Beachfront vacation rentals in Siesta Beach

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Top-rated beachfront rentals in Siesta Beach

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Guest favorite

Apartment in Siesta Key

4.99 out of 5 average rating, 141 reviews

Siesta Key #1 Beach, pickle ball & tennis paradise

Beautiful Apartment w/ Hotel Services, at Siesta Key Beach. Totally remodeled. Fully equipped to spend the best holidays with family or friends. Condo hotel, on the best beach in Siesta. Beach pool, shade pool (heated), gym, 3 tennis courts on site (2 clay, 1 hard) and 2 pickle ball courts. Master bedroom with King bed. The Mattress is a SAATVA ORGANIC. 2nd room with 2 single beds, and a queen sofa bed, in the living room. Pack n Play 600 MB Wifi. HD TV. 70” Smart TV Nesspreso, Keurig Machines

Apr 11 – 18

G$94,793 GYD per night

Guest favorite

Island in Sarasota

4.97 out of 5 average rating, 303 reviews

NEW 4 Day MAY opening Sarasota #1 Luxury Villa

Check our nearby sister properties for 2024 dates by clicking our host picture, then click picture again or "contact host". Or BOOK 2024 NOW, stay in Style magazines exclusive beachfront gem! This property OWNS THE BEACH!! UNIQUE PRIVATE POOL & BEACH combo is HEAVEN! Private ELEVATOR! 32,000/gl FREEFORM POOL, with 4 WATERFALLS, HOT GROTTO with HOT falls! NEW BBQ PIT AREA, BIKES, KAYAKS, and PADDLEBOARDS! WRAPAROUND BALCONY, CHEF kitchen. Hosted CELEBS! SHOPPING, FINE DINING, watch our VIDEOS!

Nov 11 – 18

G$131,846 GYD per night

Guest favorite

Condo in Siesta Key

4.96 out of 5 average rating, 276 reviews

On the Beach; Siesta Key SunBum Studio

STEPS TO YOUR OWN PRIVATE BEACH!! NO TRICKS or GIMMICKS LIKE OTHER LISTINGS on the KEY. This is the only studio in the Palm Bay Club tower on ground level with breathtaking views of the white sand and gulf waters. The Palm Bay Club offers 2 pools, hot tub, new gym, boat docks, fishing pier, outdoor grills, tennis/pickle ball courts; not to mention FREE parking+ beach lounge chairs. Enjoy 2 free bikes day rental with booking! You are sure to enjoy your time here on the #1 U.S. Beach.

Apr 12 – 19

G$95,744 GYD per night

Guest favorite

Condo in Siesta Key

4.83 out of 5 average rating, 122 reviews

Sarasota Surf & Racquet Club Siesta Key Condo

Sarasota Surf and Racquet Club is located on Siesta Key's award winning Crescent Beach. Our condo unit has all of the amenities of home for your convenience. The master bedroom has a king sized bed and it's own ensuite with walk-in shower. The second bedroom has 2 double beds and a large closet for all of your belongings. The complex has two heated pools, multiple charcoal grills and just steps away from the unit are 3 tennis courts and 2 pickle ball courts. Restaurants and shopping close by

Nov 4 – 11

G$84,389 GYD per night

Guest favorite

Condo in Sarasota

4.95 out of 5 average rating, 123 reviews

Cozy Beach Side 1BD/2BA, Walk to Beach & Pool

- First Floor 1 Bed/2 Bath condo w/ One King Bed( STEARNS &FOSTER MATTRESS) + One Sofa Bed - 3 Minute Walk to Private Access World Renowned Siesta Beach and Saltwater Heated Pool - Beach Side of Midnight Pass Rd - Beach Gear Provided - Patio Area - One Parking Space out front ( max to mid SUV = size similar Honda pilot) - Restaurants, bars, ice cream and seven Eleven, grocery & liquor store , pharmacy+ shops right across the street! Go to places by walking or riding a free Trolley.

Sep 13 – 20

G$42,761 GYD per night

Superhost

Condo in Siesta Key

4.88 out of 5 average rating, 122 reviews

Private Beach Siesta Key Resort Jamaica Royale

Jamaica Royale is a Beach Front Oasis, offering a private community with our own beach access and 3 heated pools . Enjoy our sidewalks, directly to the beach with no roads to cross; only residents are allowed onto the property, offering a family-safe paradise! Put your toes in the white sands of Siesta Key, where we have a private beach pavilion and lounge chairs! Look at our overview, to see our excellent location! We are in the first set of villas, closest to the beach.

Jan 3 – 10

G$94,170 GYD per night

Guest favorite

Condo in Siesta Key

4.96 out of 5 average rating, 103 reviews

2 Bed/2 Bath Condo Resort View on Siesta Key Beach

Amazing 2nd floor unit in building C at the Sarasota Surf & Racquet Club. This fully furnished 2 bed/ 2 bath condo offers a resort view and just steps away from the white sands of Siesta Key Beach. This unit is recently updated with an open floor plan, featuring stainless steel appliances, granite counter tops, kitchen bar with stools, living room, and dining room. This unit has flat screen tv's, ceiling fans, and maid service including linens and bath towels.

Dec 20 – 27

G$84,867 GYD per night

Superhost

Condo in Siesta Key

4.89 out of 5 average rating, 118 reviews

Siesta Key Beach Escape

Siesta key beach is consistently one of the top three beaches in the USA. My condo is within view of the beach and a short walk to the quaint little village. This roomy end unit has two large bedrooms, each with its own bath and walk-in closet. There is a dining room, living room, and large lanai. Walk the beach, jump in the saltwater pool, use the exercise room or enjoy the tennis and pickleball courts. No matter what you do you'll enjoy this magical place.

Dec 5 – 12

G$77,587 GYD per night

Guest favorite

Guest suite in Siesta Key

4.93 out of 5 average rating, 134 reviews

Cozy Studio - 5 min walk to #1 Siesta Key Beach!

Adorable Cabana style studio just steps from Siesta Key Village, and a 5 minute walk to Beach Access #2. Spend your day exploring the key, swimming in the ocean, and experiencing the local restaurants and shops. Enjoy coffee in the mornings on the patio, and use the available bikes to catch a beautiful sunset each night. **Please note: - No excessive noise or Parties/Events will be allowed** - No Smoking inside the unit** - Quiet hours from 10 PM to 7 AM**

Sep 27 – Oct 4

G$41,823 GYD per night

Superhost

Townhouse in Siesta Key

4.87 out of 5 average rating, 186 reviews

"Safe & Clean"- Honeymoon Suite- Siesta Key Beach

The Honeymoon Suite is located within 60 steps to #1 beach in the nation "SIESTA KEY." You will love our mini resort named "Gumbo Limbo" because of it's unbeatable location!!!! This 1 bedr/2 baths townhouse, sq ft 850 offers 2 floors, central AC, 2 balconies (Beach, pool and garden views) and a black bottom lagoon style pool which is heated during the colder winter months. Complimentary: parking (1 car), beach chairs and Wifi.

Oct 17 – 24

G$60,522 GYD per night

Guest favorite

Condo in Siesta Key

4.81 out of 5 average rating, 285 reviews

[Beach Elements] pool view + private beach & bikes

Relax & Recharge at Siesta Beach in a poolside one-story villa. + 2 beach cruiser bikes ( additional $35 each per stay) This modern studio is fully equipped with a kitchen, granite countertops & stainless steel appliances. Queen size Murphy bed and full-size sleeper sofa. Recently updated kitchen, bathroom, and a complete living area. It overlooks 1 of 3 pools Enjoy the morning sun, with your coffee on the patio

Aug 20 – 27

G$80,147 GYD per night

Guest favorite

Condo in Siesta Key

4.93 out of 5 average rating, 181 reviews

Siesta key getaway!

perfect and very comfortable 4th floor condo with elevator, screened in lanai, fully stocked kitchen and full bath. laundry facilities on the premises, a tennis court. We supply beach chairs, umbrellas, a rolling cooler and big beach bag. There is a beautiful dock on the intercoastal side of us with picnic chairs, grills, and you may even see dolphins playing !

Jun 6 – 13

G$28,405 GYD per night