Vacation rentals with a pool in Sarasota Beach

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.

2 BR Beachy Speakeasy | Rooftop Deck | Lido Beach

Step into your WINTER Holiday with a Beach Vacation! Now booking Spring! Reserve your March & April dates! Picture this: a rooftop deck, just a 5min walk to the pristine sand of Lido Beach, and surrounded by the charm St Armand's Circle with boutiques, and eateries, all within walking distance. Forget the conventional - this condo's got a secret. Tucked behind an unassuming door lies a vibrant space, drawing inspiration from speakeasy culture fused w/ a beach vibe. Your adventure starts now

Luxury Queen Suite

Wake up with a fresh cup of coffee, then take a short stroll to Siesta Key’s world-famous white sands. Feel the cool, powder-soft quartz beneath your feet as the ocean breeze melts your worries away. Spend your days basking in paradise, swimming in crystal-clear water and watching breathtaking sunsets. Afterward, return to your spotless luxury condo, refresh, and enjoy Siesta Key’s vibrant nightlife. A true beach oasis in the perfect location—book now before it’s gone! Note: No parking available

Magical Guesthouse 1 mi from SRQ airport

@Aloe_Stranger Dreamy + fresh! This 1-bedroom guesthouse has a king bed, full bath, kitchen, washer/dryer, daybed + sleeper sofa. NEW STOCK TANK POOL! Full of style - it feels like you're in your own art installation. 1 mile from SRQ Airport, it boasts a great location as well cushy comforts. 1/2 mile from Sarasota Bay, 15 min from Lido Beach, 15 min from Siesta Key and many beaches around the Sarasota/Bradenton area. 10 min from downtown Sarasota, 1 mile from the historic Ringling Museum

Walk to beach. Pool view. Daily rentals V2

Villa 2 is overlooking the swimming pool Private entrance with self check in key pad entry King size bed Featuring 1 bedroom, 1 bathroom, large living room, Smart TV, A/C, fridge, freezer, toaster, free wifi Own parking space 2 minutes walk from your door to the beach access #13 Only 6 rentals in total Max 2 guest No smoking No pets Electronic Key Pad Entry No car needed Ground Floor, Good Value Great Location, walk to beach , shops, restaurants and bars. Bike rack available outside.

Tropical Oasis Heated Pool Hot Tub Near Siesta Key

Escape to The Funky Fish House! Your private 2BR/3BD/2BA tropical oasis boasts a heated saltwater pool, bubbling hot tub, outdoor shower, and BBQ grill for endless fun, relaxation, and sun-soaked adventures. Just 5 miles from world-famous Siesta Key Beach and steps from Trader Joe’s, this elegantly renovated, fully stocked, stylish retreat invites families or couples to lounge, entertain, soak up the Florida sunshine, and enjoy the ultimate Sarasota vacation in absolute comfort and style!

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!

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

This beautifully designed open-concept space blends modern comfort with stylish elegance. The seamless flow between the living and dining areas creates a welcoming atmosphere, perfect for relaxation or entertainment. The cozy bedroom, featuring soft colors and plush furnishings, offers a peaceful retreat. Large windows bathe the space in natural light. For added convenience, we offer a queen airbed for additional guests, ensuring everyone enjoys a comfortable stay.

Oasis by Siesta Key Beach and Downtown SRQ w/pool

Enjoy Sarasota in one of the most desirable neighborhoods by Siesta Key! Truly an elite location, take Siesta Dr down to the well-documented #1 beach in the US in around 10 mins. Flourishing Downtown Sarasota is just 5 mins away. The house features a brand new heated pool, fenced in back yard with pavers, open concept living, beautiful kitchen with everything you need, upgraded bathrooms and plenty of space for a big family. We look forward to hosting you and yours!

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!

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.

Lido Key/St. Armand's Studio 17

Steps to the beach, restaurants and dining, family-friendly activities, and public transport. This is a 2025 remodel. Great for kayaking and biking. Walking or biking distance to Lido Beach, St. Armand's Circle and Ted Sperling Kayak Park. The one room studio is good for a couple and solo adventurers. Short drive to downtown Sarasota and LBK. Great for budget and value conscious travelers and still close to the beach