
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.

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.

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. *Brand new pool* VR24-00265

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!

Siesta Key Condo: Beach, Pool & Village Fun!
Escape to paradise in our newly renovated 2-bedroom condo, perfectly situated a block from Siesta Key Village. Enjoy the convenience of walking to bars and restaurants, plus two parking spots if you prefer to drive. Relax by the community heated pool or take an 8-minute stroll to the award-winning beach. Explore the area using the free trolley, or venture to downtown Sarasota. This dog-friendly condo offers Wi-Fi, a smart TV, in-unit laundry, and essential home and beach gear.

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.

Modern Studio · 5 min from Siesta Beach
Stylish ground-floor studio designed for couples or solo travelers, just a 5-minute drive from world-famous Siesta Key Beach. A great choice if you’re looking for a calm, well-located space with thoughtful comfort. Pet-friendly stay – $10 one-time pet fee per booking, unlimited pets. An ideal base for beach days, local dining, or a relaxed Florida getaway. About 1 mile from the property, guests may also enjoy access to a beautiful community pool that is heated.

Siesta Key Quaint Beach House
This home, built in the 1950’s, has old Florida highlights including cypress wood walls and terrazzo floors located in a peaceful neighborhood. It is all on one level and sleeps 4 adults with a private patio including a gas grill. It’s only a 5 minute walk to Siesta Key beach and includes a beach cart, chairs, umbrella, towels and a cooler. Only a 10 minute walk or 2 minute ride to the village with shops, restaurants, music and nightlife.

Enchanting Coastal Ambiance & Breathtaking Sunsets
Welcome to your slice of paradise! Our stunning vacation rental offers the ultimate beachside getaway, providing you with a luxurious and unforgettable experience right on the main strip of the world-renowned Siesta Key Beach and the vibrant Siesta Key Village. The apartment or best referred to as CasaPlaya, features open concept living, a chic kitchen, fully upgraded bathroom and screened in Florida Room for your enjoyment.

On the Beach; Siesta Key SunBum Studio
Welcome back to paradise ! STEPS to your private beach without the tricks or gimmicks found elsewhere on the Siesta 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, gym, boat docks, fishing pier, outdoor grills, tennis/pickle ball courts; not to mention FREE parking+ beach lounge chairs.
Popular amenities for rentals with outdoor seating near Siesta Beach
House rentals with outdoor seating

Siesta Key Beach Getaway

4BR Waterfront Retreat - Hot Tub, Dock, Pool

Stylish & Bright: Steps to Beach ~ Pool ~ Hot Tub!

Rustic Sands - 650

Modern, Bright Downtown SRQ A-Frame West of Trail

[lounge like locals]walk to siesta beach +bikes

Siesta Beach House

Walk To Siesta Key Beach & Village ; Renovated 2BR
Apartment rentals with outdoor seating

Free Prkn, Early Chkin, Elevator-4th fl airport/DT

VILLA 5 · Pool view. King bed. Daily rentals

Near Siesta Key Beaches - Quiet 1 BR apt

Sandy Toes: Open July 26th - 31st!

Lido Key FL Studio/Efficiency 5

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

Siesta Key Escape | 2BR + Den | Pool & Gulf Views

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

Gulf Views | Walkable | Spacious

Siesta Key For Me @ The Palm Bay Club

Sarasota Surf & Racquet Club Siesta Key Condo

Lovely 2-Bedroom Condo, 7 min from Siesta Beach

KING Bed + Anna Maria Island Beaches + Beach Gear!

Siesta Key Ground Floor Condo 2BR On Trolley Line

★Right on the beach ★ Relax and Enjoy ♥ Sunsets!

Perfect Location in Siesta Key
Other holiday rentals with outdoor seating

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

Near Siesta Key | Palm-Lit Nights, Pool & Spa

Private Heated Pool Retreat for Two Families

Sarasota Pool Home| Hot-tub| 2-miles to Siesta

siesta breeze suite

Siesta Key Luxury Penthouse, walk to Beach&Village

The Ashton Retreat

Tiki Bar Paradise! Heated Pool & Gaming Oasis!
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 €97 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
- Anna Maria Island
- Raymond James Stadium
- Anna Maria Island Beach
- Coquina Beach
- Lido Key Beach
- Bean Point Beach
- Turtle Beach
- Amalie Arena
- Caspersen Beach
- Vinoy Park
- Tampa Convention Center
- Manasota Key Beach
- Crescent Beach
- John's Pass
- Tropicana Field
- Fort De Soto Park
- Englewood Beach
- Anna Maria Public Beach
- River Strand Golf and Country Club
- Jannus Live
- Img Academy
- Cortez Beach
- North Beach At Fort DeSoto Park
- Splash Harbour Water Park





