Vacation Rentals By Owner In Siesta Key, FL

Palm Shade Cottage | 0.1 Miles to Siesta Key Beach + Shared Heated Poolbrbr Why You'll Love This HomebrStep into your private Siesta Key cottage, a cozy retreat with lush landscaping and a screened-in heated pool shared with Coconut House. This 1-bedroom home offers a charming escape for couples or a small family, just 0.1 miles from the world-famous white sands of Siesta Key Beach.brbr ‍ ‍ Perfect ForbrCouples or small families seeking an intimate space with private indoor living, shared outdoor amenities, and walkable access to the beach and Siesta Key Village.brbr ️ Imagine ThisbrStart your day with a fresh cup of coffee on your private patio, surrounded by tropical greenery. Walk just 0.1 miles to Siesta Key Beach and sink your toes into soft white sand.brbrSpend the afternoon exploring boutiques and cafés in Siesta Key Village, then return to the cottage to grill a meal in the shared BBQ area. End your day with a relaxing dip in the heated pool under the stars.brbr Where You'll Sleepbr • Bedroom 1: Queen Bed, Ensuite Bathroom, Upstairs via Spiral Staircase, TVbr • Bonus Room: Full Murphy Bed, Shared Hall Bath, Ground Floor, TVbrbr Explore the Areabr • 0.1 miles to Siesta Key Beach – White sand, turquoise water, public accessbr • 0.3 miles to Siesta Key Village – Boutique shops, local eateries, nightlifebr • 0.2 miles to Local Cafés and Bakeries – Fresh coffee, pastries, and ocean viewsbr • 0.4 miles to Siesta Public Beach Park – Kayak rentals, picnic areas, family-friendly activitiesbr • Coastal energy with quiet residential streets for leisurely strollsbrbr⌛ Don't Wait - This home is part of our CottageClean™ Program: a 6-hour deep clean followed by a 35-point inspection for total peace of mind. Homes this close to the beach with a heated pool book quickly!brbr Need to Know: Palm Shade Cottage is part of a two-unit duplex and shares outdoor space and amenities with Coconut House. The pool is heated November 15–April 15. The upstairs bedroom is accessed via a spiral staircase; please contact us if stairs are an issue. Starter packs of kitchen and toiletry essentials are provided for a seamless first couple of nights.

Cottage

Palm Shade Cottage | Charming 1-Bedroom in SK, Access to Pool, Walk to Beach!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$1033.24

Tropical Retreat | Heated Pool + 1 Block to Siesta Key Beachbrbr Why You'll Love This HomebrTwo charming cottages, one unforgettable escape—Tropical Retreat brings together private indoor space and outdoor serenity just one block from Siesta Key Beach. With a screened-in heated pool, BBQ area, and alfresco dining, your group can unwind in complete exclusivity just steps from white sands and turquoise waters.brbr ‍ ‍ Perfect ForbrIdeal for multi-family vacations, couples traveling together, or groups wanting a flexible layout with separate spaces and shared outdoor amenities.brbr ️ Imagine ThisbrWake up to the sounds of palm trees swaying and take your coffee to the poolside patio. The kids splash in the heated pool.brInside Coconut House, sunlight fills the open kitchen as you prepare lunch for the group. Meanwhile, a friend naps in the sunny bedroom upstairs at Palm Shade Cottage, enjoying the privacy of a separate retreat.brCome evening, gather around the outdoor table for a tropical dinner under the stars as food sizzles on the grill. Take a sunset stroll to the beach—just one block away.brbr Where You'll SleepbrCoconut Housebr • Bedroom 1: King Bed, Ensuite Bathroom, Ground Floor, TVbr • Bedroom 2: Queen Bed, Shared Hall Bath, Ground Floor, TVbr • Bedroom 3: Two Twin Beds, Shared Hall Bath, Ground Floor, TVbrPalm Shade Cottagebr • Bedroom 4: Queen Bed, Ensuite Bath, Second Floor, TVbr • Common Space: Full Murphy Bed, Hall Bath, Ground Floorbrbr Explore the Areabr • 0.1 miles to Siesta Key Beach – White sand, turquoise water, beach accessbr • 0.4 miles to Siesta Key Village – Boutique shops, island eateries, and nightlifebr • 0.2 miles to Siesta Public Beach Park – Kayak rentals, picnic tables, and family-friendly park spacebr • 0.3 miles to Local Cafés and Bakeries – Fresh coffee, pastries, and ocean viewsbr • 0.5 miles to Turtle Beach Trail – Scenic walking path and coastal wildlifebr • Coastal energy meets quiet, residential surroundings for a relaxing strollbrbr⌛ Don't wait—this home books fast. Your reservation includes peace of mind with our CottageClean™ program: a 6-hour deep clean and 35-point inspection.brbr Need to Know: Starter packs of kitchen and toiletry essentials are provided for a seamless first couple of nights. Free high-speed WiFi is included. This pool is heated between November 15–April 15. This is a combined duplex property—Coconut House (606B) and Palm Shade Cottage (606A) are accessed by separate entrances and do not share interior space. Coconut House is a single-floor unit. If any guest has difficulty with stairs at Palm Shade Cottage, please contact us for alternative accommodations.

Tropical Retreat | Private Pool, 1 Block to Siesta Key Beach, Quick Access to Village!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$360.03

Located on the famous Crescent Beach of Siesta Key, this beachfront garden-view property comfortably hosts 4 adults or a family with children. With amenities such as tennis courts, a saltwater pool, a white-sand beach with private chairs, and a large bar-b-q and sunbathing deck to watch the incredible sunset and share meals with friends, you can please all of your guests. You can also just walk the beach for miles and take photos of the dolphins. And a short drive takes you to the quaint Siesta Key Village with its shops, restaurants, and service establishments. The property has 24 hour security. Renovated in 2018, this condo is clean and well equipped. Come and create your memories here with us!

Condo located on the best beach in the United States

Siesta Key, Florida, United States

Bed

Bath

4

Sleeps

$261.38

Easy access -- park in front of your condo. No steps. No elevators. brbrPrivate access to Siesta Key Beach.br brLocation and value. This 1st floor bayside condo offers both. Comfortable and modern amenities await your arrival. There are updates throughout including leather living room furniture, new window treatments and bedspreads. A fully equipped, remodeled kitchen and baths complete with granite countertops add a touch of luxury at an affordable price. Did I mention that the condo is very polished and clean You don’t have to break the budget staying with us.brbrCondo amenities include: leather furniture; flat screen tvs and dvd player; wi-fi internet access; free local and long distance calling throughout the United States; bed linens and towels; and cookware and dishes. Basic supplies are provided for guests so you don’t have to rush out to shop. Come as you are, sit back, and soak up the sun.brbrThe property is centrally located on Siesta Key in a resort style complex. Relax on your patio surrounded by a beautiful courtyard, fountains and bay views. Walk along the beautiful majestic royal palms to the most beautiful sandy white Siesta Key beach or simply call for a free pickup by a tip-only driver. brbrBask in the endless amenities of Palm Bay Club. The condominium community has 2 pools, tennis courts, boat and fishing dock and a recreation/exercise facility all on a beautifully maintained property. Relax on the sugar soft beach or chill by the bayside pool. Beach chairs and loungers are available for guests and cabanas are available for rent.brbrPalm Bay Club’s resort style offers the best of both worlds – beach and bayside relaxation. There are beach activities galore ranging from lazing in the sun or sauntering along the beach to jet skiing or parasailing and everything in between. The nearby newly remodeled public beach area has tennis courts, picnic areas, playgrounds, plus many more features. The bayside features a pool and hot tub, grill area, and boat docks. brbrSiesta Key is conveniently located for enjoying all kinds of activities—nature, cultural, sports, recreational shopping and nearby restaurants for every budget and taste! brbrContact us regarding any special needs. brbrNature:brbrMyaaka River State ParkbrSelby Botanical GardensbrMote Marine LaboratorybrBig Cat HabitatbrSave Our Seabirds brJungle GardensbrLegacy Trail (rail to trail) biking and hikingbrbrSports:brbrGolf (over 50 courses in the Sarasota/Bradenton area)brFishing chartersbrTennis brOriole baseball spring training (Sarasota)brPirates baseball spring training (Bradenton)brbrCultural:brbrRingling Museum of ArtbrVan Wezel Performing Arts HallbrCircus SarasotabrHistoric Spanish PointbrSarasota balletbrSarasota operabrFlorida Studio TheaterbrAsolo Repertory TheaterbrbrDining and shopping:brbrSiesta VillagebrSt. Armand’s CirclebrDowntownbr3 area mallsbrNearby restaurants for every budget and tastebrbrDay trips to Tampa and Orlando offer even more great experiences.brbrbrKeywords: Best beach, Palm Bay Club, bayside

Siesta Key Serenity At The Palm Bay Club

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$307.2

IN-GROUND POOL brbrThis is THE location! Just steps to the Village Cafe and the Hub Bar and Grille, and a short walk to the beach 3.5 Blocks to the Beach. Our 2 bedroom 2 bath beautifully updated property offers a coastal theme and open floor plan. A queen size sofa bed is included for the overnight guest. Granite countertops, stainless steel appliances, fully supplied kitchen and a Keurig machine add to the feel of this house. Primary suite with full bath, large family dining room looking over the canal. Enjoy grilling out, playing a game of corn hole or fish on the canal. This home is pet friendly. NOTE: There is a $250 fee for up to 2 dogs. Must state you are bringing a pet at time of inquiry/booking. An additional $100 will be charged if not notified about pet. The canal and pool area is a shared space with our other location - Unit A (VRBO# 1077749). Need more rooms The Units are attached, but have separate private entrances. There are no shared walls to any rooms of the Units. For guest safety, there are outside security cameras, including the pool area. Unit is smoke free. No smoking is permitted inside the units. Enjoy your stay!! :-)brbrNote: The pool temperature is dependent and subject to the outside temperature during the cooler months in Florida. When the temperature dips into the low 60’s and below during the evening, the pool may not get up to a comfortable temperature during the day.

301 Avenida Madera B -2Bed/2Bath in the center of SK Village!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$334.74

6th Floor condominium overlooking the pool and Gulf of Mexico on the best beach in the United States. 2 Bedroom (1K, 2Full) two bathrooms. Unit includes a washer/dryer, full kitchen with refrigerator & dishwasher. Television with cable & high speed wireless internet. Has a wonderful screened in balcony with chairs and tables that are nice to use to play cards after a fun day at the beach! Great for families of all sizes.

Siesta Key Midnight Cove Condo!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$289.06

**PLEASE do NOT request to book before contacting hosts. USE Contact Host button (blue letters under book now button - scroll down) BEFORE requesting to book so we can assure this special spot is a good fit for you.**br*NO dogs over 20 pounds and ONE dog only. NO more than 2 guests with ONE car.*brLOCATION!! Just steps to beach access #7 and a block from Siesta Village. CUTE one story fishing cottage takes you back to the old Key with a private Key West style courtyard with swing and small pond. Inside, you'll find original pickled cypress walls and heart pine floors, but modern amenities; HDTV, Keurig, Nespresso & conventional coffee pots, in unit washer/dryer, wifi & printer, mini split HVAC, updated zero entry bath & totally new kitchen. Walk to the Village restaurants and shops or just cross the street to the number one beach in the U.S. with powder white sand. One large bedroom with queen bed.brOne week minimum rental in peak season, 5 days off season.brIdeal for one person or 2 people MAX (no additional overnight guests please). ONE pocket-book sized dog considered (under 20 pounds). NO Cats, NO smoking indoors.brThis is our very special getaway that we treat with love and care, and we are super protective. br*Note - there is an exterior security camera inside the garden gate at the entrance.brSee virtual tour at link!

Cottage

Key West style beach cottage JUST STEPS from #1 SIESTA KEY BEACH!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$385.49

Welcome to your slice of paradise! Our stunning vacation rental offers the ultimate beachside getaway, providing you with a luxurious and unforgettable experience right on the main strip of the world-renowned Siesta Key Beach and the vibrant Siesta Key Village. The apartment or best referred to as CasaPlaya, features open concept living, a chic kitchen, fully upgraded bathroom and screened in Florida Room for your enjoyment.

Enchanting Coastal Ambiance & Breathtaking Sunsets

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$370.59

This Siesta Key gulf side rental is located on one of the widest and most beautiful stretches of beach in the world. Beachaven is located at the ‘center’ of Siesta Key’s Crescent Beach (giving it the best vantage point for sunsets), and enjoys the widest private beach on all of Siesta Key, and likely the largest private beach in the entire world. The crystal clear aqua water of the Gulf of Mexico and unique pure white sand made of 99% quartz (so it never gets hot on your bare feet) will be your private playground. brbrMost complexes on the gulf side of Siesta Key have a pool located at the center of the complex or at the beginning of the complex near the road. This complex has one of the few pools that is literally located directly on the beach so you can watch another spectacular sunset while floating in your own private pool. Or take a dip in the ocean and come back to the pool when you're done with the salt water. brbrThis incomparable two story villa, is steps from the #1 rated beach in the USA. This 1800 square foot, 2 bedroom 3.5 bath condo has undergone a complete gut renovation down to the studs with all new plumbing, electrical, and unique open concept living that includes an attached garage and laundry that you won't find at any other condo with this incredible location. The kitchen on the second floor is simply spectacular and looks like something out of magazine with professional decorating adding to the upscale feel. Gather friends around the large ten foot kitchen island with Cambria Quartz countertops while watching a game on the large 60 TV or watching the sunset out your window. Everything is brand new with ocean views from the second level of this two level condo. Very open floor plan with two bedrooms, a murphy bed on the first floor that provides even more sleeping and a pull out sofa. Two 60 HD tvs as well as a 50 in the bedroom. All new furniture, chefs kitchen, 3.5 baths, W/D in unit. Sleeps up to 6. No pets no smoking. This is truly a one of a kind property with nothing like it on Siesta Key! Inquire today!! One month minimum. Now accepting booking for 2026 and 2027, this unit will not last!brbrThere is plenty to enjoy in Siesta Key! Whether it’s walking the beach, basking in the sun, paddle boarding, shelling, fishing, restaurants, shopping, or just watching the spectacular sunsets! There is also a smaller unit (VRBO # 7946264) that is newly renovated right next to this two story unit that would make a perfect Mother-in-Law, nanny or additional family suite. Combine the two rentals for a 3 bedroom, 4.5 bath, over 2300 Sq foot experience for weddings, family reunions and beach vacations. brbrLounge chairs and seating are provided at both pools and the beach. The complex is just 1.5 miles south of The Village, where you will find plenty of local dining spots and shops. brPlease call or e-mail with questions. Must see to appreciate this one of a kind property. brbrPAYMENT SCHEDULEbrRefundable security deposit of $500.00 due within 14 days from the date you receive the contract plus $300 for each rental month.brbrStay must be continued occupancy in the same villa.brbrbrbrCANCELLATIONbrIf cancellation is 90 days or more prior to the rental start date, all monies will be refunded less $50.00 clerical fee.brIf cancellation is less than 90 days of rental start date, no refund of monies collected shall be made.brNo refunds for early departures.brSecurity deposit ($500.00) will be refunded in full for all cancellations. Any changes to the initial contract will be a charge of $50 per changebrbrOccupancy Rates quoted are for:brfour (4) people for a two (2) bedroom villabrbrMaximum Occupancybr2 bedroom villa - 6 peoplebrMust be 21 years of age to rent a villabrRecycling Guidelines and Rules & Regulations will be available in each villa. Cleaning fee included in rent.brbrNO PETSbrNO SMOKING IN VILLAbrbrTop 10 Beaches in the World 2022 by Big 7 Travel Travel! Siesta Key #1 and only beach in the United States recognized!br1. Playa Conchal, Guanacaste, Costa Ricabr2. Turquoise Bay, Exmouth, Austrailiabr3. Grace Bay, Providenciales, Turks and Caicosbr4. Siesta Beach, Siesta Key, Florida, United Statesbr5. Punta Mosquito, Holbox, Mexicobr6. Secret Lagoon, Miniloc Island, El Nido, Palawan, Philippinesbr7. San Fruttoso, Liguria, Italybr8. Pedn Vouder, Cornwall, Englandbr9. Boulders Beach, Western Cape Province, South Africabr10. Reynisfjara Beach, Vik I Mydral, Iceland

Newly renovated Siesta Key 2br 3.5 bath condo! 1800 sq ft. #1 beach in the USA!

Siesta Key, Florida, United States

Bed

3

Bath

Sleeps

$696.91

Luxury 4BR Home with Private Pool & Spa on Palm Island – Walk to Beach & Village!brbrWelcome to your perfect Siesta Key getaway on exclusive Palm Island! This elegant and spacious 4-bedroom, 3-bathroom vacation home comfortably sleeps up to 8 guests and offers the ultimate combination of privacy, luxury, and unbeatable location—just a short stroll to Siesta Key Beach and the vibrant Village.brbrStep into the beautifully appointed main house, featuring 2 bedrooms and 2 bathrooms. The master suite boasts a king-sized bed and a private en suite bathroom, while the guest bedroom includes two twin beds—ideal for families or friends. A second full bathroom also doubles as a convenient pool bath.brbrStep outside to your private oasis—complete with a sparkling pool and a built-in hot tub. The pool can be heated to a cozy 84 degrees during cooler months for just $25/day. It's the perfect space to relax after a day at the beach or exploring the island.brbrUp a private staircase, you'll find a separate guest retreat with 2 additional bedrooms. One bedroom features a king bed, while the other offers a queen bed and a sleeper sofa—perfect for extra guests. Whether you're traveling as a family or with friends, this layout provides flexibility and privacy for everyone.brbrThe home is always rented as one unit, so you’ll have the entire property to yourself.brbrLocated on serene Palm Island, you're just a short walk or bike ride to both the world-famous Siesta Key Beach and the lively Village area filled with restaurants, shops, and nightlife.brbrRental Details:brbrSleeps 8 comfortablybrbrPrivate heated pool & spa ($25/day heating fee)brbrWeekly rentals available in the off-seasonbrbrWe dont allow Pets or animals of any kind, no RVs or Campers Allowed on Site, No Weapons, No Smoking. brbrBook your next island escape and experience the best of Siesta Key from the comfort and privacy of this exceptional Palm Island retreat!

Luxury 4BR Home with Private Pool Siesta Key

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$617.06

This apartment has been decorated to make feel like home with very cozy atmosphere. Has beautiful over sized closed in lanai. You can enjoy morning coffee and breakfast or just relax a in the afternoon or evening breathing fresh air. Ideal location, right in the center of Siesta with all restaurants, bars, live music, shopping, biking and so much more. You will be right on the Siesta Beach, to enjoy fresh tropical breeze, whitest, finest, crystal sand #1 Beach in United States. brWe constantly remodeling and redecorating. Your needs and comfort is our priority. This apartment is very clean and supplied with all you might need, while you stay here. Fully equipped kitchen, fresh sheets, all towels and beach towels, beach chairs ,and so much more. We just did huge downstairs decking and entire landscaping, so you van enjoy to sit privately with more friends or family.brbrWe appreciate and respect your privacy, but we are available to help you any time, that you might need us. We care, that your vacation is most pleasurable and memorable as possible.br

Prime Location on Siesta Beach, Includes everything, you possibly want!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$345.15

Our condo is located in Sunset Royale Condominiums at 711 Beach Road, Siesta Key, Florida 34242.brbrWelcome to our charming 1-bedroom, 1-bath condo, a contemporary oasis just steps away from the renowned Siesta Key Public Beach. This stylish vacation retreat is perfect for couples or small families seeking a tranquil and convenient escape. brbrWith a comfortable king bed in the main bedroom, and additional sleeping spaces (a twin bunk bed, and a queen sized sleeper sofa) in the living room, this condo can comfortably sleep up to 6 people.brbrOur fully equipped kitchen boasts sleek countertops, stainless steel appliances, and all the amenities you need to whip up a delicious meal. Enjoy your culinary creations at the dining area, or take advantage of the warm Siesta Key weather and pack a picnic to enjoy on the beach!brbrWhile our property doesn't have a pool or a hot tub, we are thrilled to highlight its prime location mere steps from the beach. The stunning beach with it's warm ocean waters just a stone's throw away offers a serene and captivating setting, creating a unique experience where you can unwind, relax, and embrace the natural beauty surrounding you. We believe that the enchanting beach will provide an extraordinary atmosphere that rivals the need for a pool, allowing you to immerse yourself in the calming sounds of the ocean and the invigorating sea breeze throughout your stay.brbrConvenience is key, and with our condo's unparalleled location you will have easy access to the island's attractions, shopping districts, and entertainment options. Whether you're seeking a romantic getaway or a family vacation, our Siesta Key retreat provides the perfect blend of modern luxury and coastal charm. Book your stay now and make lasting memories in this coastal paradise!brbrWe own another unit that is the same size as this condo in the same building. If you are interested in booking two condos that are nearby each other for your larger party, please send me a message to check for availability and preview our other listing.

Good Vibrations- Stay right ON the beach in Siesta Key! Sleeps 6

Siesta Key, Florida, United States

1

Bed

1

Bath

Sleeps

$2625.92

The Village Breeze 8BR (REMODELED '25). No car required! Four side by side 2BR Siesta Key vacation rental units near shopping dining and attractions, with heated Pool, near Beach, but just 250ft to the world famous Siesta Key Village. A true favorite of initiated guests, and sure to provide a combination of fun and rejuvenation you won't find in other getaways. *NEW LISTING!! Please read the other Gertrude Rentals reviews. We are very proud of them!brbrWhat Guests Lovebr∙ The Village – 1-min walk to 25 restaurants in world famous Siesta Villagebr∙ The Fun – steps to live music, daiquiris, oysters, stone crab, craft beer, ice cream & donutsbr∙ Space - 4 separate private units (8BR total) perfect for larger groups who enjoy spacebr∙ Decor – beautifully remodeled thru-out in May 2025br∙ Sunsets – 8-min walk to Siesta Key's best sunsets & 300-degree Gulf viewsbr∙ Exploring - sand dollars, shells, dolphins, occasionally manatees and live conchbr∙ Activities - kayak, bike, paddleboard, scooter, golf cart rentals nearby br∙ No Car Required - you're already where everyone on Siesta Key wants to be:)br∙ The Memories - one of a kind Siesta Key experience, the favorite of initiated visitorsbrbrThe LocationbrThe possibilities are endless! Enjoy the best Beaches, Seafood, Drinks, Ice-Cream, Shopping, Oysters, Live-Entertainment, fresh-Donuts, Daiquiris, big-Breakfast, and the Coldest-Beer on the Island. Rare secluded street in the heart of Siesta Keys world famous Village. Just a short walk to two of the best beaches on the planet and only 250 feet to all the best of the Village. One of only four units in this building. The beaches at this location are the widest and have panoramic views of the gulf to the North-West-and-South and are the top spot in North America for viewing sunsets. You can swim or “often” wade to Sand Dollar Island, a naturally occurring white sand cay popular with dolphin's sand-dollars and “occasionally” giant-conch. The water is shallow clear and calm with white quartz-sand tide-pools perfect for sleeping drinking or playing. This is the only Siesta neighborhood where you can go from the water to lunch or dinner and back to the sand without putting on your shirt and shoes. brbrProperty TruthsbrOur front is residential but the back is alley access for stores. This is the heart of Siesta Village with many nearby shops restaurants stores and attractions. It won't be noisy, makes shopping and other activities convenient, but we want you to be aware.brbrPossible Siesta Key ItinerarybrWakeup, decide if you will wear shoes today, then head to Sun Garden Café for a Crab Cake Benedict. Theirs is the best and they serve breakfast til 12 so there's no rush. Eat there Al Fresco, return to the pool, or walk over to the beach and look for dolphins, swim, bike, or just or just go back to sleep. This is a special spot so exploring a little will be worth your while. I like wading out to the sand bar at low tide. Bike rides on the beach are also amazing. Bike south to check out Point of Rocks or north and east to Big Pass. I usually skip lunch and have a 3PM happy hour meal at SKOB or the Hub, after drinking my fill I grab a real dinner, then walk back down to the beach to watch the sunset and digest. The sunsets are amazing, it's what leaf season in the north would be like if it happened every day, and if they had dolphins and great weather there. Now it's dark and you can go out or go to bed, but you have to make a decision. While deciding consider my grandmothers advice “Life is a string of pearls and you never know how many you have left.”- GVLJbrbrBedroom DetailsbrThis is four ground floor 2BR units (8BR total, sleeps 24). Each unit has a king bedroom, a queen bedroom, and a queen sleeper sofa in the living room. If you need more space, I can get an additional unit nearby. brbrBeach GearbrThis vacation rental comes with beach towels and beach chairs at every location, umbrellas and carts. Correction for Air-b-n-b listings, we do not provide snorkeling gear at any locations. Sorry for the confusion. Snorkeling gear can be rented or purchased nearby.brbrSupport Post BookingbrI understand vacation time is precious and I will make sure you get the most out of it. My number is the only contact information you need. My units are at the top attractions on the island. Cars are never required, but you will have private parking near the unit. Check-in any day of the week at any time using your private door-code. No requirement ever at checkout. Free early check-in when possible. Never hidden fees or solicitations. Every unit including this one is available for instant booking. brbrEventsbrMany of our properties are wonderful locations for gatherings, unfortunately this unit cannot allow gatherings involving third party vendors or visitors outside your occupancy limit.brbrTermsbrPayments 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. brbrTravel InsurancebrIf 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.

NEW LISTING! The Village Breeze 8BR with heated Pool, near Beach, 250ft to Siesta Key Village!

Siesta Key, Florida, United States

8

Bed

Bath

24

Sleeps

$1011.87

The Village Breeze 4BR (REMODELED '25), a Gertrude Rentals property. No car required! Two side by side 2BR/1Bath units in an enviable location on quiet street, with heated Pool, near Beach, but just 250ft to the world famous Siesta Key Village. A true favorite of initiated guests, and sure to provide a combination of fun and rejuvenation you won't find in other getaways. *NEW LISTING!! Please read the other Gertrude Rentals reviews. We are very proud of them!brbrWhat Guests Lovebr∙ The Village – 1-min walk to 25 restaurants in world famous Siesta Villagebr∙ The Fun – steps to live music, daiquiris, oysters, stone crab, craft beer, ice cream & donutsbr∙ Space - 2 separate private units (4BR total) perfect for larger groups who enjoy spacebr∙ Decor – beautifully remodeled thru-out in May 2025br∙ Sunsets – 8-min walk to best sunsets in America & 300-degree Gulf viewsbr∙ Exploring - sand dollars, shells, dolphins, occasionally manatees and live conchbr∙ Activities - kayak, bike, paddleboard, scooter, golf cart rentals nearby br∙ No Car Required - you're already where you want to be:)br∙ The Memories - one of a kind Siesta Key experience, the favorite of initiated visitorsbrbrProperty Truths - Our front is residential, but the back is alley access for stores. This is the heart of Siesta Village with many nearby shops restaurants stores and attractions. It won't be noisy, makes shopping and other activities convenient, but we want you to be aware.brbrbrThe Location – The possibilities are endless! Enjoy the best Beaches, Seafood, Drinks, Ice-Cream, Shopping, Oysters, Live-Entertainment, fresh-Donuts, Daiquiris, big-Breakfast, and the Coldest-Beer on the Island. Rare secluded street in the heart of Siesta Keys world famous Village. Just a short walk to two of the best beaches on the planet and only 250 feet to all the best of the Village. One of only four units in this building. The beaches at this location are the widest and have panoramic views of the gulf to the North-West-and-South and are the top spot in North America for viewing sunsets. You can swim or “often” wade to Sand Dollar Island, a naturally occurring white sand cay popular with dolphin's sand-dollars and “occasionally” giant-conch. The water is shallow clear and calm with white quartz-sand tide-pools perfect for sleeping drinking or playing. This is the only Siesta neighborhood where you can go from the water to lunch or dinner and back to the sand without putting on your shirt and shoes. brbrPossible Itinerary - Wakeup, decide if you will wear shoes today, then head to Sun Garden Café for a Crab Cake Benedict. Theirs is the best and they serve breakfast til 12 so there's no rush. Eat there Al Fresco, return to the pool, or walk over to the beach and look for dolphins, swim, bike, or just or just go back to sleep. This is a special spot so exploring a little will be worth your while. I like wading out to the sand bar at low tide. Bike rides on the beach are also amazing. Bike south to check out Point of Rocks or north and east to Big Pass. I usually skip lunch and have a 3PM happy hour meal at SKOB or the Hub, after drinking my fill I grab a real dinner, then walk back down to the beach to watch the sunset and digest. The sunsets are amazing, it's what leaf season in the north would be like if it happened every day, and if they had dolphins and great weather there. Now it's dark and you can go out or go to bed, but you have to make a decision. While deciding consider my grandmothers advice “Life is a string of pearls and you never know how many you have left.”- GVLJbrbrBedroom DetailsbrThis is two side by side, ground floor 2BR units (4BR total, sleeps 12). Each unit has a king bedroom, a queen bedroom, and a queen sleeper sofa in the living room. If you need more space, I can get an additional unit nearby. brbrBeach Gear - Correction for Air-b-n-b listings. We provide beach towels and beach chairs at every location, umbrellas and carts at most locations, and do not provide snorkeling gear at any locations. Sorry for the confusion. Snorkeling gear can be rented or purchased nearby.brbrSupport Post Booking - I understand vacation time is precious and I will make sure you get the most out of it. My number is the only contact information you need. My units are at the top attractions on the island. Cars are never required, but you will have private parking near the unit. Check-in any day of the week at any time using your private door-code. No requirement ever at checkout. Free early check-in when possible. Never hidden fees or solicitations. Every unit including this one is available for instant booking. brbrEvents - Many of our properties are wonderful locations for gatherings, unfortunately this unit cannot allow gatherings involving third party vendors or visitors outside your occupancy limit.brbrTerms - 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. brbrTravel 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.

NEW LISTING! The Village Breeze – 4BR/2BA, Pool, Walk to Beach & Siesta Key Village (2 Units)

Siesta Key, Florida, United States

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$601.05

Beautiful brand new three bedroom which has three king-size beds three full bathroom penthouse condo At the #1 beach. Enjoy one-of-a-kind views from the top floor spacious patio balcony, or come enjoy a meal inside watching the sunset from the Florida ceiling windows. This condo is fully furnished, kitchen has top-of-the-line appliances and large flatscreen TVs in every room. Beach chairs and beach towels also provided. Laundry machines on same floor of building. brbrSecond bed and bath shower is wheelchair accessible.

Beach front paradise located in a Condo Building Beach front Penthouse!

Siesta Key, Florida, United States

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Sleeps

$240.3

New to Vrbo, be one of the first guests to stay! The Coastal Cottage is newly renovated, first floor unit located in the popular White Sands Village! Premium upgrades include oversized quartz island, open floor plan, high quality finishes in both bathrooms, smart refrigerator with built in Keurig, designated built-in office space with queen-sized Murphy bed, custom closets & washer/dryer in private enclosed mud room! Short walk across the street to the beach, tennis courts and private community marina!brbr*Small dogs under 20lbs are welcome, $250 pet fee is required prior to check-in. Please let host know if you plan on bringing your pet so that the office may be notified. brbr*A starter kit of paper towels, toilet paper, trash bags, laundry detergent, and coffee are provided. Travel sized shampoo/comditioner and soap are also provided. Any additional items that you may need througout your stay can be purchased at one of the local grocery stores.

Coastal Cottage-Steps to Siesta Key Beach

Siesta Key, Florida, United States

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Bath

Sleeps

$198.47

Welcome to Little Sandy Cove, a modern condo on Siesta Key. Walk to Siesta Key Village, then unwind with direct access to a private sandy cove and community fishing pier. Spend your days fishing, watching dolphins, and catching Gulf sunsets. brbr brbrNote: Second-floor unit, stair access only; no elevator. brbr brbrProperty Highlights brbr- Private Beach Cove: Enjoy exclusive access to a sandy beach just steps away from your door. brbr- Private Fishing Pier: Perfect for fishing enthusiasts with some of the best fishing on Siesta Key. brbr- Modern, Standalone Condo: No shared walls for ultimate peace and privacy. brbr- Vaulted Ceilings & High-End Finishes: Contemporary design with wood flooring throughout. brbr- Private Carport: Includes a convenient storage locker and a private washer/dryer. brbr- Peek-A-Boo Ocean Views: Relax on your main balcony with partial views of the Gulf. brbr- Short Walk to Siesta Key Village: Just 6 minutes to shops, restaurants, and entertainment. brbr- Proximity to Public Beach Access: A quick walk, less than 1-mile to the popular Beach Access #2. brbr brbrCondo Features brbr- Master Bedroom: Comfortable queen bed with hardwood floors, closet, dresser, and direct access to the bathroom. brbr- Living Room: Relax on the sofa sleeper with a new coffee table, vaulted ceilings, and a Samsung Smart TV with WiFi and cable. brbr- Kitchen: Fully equipped with high-end Thermidor & Wolf stainless appliances, Onyx countertops, a pantry, and a wine refrigerator for your convenience. brbr- Bathroom: Features a modern Onyx-tiled shower and vanity with a second access door to the living room for guest convenience. brbr- Balconies: Enjoy multiple balconies offering peaceful outdoor spaces, including a front balcony with partial Gulf views. brbr- Beach Gear: We provide towels, 2 beach chairs, and a sun umbrella for your beach days. brbr- Parking: Assigned covered carport with private washer/dryer in a storage locker. brbr brbrCommunity Amenities brbr- Private Beach: Relax and unwind on the private sandy beach with stunning views of Big Pass and Lido Key. brbr- Fishing Pier: Perfect for fishing and watching the dolphins play in the Gulf. brbr- Lake with Fountain: A serene spot to enjoy nature and unwind. brbr brbrLocation brbr- Siesta Key Village: Only a 5-minute walk to local shops, dining, and entertainment, including The Salty Dog pub and Morton’s Siesta Market. brbr- Beach Access: A 15-minute walk, bike ride, or free shuttle ride to the public beach, or just stroll down to Beach Access #2. brbr- Proximity to Sarasota: Conveniently located near the north bridge for easy access to downtown Sarasota's shops, dining, and theatre. brbr brbrAdditional Information brbr- No Smoking, No Pets: This property is smoke-free, including vaping, and does not allow pets. brbr- Booking Restrictions: An approved HOA application is required for occupancy, which may take up to 3 weeks. If there are any delays, we’ll adjust your trip accordingly.brbrIMPORTANT: The min age to rent is 25 years old. No parties, large gatherings. Please reach out if you have any questions.

Condo with Private Beach | Walk to SK Village | Stand Alone Unit | Fishing Pier | Monthly Visitors

Siesta Key, Florida, United States

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Sleeps

$465.27

Enjoy our little slice of paradise on 4 miles of white sandy beaches with breathtaking sunsets. Beautifully updated and tastefully decorated 2nd floor beachfront condo with easy access to a covered parking spot and the beach. Well-equipped and recently updated kitchen with stainless steel appliances and hardwood cabinets that is perfect for those who love to cook. Two beautifully decorated and updated bedrooms with king size Serta Foam mattresses. The bathrooms are recently updated with granite countertops. High speed wireless Internet, large flat screen Smart HDTV in the living room, and flat screen TV’s in both bedrooms. Beautiful crown molding, tile floors, plantation shutters and six panel doors throughout. Free long distance calls in the US, Canada, and Mexico.

Little slice of paradise, Siesta Dunes 2-209.

Siesta Key, Florida, United States

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Bath

Sleeps

$392.15

Newly Renovated Siesta Key Condo | Ocean & Bay Views | Sleeps 6 | The Palm Bay ClubbrExciting Updates May 2025!brOur condo underwent a full renovation, including brand new bathrooms, flooring, doors, trim, and sleek granite kitchen countertops. Get ready for an even better beach getaway!brbrWelcome to Siesta Key For Me Condo #310brLocated at the iconic Palm Bay Club, one of Siesta Key’s premier waterfront resorts, this stylish 2-bedroom, 2-bathroom Bayside Suite sleeps up to 6 guests. Enjoy a coastal retreat with breathtaking views, just steps away from both the Inter-coastal Waterway and our private Gulf beach.brbrSleeping ArrangementsbrMaster Suite: King bed with private bathbrSecond Bedroom: Two full beds with private bathbrbrFully Equipped KitchenbrEnjoy cooking and entertaining in our open-concept kitchen with stainless steel appliances and granite countertops, all while soaking in the water views from the living area.brbrInterior HighlightsbrAll-new furnishings, paint, window blinds, and beddingbrbrDining set for family mealsbrbrHigh-speed WiFi and flat-screen TVsbrbrFresh linens & towels providedbrbrResort Amenitiesbr2 Swimming Pools (1 beachside, 1 bayside)brbrCustom Hot Tub overlooking the baybrbrPrivate Beach Access with lounge chairs providedbrbrFitness Center & Tennis CourtsbrbrLaundry Facilities with new machinesbrbrWe even provide coolers and a beach wagon to make your beach days stress-free!brbrPrime Locationbr4-5 minute walk to the beach via crosswalkbrbr2 miles to Siesta Key Village – shops, restaurants, and nightlifebrbrGated resort with on-site parking (1 car per unit)brbrPlanning Your Stay brFor added peace of mind, we highly recommend purchasing travel insurance.brbrStay Connected:brFollow us on Facebook for updates, photos, and last-minute deals:brSiesta Key For MebrbrCome experience the best of Siesta Key—soft white sands, endless sunshine, and the beautiful Palm Bay Club. Your dream vacation starts here!

Siesta Key For Me @ The Palm Bay Club

Siesta Key, Florida, United States

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