Gertrude's Siesta | Pool & Spa, 100% Private, 5-min bike to Siesta Key Beach, 3-miles to Village!
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.
Our prices include all fees. No hidden fees.
Add dates for prices
Have a question?
AI iconBetaBeta
Get instant answers with AI powered search of property information and reviews.
If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with UK consumer law, property booking services are not subject to the right of withdrawal.
This property is managed by a professional host. The provision of housing is linked to their trade, business or profession.
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit and a deadlock
About the area
Siesta Key
Located in Siesta Key, this holiday home is near theme parks and near the beach. St. Armands Circle and Mall at University Town Center are worth checking out if shopping is on the agenda, while those wishing to experience the area's natural beauty can explore Siesta Key Beach and Crescent Beach. Travelling with kids? Consider Mote Marine Laboratory & Aquarium, or check out an event or a game at Ed Smith Stadium. Jet skiing and kayaking offer great chances to get out on the surrounding water, or you can seek out an adventure with hiking/biking trails and horse riding nearby.
St. Boniface Episcopal Church Labyrinth - 15 min walk - 1.3 km
Siesta Key Beach - 2 min drive - 2.1 km
Irma Beach - 2 min drive - 1.8 km
Siesta Key Beach Playground - 3 min drive - 2.1 km
Crescent Beach - 7 min drive - 4.8 km
Getting around
Sarasota, FL (SRQ-Sarasota-Bradenton Intl.) - 28 min drive
Restaurants
Circle K - 4 min drive
Gilligan's Island Bar & Grill - 4 min drive
Siesta Beach Pavilion - 2 min drive
Siesta Key Oyster Bar - 4 min drive
Daiquiri Deck Siesta Key Village - 4 min drive
Frequently asked questions
Does Gertrude's Siesta | Pool & Spa, 100% Private, 5-min bike to Siesta Key Beach, 3-miles to Village! have a pool?
Yes, this property has a pool. Pool types include heated pools.
How much does it cost to stay at Gertrude's Siesta | Pool & Spa, 100% Private, 5-min bike to Siesta Key Beach, 3-miles to Village!?
As of 1 Sept 2026, prices found for a 1-night stay for 2 adults at Gertrude's Siesta | Pool & Spa, 100% Private, 5-min bike to Siesta Key Beach, 3-miles to Village! on 2 Oct 2026 start from £1,665, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
Is Gertrude's Siesta | Pool & Spa, 100% Private, 5-min bike to Siesta Key Beach, 3-miles to Village! pet-friendly?
Yes, pets are allowed at this property.
How much is parking at Gertrude's Siesta | Pool & Spa, 100% Private, 5-min bike to Siesta Key Beach, 3-miles to Village!?
On-site parking is available at the property.
What time is check-in at Gertrude's Siesta | Pool & Spa, 100% Private, 5-min bike to Siesta Key Beach, 3-miles to Village!?
Check-in begins at 3:00 PM.
What time is check-out at Gertrude's Siesta | Pool & Spa, 100% Private, 5-min bike to Siesta Key Beach, 3-miles to Village!?
Checkout is at 10:00 AM.
Where is Gertrude's Siesta | Pool & Spa, 100% Private, 5-min bike to Siesta Key Beach, 3-miles to Village! located?
This family-friendly Siesta Key holiday home is located by the sea, within 1 mi (2 km) of St. Boniface Episcopal Church Labyrinth, Irma Beach and Siesta Key Beach Playground. Siesta Key Beach is 1.4 mi (2.3 km) away.