includes a well-equipped, full kitchen, a dining area with a table for four, and a living area with matching sofas - all illuminated by floor-to-ceiling sliding glass doors overlooking the marina.brbrOn-site, take a relaxing stroll through the property's 11 acres and then indulge in a variety of resort amenities, including a sparkling, outdoor pool, hot tub, sports courts, and a picnic area with gas grills for perfect cookouts in the abundant Florida sunshine.brbrRESORT AMENITIESbr- Outdoor poolbr- Hot tubbr- Tennis courtsbr- Basketball courtbr- Picnic area with gas grillsbr- Fitness roombrbrTHINGS TO KNOWbrStreaming TV services require guest accounts to access.brOn-site coin-operated laundry facilities.brThe thermostat will only cool to 73 degreesbrbrParking notes: There is free parking available for 1 vehicle.brThis rental is located on floor 2.brbrbrbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 21 years of age to book. Guests under 21 must be accompanied by a parent or legal guardian for the duration of the reservation.

Harbor-view condo with pool, sports courts & fitness room - snowbirds welcome

Siesta Key, Florida, United States

Bed

1

Bath