4BR- 5156 House Featuring Wheelchair Accessible, Air Conditioned, Pet-Friendly Vacation Lodgings

4BR- 5156
4BR- 5156
4BR- 5156
USA's #1 Beach, Siesta Key 4BR

4BR- 5156 House Featuring Wheelchair Accessible, Air Conditioned, Pet-Friendly Vacation Lodgings

Explore the spacious 2300 sq ft house at Siesta Key, FL. Accommodates whole family languorous enjoyment with Grill, Internet, Television & more amenities.


Vacation Home in Siesta Key Florida

5156 Siesta Woods Drive
How Many Bedrooms? 4 Bedrooms • Sleeps 10
How Many Bathrooms? 3 Full Bathrooms
How Much Living Space? 2300 sqft.
Air Conditioning: Yes
Pool: Pool, Pool (Private)
Internet: Internet Access
Television: Television
Wheelchair Accessible: Yes
Pet Friendly: Yes
Washer/Dryer: Yes

Rates & Availability  
(Displayed in USD)

  • Rates From $166 to $2,155 per night

Rates from $166 per night
Additional fees may apply
Book Direct 47 Rentals Available
Reservations and Guest Services at Gertrude Rentals

Daytime Phone Number
Evening Phone Number
Reference this Property as:

Property #176182
4BR- 5156


Availability details can be found on the Gertrude Rentals website.

Book Direct through Gertrude Rentals for maximum savings and service!

Availability Details

Available
Already Booked
Season Nightly Weekly Monthly
SK PEAK- PLUS 2025
Apr 01, 2025 - Apr 17, 2025
$986 n/a n/a
EASTER 2025
Apr 18, 2025 - Apr 20, 2025
$2,155 n/a n/a
SK PEAK- PLUS 2025
Apr 21, 2025 - May 08, 2025
$986 n/a n/a
MOTHER'S DAY 2025
May 09, 2025 - May 11, 2025
$511 n/a n/a
SK PEAK- PLUS 2025
May 12, 2025 - May 22, 2025
$986 n/a n/a
MEMORIAL DAY 2025
May 23, 2025 - May 25, 2025
$511 n/a n/a
SK PEAK- PLUS 2025
May 26, 2025 - May 31, 2025
$986 n/a n/a
SK PEAK 2025
Jun 01, 2025 - Jun 12, 2025
$537 n/a n/a
FATHER'S DAY 2025
Jun 13, 2025 - Jun 15, 2025
$511 n/a n/a
SK PEAK 2025
Jun 16, 2025 - Jul 02, 2025
$537 n/a n/a
JULY 4 2025
Jul 03, 2025 - Jul 05, 2025
$1,620 n/a n/a
SK PEAK 2025
Jul 06, 2025 - Jul 31, 2025
$537 n/a n/a
SHOULDER 2025
Aug 01, 2025 - Aug 28, 2025
$280 n/a n/a
LABOR DAY 2025
Aug 29, 2025 - Aug 31, 2025
$511 n/a n/a
SK OFF 2025
Sep 01, 2025 - Oct 09, 2025
$166 n/a n/a
COLUMBUS DAY 2025
Oct 10, 2025 - Oct 12, 2025
$511 n/a n/a
SK OFF 2025
Oct 13, 2025 - Nov 13, 2025
$166 n/a n/a
SAND CASTLE FEST 2025
Nov 14, 2025 - Nov 17, 2025
$511 n/a n/a
SK OFF 2025
Nov 18, 2025 - Nov 23, 2025
$166 n/a n/a
THANKSGIVING 2025
Nov 24, 2025 - Nov 29, 2025
$819 n/a n/a
SK OFF 2025
Nov 30, 2025 - Dec 18, 2025
$166 n/a n/a
CHRISTMAS 2025
Dec 19, 2025 - Dec 25, 2025
$420 n/a n/a
NEW YEARS 2025
Dec 26, 2025 - Jan 03, 2026
$1,785 n/a n/a
SHOULDER 2026
Jan 04, 2026 - Jan 14, 2026
$280 n/a n/a
SHOULDER-PLUS 2026
Jan 15, 2026 - Jan 15, 2026
$263 n/a n/a
MLK 2026
Jan 16, 2026 - Jan 18, 2026
$840 n/a n/a
SHOULDER-PLUS 2026
Jan 19, 2026 - Jan 31, 2026
$263 n/a n/a
SK PEAK 2026
Feb 01, 2026 - Feb 12, 2026
$537 n/a n/a
PRESIDENTS 2026
Feb 13, 2026 - Feb 15, 2026
$1,271 n/a n/a
SK PEAK 2026
Feb 16, 2026 - Feb 18, 2026
$537 n/a n/a
SK PEAK- PLUS 2026
Feb 19, 2026 - Feb 28, 2026
$986 n/a n/a
SK SUPER-PEAK 2026
Mar 01, 2026 - Mar 19, 2026
$1,763 n/a n/a
SK SUPER-PEAK-PLUS 2026
Mar 20, 2026 - Mar 27, 2026
$1,609 n/a n/a
EASTER 2026
Mar 28, 2026 - Apr 11, 2026
$2,155 n/a n/a
SK PEAK 2026
Apr 12, 2026 - May 07, 2026
$537 n/a n/a
MOTHER'S DAY 2026
May 08, 2026 - May 10, 2026
$511 n/a n/a
SK PEAK 2026
May 11, 2026 - May 21, 2026
$537 n/a n/a
MEMORIAL DAY 2026
May 22, 2026 - May 24, 2026
$511 n/a n/a
SK PEAK 2026
May 25, 2026 - Jun 18, 2026
$537 n/a n/a
FATHER'S DAY 2026
Jun 19, 2026 - Jun 21, 2026
$511 n/a n/a
SK PEAK 2026
Jun 22, 2026 - Jul 01, 2026
$537 n/a n/a
JULY 4 2026
Jul 02, 2026 - Jul 05, 2026
$1,620 n/a n/a
SK PEAK 2026
Jul 06, 2026 - Jul 31, 2026
$537 n/a n/a
SHOULDER 2026
Aug 01, 2026 - Aug 31, 2026
$280 n/a n/a
SK OFF 2026
Sep 01, 2026 - Sep 03, 2026
$166 n/a n/a
LABOR DAY 2026
Sep 04, 2026 - Sep 06, 2026
$511 n/a n/a
SK OFF 2026
Sep 07, 2026 - Oct 08, 2026
$166 n/a n/a
COLUMBUS DAY 2026
Oct 09, 2026 - Oct 11, 2026
$511 n/a n/a
SK OFF 2026
Oct 12, 2026 - Dec 17, 2026
$166 n/a n/a
CHRISTMAS 2026
Dec 18, 2026 - Dec 25, 2026
$420 n/a n/a
NEW YEARS 2026
Dec 26, 2026 - Jan 02, 2027
$1,785 n/a n/a

Property Description

&nbsp;<br />
The Island Time<br />
Breathtaking pool-spa 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!<br />
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What Guests Love<br />
∙ Private Pool Spa heated pool, jacuzzi, and stunning marble hard-scape *Jacuzzi not open until May 1!<br />
∙ Balconies tropical balcony, 2nd floor lounging deck, and covered alfresco area<br />
∙ Privacy two units for price of one, includes upstairs 3BR and downstairs 1BR<br />
∙ Beach world famous Siesta Key Beach, 5-min bike or 20-min walk<br />
∙ Restaurants 1-mile to free trolley for all 40 of Siesta s bars and restaurants<br />
∙ Sunsets 20-min walk to best sunsets in America or just enjoy from your pool deck<br />
∙ Activities scooter, bike, boat and kayak rentals nearby<br />
∙ Exploring - sand dollars, shells, dolphins, occasionally manatees and live conch<br />
∙ The Fun - live music, daiquiris, oysters, stone crab, craft beer, ice cream, fresh donuts<br />
∙ The Memories perfect for large groups, quiet, comfort, access to all top attractions<br />
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The Beach<br />
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.<br />
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The Home<br />
This listing is a 3BR unit above and 1BR suite below for a total of 4BR. Large and 100% private. Heated pool and jacuzzi (*Jacuzzi not open until May 1!) 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.<br />
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Property Truths and Limits<br />
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 Jacuzzi (*Jacuzzi not open until May 1!) is maintained near 100 and the pool is heated November 15 to April 15 to a target temperature near 80 . 4) Sorry, it s too to allow 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.<br />
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Bedroom Details<br />
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.<br />
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Beach Gear Provided<br />
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.<br />
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Household Items Provided<br />
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.<br />
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What to Bring<br />
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.<br />
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Post Booking Support<br />
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.<br />
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Terms<br />
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.<br />
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Travel Insurance<br />
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.


Activities and Special Interests

This property provides access to the following activities and special interests:

» Wheelchair Accessible
» Biking
» Fishing
» Golfing
» Hiking
» Scuba Diving
» Sailing
» Surfing
» Wind Surfing
» Kayaking
» Beach
» Horseback Riding
» Boating
» Pet Friendly

Property Features

» Towels/Linens
» Ceiling Fan(s)
» Refrigerator
» Coffee Maker
» Microwave
» Dishes/Utensils
» Stove
» Highchair
» Toaster
» Oven
» Freezer
» Blender
» Parking
» Hair Dryer
» Iron / Ironing Board
» Balcony

Suitability

» Children Welcome

Featured Amenities

» Wheelchair Accessible
» Air Conditioning
» Pets Allowed
» Television
» Dishwasher
» Grill
» Internet Access
» Washer/Dryer
» Pool
» Hot Tub
» Pool (Private)

Entertainment

» Books

Outdoor

» Playground