Vacation Condo Rentals By Owner In Siesta Key, FL

Welcome to Pass Key Retreat at Sandy Cove II! brbr brbrExperience waterfront island living at Sandy Cove, a rare Siesta Key Village gem with private gulf access perfect for fishing, dolphin watching, and sunset lounging. This beautifully furnished 2-bedroom, 2-bath townhouse offers two balconies with peek-a-boo Gulf views and easy access to restaurants, shops, and Siesta Key Beach—just a short stroll or trolley ride away. Enjoy resort-style relaxation in a peaceful, gated coastal setting with unbeatable location and charm. brbr brbrLOCATION HIGHLIGHTS: brbr - Waterfront community on Siesta Key brbr- Private water access for fishing brbr- Direct access to Big Pass brbr- Partial Gulf of Mexico views brbr- Quick stroll to Siesta Key Village brbr- Close to north bridge for easy mainland access brbr- Near downtown Sarasota shops and dining brbr- Sunset viewing on-site brbr- Dolphin and wildlife watching spot brbr brbrPROPERTY FEATURES: brbr- 2 bedroom/ 2 bathroom, second-level 2-story townhouse (1108 SQ FT) brbr- Split master suites layout, accessible by stairs brbr- Loft-style upper master brbr- Two balconies with peek-a-boo gulf views brbr- Assigned parking plus guest spaces brbr- Washer and dryer inside loft brbr- Private beach access and fishing pier brbr- Dedicated WIFI and cable brbr- Central Air with ceiling fans brbr brbrLIVING ROOM: brbr- Vaulted wood ceilings, Bright and open layout, access to standing balcony brbr- Cozy sofa seating, large Vizio Smart TV brbr- Games and puzzles available brbr brbrKITCHEN AND DINING: brbr- Modern galley kitchen, new white cabinetry, solid stone countertops brbr- Stainless appliances throughout brbr- Breakfast bar for 2, dining table for 4 brbr- Balcony access from kitchen with café seating brbr brbrBEDROOMS AND BATHROOMS: brbr- Upstairs loft master with king bed, washer and dryer, access to balcony, TV brbr- Master ensuite bath with tub/shower combo, Stone counters and updated vanity brbr- Downstairs guest bedroom with two queen beds, ensuite bathroom, TV, access to balcony brbr- Guest ensuite bathroom with oversized rain shower head brbr brbrEXTRA PERKS: brbr- Private community fishing area, Lounge seating by the water brbr- Small beach launch for kayaks brbr- Coin-operated laundry in complex brbr- Complimentary beach items provided: a couple of beach chairs, a beach umbrella, and beach towels brbr brbrLOCAL FAVORITES brbr- Free Siesta Key trolley service nearby brbr- 5-minute walk to The Salty Dog pub brbr- Morton’s Siesta Market within walking distance brbr- Ocean Blvd dining and shopping close by brbr brbrIMPORTANT INFO: brbr- Kids not permitted in loft unattended brbr- No pets due to severe allergies brbr- No smoking allowed brbr- Vehicle restrictions enforced by HOA, no trailer, boats, oversized trucks, work vehicles, etc. brbr- HOA notification required for guests, application approval required brbr brbrDON’T MISS OUT—THE BEACH IS CALLINGbrbrIMPORTANT: The min age to rent is 25 years old. No parties, large gatherings. Please reach out if you have any questions.

Private Fishing Pier Paradise! Gulf Front with Views from Balcony | Renovated | Walk to Village

Siesta Key, Florida, United States

Bed

Bath

4

Sleeps

$293.85

This spacious 1 bedroom 1 bath offers an efficient kitchenette to cook and prepare most meals in or if dinner out is preferred the Siesta Key Village is literally at your finger tips being 1 block away! The cottage feel with vintage Florida vibe you will be sure to feel immersed in the Florida beach life style. This room offers a king size bed in the bedroom, stand up shower, living room with TV and private patio with hot tub and divider. This is the perfect getaway for special occasions or couples travelling

Beach Tree across street from beach

Siesta Key, Florida, United States

1

Bed

1

Bath

Sleeps

$497.51

Jamaica Royale Unit 206 by Tropical Sands AccommodationsbrbrWelcome to the updated Jamaica Royale Unit 206, a bright and inviting two bedroom, two-bathroom condo with a partially enclosed private balcony overlooking the pool and glimpses of the Gulf. Recently refreshed and designed for comfort, this coastal retreat offers modern convenience, easy access to Siesta Beach, and a prime location just minutes from Siesta Key Village. With upgraded features throughout, this unit provides the perfect blend of relaxation and style.brbrHighlightsbr• 5-minute walk to Siesta Beachbr• Updated unit with modern featuresbr• Private balcony with pool and Gulf viewsbr• 2 Bedrooms / 2 Bathroomsbr• 1 King, 1 Queenbr• Washer and dryer in unitbr• Primary bath with built in shower seatbr• Access to 3 heated poolsbr• Shared BBQ grills and shuffleboardbr• Assigned covered parkingbr• 2 miles to Siesta Key VillagebrbrJamaica Royale is known for its private beachfront and exceptional community amenities. Enjoy three heated pools, shuffleboard courts, beachside grilling stations, and beautifully landscaped grounds ideal for morning walks and sunset strolls. Direct beach access makes it easy to enjoy the award-winning white quartz sand of Siesta Beach, while the covered parking and elevator access add convenience to your stay.brbrThis cheerful and airy condo welcomes guests with an open living area featuring comfortable seating, natural light, and access to the private balcony. Perfect for enjoying morning coffee or evening views of the pool and Gulf. The fully equipped kitchen includes essential appliances and cookware, while the dining area provides space for shared meals after a day in the sun.brbrThe primary bedroom offers a serene retreat with a king bed, balcony access, and an ensuite bathroom featuring a walk-in shower with a built-in shower seat for added comfort. The guest bedroom includes a queen bed and easy access to the hallway bathroom, which also offers a walk-in shower and single vanity.brbrRoom Detailsbr• Primary Bedroom: King bed, ensuite bathroom with walk in shower and built in shower seatbr• Second Bedroom: Queen bedbr• Bathroom 2: Hallway bath with walk in showerbrbrUnit 206 includes a washer and dryer, private balcony with partial enclosure, complimentary Wi-Fi, covered parking, and access to all Jamaica Royale amenities including heated pools, shuffleboard, grills, and private beach access.brbrWith its relaxing coastal atmosphere, stunning views, and ideal location steps from Siesta Beach, Jamaica Royale Unit 206 is the perfect home base for your Siesta Key vacation. Book your stay with Tropical Sands Accommodations today and experience island living at one of the most desirable communities on the Gulf Coast.

Private Beach Access-Jamaica Royale 206

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$385.82

Enjoy a beach retreat at Palm Bay Club! This condo is a 5 minute walk to the private beach by crossing the main road and following a brick paver path through the resort property. Relax and enjoy the beach in lounge chairs that are available to all guests. The condo is private, quiet, and very close to the beautiful bayside pool and outdoor grill area. A large second pool, tennis/pickle ball courts, and fitness center are also located on the property. This condo has a king bed in the main bedroom and bunk beds (twin over double) in the second bedroom. Comfortable and clean furniture, wifi, A/C, smart TVs, and outdoor patio seating make the space a home away from home. This condo is great for families or smaller groups who want a getaway!brbrMinimum age requirement: At least one guest in the party must be age 25 or older as required by The Palm Bay Club condo association.

2-bedroom condo in Siesta Key with 2 pools, hot tub, 5 min walk to beach

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$245.17

Welcome to Midnight Cove II 610F! This coastal 2-bedroom, 2-bathroom ground floor condo is perfect for families or couples looking to escape to beautiful Siesta Key. Located just steps away from our dedicated beach access, you can easily enjoy the renowned quartz-white sands and vibrant local culture, filled with shopping, dining, and art. brbrHighlights br• Private Beach Walkwaybr• 10-15 min walk to the beach via private path, plus 0.2 mile to Public Beach Access #12br• Heated community pool (84°F) from November to Maybr• Tennis, pickleball, and basketball courts (equipment available at rental office)br• Fitness Center br• Boat dock rentals available br• Beach chairs in unitbr• Picnic/Grilling Areabr• Bike racks throughout propertybr• CornholebrbrThe inviting interior features a cozy living area and a stylish kitchen, ideal for preparing meals together. The primary bedroom boasts a king bed, while the second bedroom offers a comfortable queen bed. A bonus queen sleeper sofa in the living room ensures ample sleeping space for up to six guests. Step onto the lovely lanai, complete with a dining table and lounge chair perfect for relaxing with a book or enjoying your morning coffee.brbrMidnight Cove II is a spectacular bayside condominium complex with private beach access to Crescent Beach on Siesta Key and its world renowned pure white sands and breathtaking sunsets. This complex offers a heated pool, two tennis courts, pickleball, basketball, bike racks, BBQ area with grills and tables, fitness room, and a beautiful observation deck and even private docks available to rent (contact for details). brbrBook your stay at Midnight Cove II 610F today and experience your dream beach getaway! Your ultimate relaxation awaits!

Midnight Cove II 610F: 2 Bed Condo with Lanai and Shared Amenities

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$236.66

Nestled in Siesta Key, this wonderful condo offers a tranquil retreat for guests. With two bedrooms featuring a king, queen, and twin bed, plus two living rooms each with sofa beds, there’s plenty of space for everyone. The two bathrooms include both a shower and a bathtub, perfect for relaxing after a day of adventure. Guests enjoy the comfort of air conditioning and heating, making it cozy year-round. Whether you’re lounging inside or exploring nearby, this amazing condo provides a peaceful home base. It’s easy to see why you’ll be able to unwind at our place. All new appliances including washer/drywr

Beachfront condo - walk out back door directly on the beach w/kayaks, SUP & dock

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$290.54

Indulge in luxury with Unit 1D, an in-demand ground floor condo boasting two bedrooms, two bathrooms, and 1,210 square feet of pure elegance. The sophisticated interior exudes a timeless charm, complemented by a high-end kitchen that caters to culinary enthusiasts. Situated just moments from the renowned Siesta Key beach, celebrated as a gem of the United States.brbrBut there's more to discover! The screened-in lanai provides a serene retreat to admire breathtaking sunsets, with a private entrance offering direct access to the beach for your convenience. This condo also includes beach equipment for your convenience: beach chairs, a beach umbrella, beach towels, and a beach wagon.brbrCentrally located in Siesta Key, Crescent Royale places you amidst vibrant dining, nightlife, and shopping options in the Village. Not to mention, the screened-in lanai presents a perfect vantage point for enjoying the spectacular sunsets.brbrWith our dedicated on-site team prepared to ensure a seamless experience, why hesitate Secure Unit 1D now and prepare to be enamored from the moment you arrive!

Charming 2 Bed 2 Bath Ground Floor Steps to Siesta Key Beach

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$459.7

Enjoy automatic discounts based on your stay length, no codes needed, and the price you see already includes your savingsbrbrWelcome to Siesta Dunes Modern Coastal Retreat! brbr brbrEscape to Siesta Dunes, a gated resort offering a private beach on Siesta Key’s stunning Gulf Coast. Enjoy direct beach access, a saltwater pool, a hot tub, and tennis courts, all just steps away from this beautifully updated first floor, end unit condo. With a spacious layout, modern amenities, and a private outdoor space, this vacation home offers the perfect blend of relaxation and adventure. brbr brbrLOCATION HIGHLIGHTS: brbr- Gated community with private beach access brbr- Heater community pool and hot tub, tennis/pickleball courts brbr- Sun decks, loungers, and BBQ grills just minutes from the unit brbr- 6 minute drive to Siesta Key Village brbr- Assigned parking spot brbr brbrPROPERTY FEATURES: brbr- 2 bedroom/ 2 bathroom ground floor unit brbr- Close to complex entrance gate, easy access to Midnight Pass Road brbr- Short couple minutes walk to the beach access and pool brbr- Keyless entry brbr- Dedicated WIFI and cable brbr- Private washer and dryer brbr brbrLIVING ROOM: brbr- Coastal furnishing with access to screened lanai outlooking the back area brbr- Smart TV with cable brbr- Floor to ceiling sliders to let in natural light brbr brbrKITCHEN AND DINING: brbr- Fully equipped modern kitchen with quartz countertops brbr- Stainless steel appliances and all cooking essentials brbr- Dining area with seating for 4, plus 2 more at the breakfast bar brbr brbrBEDROOMS AND BATHROOMS: brbr- Master Suite: Double queen bed, flat-screen TV, walk-in closet, en-suite bath, direct access to open-air deck brbr- Guest Bedroom: Two twin beds, flat-screen TV, walk-in closet brbr- Master ensuite bathroom: large rain shower and separate water closet brbr- Guest bathroom: tub/shower combo brbr brbrEXTRA PERKS: brbr- Complimentary beach items provided: a couple of beach chairs, a beach umbrella, and beach towels brbr brbrNEARBY FAVORITES: brbr- Clayton’s Grill, Miguel’s, Captain Curt’s, Anna’s Deli, Orange Octopus, Crescent Beach Grocery, and more within walking distance brbr- Boat & water sport rentals nearby brbr- Post office close by for sending postcards home brbr brbrIMPORTANT INFO: brbr- No pets allowed brbr- No smoking or vaping brbr- Weekly minimum stay off season, 2 week min during high season brbr- Guests must follow resort rules (including parking limits) brbr- Rental registration and parking passes required brbr- No boats, trailers, jet skis, golf carts, motorcycles, or oversized/commercial vehicles. No golf carts allowed brbr- Roofing project is scheduled to start the first week of May 2026 (completion in about a month, weather permitting) brbr brbrWHETHER YOU'RE ENJOYING THE SUNSET ON THE BEACH, GRILLING UP A MEAL, OR RELAXING IN THE COMFORT OF YOUR CONDO, THIS PROPERTY OFFERS THE PERFECT ESCAPE FOR YOUR NEXT BEACH VACATON!brbrWe help make the most of your vacation by providing Xplorie's Free Admission to some of the area’s top attractions each and every day including a choice of a free bike rental, kayak rental, a dolphin cruise tour, or admission to the Ringling Museum ! Round-trip airport transportation provided for up to 3 passengers from SRQ or TPA with advance reservation. The fare is free but please tip the driver. Limited to one activity for just one person each day (other members of the group can partake but will need to pay). Create exciting memories, have more fun, and truly experience the Beaches of Sarasota! Book now for an amazing vacation experience! Activities are subject to change and based on availability; non-cumulative and non-transferrable.brbrbrbrimg src=https://admin.itrip.net/upload/360/marketingimageitripsarasota.1718820503.jpg alt=marketing /brbrbrbrFeel free to book for a month or longer but Xplorie is not available for booking 25 days or longer.brbrIMPORTANT: The min age to rent is 25 years old. No parties, large gatherings. Please reach out if you have any questions.

Siesta Dunes Modern Condo | Private Beach | Heated Pool | Ideal Location | Beach Gear Provided!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$227.34

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* Sixth Floor Condo with balcony overlooks Southern Siesta Keybr* Fully equipped Kitchen with seating for 4 at the dining table and 4 at kitchen islandbr* Beach Supplies include- 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* Elevatorbr* 25-year minimum age to rent restrictionbrbrBEDROOMS (Sixth Floor Condo)brBedroom 1: One King Bed (Ensuite Bathroom) / Balcony Access / 55 Smart TVbrBedroom 2: Two Queen Beds / Balcony Access / 50 Smart TVbrbrThe 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 onlybr brbrDistances 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. 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 2 Bedroom Condo 6th Flr, Beach Access, Pool

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$426.1

Upon entering this unit, you experience the fantastic view of shining gulf waters and the powder white crystal sand beach. Master bedrooms offers king bed and beautifully remodeled bathroom and boasts more of the stunning beach views, including direct access to the balcony! brbrYou can enjoy waking up to a fresh cup of coffee as you listen to waves roll in from offshore or unwind at the end of each day sipping your favorite glass of wine as you watch the sunsets over the Gulf of Mexico. brbrOur Accommodations are just 2 miles from the popular Siesta Key Village with shops, restaurants, bars, coffee shops and more or a short walk to nearby restaurants, convenience stores, and water sports rentals! Siesta Key also provides free trolley service that stops right in front of the resort.brbrCrystal Sands' resort-like amenities include private access to Siesta Key's famous powdery, white-sand beaches and 2 heated swimming pools. If you are looking for a family vacation or a romantic getaway Crystal Sands is the perfect place for you. Come stay with us at the most exclusive resort on Siesta Key that offers the best beachfront views on the island!br

Crystal Sands Tower Unit 1002 - Beachfront

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$246.51

Never miss a beach-scape sunset when you are just a couple hundred meters from Americans #1 beach, Siesta Key Beach. Enjoy this two bedroom two bathroom condo style unit in a great location: a short walk to the beach on a quiet street but just minutes from shops, bars, and restaurants. The unit offers a full kitchen large enough for TWO cooks in the kitchen..., breakfast bar, an open dining area and living room. The living room is furnished with a flat screen TV. Open the large sliding glass doors out to the spacious screened patio with lounge seating and table. The master bedroom with ensuite bathroom is furnished with a king-size bed and TV. The guest bedroom is furnished with a Queen-size bed and TV. The backyard of the property offers a heated pool, plenty of sun bathing spots, and a BBQ area. There are two twin-size rollaway beds available for guests. Free high speed WiFi is available throughout the property including the pool area.brbrMinimum Reservation Requirement: 1 week minimum Saturday to Saturday during peak season.

Fully Renovated Beachside Getaway with Heated Pool – Walk to Restaurants

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$266.03

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.brAnchorage Resort Condo - Corner Unitbr2 bedrooms / 2 bathroomsbrSpacious Balcony overlooking Southern and Western Siesta KeybrThird Floor Condo overlooks the canal and Gulf of MexicobrFully equipped Kitchen with seating for 4 at the dining tablebrBeach Supplies include- Chairs, Umbrella, Raft/Float Items, Beach TowelsbrCommunity Pool- Largest pool on the Key!brGated CommunitybrSiesta Key Trolley- free pickup in front of the resort entrancebrPrivate Beach access to Crescent Beach across the streetbr25-year minimum age to rent restrictionbrbrBEDROOMS (Third Floor Condo)brBedroom 1: One King Bed (Attached Bathroom) / Balcony AccessbrBedroom 2: Two Double Beds (Attached Bathroom) / Balcony AccessbrbrPool 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 onlybrbrThe 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 3rd Floor 2 Bedroom Condo South/West Balconies

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$372.03

Our 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.brAnchorage Resort Condo on Siesta Key br2 Bedrooms / 2 BathroomsbrEighth Floor Condo with Balcony overlooking North-Western Siesta KeybrFully equipped Kitchen with Seating for 4 at the Dining TablebrBeach Supplies include - 4 Beach Chairs, Beach Towels, Beach Umbrella, Cooler & Beach CartbrCommunity Pool- Largest pool on the Key!brGated Community and Parking includedbrSiesta Key Trolley- Free pickup in front of the Resort entrancebrPrivate Beach access to Crescent Beach across the street!brbrbrGuests staying at The Anchorage on Siesta Key have access to America’s #1 beach.brbrEasily accessible by one of two bridges connecting to the mainland of Sarasota, Siesta Key is an 8-mile long, crescent-shaped barrier island with four main areas – Siesta Beach, Crescent Beach, Turtle Beach, and Siesta Key Village.brbrbrREFUNDABLE DAMAGE DEPOSIT: $300 will be added to total as a refundable damage deposit. This amount will be refunded after the check out, if no damage to the property has been detected during your stay.brCommunity Pool- Largest pool on the Key!brGated CommunitybrSiesta Key Trolley- free pickup in front of the resort entrancebrPrivate Beach access to Crescent Beach across the street

Lovely 2bd condo close to the beach (AN1145)

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$351.43

Our 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.brAnchorage Resort Condo br2 bedrooms / 2 bathroomsbrNinth Floor Condo with balcony overlooks North-Western Siesta Key- Gulf Views!brFully equipped Kitchen with seating for 4 at the dining tablebrBeach Supplies include- 4 Chairs, Umbrella, Beach CartbrCommunity Pool- Largest pool on the Key!brGated CommunitybrSiesta Key Trolley- free pickup in front of the resort entrancebrPrivate Beach access to Crescent Beach across the streetbrbrbrGuests staying at The Anchorage on Siesta Key have access to America’s #1 beach.brbrEasily accessible by one of two bridges connecting to the mainland of Sarasota, Siesta Key is an 8-mile long, crescent-shaped barrier island with four main areas – Siesta Beach, Crescent Beach, Turtle Beach, and Siesta Key Village.brbrbrREFUNDABLE DAMAGE DEPOSIT: $300 will be added to total as a refundable damage deposit. This amount will be refunded after the check out, if no damage to the property has been detected during your stay.brCommunity Pool- Largest pool on the Key!brGated CommunitybrSiesta Key Trolley- free pickup in front of the resort entrancebrPrivate Beach access to Crescent Beach across the street

Gorgeous 2bd condo near the beach (AN1079)

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$316.54

Our House at the Beach E-302 by Tropical Sands Accommodationsbr1055 Beach Road, Sarasota, FL 34242brbrWelcome to Our House at the Beach E-302, a recently refreshed two-bedroom, two-bath condo located directly across from world-famous Siesta Beach. This bright coastal retreat sits within the coveted Our House at the Beach community, offering stunning beach views, easy walkability to Siesta Key’s sugar-white shoreline, and quick access to Siesta Village for dining, shopping, and island activities. Fresh interiors, comfortable furnishings, and desirable shared amenities make this a perfect choice for couples, small families, or guests seeking a relaxing Siesta Key escape.brbrHighlightsbr• Less than a 5-minute walk to Siesta Beachbr• 2 Bedrooms / 2 Bathroomsbr• 1 King bed, 2 Full bedsbr• Beach viewsbr• Shared heated community poolbr• Shared pickleball and tennis courtsbr• Beach chairs providedbr• Washer and dryerbr• 1 covered carport parking spacebr• Newly refreshed interiorbrbrGuests will enjoy access to the heated community pool, perfect for morning laps or an afternoon cool-down after a beach day. The community also features shared pickleball and tennis courts, ideal for friendly matches during your stay, as well as a grilling area for relaxed outdoor meals. With beach views and quick access to the shoreline, this condo offers the best of coastal living in a highly desirable Siesta Key location.brbrStep into a bright and newly refreshed living area designed for comfort and easy relaxation. The open-concept layout features cozy seating, a flat-screen TV, and large windows that bring in natural light and beach views. The fully equipped kitchen offers everything needed for home-cooked meals, including a refrigerator, stove, oven, dishwasher, microwave, toaster, regular drip coffeemaker, and Keurig. Enjoy meals at the dining table or take your morning coffee to the balcony overlooking the water.brbrThe primary bedroom offers a peaceful retreat with a king bed, ample storage, and an ensuite bathroom for added privacy. The second bedroom features two full beds, making it ideal for families or groups. The additional bathroom is conveniently located and equipped with a shower and bath combination, providing comfort for all guests.brbrRoom Detailsbr• Primary Bedroom: King bed, ensuite bathroombr• Second Bedroom: Two full beds, access to hallway bathroombrbrThis condo includes a washer and dryer, beach chairs, and one covered carport parking space. Its central Siesta Key location places guests minutes from Siesta Village, Beach Road dining spots, island boutiques, and beautiful Gulf-front walking paths.brbrWith its newly refreshed interior, beach views, and unbeatable proximity to Siesta Beach, Our House at the Beach E-302 offers the perfect blend of comfort, convenience, and classic Siesta Key charm. Reserve your stay with Tropical Sands Accommodations today and enjoy a relaxing coastal retreat steps from one of the nation’s top-ranked beaches.

Our House at the Beach E-302 by Tropical Sands Accommodations

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$398.12

Prepare to embark on an unforgettable beach escapade at Siesta Key Beach, the epitome of all beaches, with its sparkling quartz sand and stunning sunset views. Nestled away on the third is the ultimate luxurious hideaway, Unit 3C. With two bedrooms, two full bathrooms, and 1220 sq. ft. of living space, you'll experience an opulent lifestyle.brbrThe beach is just a short walk away, and the lanai and bedroom offer breathtaking views of the Gulf. The Master Bedroom features 2 Queen Beds, while the guest room has an additional queen.brbrThe Kitchen is equipped with full-sized appliances, a kitchen island for social gatherings, 3 TVs, and Free WIFI.brbrWe cater to all your beach needs, providing beach towels and chairs, allowing you to enjoy your time at the beach to the fullest. And after a day of fun, take a dip in the heated pool, fire up the BBQ grill, or work out in the gym. You can even challenge your friends to a game of shuffleboard on the court available for guests.brbrLocated in the heart of Siesta Key, the Village is just a short ride away on the free trolley, offering a variety of restaurants, nightlife, and shopping. And the cherry on top The enclosed lanai provides panoramic Gulf views, displaying some of the world's most beautiful sunsets.brbrOur onsite team at Crescent Royale is eager to assist you, ensuring you have the best vacation experience. So, pack your bags and book your stay today - paradise awaits you at Siesta Key!

Steps to the Beach 2 Bed 2 Bath at Siesta Key Beach with Full Gulf Views

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$283.25

Prepare to be whisked away to a beachy paradise penthouse Condo 508 in stunning Siesta Key Beach! This top-floor one-bedroom unit offers up a whopping 820 square feet of pure relaxation and cozy comfort. With Gulf and beach views that'll make your heart skip a beat, you'll be feeling like a brand new person in no time.brbrThe master bedroom boasts a king-sized bed that's guaranteed to give you the best sleep of your life, and there's a sofa sleeper available for any extra guests. You won't have any trouble staying entertained with two TVs, free WIFI, and basic cable.brbrThe kitchen is fully equipped for all your culinary needs, and extras like towels, linens, beach chairs, and umbrellas are all provided so you can enjoy the beach to the fullest.brbrSpeaking of the beach, it's only 100 steps away and offers up soft white sand and stunning Gulf sunsets that you can admire from the comfort of the screened lanai or while lounging on the beach.brbrOnce the sun starts to set, treat yourself to a glass of wine on the screened-in lanai and watch the sky transform into a painting. And for those looking for a bit more excitement, Siesta Key Village is just a short trolley ride away, offering up a plethora of dining, shopping, and nightlife options.brbrThe condo complex has a heated pool and an on-site gym for all the fitness gurus out there. Our team is dedicated to making sure your stay is both carefree and enjoyable.brbrDon't wait another second to book your beach vacation at Condo 508! This dreamy spot won't be available for long, so reserve your spot now!

Incredible Siesta Key Beach Gulf Views 1 Bed 1 Bath Top Floor Steps to Beach

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$290.54

Check out this completely renovated 2nd floor condo! Unit 203 has had a complete facelift! This open floor plan allows beach visibility as soon as you walk in the door. New everything, furniture, TVs, stainless steel appliances, flooring, remodeled bathrooms and kitchen. brbrEnjoy the beach from the lanai with a short walk to the white sands of the incredible Siesta Beach. This condo also includes beach equipment for your convenience: beach chairs, a beach umbrella, beach towels, and a beach wagon. If the beach isn't your thing, take a short elevator ride or get your steps in by taking the stairs down to the heated pool. You will also have a designated parking spot. brbrThe Master and guest suites each have new King size beds, a walk in closet and their own bathroom. Chairs, umbrellas, mat, cooler and beach cart are provided and ready for beach fun as well!brbrWe want to accommodate your vacation needs while being our guest. If you need something, please ask.brbrCome to Siesta Key, with or without your car. It's a short walk to the vibrant Siesta Key Village and all of the cafes, restaurants, bars and shopping. Take the free trolley anywhere on the island as well. Once you're here, you'll never want to leave!

Modern Siesta Key Beach Retreat 2 Bed 2 Bath Gulf and Beach Views

Siesta Key, Florida, United States

Bed

Bath

4

Sleeps

$500.56

This is your chance to enjoy one of the best views on Siesta Key from the comfort of a spacious 7th-floor penthouse. With 3 bedrooms, 2 bathrooms, and over 1,700 square feet, this beachfront condo offers unmatched Gulf of Mexico vistas and all the space you need for a relaxing coastal escape.brbrWhile the decor and furnishings may be dated, the unit is clean, well-maintained, and priced accordingly. Guests who prioritize spectacular views and prime location over modern upgrades will find exceptional value here. The condo needs to be rennovated and is priced to reflect it's lack of modernization.brbrThe Master Suite features a king-sized bed, with queen beds in the two guest rooms. A fully stocked kitchen, free Wi-Fi, and three flat-screen TVs provide the essentials for a comfortable stay. The unit also includes a full beach kit—chairs, towels, and umbrella—for your days on the sand, just steps away from your front door.brbrEnjoy resort-style amenities at Crescent Royale, including a heated pool, fitness center, BBQ area, shuffleboard, and the convenience of onsite management. Siesta Key Village is just a trolley ride away, offering dining, shopping, and entertainment.brbrBook this rare penthouse today and enjoy million-dollar views at a fraction of the cost.

Top Floor Views 3 Bedroom 3 Bath at Siesta Key Beach

Siesta Key, Florida, United States

3

Bed

Bath