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Condo holiday rentals in Saint Armands Key

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Top-rated condo rentals in Saint Armands Key

Guests agree: These condos are highly rated for location, cleanliness and more.

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Top Guest favourite
A modern living room features a light-colored leather sofa and armchairs, complemented by a colorful area rug. A wall-mounted TV is positioned against a textured stone wall, with natural light filtering through sliding glass doors that lead to a screened-in patio.
Condo in Siesta Key
5.0 out of 5 average rating, 169 reviews

❤️ Hidden Gem steps away from #1 beach 🏖 Siesta Key

Welcome to Mi Casa Siesta on Siesta Key, the #1 beach in the country! Gorgeous newly renovated one-bedroom condo within a 5 min walk to the powdery white sandy beach and stunning sunsets. Also next to restaurants, bars, kayak & jet ski rentals, and much more! Contact for monthly rentals available. Experience this modern oasis: • Chic Living Room • Quartz Kitchen Countertops • King Size Mattress • Beach gear • Wifi • Private Parking • Smart TVs • Screened-in Patio • Coin Laundry room on premises

ValueFamilySleep quality

Top Guest favourite
A spacious living area features a comfortable sofa and two cozy armchairs. A wooden coffee table sits at the center, complemented by a geometric area rug. Large sliding glass doors provide natural light and lead to an outdoor seating area, showcasing a view of the beach.
Condo in Siesta Key
4.95 out of 5 average rating, 146 reviews

NO Stairs, Siesta beachfront. Walk to the village!

Welcome to your own private getaway directly on Siesta Beach! This ground floor unit is just steps from the powdery sands of Siesta Key. NO STAIRS Enjoy the updated bathroom with quartz countertops, new fixtures, paint, new furnishings, and décor. You literally walk out your door and directly onto the beautiful, fine, powdery white sand of Siesta Key Beach. Private Paradise directly on the white powdery sand of Siesta Key! 2 bedrooms 1.5 bathroom beachfront home with Gulf views that sleeps 6.

ValueFamilyBeach

Guest favourite
A light-filled bathroom is visible, featuring a modern sink with a glass basin. Towels are neatly hung on the wall. A doorway leads to a bedroom with a spacious bed, complemented by a ceiling fan and natural light flowing through a large window.
Condo in Siesta Key
4.85 out of 5 average rating, 428 reviews

[Sunny in Siesta] King bed+5 minute walk to beach

Your relaxing beach vacation awaits! Enjoy the island life from a freshly remodeled condo. Quick stroll to the #1 beach in the US. Public Access #12 (5 min walk) or hop on the free trolley to Siesta Beach & the Village. Can’t beat this location...Walk to Crescent Club, Captain Curt’s, Big Water Fish Market, Daquiri Deck & more. Beach gear includes- wagon., 2 chairs, small cooler and beach towels. 2 Bikes available to rent (40 per bike) King bed BEAUTY REST BLACK & queen sofa bed.

FamilyValueDecor

Guest favourite
The exterior of the condo displays a modern design with a light color palette. Palm trees are positioned around the landscaped area, and two garages are visible, along with a walkway leading to the entrance. The sunny sky enhances the welcoming appearance of the property.
Condo in Siesta Key
4.85 out of 5 average rating, 110 reviews

Comfy Siesta Key Condo

Ground floor 2 bedroom 2 bath condo in the heart of Siesta Key. Master suite with recently remodeled en suite bath. King bed in master. 2nd bedroom has a double bed and easy access to the full bath. Enjoy your morning coffee on the lanai before taking the easy walk Siesta Key private beach. Or just walk out the front door and spend the day at pool. Garage is stocked with beach and pool supplies like chairs, toys and a cooler. We have done some recent freshening up with new furniture.

ValueLocationPool

Guest favourite
A sandy pathway leading to a beach is framed by lush dune vegetation. The scene captures a vibrant sunset over calm waters, with soft clouds reflecting warm hues. Natural light creates an inviting atmosphere, highlighting the serene transition from land to sea.
Condo in Longboat Key
4.8 out of 5 average rating, 142 reviews

Gulfront Views! BEACHFRONT BARGAIN HUNT NOMINATED

THIS UNIT WAS NOMINATED TO BE FEATURED ON BEACHFRONT BARGAIN HUNT! Unit #102 Features: Full-size kitchen and Gulf-front views Bedding: 1 Queen Murphy Bed and a Sleeper Sofa Savor warm Gulf breezes while resting lavishly in this Gulf-front condo complex. Located directly on the beach, this resort features beautiful Gulf-front views. You are only steps from the white-sand beaches, placid turquoise waters and beautiful sunsets that will have you daydreaming about your next beach vacation.

ValueLocationAccess

Top Guest favourite
A dining setting on a patio table showcases a plate of breakfast foods, including a toasted bagel, fruit, and a drink. Soft, rolled towels are stacked nearby, with a view of the beach and pool visible in the background.
Condo in Longboat Key
4.98 out of 5 average rating, 251 reviews

Island Time: Discounted August & September!

This sublime oceanfront studio is directly on the pristine white sands and serene blue waters of the Gulf of Mexico in Longboat Key, Florida! On the second floor, overlooking the heated pool and ocean, this dreamy studio condo is optimal for sunset viewing from a private lanai. Take a 30-second walk to the pool and secluded beach. Enjoy a relaxing vacation at our peaceful condo at The Beach at Longboat Key Resort! To see all four of our listings, click on my Host photo and scroll down...!

FamilyValueBarbecue

Guest favourite
A spacious living area features a light-colored sofa against a vibrant tropical leaf mural. A sleek white entertainment unit holds a flat-screen TV, complemented by a decorative lamp and a colorful area rug underfoot. Natural light filters through window blinds.
Condo in Bradenton
4.98 out of 5 average rating, 183 reviews

KING Bed + AMI Beaches + Beach Gear!

🎙️🦩Welcome to the Retro Flamingo! Your tropical getaway that combines style, fun, and the serene beauty of the Gulf Coast. This cozy, vibrant themed condo is the perfect destination for your next Beach vacation. Walking distance to Palma Sola Beach Causeway, where you can enjoy sun-bathing, horseback riding, jet skiing, and fishing! 5 mins or less from the Gulf of Mexico and powdery white sand beaches of Anna Maria Island! Kick back and relax in this retro “Old Florida” themed condo!

FamilyLocationLong stay

Guest favourite
Condo in Siesta Key
4.86 out of 5 average rating, 137 reviews

Beach Retreat - Jamaica Royale Unit #52

Casually elegant condo fully remodeled in 2025, and very close to beach! One bedroom, one bath unit includes quartz kitchen counters, new appliances, king bed and relaxing patio. Perfect size for 2 guests! No need to cross busy roads to get to stunning white sand; just a 5 -10 minute walk along lush grounds which boast 3 heated pools. Beach gear provided, and unit is stocked with linens and kitchen utensils. Minutes away from Siesta Village and other wonderful dining and activities.

ValueLocationLaundry

Top Guest favourite
Condo in Longboat Key
4.98 out of 5 average rating, 107 reviews

Beach Condo with Quiet, Private Beach

Escape to our serene 2-BR beachfront condo on Longboat Key. This corner unit offers stunning Gulf of Mexico views and sleeps 6. Enjoy direct beach access, a heated pool, and a private patio perfect for sunsets. Located in the quiet Beach Castle Resort, it's the ideal beach vacation rental for families or couples seeking a tranquil getaway. Walk to local restaurants and cafes from your peaceful retreat. A guest-loved home, consistently rated top 5% among Airbnb’s homes.

LocationFamilyWalkability

Top Guest favourite
A serene pool area is bordered by palm trees, reflecting the gentle hues of a sunset. Lounge chairs are arranged around the pool, and a shaded cabana is visible in the background. The tranquil water mirrors the evening sky, enhancing a peaceful atmosphere.
Condo in Siesta Key
4.97 out of 5 average rating, 134 reviews

Private Beach with Loungers · 2 Pools & Bay View

Beachside resort life for families, groups and remote workers seeking easy beach access and active days. This oversized & Fully Renovated 2‑bed, 2‑bath condo sits in a gulf-to-bay complex so you can walk to the famed Siesta Key sand and hop the island trolley outside your door. Enjoy bay views, unwind in heated pools and the hot tub, use the on-site gym and courts, and take advantage of provided beach chairs, umbrella and wagon for effortless beach days.

FamilyLocationLayout

Top Guest favourite
An aerial view shows a two-story beachfront property with direct access to the beach. A shared pool is visible in the center, surrounded by lounge chairs. The studio unit is indicated with a blue circle on the left, featuring a patio area and proximity to the sandy beach.
Condo in Longboat Key
4.87 out of 5 average rating, 209 reviews

The Beach Condo #107 Beachfront Full View

Unit #107 has private beach access. Only a few steps to the beach will full gulf view. This end condo unit is quiet, ground floor . It is a small studio: new queen murphy bed and queen sofa bed. No separate bedroom. Limited initial limited supply of products/soaps/towels. Common use W/D across from unit. This is a small studio at 330 sq ft. It has been recently remodeled. Grounds, unit, pool recently renovated due to hurricanes.

LocationFamilyHospitality

Guest favourite
A cozy sleeping area features a spacious bed topped with neutral linens and a colorful towel. A small table and chairs are positioned near a large window adorned with blinds, allowing natural light to fill the room. A flat-screen TV is mounted on the wall.
Condo in Lido Key
4.89 out of 5 average rating, 102 reviews

Lido-Key- Tiny, Yet Charming Studio-B

Lido-Key- Newly remodeled TINY (smaller than a hotel room) Studio. 7-10 min walk to the beach and St.Armands Circle. Quaint main floor tiny studio in a great location. This is an affordable way to enjoy this popular area. This cozy cottage features a Queen bed, refrigerator, stove, microwave, coffee maker, fully stocked cooking items & dishes, along with beach chairs, towels, Located at 170 Roosevelt Dr., Sarasota

FamilyValueParking

Popular amenities for Saint Armands Key condo rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Weekly condo rentals

Guest favourite
The studio features a modern kitchen with white cabinetry and a large countertop. A flat-screen TV is mounted on the wall, and natural light enters through sliding glass doors that lead to the private garden. A compact dining table and a plush blue ottoman add functionality.
Condo in Gulf Gate Estates
4.95 out of 5 average rating, 148 reviews

Modern Studio · 5 min from Siesta Beach

ValueLocationParking

Guest favourite
A bright and airy living space features a modern sofa facing a sleek coffee table. The open kitchen is visible in the background, showcasing white cabinetry and bar seating with stylish stools. Light fills the room through large windows, enhancing the spacious feel.
Condo in Sarasota
4.96 out of 5 average rating, 159 reviews

Your Modern Beachside Getaway!

FamilyValueHeating

Top Guest favourite
Condo in Longboat Key
4.89 out of 5 average rating, 122 reviews

Beachfront Escape – Private Balcony, Gulf Views

ValueLocationIndoor spaces

Top Guest favourite
Condo in Sarasota
4.98 out of 5 average rating, 130 reviews

Lovely 2-Bedroom Condo, 7 min from Siesta Beach

FamilyLocationIndoor spaces

Guest favourite
An open concept living area features a blend of modern and comfortable furnishings. A dark wooden coffee table is centered on a textured rug, with a stylish mirror and a ceiling fan overhead. Large glass doors allow natural light and views of the screened Florida Room.
Condo in Siesta Key
4.88 out of 5 average rating, 103 reviews

Enchanting Coastal Ambiance & Breathtaking Sunsets

BeachCleanlinessLocationWalkabilityNearbyHospitalityComfortAccuracyDecorSleep qualityGetting aroundQuietConditionKitchenIndoor spacesAmenitiesAir conditioningFamilyBathroomParkingLaundryViewAccessValueCheck-inTVOutdoor spacesLayoutHeatingWi-FiLong stayNoiseCheckout

Top Guest favourite
A spacious living area features a blue sofa and striped armchair, complemented by a wooden coffee table. Large windows allow natural light to illuminate the room, showcasing views of the turquoise Gulf. Light-colored cabinetry and decorative shelving enhance the inviting atmosphere.
Condo in Bradenton Beach
4.99 out of 5 average rating, 179 reviews

★Right on the beach ★ Relax and Enjoy ♥ Sunsets!

BeachHospitalityViewCleanlinessLocationNearbyWalkabilityComfortAccuracyAmenitiesGetting aroundKitchenQuietSleep qualityDecorIndoor spacesAccessCheck-inFamilyConditionParkingValueBikingHot tubCheckoutTVOutdoor spacesHikingWi-FiPoolShared spacesAir conditioning

Guest favourite
Condo in Bradenton Beach
4.87 out of 5 average rating, 116 reviews

Steps 2 Beach/Charming Walkable Coastal Ctg

BeachLocationWalkabilityHospitalityCleanlinessNearbyOutdoor spacesComfortIndoor spacesKitchenCheck-inQuietGetting aroundBarbecueAmenitiesAccuracyAccessSleep qualityDecorViewShared spacesValueAir conditioningBathroomLaundryFamilyParkingConditionTVLayoutLong stayCheckoutBiking

Top Guest favourite
A spacious living area features a light-colored sofa and armchairs, with decorative pillows adding color. A coffee table sits in the middle, and a flat-screen TV is mounted on the wall. Natural light streams through windows, complementing the neutral-toned decor and beach-themed accents.
Condo in Saint Armands
4.96 out of 5 average rating, 28 reviews

Lido Beach/St. Armands Condo

BeachHospitalityLocationNearbyWalkabilityComfortCleanlinessDecorKitchenFamilyAmenitiesParkingSleep qualityAccuracyLaundryPoolQuietIndoor spacesGetting aroundAccessBarbecueHeatingLong stayConditionViewHot tubNoiseValueAir conditioning

Pet-friendly condo rentals

Guest favourite
A modern living area features a blue sofa with decorative pillows and a low coffee table. A dining set with white chairs is visible in the background. Bright natural light filters through sheer curtains, enhancing the neutral grey walls and stylish artwork.
Condo in Gulf Gate Estates
4.87 out of 5 average rating, 153 reviews

Heated Pool Apartment Near Siesta Key | 1BR

HospitalityCleanlinessLocationBeachPoolComfortNearbySleep qualityCheck-inAccuracyFamilyGetting aroundDecorIndoor spacesConditionValueAmenitiesCheckoutBathroomQuietParkingPetsLaundryKitchenWalkabilityTVAccessOutdoor spacesWi-FiBackyardViewNoiseShared spacesAir conditioningBiking

Top Guest favourite
A brightly colored three-story building stands under a starry night sky, surrounded by palm trees. Exterior lights illuminate the vibrant walls and large windows. A paved driveway leads up to the garage, flanked by landscaped greenery.
Condo in Siesta Key
4.88 out of 5 average rating, 126 reviews

5209B Menorca Street - Siesta Key Village Condo

LocationBeachCleanlinessPoolNearbyWalkabilityHospitalityComfortAccuracySleep qualityFamilyOutdoor spacesBackyardGetting aroundDecorKitchenIndoor spacesNoiseConditionAmenitiesBathroomCheck-inPetsQuietLaundryViewValueTVParkingBarbecueLong stayAccessBiking

Guest favourite
A modern living area features a comfortable sectional sofa, accented by textured cushions. A flat-screen TV is mounted on the wall above a wood panel, while large sliding doors invite natural light and provide access to the patio. Indoor plants add a touch of greenery.
Condo in Siesta Key
4.85 out of 5 average rating, 153 reviews

Siesta Key Condo: Beach, Pool & Village Fun!

LocationBeachWalkabilityCleanlinessNearbyHospitalityComfortSleep qualityAccuracyFamilyConditionAmenitiesQuietIndoor spacesPoolBathroomDecorGetting aroundCheck-inKitchenParkingValuePetsNoiseLayoutAccessCheckoutTVOutdoor spacesAir conditioningHeatingLaundryView

Guest favourite
A fire table is positioned near large glass windows that frame a stunning sunset over the water. The reflection of the vibrant sunset is visible in the water, while the outdoor landscape is softly illuminated by the fading light.
Condo in Bradenton
4.97 out of 5 average rating, 209 reviews

Luxury 3/3 Margaritaville Resort

HospitalityViewLocationBeachCleanlinessFamilyPoolNearbyAmenitiesKitchenIndoor spacesComfortAccuracyDecorBikingQuietGetting aroundBathroomOutdoor spacesConditionCheck-inSleep qualityBarbecueParkingLayoutWalkabilityAccessValueLaundryCheckoutTVWi-FiLong stayShared spacesAir conditioningPetsParksHiking

Top Guest favourite
Condo in Holmes Beach
4.96 out of 5 average rating, 110 reviews

Steps to the beach! Condo with pool at The Terrace

BeachLocationNearbyWalkabilityHospitalityPoolFamilyCleanlinessGetting aroundComfortKitchenParkingValueAmenitiesSleep qualityDecorQuietIndoor spacesBikingAccuracyBathroomNoiseOutdoor spacesLaundryConditionCheck-inTVLayoutViewAccessCheckoutShared spaces

Top Guest favourite
The living area features a seating arrangement with two blue sofas and a light coffee table. A ceiling fan is present, along with a beige recliner. Large glass doors open to a lanai, allowing natural light to fill the room, complemented by coastal-themed art on the walls.
Condo in Holmes Beach
4.98 out of 5 average rating, 107 reviews

A Coastal Retreat Steps From the Sea

BeachHospitalityCleanlinessLocationNearbyWalkabilityPoolFamilyComfortGetting aroundDecorIndoor spacesKitchenOutdoor spacesAccuracySleep qualityAmenitiesQuietCheck-inLaundryViewCheckoutBathroomConditionValueParkingShared spacesBarbecueLayoutLong stayAccessAir conditioning

Top Guest favourite
The outdoor area features a heated pool with a rock waterfall, surrounded by lounge chairs. A thatched Tiki hut provides shaded seating, set within tropical landscaping. The villa's light blue exterior and white furnishings enhance the inviting atmosphere of the space.
Condo in Holmes Beach
4.93 out of 5 average rating, 159 reviews

Blanco at Sunset Villas on Anna Maria Island

BeachLocationPoolCleanlinessWalkabilityNearbyHospitalityComfortFamilyAmenitiesDecorSleep qualityKitchenOutdoor spacesQuietConditionIndoor spacesGetting aroundCheck-inBarbecueShared spacesAccuracyBathroomBackyardLaundryTVHeatingParkingLong stayCheckoutAir conditioningPetsBreakfastViewAccessValueBiking

Guest favourite
Condo in Nokomis
4.87 out of 5 average rating, 189 reviews

Private Beachside Kitchenette

BeachCleanlinessLocationHospitalityComfortFamilyPoolIndoor spacesNearbyViewParkingWalkabilitySleep qualityBathroomConditionKitchenQuietValuePetsBarbecueCheck-inAccuracyOutdoor spacesAmenitiesAccessAir conditioningCheckoutDecorTVNoiseWi-FiGetting aroundBikingLaundrySolo travelBreakfast

Condo rentals with a pool

Top Guest favourite
A heated pool is surrounded by a tiled deck, with lounge chairs available for guests. Palm trees and blue umbrellas create a tropical atmosphere, while the beach and ocean are visible beyond the pool area under a clear blue sky.
Condo in Siesta Key
4.94 out of 5 average rating, 155 reviews

2 Bed/2 Bath Condo Resort View on Siesta Key Beach

BeachLocationCleanlinessPoolHospitalityComfortFamilyWalkabilityCheck-inNearbyGetting aroundAccuracyAmenitiesSleep qualityIndoor spacesConditionViewCheckoutKitchenAccessBathroomBarbecueLaundryTVOutdoor spacesValueQuietLayoutParkingBackyardNoiseAir conditioning

Superhost
A modern dining area is highlighted by a marble table with an elegant vase and tableware arranged for a meal. Stainless steel appliances and a large television are visible in the background, with natural light flowing in from sliding glass doors leading to an outdoor space.
Condo in Siesta Key
4.88 out of 5 average rating, 146 reviews

Crystal House on Siesta Key Beach

HospitalityBeachLocationCleanlinessPoolFamilyGetting aroundComfortWalkabilitySleep qualityNearbyAccuracyParkingCheck-inKitchenAmenitiesAccessIndoor spacesCheckoutBathroomQuietViewOutdoor spacesBikingConditionValueDecorLaundryLong stayTVBarbecueWi-FiAir conditioning

Guest favourite
Condo in Siesta Key
4.92 out of 5 average rating, 148 reviews

Siesta Key condo, beach access, heated pool

HospitalityBeachLocationPoolCleanlinessWalkabilityAccuracyFamilyKitchenGetting aroundComfortNearbyOutdoor spacesIndoor spacesAccessConditionQuietViewSleep qualityAmenitiesValueTVParkingCheck-inBathroomDecorBarbecueCheckoutLayoutHeatingLaundryNoise

Guest favourite
Condo in Longboat Key
4.88 out of 5 average rating, 137 reviews

Sunset and beach view from your balcony Unit 403

ViewBeachLocationCleanlinessHospitalityComfortAccuracyConditionKitchenQuietPoolIndoor spacesNearbyFamilySleep qualityAmenitiesCheck-inGetting aroundBathroomParkingWalkabilityAccessDecorTVOutdoor spacesBarbecueNoiseCheckoutValueLaundryAir conditioningParks

Guest favourite
Condo in Siesta Key
4.79 out of 5 average rating, 108 reviews

Beachwalk Townhouse with view of Gulf of Mexico

HospitalityLocationBeachWalkabilityFamilyCleanlinessViewPoolKitchenComfortNearbyAccuracyAccessBathroomGetting aroundConditionIndoor spacesShared spacesValueLaundrySleep qualityAmenitiesDecorQuietCheckoutOutdoor spacesLayoutParkingBikingBarbecueNoiseAir conditioningCheck-in

Top Guest favourite
A spacious sleeping area features a plush king bed with silky white linens and decorative blue accents. A blue ottoman sits at the foot of the bed, while a large TV is placed on a dark wood dresser. Natural light filters in through the nearby balcony doors.
Condo in Longboat Key
4.93 out of 5 average rating, 30 reviews

Waterfront Coastal Retreat | Steps from LBK Beach

HospitalityViewBeachCleanlinessLocationWalkabilityAccuracyIndoor spacesDecorSleep qualityQuietConditionKitchenComfortPoolAmenitiesLayoutNearbyLaundryFamily

Top Guest favourite
Aerial view captures the pristine beach alongside the expansive manicured grounds of a gated community. The layout features several buildings with red roofs, centered around a heated salt water pool. The shoreline and beach-goers are visible in the distance.
Condo in Siesta Key
4.98 out of 5 average rating, 63 reviews

Siesta Dunes 1st Floor Beach Front Retreat

BeachHospitalityLocationCleanlinessPoolWalkabilityComfortFamilyKitchenNearbyAmenitiesSleep qualityIndoor spacesGetting aroundAccessBarbecueConditionAccuracyOutdoor spacesCheck-inQuietViewHot tubBikingTVCheckoutBathroomParkingLaundry

Guest favourite
A spacious patio provides a serene view overlooking Whitaker Bayou, with boats moored along the water. A round dining table, surrounded by white chairs, offers an inviting spot for meals while enjoying the scenery. The area is complemented by a colorful artwork piece on the wall.
Condo in Sarasota
5.0 out of 5 average rating, 17 reviews

Modern 1/1.5 Waterfront at The Strand

HospitalityViewLocationQuietAmenitiesAccuracyComfortIndoor spacesFamilyDecorLong stayConditionOutdoor spacesKitchenSleep qualityCleanliness

Destinations to explore