We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.

Airbnb your place

Mansion vacation rentals in Siesta Key

Find and book unique mansions on Airbnb

Top-rated mansion rentals in Siesta Key

Guests agree: these mansions are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Home in Holmes Beach

4.87 out of 5 average rating, 103 reviews

New Golf cart + 4bd/3b w pool/2100 sq ft home

Urban Oasis is a privately owned 2100 sq ft 4 bd, 3 bth on Anna Maria Island. 4 minute walk on a quiet residential street to walk to the beach.This home features grey blue hues, coastal furniture, driftwood accents, themed rooms and designer accents. A brand new 2024 6 str golf cart is included in your rental as well as a premium linen service including all towels and linens. Urban Oasis is truly a turnkey Vacation Rental! We also have a second property, Urban Oasis Too, if you like our style!

Home in Bradenton

4.97 out of 5 average rating, 118 reviews

Near downtown! Saltwater Pool! HOT TUB! Games!

Beach! River! Heated Saltwater Pool! Hot Tub! Your tropical beach vacation awaits! Prime location in proximity to local restaurants, attractions & sparkling waters. Nathan Hejl Interior Designer has updated this spacious 5BR/3.5BA vacation oasis to blend luxurious furniture & finishes w/ a barefoot, tropical vibe. Located in Historic River District in W Bradenton, walking distance to Manatee River, 2mi to Bradenton Convention & only 8mi to the famous Anna Maria Island beaches, 20mi to #1 Siesta

Home in Bradenton

4.87 out of 5 average rating, 118 reviews

IMG golf & close to AMI- Ocean View | Slt Wtr Pool

Welcome to The Beachview @ Bayside in beautiful Bradenton, Florida—a true slice of paradise with stunning views of the inner coastal waterway, Longboat Key, and Anna Maria Island! This spacious beach retreat offers 3 main-level bedrooms and an exclusive Master/Family Suite upstairs, providing the perfect setup for families or groups of friends. Comfort & Relaxation Await Each of the three main bedrooms features a private deck, ideal for sipping your morning coffee or enjoying a sunset cockta

Home in Holmes Beach

4.97 out of 5 average rating, 128 reviews

Twin Palms: Big House Steps to Beach w/Lush Pool

Twin Palms is home to NY Times best-selling food writer and chef and her tech husband. Infant/kid/pet-friendly (to 35 lbs) in a great location 5 min. walk to the beach. Private lagoon-style *heated* pool amid lush landscaping with gorgeous rock waterfall. Fully updated kitchen, 60-inch Sony HDTV, 55'' Samsung Frame TV, Italian leather reclining sofas, BBQ, beach gear, updated bathrooms, three king bedrooms. Classic Florida one-level home - no stairs. Managed directly by owners. No crazy fees!

Home in Sarasota

4.96 out of 5 average rating, 143 reviews

La Hacienda / heated pool, hot tub, 6mi to beach

Experience the allure of La Hacienda, a charming rental with a warm Southwestern-inspired interior with unique touches. This 4-bedroom, 2-bath home features a spacious living room with comfortable seating and multiple smart TVs. The private backyard awaits with a heated pool, hot tub, and outdoor kitchen for ultimate relaxation and entertainment. Located near downtown, you'll have easy access to beaches and dining. Indulge in the perfect blend of chillin', grillin' and sippin' at La Hacienda!

Home in Sarasota

4.97 out of 5 average rating, 152 reviews

LUXE home 6mi to Siesta w/ incredible pool area!

Welcome to The Palmieri - the ideal Sarasota family vacation destination! Minutes from DT, Siesta & Lido beach, our beautifully styled home features an incredible backyard with a heated saltwater pool, hot tub, fire pit, playland, and a shaded lounge. Spacious and open inside, with a fully equipped kitchen, and all the cozy feels of home. The finished garage houses beach supplies for your convenience, and thoughtful touches throughout combine comfort & luxury for an unforgettable experience.

Home in Bradenton Beach

4.97 out of 5 average rating, 159 reviews

BACK Jan 1! Newly Renovated! STEPS 2 Private Beach

NEW Pics Coming! Less than a 2 min WALK to the white sand beaches of the Gulf, this 4 BR home comfortably sleeps 8. Large bedrooms & a spacious floor plan (the kitchen, dining and living rooms flow together), the house is perfect for families. The bedrooms are split 2+2 & paired with bathrooms on opposite ends of the house (a pocket door adds privacy). Private heated saltwater pool sits amidst the lush tropical yard. Hop on the free trolley and explore Florida's gorgeous Anna Maria Island.

Home in Sarasota

4.94 out of 5 average rating, 186 reviews

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 and more. Walk to the Sarasota Arts Museum, grocery, Southside and downtown Restaurants & shops, Selby Botanical Gardens, Bayfront Park, & Marina Jack.

Home in Bradenton

5 out of 5 average rating, 118 reviews

HTDPool~2KingSuites~3BathRm~FIREpit~Airhockey~CRIB

We have been very fortunate and our home has not been affected by hurricane Helene. Our home is available for rent now. ▪️2 Game Rooms ▪️2KingSuites ▪️7 miles to Beach ▪️Blackout curtains ▪️BabyMonitor▪️Crib/Pack N Play/HighChair ▪️RokuTV’s▪️Self Checkin ▪️AirHockey ▪️Grill ▪️FirePit ▪️Washer/Dryer ▪️Coffee Bar▪️Cable ⭐️Short Checkout List⭐️ Book your family's fun beach vacation TODAY.🏖️ And create memories for a lifetime!😀 Ask us about any special offers!⛱️👌

Home in Siesta Key

4.93 out of 5 average rating, 27 reviews

Stunning Siesta Home | 4 Bedroom | Walk to Village

This newly remodeled, Siesta Key three-story, family home, just minutes to the #1 beach in the USA Siesta Key village, is ready to welcome you and your family to Paradise! Step into this updated designer home close to everything Siesta Key has to offer. The home boasts several large living areas perfect for family movie night, a garage packed full of beach toys, comfy bedrooms, a well equipped chefs kitchen, four large bedrooms, an extra large lanai and much much more!

Home in Sarasota

4.82 out of 5 average rating, 161 reviews

☀ Pet and Family Friendly Home with Pool ☀

Our spacious single-level house is perfect for families as it comfortably sleeps 10 people. The home features a renovated caged pool, an outdoor seating area with a BBQ grill, three 4K smart TVs, a game room and a fire pit. The backyard is fenced and well-behaved dogs are welcome. We are a short drive away from some of the best beaches in the country, amazing kayaking, bike riding and hiking trails. The pool can be heated up to 78-82F for an extra charge ($25/day).

Rental unit in Siesta Key

5 out of 5 average rating, 22 reviews

Coastal Luxury Penthouse

This luxury Penthouse condo is in the heart of Siesta Key Village. There is no other property in Siesta Key that can compare to this one in location, amenities, and size that can not only house your entire party, it provides every piece of luxury needed to make your trip the most memorable experience. This 2 floor, 4 Bedroom, 3.5 bathroom Penthouse is equipped with a private entrance elevator, 2 car garage, private rooftop terrace, and 6 exterior balconies to enjoy.

Vacation rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Bungalows

Intimate homes. inviting architecture

Apartments

Convenient locations with everyday essentials

Popular amenities for Siesta Key mansion rentals

Free parking on premises

Air conditioning

Luxury mansion rentals

Home in Anna Maria

5 out of 5 average rating, 22 reviews

Veselka - Canal front w private heated pool & dock

Home in Siesta Key

4.83 out of 5 average rating, 58 reviews

A Family Island Treasure

Home in Sarasota

5 out of 5 average rating, 48 reviews

Luxury villa near Siesta - heated, screened pool

Home in Sarasota

4.97 out of 5 average rating, 69 reviews

Minutes to Siesta Key, heated pool & tiki on water

Villa in Sarasota

4.79 out of 5 average rating, 33 reviews

Relaxation awaits in this bohemian inspired villa

Home in Anna Maria

4.87 out of 5 average rating, 15 reviews

Luxe Island Escape by Beach Boutique Rentals

Home in Bradenton

4.94 out of 5 average rating, 119 reviews

Spa & Pool+By The River+Near Beaches+Gameroom

Home in Sarasota

5 out of 5 average rating, 30 reviews

Family friendly with large pool

Pet-friendly mansion rentals

Home in Bradenton

4.9 out of 5 average rating, 110 reviews

4BR Htd Pool- IMG Acad Golf View/16ppl/Near Beach

Home in Sarasota

5 out of 5 average rating, 15 reviews

Luxe Oasis Mins to Beach & Downtown w/Heated Pool

Home in Anna Maria

5 out of 5 average rating, 22 reviews

༄ Sunset Shore on Anna Maria Island ༄

Home in Bradenton

4.86 out of 5 average rating, 146 reviews

Resort Style Backyard Oasis w/Heated Pool/Tiki Bar

Home in Sarasota

5 out of 5 average rating, 3 reviews

Pura Vida Near SK

Home in Sarasota

4.97 out of 5 average rating, 70 reviews

Renovated Ranch near Downtown Sarasota and Siesta

Home in Indian Beach-Sapphire Shores

5 out of 5 average rating, 16 reviews

Private Resort

Home in Sarasota

4.82 out of 5 average rating, 111 reviews

4bd/3bth Renovation With Heated Pool near Downtown

Mansion rentals with a pool

Home in Sarasota

4.95 out of 5 average rating, 39 reviews

Luxurious Summer Family Oasis w/ Private Pool!

Home in Sarasota

4.95 out of 5 average rating, 20 reviews

Large Pool Home near the Siesta Key beach

Home in Sarasota

4.91 out of 5 average rating, 47 reviews

Hideaway House Boho Retreat Pool Spa Siesta 3.5m

Home in Bradenton

4.97 out of 5 average rating, 30 reviews

Pool, putting green, pickleball, tiki bar, hot tub

Home in Sarasota

4.9 out of 5 average rating, 62 reviews

[The Bay St. Hideaway]Private Swimming Pool& Patio

Home in Sarasota

4.81 out of 5 average rating, 74 reviews

Fern Retreat 5/2 Home with Heated Pool

Home in Sarasota

5 out of 5 average rating, 23 reviews

Urban Oasis, Pool, 6mi>Beach

Home in Sarasota

4.97 out of 5 average rating, 70 reviews

Serenity 4BR HOME Amazing Pool and Relaxing Spa

Destinations to explore