
Holiday rentals with outdoor seating near Siesta Beach
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Top-rated rentals with outdoor seating near Siesta Beach
Guests agree: these stays are highly rated for location, cleanliness and more.

❤️ Hidden Gem steps away from #1 beach 🏖 Siesta Key
Welcome to Mi Casa Siesta on Siesta Key, the #1 beach in the country! Gorgeous newly renovated one-bedroom condo within a 5 min walk to the powdery white sandy beach and stunning sunsets. Also next to restaurants, bars, kayak & jet ski rentals, and much more! Contact for monthly rentals available. Experience this modern oasis: • Chic Living Room • Quartz Kitchen Countertops • King Size Mattress • Beach gear • Wifi • Private Parking • Smart TVs • Screened-in Patio • Coin Laundry room on premises

The Honeymoon Suite on Siesta Key Beach
This is a recently renovated honeymoon suite located directly across from the big end of Siesta Key. It is an elegant ground floor pool unit. This unit is equip with marble countertops, tigers eye, lapis lazuli tables, bladeless ceiling fan, alabaster lighting and giant TVs. All of the appliances are stainless/smart and the microwave can cook steaks. There is a gym. The geographic location on the key can not be beat! There is a floating television over the California King luxury memory foam bed.

[Beach Retreat] modern condo +5 min. walk to beach
5 min walk to beach and bikes onsite to rent.. Relax and recharge at this beautiful modern two bedroom Siesta Key condo. This is a fully remodeled second floor end unit with no unit above. The open layout provides excellent light throughout. Wonderful tile wood floors and a private screened in patio to sip your morning coffee. The warm sun and white sand beach awaits... beach gear (2chairs, towels, beach wagon)included complimentary -plus 2 beach cruisers to rent ($40 each per stay)

NO Stairs, Siesta beachfront. Walk to the village!
Welcome to your own private getaway directly on Siesta Beach! This ground floor unit is just steps from the powdery sands of Siesta Key. NO STAIRS Enjoy the updated bathroom with quartz countertops, new fixtures, paint, new furnishings, and décor. You literally walk out your door and directly onto the beautiful, fine, powdery white sand of Siesta Key Beach. Private Paradise directly on the white powdery sand of Siesta Key! 2 bedrooms 1.5 bathroom beachfront home with Gulf views that sleeps 6.

The Mango House Beach Cottage
Our cozy boho beach cottage, The Mango House is the perfect place for a couple or small family to relax and enjoy all the best Sarasota amenities. It’s conveniently located right between both Siesta Key entrances, walking distance to restaurants, grocery stores, Trader Joe’s, gym and a block from the popular Walt’s Fish Market. This gorgeous bungalow is the front house of a duplex on a large lot with plenty of cozy private outdoor space to relax and take in all the wonderful Florida weather!

Beachwalk Townhouse with view of Gulf of Mexico
Townhouse with 1550 sq. ft. Private elevator, all new flooring, quartz countertops, sinks, faucets, shower. View of the Beach and Gulf of Mexico from Lanai and Master Bedroom. Only a few steps to Siesta Key Beach Heated Pool, garage, grill, all beach accessories. Relax on the lanai with a view of the beach/gulf or in the downstairs Florida room by the pool. Walking distance to the village of Siesta Key to the many restaurants and amenities. Have a relaxing stay on a wonderful island.

Luxury 4B Home & Heated Pool, Resort for 10 guests
Minutes to Siesta Key Beach, this Sarasota home is made for effortless group getaways. Start your mornings by the private screened pool, unwind on the cabana daybed, and gather in bright open living spaces designed for connection. Enjoy a fully equipped kitchen, 3 full bathrooms, and a separate studio offering extra space and privacy. Centrally located with quick access to St. Armands Circle, The Ringling, and Mote Marine Laboratory & Aquarium—perfect for dining, culture, and family fun 🌴

Your Modern Beachside Getaway!
Search no more… we have it all! Enjoy this spectacular, newly remodeled beachside home in Siesta Key, equipped with a modern kitchen, hotel luxury pillow-top bed, and high-end finishes throughout! Amenities include private beach access (beachside 3 minute walk), pool access, patio, courtyard, BBQ, parking, and more. And the cherry on top, you’re right across the street for a plethora of restaurants, shops, and conveniences giving you everything you need to enjoy the best of Siesta Key!

Modern, Bright Downtown SRQ A-Frame West of Trail
Enjoy this bright, newly renovated unique pool home on a street with mostly waterfront homes featuring 4 beds & 3 baths, office area options, loft reading nook, Bosch appliances, bedroom skylights, artful light fixtures and fully fenced with heated pool. Central to & minutes from Siesta Key, St. Armand's Circle/Lido Key, downtown. Walk to the Sarasota Arts Museum, grocery, Southside and downtown Restaurants & shops, Selby Botanical Gardens, Bayfront Park, & Marina Jack. VR24-00157

Pool, Shuffleboard, EV charg, Near beach, UTC mall
Welcome to Vistalodgings Villa Del Sol where families have fun ☀ 3 bedrooms: 1 king, 1 queen, 1 full, 1 twin bed and 2 full bathrooms ☀ Fully equipped kitchen: Keurig dual coffee maker, waffle maker, air fryer, electric kettle, blender, mixer, pots and pans ☀ Dining area for 8 ☀ Fast speed internet Wi-Fi ☀ Heated pool free of charge ☀ EV charger ☀ Shuffleboard, Pac-man arcade ☀ 5 Smart TVs with Disney Plus ☀ Bikes, beach chairs, umbrellas, cooler, beach toys ☀ Iron

Modern 4BR Home *Heated Pool & Spa*
Discover elegance in this centrally located Sarasota gem, featuring four bedrooms and two bathrooms to accommodate up to eight guests. Enjoy a laid-back vibe while lounging at Sarasota's beaches or immersing yourself in local attractions. Siesta Beach and Lido Beach are within easy reach at 7.6 and 6.4 miles respectively. Rest easy knowing commitment to cleanliness aligns with your travel priorities. Your serene vacation awaits in this beautifully adorned home. VR24-00265

Siesta Key Beach & Village 2BR/2BA Steps to Beach
This charming tropical 1,320 sq.ft. 2 bedroom 2 bath home is located in the heart of Siesta Key Village. You will be within a 2 minute walk to Siesta Key Beach and Siesta Village. With a beach house décor and equipped with 3 smart TVs, WIFI, cable, refrigerator, microwave, W/D, grill, beach chairs, toys for the kids, beach wagon, 1 queen bed, 2 twin beds and sleeper queen sofa. This private beach home has everything you need for a beach vacation. Local ownership.
Popular amenities for rentals with outdoor seating near Siesta Beach
House rentals with outdoor seating

Gulf Front! Sunset Deck! + Walk to Bridge St Pier!

Luxury 3B/3B waterfront home w/ pool + boat access

Luxury Lido Key Getaway on St. Armands Circle

Luxury Canal-Front Home + Heated Pool Near Beach

Mid-Century Modern, Pool, Mins to Siesta Key Beach

Siesta Key, FL - Casa Berano

Luxury Pool Family Oasis-Siesta Beach/DT-3BR/2BA

Siesta Beach House
Apartment rentals with outdoor seating

Near Siesta Key Beaches - Quiet 1 BR apt

VILLA 5 · Pool view. King bed. Daily rentals

Cosy “Hide-A-Way Suite” Siesta Key Beach

Sandy Toes Open Next Wed & Thurs, $225/nt + Fees!

Come Enjoy Our Peaceful Retreat

Lido Key FL Studio/Efficiency 5

Minutes to Siesta or DT w/heated pool and Hot Tub

Modern Chic Getaway 2 Min. Walk to Beach & Village
Apartment rentals with outdoor seating

6 Siesta Breakers - Condo, Ocean View, Heated Pool

Gulf Views | Walkable | Spacious

Siesta Key For Me @ The Palm Bay Club

Lovely 2-Bedroom Condo, 7 min from Siesta Beach

Siesta Key Ground Floor Condo 2BR On Trolley Line

Heated Pool Apartment Near Siesta Key | 1BR

Perfect Location in Siesta Key

★Right on the beach ★ Relax and Enjoy ♥ Sunsets!
Other holiday rentals with outdoor seating

Sarasota's Luxury Oasis

Beach Rd, 300ft to Beach Access & 500ft to Village

Serenity Springs | Private Heated Pool + Waterfall

Bike to Beach Double King Suites, Pool & Mini Golf

Is this Heaven? No, it's Longboat Key

Siesta Key House, Pool & Hot Tub, 1 mile to beach

Private Heated Pool Retreat for Two Families

siesta breeze suite
Quick stats about holiday rentals with outdoor seating near Siesta Beach

Total holiday rentals
Explore 720 holiday rentals in Siesta Beach

Nightly prices starting at
Siesta Beach holiday rentals start at €95 per night before taxes and fees

Verified guest reviews
Over 21,850 verified reviews to help you choose

Family-friendly holiday rentals
580 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 160 rentals that welcome pets

Holiday rentals with a pool
640 properties feature pools

Rentals with dedicated workspaces
420 properties have a dedicated workspace

Wifi availability
720 of Siesta Beach holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Siesta Beach rentals

4.8 Average rating
Siesta Beach stays are highly rated by guests – averaging 4.8 out of 5!
Destinations to explore
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- Rentals with outdoor seating Sarasota County
- Rentals with outdoor seating Florida
- Rentals with outdoor seating United States
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