Gertrude's Siesta | Pool, Jacuzzi | 1 Min to Beach | 4 Min to Dining & Music!

Siesta Key, Florida
$451 avg/night
Bed 2

Bed

Bath 2

Bath

Home Private Vacation Home

Property Type

Sleep 5

Max Sleeps

Kaia's Sun and Sea
Newly remodeled with pool and jacuzzi, just 1-minute walk to Siesta Key beach! Poolside lounging and grilling, sunsets, sandbars, and on reef snorkeling and paddling. Just 4-min walk to shopping dining bars and live music. Book your getaway now! - Tollbooth by VRBOCorpMiddlemen, but this property is from GertrudeRentalsSiesta

What Guests Love
∙ Front Porch – southwesterly porch on the palms (shared)
∙ Beaches – 1-min walk to award winning beaches, white sand, calm water
∙ Relaxing – private balcony and patio with dining and lounging
∙ Pool – beautiful heated pool with tropical plants just 1-minute walk
∙ Reef Snorkeling – 70-yard walk to Point of Rocks, free snorkel gear provided
∙ The Food –12 restaurants within 0.5 miles, 3 waterfront restaurants within 4 miles
∙ Activities – Boat bike jet-ski & sport-fishing tours, marina and rentals 7-min away
∙ Sunsets –1-minute walk to best sunsets and whatever comes next
∙ The Fun - live music, daiquiris, oysters, stone crab, craft beer, ice cream, fresh donuts
∙ The Memories – access Siesta Key's top attractions and beaches guaranteed fun for all

The Beach
Access to two private Siesta Key beaches. With no public parking nearby, this cove is one of Siesta's more exclusive beaches. The white quartz sand, tide pools, and calm, clear water are perfect for relaxing. A livelier scene with food, drinks, and the weekend drum circle is just a short beach walk north. Point of Rocks reef is only 60 yards south.

The Location
No car needed. Nestled on a quiet street with no traffic, businesses, or public parking. Walk 4-minutes two 12 bars and restaurants. Walk 7-minutes to Siesta's top eco-adventures boat, bike, jet-ski, and fishing tours. Prefer to relax Sunbathe at the beach, nap by the pool or enjoy Siesta s top-rated seafood, ice cream, and waterfront dining. Just a short stroll to favorites like Daiquiri Deck, Sniki-Tiki, Crescent Club, and Orange Octopus.

Reef Snorkeling
Siesta Key is already paradise now add one of the Gulf Coasts best snorkeling spots! Just 60 yards south, Point of Rocks offers safe, shallow waters filled with tide pools, colorful marine life, and shelling treasures. Most days you'll spot chameleons, sponges, mother-of-pearl shells, conch, and maybe even dolphins or turtles. Ideal for exploring by foot, snorkel, paddleboard, or kayak.

Bedroom Details
This unit is two flights up with no one above it. There is a king bedroom, a queen bedroom and a sectional sofa. Need more space We can get you an additional unit nearby.

Beach Gear Provided
We provide beach towels and the resort supplies chairs and umbrellas. If you don't have what you need, just reach out and we can usually get it for you. Correction for Air-b-n-b listings this location doesn't provide snorkeling gear but this and anything you need can be rented or purchased nearby.

Household Items Provided
We provide bedding, kitchen items, most major and minor appliances, blow dryers, and hangers. Simple soaps and paper products come in starter-supply that will get you through a short stay and anything you need can be purchased nearby.

What to Bring
It's a laid-back island so pack as lite as you like. Our fashion is casual, wash and wear, and all units have laundries. Also, anything you forget to bring can be found nearby in good supply and fair prices.

Post Booking Support
We understand vacation time is precious and will make sure you get the most out of it. Our number is the only contact information you need. All units are at the top attractions on the island. Cars are never required, but you will have private parking near the unit. No check-in restrictions, check-in any day of the week at any time using a private door-code. Never a cleaning requirement at checkout. Free early check-in when possible. No hidden fees or solicitations. Every unit including this one is available for instant booking. We can recommend the best spot for fishing or fresh fish, Michigan or Ohio State games, romantic-dinners marriage-proposals or singles, eco-tourism, family friendly activities, or safe ways to lose your kids when you(they) need alone time.

Travel Insurance
If you prefer insured bookings, we also offer travel insurance. Basic Travel Insurance- cost is 7%, covers 30 different issues, coverage begins only after protection has been purchased. CFAR (cancel for any reason) insurance is available in states applicable- cost is approximately 11% (7% basic plus additional 3.8% to add CFAR). Basic and CFAR must be purchased together as CFAR cannot be purchased individually. CFAR covers 60% of the trip cost with no questions asked. Travel insurance must be purchased within 14 days of booking and 30 days before check-in. Claim must be filed two days prior to arrival, available to U.S. citizens only.

Terms
Payments are 50% refundable when canceled at least 60 days before arrival. Payments are not refundable when canceled less than 60 days before arrival. Events or gatherings involving outside guests are only allowed with prior approval from the management. Guest agrees to hold the Property Manager and Owner harmless from any liability for injuries while on vacation. Sorry but events involving guests in excess of your unit occupancy limit are not permitted at this location.

Read More Expand
  • Feature Features
  • Map Map
  • School District Rates & Availability
  • Review Review

Feature Features

  • PETS

    No Pets Allowed
  • BEACH

    Near The Beach
  • DINING

    Dining Table
  • SAFETY

    Carbon Monoxide Detector Installed (host Has Indicated There Is A Carbon Monoxide Detector On The Property) Deadbolt Lock Fire Extinguisher Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    2 Bedrooms Bed Sheets Provided Sofa Bed
  • GENERAL

    Unit Size: 900 Sq Ft (84 Sq M)
  • KITCHEN

    Coffee/tea Maker Cookware/dishes/utensils Dishwasher Microwave Oven Refrigerator Stovetop Toaster
  • LAUNDRY

    Laundry Facilities Near Laundromat Washing Machine And Dryer
  • PARKING

    Onsite Parking
  • INTERNET

    Free WiFi
  • OUTDOORS

    Balcony Garden Gas Grill
  • POOL/SPA

    Hot Tub Shared/communal Pool
  • BATHROOMS

    2 Bathrooms Hair Dryer Shower Towels Provided
  • LANGS SPOKEN

    English French
  • THINGS TO DO

    Birdwatching Nearby Ecotours Nearby Jet Skiing Nearby Parasailing Nearby Power Boating Nearby Sailing Nearby Scuba Diving Nearby Snorkeling Nearby Surfing/body Boarding Nearby
  • ENTERTAINMENT

    Games Smart TV With Cable/satellite Service
  • LIVING SPACES

    Living Room
  • CLIMATE CONTROL

    Air Conditioning Heating
  • FAMILY FRIENDLY

    Highchair Travel Crib
  • LOCATION HIGHLIGHTS

    In A Village In The City Center Near A Hospital Near A Zoo Near The Sea
  • SERVICES AND CONVENIENCES

    Iron/ironing Board
  • SUITABILITY/ACCESSIBILITY

    Smoke-free Property

CheckIn Check-in : 03:00 PM CheckOut Check-out : 10:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 5

Map Map

School District Rates & Availability

Review Review

  • Chanda

    Submitted Jan 20, 2026

    Stayed Jan 13, 2026

    Very cute, clean and comfortable! Amazing porch to sit on, within walking distance to the beach. The hot tub and heated pool really made the stay!

  • Leanna

    Submitted Jan 5, 2025

    Stayed Oct 2, 2024

    Loved it!

  • Bryan W.

    Submitted Dec 24, 2025

    Stayed Dec 19, 2025

    Loved the area. Very quiet. Hot tub and grill were great to have. Beach chairs and towels for use also. Host was very helpful on a missing kitchen item, replacement was dropped off just a few hours later. Room was spotless. We were able to get in the ocean during our stay, not for the weak of heart though. We will be back.

  • Richard K.

    Submitted Sep 14, 2025

    Stayed Sep 7, 2025

    This 2 bed/2 bath condo was perfect for our stay in Siesta Key. Clean/ fully equipped kitchen/ comfortable living room and 2 large bedrooms all complete with TV's. Steps to the beautiful beach….. just so convenient to restaurants and stores as well. Great communication with owner as well. Definitely recommend!!!

  • Lisa D.

    Submitted May 26, 2025

    Stayed May 23, 2025

    Nice unit! We enjoyed our stay

  • Tracy P.

    Submitted Apr 21, 2025

    Stayed Apr 17, 2025

    Great place, perfect for our quick family getaway.

  • Patrik F.

    Submitted Apr 13, 2025

    Stayed Apr 9, 2025

    we had a great time at Crescent beach Siesta, the Condo was spacious and well equipped. The location close to the beach and near to many good restaurants is perfect. We loved our stay here!

  • Loren K.

    Submitted Mar 25, 2025

    Stayed Mar 22, 2025

    Everything here was great. Updated, clean, and great location to the beach, restaurants, and convenience stores. The owner was very helpful, answering all my questions quickly. Would stay here again!

  • Abby P.

    Submitted Mar 25, 2025

    Stayed Mar 18, 2025

    Our unit was exactly as pictured and described. Dan was great with any questions or concerns we had before and during our stay. We will definitely return and book with Gertrude Rentals!

  • Amanda H.

    Submitted Mar 13, 2025

    Stayed Mar 2, 2025

    This was our first time to Siesta Key & the Gertrude Rentals team went above & beyond to make our stay so great! Check in was seamless. We had a few questions throughout our stay & always got quick responses. Love that there was no “Check out checklist” as well. We will be back!

  • David B.

    Submitted Mar 6, 2025

    Stayed Feb 10, 2025

    The accommodations were very clean and comfortable, the location was very accessible to the beach And an easy walk to the market area and some very good eateries. Just a short trolley ride up the road to some additional great restaurants in the village area. A highly recommended vacation spot.

  • Joan B.

    Submitted Jan 10, 2025

    Stayed Jan 3, 2025

    We thoroughly enjoyed our stay. It was quiet, clean and well maintained. The only thing missing was a kitchen trash can.

  • Tonya A.

    Submitted Dec 22, 2024

    Stayed Dec 19, 2024

    Traveled to area to search for apartments for our son moving to Florida. Booked on short notice and everything was great. Great communication. All of our needs met. Great location. Pool and hot tub very nice. Beds super comfortable. Great shower. Definitely would stay again and book for longer stay. Easy access to the beach

  • Brandon C.

    Submitted Dec 16, 2024

    Stayed Dec 9, 2024

    Last minute trip to Siesta Key and had another great stay. Visited new restaurants along the Crescent beach area that I'll add to our list of places to continue eat at. Each time we come we find something new!

  • hillary f.

    Submitted Dec 16, 2024

    Stayed Nov 26, 2024

    This property was clean and comfortable. It had everything you needed to enjoy your stay. The new furniture was comfortable and cute! Communication with the property manager was 5 star!

  • Gregory C.

    Submitted Nov 22, 2024

    Stayed Dec 31, 1969

    Nice condo in a very quiet neighborhood extremely close to the beach. The grandkids really enjoyed the pool and hot tub.

  • Brandon C.

    Submitted Sep 19, 2024

    Stayed Dec 31, 1969

    We loved the ability to park our car and never have to drive again. This property was so close to everything. The beach is right out in front and the restaurants we really enjoyed are less than 2 blocks away. Somehow it still keeps its unique calm and quiet character even with being so close to the typically busy and loud areas. We loved the resort style pool and the large bedrooms. When we did have to drive it only took 2 minutes to get across the bridge back into Sarasota! Perfect spot for our vacation.

  • Kade H.

    Submitted Sep 19, 2024

    Stayed Dec 31, 1969

    Great location. Danny and his team are super friendly and responsive to my needs. Unit was clean and met my needs on a short getaway! Will come back and use Gertrude again.

Your dates are Available!

Total

Includes taxes and fees
$451+
View details