
Condo holiday rentals in Siesta Key
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Top-rated condo rentals in Siesta Key
Guests agree: These condos are highly rated for location, cleanliness and more.

Crystal House on Siesta Key Beach
This is an updated and renovated two bedroom suite on Siesta Key. Complete with marble dining table, stainless appliances and large televisions. There is a computer in the spare bedroom for your convenience along with an Xbox and DVD player. We tried to think of everything so please feel free to make suggestions after your stay. Your satisfaction is our number one concern. The sofa is a Laz-Y-Boy and is not a sleeper but is very comfortable!!! There is a set of twin-twin bunks in the main room!

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.

Oceanfront: Open Wednesday, $150/nt + Fees!
This sublime oceanfront studio is directly on the pristine white sands and serene blue waters of the Gulf of Mexico in Longboat Key, Florida! On the second floor, overlooking the heated pool and ocean, this dreamy studio condo is optimal for sunset viewing from a private lanai. Take a 30-second walk to the pool and secluded beach. Enjoy a relaxing vacation at our peaceful condo at The Beach at Longboat Key Resort! To see all four of our listings, click on my Host photo and scroll down...!

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!

❤️ Hidden Gem steps away from #1 beach 🏖 Siesta Key
Welcome to beautiful 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 Flamingo's Nest at Sea Club II
The Flamingo's Nest at Sea Club II features a beautiful new pool on the intracoastal waterway, a tiki hut for on-site cocktail hours, a plethora of boats and sea birds to enjoy while cooking on our new charcoal grills, a fishing pier, boat basin, and private beach access directly across the street. We are located 1.5 miles from the Village, loaded with amazing shops, restaurants, and night life. Condo remodeled top to bottom in 2019. Beach towels, chairs, and accessories provided.

KING Bed + Anna Maria Island Beaches + Beach Gear!
⚓️🦩Welcome to the Coastal Flamingo! Your nautical getaway that combines style, fun, and the serene beauty of the Gulf Coast. This cozy, vibrant themed condo is the perfect destination for your next Beach vacation. Walking distance to Palma Sola Beach Causeway, where you can enjoy sun-bathing, horseback riding, jet skiing, and fishing! 5 mins or less from the Gulf of Mexico and powdery white sand beaches of Anna Maria Island! Kick back and relax in this coastal escape!

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.

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. Enjoy 2 free bikes day rental with booking!

Palm Bay Club! Resort Style Living on Siesta Key!
Meticulously Renovated Oversized, 2 Bedroom 2 Bath, Beach to Bay unit! Walk to the Famous Siesta Key beach, voted #1 beach in the US, with the worlds softest sand! This complex spans from the magnificent Bay with yachts and boats to the private beach with free access to Chairs and loungers, Cabanas are available to rent. Nearby Siesta Key Village has great shopping and restaurants. Access to free transportation around the island is right outside your door.

Cozy 1BR Beach Condo on Siesta Key!
Experience the best of both worlds in this beautiful bayside 2nd floor unit! Sea Club II offers the charm of Old Florida with its shell driveway and old oak and palm trees throughout the property. Relax by the upgraded bayside pool or enjoy Happy Hour by the Tiki Hut or on the open lawn and watch the boats (BIG and small) pass by on the intercoastal. Grills are available for guests to use by the pool area. We also have a new fishing pier and boat dock.

Cottage on Siesta Key Beachside & Stunning sunsets
Come experience Siesta Key and relax in our beachside cottage. It is sure to refresh you , whether you prefer an incredible one of a kind sunset or a long leisurely walk on the beach with the cool sugar white sand beneath your toes! This is an escape you deserve. The pool is beautiful and conveniently located on your stroll to the beach. If you enjoy music , we are close to several places you can sit & enjoy under the Tiki Huts with refreshments!
Popular amenities for Siesta Key condo rentals
Weekly condo rentals

2 BR condo in Siesta Key w/ Private beach access

Enchanting Coastal Ambiance & Breathtaking Sunsets

Siesta Key Village, Pool, Beach Access 4-min Walk

Bayside Escape-Condo w/ Dock, Pool, and Near Beach

615 Luxury Condo With Ocean View, Heated Pool +++

Siesta Dunes 1st Floor Beach Front Retreat + Bikes

Location! Gulf Condo @ S. Jetty 30 day minimum

Waterfront w/ Pool, mins to SK Beaches, bikes/sups
Pet-friendly condo rentals

5213B Menorca Street - Siesta Key Village Condo

Dreamview • 1BR - Siesta Key Beach Sunset View

Short walk to beach 4, King bed, Dog Friendly

Siesta Key w heated pool arcade & pet friendly

Siesta Key Condo: Beach, Pool & Village Fun!

Lake View 1BR Condo | Heated Pool Near Siesta

Condo Downtown Sarasota. Sunsets, GYM, POOL/SPA

New Luxury 3/3 Condo in Margaritaville Resort
Condo rentals with a pool

Walk to Siesta Beach, Heated Pool, Tennis, Balcony

Upscale Villa in the heart of Siesta Key!

Gulf View! 2/1 with Heated Pool, Kayaks and SUP

Your Beachside King Suite Retreat!

Top Floor Beautiful View Condo-Shore To Please

Anchorage Resort 2 Bdrm Condo 9th Flr, Pool, Beach

The Key to a Great Vacation!

Sleep 6, walk to beach, restaurants/bars, new reno
When is the best time to visit Siesta Key?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $382 NZD | $521 NZD | $521 NZD | $433 NZD | $344 NZD | $346 NZD | $353 NZD | $313 NZD | $301 NZD | $276 NZD | $304 NZD | $330 NZD |
| Avg. temp | 16°C | 18°C | 20°C | 22°C | 25°C | 27°C | 28°C | 28°C | 27°C | 24°C | 20°C | 18°C |
Quick stats about condo rentals in Siesta Key

Total holiday rentals
Explore 1,060 holiday rentals in Siesta Key

Nightly prices starting at
Siesta Key holiday rentals start at $122 NZD per night before taxes and fees

Verified guest reviews
Over 16,790 verified reviews to help you choose

Family-friendly holiday rentals
850 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 50 rentals that welcome pets

Holiday rentals with a pool
890 properties feature pools

Rentals with dedicated workspaces
400 properties have a dedicated workspace

Wi-Fi availability
1,050 of Siesta Key holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Siesta Key rentals

4.8 Average rating
Siesta Key stays are highly rated by guests—averaging 4.8 out of 5!
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