House in Siesta Key, FL
10 guests · 4 bedrooms · 3 baths
Reasons to book
Guests love it hereGuests give this property a top rating
Great for petsBring all your friends and family, even the furry ones
Top-tier experienceA high end property in this area
About this house rental
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.
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.
Amenities at Gertrude's Siesta | Pool & Spa, 100% Private, 5-min bike to Siesta Key Beach, 3-miles to Village!
Non-smoking
Pets allowed
Family friendly
Map of Siesta Key, FL
Ratings and reviews
10 / 10Outstanding·Feb 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.
10 / 10Outstanding·Dec 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
10 / 10Outstanding·Dec 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
10 / 10Outstanding·Oct 2025
We love all off the site and the property
$$$$
Top rated by guests
9.6Outstanding
(30 Ratings)
"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 approac..."
Rhonda S.Don't miss out! Price and availability may change
