Gertrude's Siesta | Pool & Spa, 100% Private, 5-min bike to Siesta Key Beach, 3-miles to Village!

Siesta Key, Florida
$650 avg/night Minimum Stay 2 Nights
Bed 4

Bed

Bath 3

Bath

Home Private Vacation Home

Property Type

Sleep 10

Max Sleeps

Night 2 nights

Min Stay

The Island Time
Breathtaking pool at large 100% private Siesta Key home! Spacious, tropical, just 5-min bike or 20-min walk to world famous Siesta Key Beach, and 1-mile to free Island trolley! Elevated deck, balcony, and covered alfresco area. Property includes 3BR unit above and 1BR suite below. Perfect for larger groups. Book a getaway now!

What Guests Love
∙ Private Heated Pool, and stunning marble hard-scape
∙ Balconies tropical balcony, 2nd floor lounging deck, and covered alfresco area
∙ Privacy two units for price of one, includes upstairs 3BR and downstairs 1BR
∙ Beach world famous Siesta Key Beach, 5-min bike or 20-min walk
∙ Restaurants 1-mile to free trolley for all 40 of Siesta s bars and restaurants
∙ Sunsets 20-min walk to best sunsets in America or just enjoy from your pool deck
∙ Activities scooter, bike, boat and kayak rentals nearby
∙ Exploring - sand dollars, shells, dolphins, occasionally manatees and live conch
∙ The Fun - live music, daiquiris, oysters, stone crab, craft beer, ice cream, fresh donuts
∙ The Memories perfect for large groups, quiet, comfort, access to all top attractions

The Beach
Our closest beach is the Siesta Key Public Beach on Beach Rd., just 1-mile away. It s the most lively on the island, but also the widest so plenty of room to sit and relax. What makes this beach amazing is it is the only beach on the island that serves food and drinks. That s right! For the first time since the 1970s, you can get beer, frozen cocktails, gourmet sandwiches and burritos, snacks and more at a Siesta Key beach location! The water at this beach is also shallow clear and calm with white quartz-sand and tide-pools perfect for sleeping drinking or playing.

The Home
This listing is a 3BR unit above and 1BR suite below for a total of 4BR. Large and 100% private. Heated pool with stunning marble hard scape. Out-door grilling and dining, tropical balcony, 2nd floor lounging deck and covered alfresco area. Perfect for bigger groups, surrounded by palms, and accessible to all Siesta Key s top attractions.

Property Truths and Limits
If any of these limits are not a fit for you, just let us know and we ll find you something a little more laid-back - 1) If you re looking for a party spot this property is not for you. However, if you want a quiet getaway, you found the perfect fit and we would love to host you. 2) The Siesta Woods neighborhood agreement requires the pool and all outdoor areas to close promptly at 9 PM. After 9 PM, please move the party to the nearby beaches, to the village, or just move into your unit. 3) The island of Siesta Key does not allow overnight parking of recreational vehicles or motorhomes, no matter what. People attempting to park. These vehicles overnight will almost definitely be towed by the county. 4) Sorry, no nudity in the pool or the pool area and we follow Sarasota rules for non-nude beaches. 5) The pool gate is portable, but according to state law, must stay in place. Also 6) The unit is advertised as “100% private,” and you will never share the home with other guests. Occasionally—typically about once per week—the pool or landscaping service may stop by for routine maintenance. These visits are quick, limited to exterior or storage spaces, and always completed during daytime hours.

Bedroom Details
This listing is a 3BR unit above and 1BR suite below for a total of 4BR. The upper unit has a king bedroom and two queen bedrooms. The ground floor unit is a full apartment with TV, living area, kitchen, bath, separate queen bedroom and a queen sleeper sofa in the living room. This is a large rental with 2 living rooms and 4 dining areas, including interior and exterior. You can sleep up to 12 people.

Property Truths
The unit is advertised as “100% private,” and you will never share the home with other guests. Occasionally—typically about once per week—the pool or landscaping service may stop by for routine maintenance. These visits are quick, limited to exterior or storage spaces, and always completed during daytime hours.

Beach Gear Provided
We provide beach towels, chairs, carts, umbrellas, and usually have a few bikes and a paddleboard. 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, private laundry, 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.

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.

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.

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  • Feature Features
  • Map Map
  • School District Rates & Availability
  • Review Review

Feature Features

  • PETS

    Pet Friendly
  • 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 First Aid Kit Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    4 Bedrooms Bed Sheets Provided Sofa Bed
  • GENERAL

    Unit Size: 2300 Sq Ft (214 Sq M)
  • KITCHEN

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

    Laundry Facilities Washing Machine And Dryer
  • PARKING

    Onsite Parking
  • INTERNET

    Free WiFi, With Speed Of 100+ Mbps (good For 1–2 People Or Up To 6 Devices)
  • OUTDOORS

    Balcony Barbecue Grill
  • POOL/SPA

    Heated Pool Private Pool
  • BATHROOMS

    3 Bathrooms Hair Dryer Jetted Bathtub Shower Towels Provided
  • WORKSPACES

    Desk Desk Chair Office
  • LANGS SPOKEN

    English French
  • THINGS TO DO

    Ecotours Nearby Hiking Nearby Hiking/biking Trails Nearby Horse Riding Nearby Power Boating Nearby Swimming Nearby Theme Parks Nearby Water Park Wildlife And Game Walks Nearby Windsurfing Nearby
  • ENTERTAINMENT

    Books Smart TV With Cable/satellite Service
  • LIVING SPACES

    Dining Room Living Room
  • CLIMATE CONTROL

    Air Conditioning Heating
  • FAMILY FRIENDLY

    Highchair Travel Crib
  • LOCATION HIGHLIGHTS

    Near A Hospital Near A Zoo Near Outlet Shopping Near The Bay Near The Sea
  • SERVICES AND CONVENIENCES

    Iron/ironing Board
  • SUITABILITY/ACCESSIBILITY

    If You Have Requests For Specific Accessibility Needs, Please Contact The Property Using The Information On The Reservation Confirmation Received After Booking. Smoke-free Property Wheelchair Accessible

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

Map Map

School District Rates & Availability

Review Review

  • Margaret

    Submitted Jul 20, 2024

    Stayed Jul 14, 2024

    I absolutely loved this place. We had two adults 5 kids 10-16 it was perfect! Very close to beach, spacious, clean, amenities were great, very up to date, etc 7/2024

  • Rhonda S.

    Submitted Feb 2, 2026

    Stayed Jan 30, 2026

    The host reached out to us to make sure we had everything we needed, so we knew he was available, but the place was so well appointed and maintained, that we had no need to speak with him. It approached record lows while we were here, so not the beach weekend we were hoping for, but the house was cozy and the company wonderful. Hope to stay here again.

  • Ahmed E.

    Submitted Dec 31, 2025

    Stayed Dec 22, 2025

    Great location - about 3 mins to the beach by car. Definitely walkable. The property was clean and well maintained. Host communication was great. Would definitely stay here again

  • Nikhil G.

    Submitted Dec 29, 2025

    Stayed Dec 26, 2025

    Bad experience. The hot tube took hours to heat up. Grandma's quarters had tiny lizards. Even with renovation, house felt outdated. No USB outlets.

  • Melany W.

    Submitted Dec 1, 2025

    Stayed Nov 26, 2025

    Our family gathered for Thanksgiving, and we enjoyed this beautiful home for a fun long weekend together. The home was great. Clean, spacious, and perfect for cooking and hanging out. Loved the deck and pool. A close drive to the beach. Responsive host A

  • Sandy S.

    Submitted Oct 19, 2025

    Stayed Oct 16, 2025

    We love all off the site and the property

  • Gail R. B.

    Submitted Oct 10, 2025

    Stayed Oct 5, 2025

    Seven adults gathered for a family reunion from around the country for 4 days.The house, cleanliness, furnishings and pool were even better than expected. The kitchen was well equipped, although, we only ate breakfast in. Although it wasn't heated, the pool was delightful and easy to access. The location was perfect, one mile to Siesta Key beach and close to shops and a wide variety of restaurants.The Owner was welcoming and extremely helpful and responsive. We highly recommend a stay here. We hope to come back again!

  • Eliane R.

    Submitted Sep 11, 2025

    Stayed Sep 7, 2025

    It was great location

  • Crystal C.

    Submitted Aug 19, 2025

    Stayed Aug 15, 2025

    We had a wonderful stay! How was super clean and accommodating! Great views and host was super responsive!

  • Casey m.

    Submitted Aug 7, 2025

    Stayed Aug 2, 2025

    House was very nice. Pool was 94 degrees everyday but one, the day the pool guy turned on the fountain and waterfall for us. Unfortunately it didn’t come back on the next two days. That seemed to help cool it a little bit. That warm of pool maybe common for this area, I am not sure, but really felt warm to us. 4 usable beach chairs, rusty beach wagon that was not usable. No pool floats or ocean toys. We did leave 2 buggy boards and 5 pool floats for the next people. Location in my opinion you need a car, golf cart or plan on using uber every time you leave. We did find out the last night that the frog bus will take you home for tips. I am not leaving negative review, I am just sharing information I wish we would have know on day one. We were very happy with the layout of the house. We had two families with 5 kids ranging from 15-22 and everyone enjoyed their stay.

  • Tara S.

    Submitted Jul 28, 2025

    Stayed Jul 21, 2025

    4th stay with Gertrude, 1st at this property- everything was excellent. The house was perfect- clean, spacious, conveniently located- kids and adults all enjoyed themselves. Will definitely be back.

  • Kiana L.

    Submitted Jul 15, 2025

    Stayed Jul 10, 2025

    To start Daniel's home was amazing. There was so much space for our family, the rooms and common area were clean and set up so nicely. We were thankful that he allowed us to have our pet with us and that there was a fenced yard. The pool was heated and beautiful the kids loved it so much. The location is perfect distance from the beach and all stores or eatery's in town. We will definitely be staying here again in the future for sure.

  • Brandon P.

    Submitted Jul 4, 2025

    Stayed Jun 29, 2025

    My family and I ranging from children to senior citizens enjoyed this home. It was spacious, very clean, and has a great pool! The best thing was the just Daniel. He was very responsive and super nice during all communications. I highly recommend renting this home in the quiet neighborhood very close to the beach.

  • Kimberly P.

    Submitted Jun 3, 2025

    Stayed May 30, 2025

    The home was very spacious! Kids loved the pool we spent our time there when not at the beach and we were very satisfied with distance of shops restaurants and beach it was a great experience overall!

  • Robert V.

    Submitted Apr 8, 2025

    Stayed Apr 2, 2025

    The home was beautiful, very clean, and well prepared to receive our visit. Gertrude Rentals provided and simple and seamless rental process so we could just relax and enjoy our vacation. Any questions were answered promptly and completely. Thank you!!

  • francis R j.

    Submitted Mar 10, 2025

    Stayed Mar 5, 2025

    The Home was incredible. It is completely updated and it was exceptionally clean. It is also in a great location. Also, the property managers were fantastic. Easy to reach and followed up during the stay to make sure everything was good. I highly recommend this home.

  • Tracy L.

    Submitted Jan 26, 2025

    Stayed Jan 10, 2025

    Great stay in Siesta Beach. Enjoyed hanging out in the TV room with other families. Bedrooms were very nice and roomy. Very close to Siesta Beach restaurants which was nice. Property Manager was very responsive. Definitely a great place to stay.

  • Sharon K.

    Submitted Jan 24, 2025

    Stayed Jan 20, 2025

    Very nice property. Plenty of room. Very clean. Good location. Weather was terrible but had a wonderful time with family.

  • Amanda C.

    Submitted Nov 6, 2024

    Stayed Dec 31, 1969

    We came to Siesta Key for our son's wedding. While not all of our family stayed in the house, many dropped by at various times throughout the long weekend. Plenty of seating space for us all. And we were able to grill out in the yard on our final night together.

  • Anthony F.

    Submitted Aug 19, 2024

    Stayed Aug 10, 2024

    We had a wonderful time in this very spacious home. It was very accommodating! We had a total of 8 people in our party (2 families). The beds were very comfortable and the house was super clean! Everything was provided including bedding, towels, etc. There was even plenty of beach chairs and 2 umbrellas which came very much in handy as we went to the beach every day. The family room had plenty of seating for all of us and the 65 TV was great for evening movies (we brought our own Apple TV which we hooked up to the TV so that we could us our own Netflix, etc. streaming services). There was also a deck both on the front and rear of the house which was very popular for our group. The front deck is shaded in the afternoon and therefore became the more popular hang out when waiting to dry off from the beach, etc. We also never ran out of hot water when all of us had to take showers which was amazing to me when factoring in 8 people! The kitchen, dining room and bar seating was also great for mornings while all of us were eating breakfast, drinking our coffee, etc. Please keep in mind that walking to the beach isn't very practical since it is about mile. You can rent a golf cart from one of the local rental places but they were way out of our price range. We chose the very short 3 minute drive to Siesta Key public beach (free parking) which worked out great! Just keep in mind that if you aren't familiar with Siesta Key public beach, it is still a fairly long walk from the parking

  • Nivvi N.

    Submitted May 22, 2024

    Stayed Dec 31, 1969

    The place was excellent to stay and the staff were attentive incase of any questions we had. Everything was perfect with this house. It felt like home away from home, relaxing, all needs well taken care of.

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Total

Includes taxes and fees
$650+
View details