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Siesta Key Pet Friendly Vacation Rentals

We offer Pet Friendly Rentals: Book your home securely here and save!

Stay steps from the sand in a Siesta Key with properties designed for convenience, coastal style, and those perfect Gulf sunsets — ideal for couples, families, and anyone who wants a seamless beach getaway.


Vacation Rentals by Owner in Florida.

We have partnered with a major provider for Vacation Rentals by Owner directly through Florida Vacation Rental Homes. With hundreds of short term rentals to choose from, we now have the selection and value to offer our visitors searching for .

For Pricing & Rates, follow the "Search Availability" or "View Rental" button, which will take you directly on our partner website.......All bookings are securely completed on our partners website!

Siesta Key 3BR w/ rooftop pool & beach access

This must-see home on Siesta Key offers a much sought after modern and contemporary design. With plenty of space for the entire family. This unit, located on the 1nd floor above the garage, has 3 bedroom, 2/5 bathrooms and can sleep up to 10 guests. Complete with a full kitchen, living, and dining space, make this place your home away from home and enjoy the breathtaking views from the incredible rooftop pool!

The Space:
Bedroom 1: King
Bedroom 2: King
Bedroom 3: Queen bunk
L.......

Apartment in Siesta Key
3 Bedroom Sleeps 10
Pet Friendly Pets Allowed

Siesta Key 3BR w/ rooftop pool & beach access

This must-see home on Siesta Key offers a much sought after modern and contemporary design. With plenty of space for the entire family. This unit, located on the 2nd floor above the garage, has 3 bedroom, 2/5 bathrooms and can sleep up to 10 guests. Complete with a full kitchen, living, and dining space, make this place your home away from home and enjoy the breathtaking views from the incredible rooftop pool!

The Space:
Bedroom 1: King
Bedroom 2: King
Bedroom 3: Queen bunk
L.......

Apartment in Siesta Key
3 Bedroom Sleeps 10
Pet Friendly Pets Allowed

3 BR house+ heated pool in huge private yard. 12min walk to beach. Pet friendly.

Enjoy this private pet friendly house with your own swimming pool, in beautiful Siesta Key. Oversized private lot. Renovated main bathroom and master bathroom. Custom designed high end rain showers. ** HEATED POOL ** (up to 84 degrees December to April). Walk to Crescent Beach or beach access 10 - Walk to the North Village or ride bikes. This well maintained vacation home comes fully equipped with all the amenities you could want and possibly some you did not think about. Master Bedroom has Ki.......

Vacation Home in Siesta Key
3 Bedroom Sleeps 6
Pet Friendly Pets Allowed

Beachfront 4BR home on Siesta Key w/ sunset views

Beach Front Home on Siesta Key's Sunset Beach! This Beautiful home comes equipped with a full kitchen, a dining area, and a spacious living room for you to spend time with your family and friends. Enjoy spectacular sunsets and the white sand beach right outside the front door! It’s only a short stroll into Siesta Key Village for all of the wonderful shops and restaurants the island has to offer and with views like this, this vacation home is sure to be your choice returning year after year!

Vacation Home in Siesta Key
4 Bedroom Sleeps 12
Pet Friendly Pets Allowed

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

**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.**
*NO dogs over 20 pounds and ONE dog only. NO more than 2 guests with ONE car.*
LOCATION!! 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 an.......

Cottage in Siesta Key
1 Bedroom Sleeps 2
Pet Friendly Pets Allowed

7 minute walk to Siesta Key beach. Large heated pool/spa. Very private.1/2 acre

Welcome to Lagoon House Siesta Key beach. A uniquely private, dog friendly (up to 25 lbs), one story house with guest house (and a six person golf cart available for an extra rental fee). This property is situated within a 7 minute walk to the Number 1 beach in America, Siesta Key Beach. It is also just a short 3 minute golf cart ride (or bike ride) to Siesta Key Village where you can enjoy many restaurants, shops and live music.

The Lagoon house sits on a half-acre property that has a .......

Vacation Home in Siesta Key
4 Bedroom Sleeps 10
Pet Friendly Pets Allowed

Beachfront 5BR on Siesta Key w/ sunset views

Beach Front Home on Siesta Key's Sunset Beach! This Beautiful home comes equipped with a full kitchen, a dining area, and a spacious living room for you to spend time with your family and friends. Enjoy spectacular sunsets and the white sand beach right outside the front door! It’s only a short stroll into Siesta Key Village for all of the wonderful shops and restaurants the island has to offer and with views like this, this vacation home is sure to be your choice returning year after year!

Vacation Home in Siesta Key
5 Bedroom Sleeps 14
Pet Friendly Pets Allowed

Across from Siesta Key Beach, walk to village shops

Enjoy the Gulf breezes and partial views with this lovely home directly across from our world-famous Siesta Key Beach! Beautifully decorated, this second-floor unit is right outside of the Siesta Key Village, making it a breeze to walk to all of the restaurants, shops, and live entertainment the island has to offer. Relax on the sugary white sand or swim in the crystal-clear waters. Experience brilliant colors at sunset in this beautiful home that will have you coming back year after year!

Apartment in Siesta Key
2 Bedroom Sleeps 6
Pet Friendly Pets Allowed

2Bed directly across from Siesta Key Beach, and steps from SK Village

Enjoy the Gulf breezes and partial views with this lovely home directly across from our world-famous Siesta Key Beach! Beautifully decorated, this second-floor unit is right outside of the Siesta Key Village, making it a breeze to walk to all of the restaurants, shops, and live entertainment the island has to offer. Relax on the sugary white sand or swim in the crystal-clear waters. Experience brilliant colors at sunset in this beautiful home that will have you coming back year after year!

Apartment in Siesta Key
2 Bedroom Sleeps 6
Pet Friendly Pets Allowed

Charming home on quiet street one block from Siesta Beach.

Comfortable private home on a quiet street one block from Siesta Beach. Lush tropical fully fenced in backyard has a gas grill and comfortable chairs and table, under a shade sail with cafe lights. Walk to the beach or Siesta Village. Fully furnished kitchen has everything you need to feel at home. Enjoy comfortable couches and beds, fast internet and 2 large screen cable TVs. Full size washer and dryer........

Vacation Home in Siesta Key
2 Bedroom Sleeps 4
Pet Friendly Pets Allowed

LUXURY HOUSE BY THE CANAL ☀️

Our beautiful 3 bedroom / 2 bathroom house is located in the heart of Siesta Key Village. We have place for 8 people to sleep . The house features outdoor heated , saltwater pool make you feel relaxed on the hot day. All of our bedrooms have TVs in them. Our kitchen is fully stacked for your convenience so you can enjoy home cooked meal. If you are lucky you can see dolphins 🐬and manatees from the back patio ........

Vacation Home in Siesta Key
3 Bedroom Sleeps 8
Pet Friendly Pets Allowed

Villa Castile | Private Heated Pool + Walk to Beach & Village

🏖️ Villa Castile | Private Heated Pool + Walk to Beach & Village

💖 Why You'll Love This Home
Picture yourself gathered poolside in your sunlit courtyard, the warmth of the heated pool inviting you to pause time. Just steps from Siesta Key Village and a short stroll to world‑famous Siesta Key Beach, Villa Castile blends sophisticated comfort with laid‑back island energy.

👨‍👩‍👧 Perfect For
Families, multi‑family groups, or friends looking for space, p.......

Vacation Home in Siesta Key
3 Bedroom Sleeps 8
Pet Friendly Pets Allowed

Gertrude's Siesta | 1 min walk to Beach Path | Free Bikes, Boards & Trolley!

The Oceanside 603
Large king apartment perfectly located. 12-steps to Siesta Key's best beach access! 3-min by trolley or bike (10-min walk) to Siesta Village. Remodeled in 2022. No neighbors above or below. Free, bikes, and paddle boards. Communal lounging, alfresco dining, ping-pong, and Tiki bar below. Perfect for couples looking to relax, explore and repeat. Book your getaway now! - Tollbooth by VRBOCorpMiddlemen, but this property is from GertrudeRentalsSiesta

What Guests Love.......

Apartment in Siesta Key
1 Bedroom Sleeps 4
Pet Friendly Pets Allowed

Siesta Sunrise-Just steps to the beach and village

Location, location, location! Siesta Sunrise is just steps to beautiful Siesta Key beach and a short walk to the village. Enjoy this newly remodeled 2 bedroom 2.5 bath plus bonus room with sleeper sofa. The kitchen has enough room and supplies to cook every meal and has a shared grill out back. Both bedrooms have en-suite baths with walk in showers. This property also features a heated pool shared between two units. Saturday to Saturday rentals during season........

Vacation Home in Siesta Key
2 Bedroom Sleeps 6
Pet Friendly Pets Allowed

Garden Terrace Studio Cottage - Walk To Siesta Beach & Village - Pets Welcome!

SHORT WALK TO FAMOUS SIESTA WHITE SAND BEACH & QUAINT ISLAND VILLAGE.

Situated in the quiet and welcoming neighborhood of Palm Island, the heart of Siesta Key, this Tommy Bahama styled studio efficiency has fifteen-foot sliding glass doors looking into a private brick courtyard with flowered trellis and wrought iron patio furniture. Wood and tile floors, cypress beamed ceilings, kitchenette, full bathtub/shower, full-sized bed, love seat, and dining set. It is situated in the quiet neigh.......

Apartment in Siesta Key
1 Bedroom Sleeps 2
Pet Friendly Pets Allowed

301 Avenida Madera A- Siesta Key Village House with Roof Top Deck

Siesta Key Main Village Location - No Car Needed for this fantastic, waterfront location with Heated Salt Water Pool... Generously Appointed with all the things that make a Good Siesta Key Guest Stay a GREAT Siesta Key Guest Stay...

If you are looking for the perfect location for your next vacation, then your search is over! This 2 bedroom, 2 bath property features a prime location within The Village of Siesta Key and is 3.5 blocks to the beach. Beautifully updated, this home is decorate.......

Vacation Home in Siesta Key
2 Bedroom Sleeps 4
Pet Friendly Pets Allowed

Siesta Key Escape: Spacious 2BR /2BA Near Beach + Dining

Please relax and enjoy our spacious unit, which offers an open-concept kitchen, two large bedrooms, a screened patio, and a washer and dryer. We also have a beautiful heated pool in our complex for you and your family to enjoy when you're not on the beach........

Condo in Siesta Key
2 Bedroom Sleeps 4
Pet Friendly Pets Allowed

Siesta Key beach house

Nice house as is renovated to January-2025 and there is new kitchen , bathroom, furniture and beds and private pool with tree bedrooms and tree bath close to Siesta Key Village resturants and Beach.
Canal on the backyard there you can relax and fishing or have your barbecue.
Perfekt place for you and your family........

Vacation Home in Siesta Key
3 Bedroom Sleeps 6
Pet Friendly Pets Allowed

The Lookout - 891 “Siesta Key’

KEEP READING BELOW! THIS IS NOT JUST A BASIC DESCRIPTION OF THE HOME AND CONTAINS VERY USEFUL INFORMATION THAT YOU WON’T WANT TO MISS!!

Premier local manager, Destination Paradise welcomes you to “The Lookout”… a beautiful, grand vacation home on a magnificent waterfront area of the bay with an awesome outdoor lounge and heated pool area! This 4 level home sleeps up to 13. It is located on the ultra-premium North end of the island in a super private neighborhood and is just minut.......

Vacation Home in Siesta Key
5 Bedroom Sleeps 10
Pet Friendly Pets Allowed

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

IN-GROUND POOL

This 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.......

Vacation Home in Siesta Key
2 Bedroom Sleeps 6
Pet Friendly Pets Allowed

Beachfront Home with Gulf Views Pet friendly- one pet 35 lb max

Our beach house located on the gulf side of Beach Road is directly on Crescent Beach with gulf views on 3 levels. It is a spacious 1,800 sq. ft. and newly remodeled kitchen, plus 3 1/2 baths and a 1 car garage. Each bedroom is en suite with private, newly remodeled full baths. The master suite has a very large bath with two skylights. It has the most spectacular views right from the king size bed. There is also a deck off the master bedroom with chairs, a great spot for your morning coffee.

Vacation Home in Siesta Key
3 Bedroom Sleeps 7
Pet Friendly Pets Allowed

Siesta Key Beach Duplex-Close to Sarasota Beach/Pet Friendly

Off The Hook - B by Tropical Sands Accommodations

Welcome to Off The Hook – B, your ideal sunny vacation getaway just minutes from the world famous Siesta Key Beach! This charming two-bedroom, one-bath duplex offers a delightful blend of comfort and convenience, just minutes from the beach and Siesta Key Village. Perfect for couples or families looking to explore the beautiful surroundings of Siesta Key.

Highlights
• 5-minute walk to Siesta Key Beach
• 2 Bedroom /.......

Vacation Home in Siesta Key
2 Bedroom Sleeps 4
Pet Friendly Pets Allowed

Pet Friendly home, Close to Sarasota Beach!

Off The Hook – A by Tropical Sands Accommodations

Welcome to Off The Hook – A, your cheerful vacation duplex just steps away from the world famous Siesta Key Beach! This delightful two-bedroom, one-bath home is perfectly suited for couples or families with young children, providing a fun and sunny atmosphere for your next getaway.

Highlights
• 5-minute walk to Siesta Key Beach
• 2 Bedroom / 1 Bathroom
• 1 King, 2 Twin beds
• Screened-in lanai
•.......

Vacation Home in Siesta Key
2 Bedroom Sleeps 4
Pet Friendly Pets Allowed

Walkable to Siesta Key Village, Saltwater Pool/Spa, BBQ, Pond Views, Bike to Beach in 6 mins

Welcome to Ocean Beach Gleason Home!



Newly renovated and furnished! New pics to come!



This beautiful 4-bedroom, 2-bathroom home on Siesta Key is perfect for families or groups looking for a luxurious and relaxing getaway. With over 1,900 square feet of heated space and a total of 2,500 square feet, this single-level home offers plenty of room to spread out. The property features a private saltwater pool and spa, with optional heating, overlooking a serene lake, .......

Vacation Home in Siesta Key
4 Bedroom Sleeps 8
Pet Friendly Pets Allowed

Siesta Dolce | Private Pool, Kayaks and Putting Green

🌴 Siesta Dolce | Private Pool, Kayaks and Putting Green

💖 Why You'll Love This Home
Escape to Siesta Dolce, a luxurious oasis where every detail is designed for your ultimate enjoyment. From its stunning outdoor amenities, including kayaks and a putting green, to its inviting interiors, this home promises an unforgettable Siesta Key escape.

👨‍👩‍👧 Perfect For
Families or adult groups seeking a blend of active outdoor fun and luxurious relaxation, with easy a.......

Vacation Home in Siesta Key
4 Bedroom Sleeps 8
Pet Friendly Pets Allowed

Tropical Bungalow 5 min walk Beach-15 min Village, Monthly Rental, Pet Friendly

SHORT WALK TO FAMOUS SIESTA WHITE SAND BEACH & QUAINT ISLAND VILLAGE.

The Blue Lagoon is the perfect tropical getaway right in the heart of Siesta Key in the quiet and welcoming Palm Island neighborhood - just steps away from the award-winning white sand beach or an equally short stroll to Siesta Key Village; which has amazing shops and plentiful restaurants.

The Blue Lagoon is in such a fantastic location, so close to everything Siesta Key has to offer, yet situated in a lovely p.......

Vacation Home in Siesta Key
2 Bedroom Sleeps 6
Pet Friendly Pets Allowed

Nearly Beachfront, One house from the beach! Pool and Game Room - Ocean Overlook

Ocean Overlook by Siesta Key Luxury Rental Properties

Ocean Overlook by Siesta Key Luxury Rental Properties is an exceptional eight bedroom, eight bathroom coastal retreat with two additional half baths, thoughtfully designed for large families and large group getaways seeking luxury coastal living. Located just a three-minute walk to Siesta Key Beach, this four-story Siesta Key luxury rental offers sweeping Gulf views, large balconies, and a private outdoor oasis. Guests are also a sho.......

Vacation Home in Siesta Key
8 Bedroom Sleeps 18
Pet Friendly Pets Allowed

Cabana Cottage Across street from Beach and Heated Pool

The Cabana is small but mighty! A fully equipped kitchen complete with granite countertops, and a breakfast bar, with all of the comforts of home.The master bedroom has a King size Serta ICOMFORT Memory Foam Gel bed with a flat screen TV, and an attached European Rain shower bath. The second bedroom is two, twin Serta ICOMFORT Memory Foam Gel beds with a flat screen TV. The second tub/shower bathroom is off the kitchen area. Living room and dining areas are combined, equipped with 65 flat screen.......

Cottage in Siesta Key
2 Bedroom Sleeps 4
Pet Friendly Pets Allowed

Large Pool Home- Blocks from Siesta Key Beach

Summary:
Welcome to Ocean Breeze Cottage,

This beautiful 5 bedroom 3 bath home is perfect for a family vacation to Siesta Key Beach. Ocean Breeze Cottage is a quick block and a half stroll or bike ride up the street from The Nation’s Number One Beach; where you can enjoy Siesta Key’s famous white sand, swim in the Gulf of Mexico and take in a technicolor sunset. Looking to do some shopping, grab a bite to eat, or just enjoy live music and some drinks then you will enjoy Siesta Vi.......

Vacation Home in Siesta Key
5 Bedroom Sleeps 10
Pet Friendly Pets Allowed

Walk to Siesta Key Beach & Village | Private Patio | Prime Location

The Village Studio
Top location on the island! Apartment with full kitchen, private patio, quiet gated courtyard, in world famous Siesta Key Village! Leave the car behind and walk to white-sand cays, 20 bars and restaurants, quartz-sand beach with calm water, ice-cream, shopping, daiquiris, live music, craft beer, fresh oysters and seafood. This studio apartment delivers a combination of fun ease and relaxation you can't get in other vacations so book a special getaway now! - Tollbooth b.......

Apartment in Siesta Key
1 Bedroom Sleeps 2
Pet Friendly Pets Allowed

Gertrude's Siesta | Top Location! 1-min to Best Beaches, Private Patios, Gate to Village!

Gertrude's Village House
Top location on the island with 3 patios and private gate into world famous Siesta Key Village! Leave the car behind and walk to white-sand cays, 20 bars and restaurants, quartz-sand beach with calm water, ice-cream, shopping, daiquiris, live music, craft beer, fresh oysters and seafood. Enjoy private patios off the bedrooms and living area. Gertrude's is sure to provide a combination of fun ease and relaxation you can't get in other vacations so book a special geta.......

Vacation Home in Siesta Key
3 Bedroom Sleeps 10
Pet Friendly Pets Allowed

Gertrude's Siesta | 4-min Walk to Beach & Village | Balcony & Tropical Patio!

Casa Van Lopik
Large 3BR home in the Siesta Key Village, 4-min walk to best beaches shopping dining and entertainment on the island. Leave the car behind and walk to white-sand cays, 20 bars and restaurants, quartz-sand beach with calm water, ice-cream, shopping, daiquiris, live music, craft beer, fresh oysters and seafood. Enjoy tropical “communal” patios tiki-bar and alfresco dining area. Free bikes and paddleboards. Sure to provide a combination of fun and relaxation you can't get in.......

Vacation Home in Siesta Key
3 Bedroom Sleeps 12
Pet Friendly Pets Allowed

Gertrude's Siesta | 4-min Walk to Beach & Village | Balcony & Tropical Patio!

Casa Van Lopik
Large 3BR home in the Siesta Key Village, 4-min walk to best beaches shopping dining and entertainment on the island. Leave the car behind and walk to white-sand cays, 20 bars and restaurants, quartz-sand beach with calm water, ice-cream, shopping, daiquiris, live music, craft beer, fresh oysters and seafood. Enjoy tropical “communal” patios tiki-bar and alfresco dining area. Free bikes and paddleboards. Sure to provide a combination of fun and relaxation you can't get in.......

Vacation Home in Siesta Key
3 Bedroom Sleeps 12
Pet Friendly Pets Allowed

Siesta Key Heated pool Home. Walk to Beach/Village. Check our monthly rate!

Large home on Siesta Key. Walk to Beach and Village. NEW POOL/OUTDOOR PATIO!
Our home is located in a quiet could de sac street just a few minutes walk to the beach and Village where you will find restaurants, shops, ice cream stores. Enjoy the amazing food and live music of Siesta Key Village and the world famous Siesta Key beach. Also easy access to the shopping and dining of downtown Sarasota. No need for a car to stay in this house, everything you need within a walking distance or just us.......

Vacation Home in Siesta Key
4 Bedroom Sleeps 8
Pet Friendly Pets Allowed

Nook Cottage Across street from beach and Heated Pool

This is a ground floor, one bedroom, one bath unit with King-size Serta ICOMFORT CF 3000 Memory Foam Gel Series bed in the master and full bath off of the bedroom, ensuite. Large walk-in tile shower with glass enclosure.The Nook features a fully equipped kitchen with granite counter tops and cozy dining area and beach chic laminate wood flooring throughout. This unit is naturally bright and spacious, with white-washed tongue and groove accent walls. Enjoy a flat screen, 55 inch TV in Living, DVD.......

Cottage in Siesta Key
1 Bedroom Sleeps 2
Pet Friendly Pets Allowed

Steps from Siesta Village and the Beach

Our condo is located in the heart of Siesta Key Village which has numerous restaurants, bars, shops and a grocery store and is only 1 block from the beach! The best of both worlds as everything you need is within walking distance.

Property Description - In the main room you have a queen size murphy bed with a built in couch that folds under the bed. With our small space we needed things that could function in multiple roles and will be out of the way when not in use. On either side of th.......

Condo in Siesta Key
1 Bedroom Sleeps 2
Pet Friendly Pets Allowed

Casa Leone | Heated Pool & Spa, Pet Friendly, Putting Green

Casa Leone | Heated Pool & Spa, Pet Friendly, Putting Green

Why You'll Love This Home
Tucked on the northern end of Siesta Key, Casa Leone is a four-bedroom retreat where polished interiors meet a private outdoor oasis. The heated pool and spa, screened lanai, putting green, and upper deck lounge area give everyone plenty of ways to fill the day, with Siesta Key's world-famous beach and village just a short drive away!

Perfect For
Families, multi-generational groups, or frien.......

Vacation Home in Siesta Key
4 Bedroom Sleeps 10
Pet Friendly Pets Allowed

Gertrudes Siesta Village Properties - short walk to Siesta's best beaches!

Gertrude's Village Properties
Two properties in the top location on the island with 4 patios and private gate into world famous Siesta Key Village! Leave the car behind and walk to white-sand cays, 20 bars and restaurants, quartz-sand beach with calm water, ice-cream, shopping, daiquiris, live music, craft beer, fresh oysters and seafood. Enjoy private patios off the bedrooms and living area. Gertrude's is sure to provide a combination of fun ease and relaxation you can't get in other vacat.......

Vacation Home in Siesta Key
4 Bedroom Sleeps 12
Pet Friendly Pets Allowed

Gertrude's Siesta | 4-min Walk to Beach & Village, Tropical & 100% Private!

Casa Van Lopik
100% Private 6BR duplex in the Siesta Key Village, 4-min walk to best beaches shopping dining and entertainment on the island. Leave the car behind and walk to white-sand cays, 20 bars and restaurants, quartz-sand beach with calm water, ice-cream, shopping, daiquiris, live music, craft beer, fresh oysters and seafood. Enjoy tropical patios tiki-bar and alfresco dining area. Free bikes and paddleboards. Sure to provide a combination of fun and relaxation you can't get in other.......

Vacation Home in Siesta Key
6 Bedroom Sleeps 22
Pet Friendly Pets Allowed

Mid-Century Meets Boaters’ Dream

Classic Mid-Century 2 bedroom, 2 bath home, believed to be designed by Sarasota School of Architect Ralph Twitchell or a close follower. It is located directly on Siesta Key’s Grand Canal and is nestled into a quiet, luxury neighbourhood.

We tried to preserve the “Old Florida” bungalow vibe that is steadily disappearing. Decorated with furniture of the era, alongside modern elements from European designers. Sunlight floods into the panoramic windows from both sides of the house. .......

Vacation Home in Siesta Key
2 Bedroom Sleeps 4
Pet Friendly Pets Allowed

Siesta Key Beach IDEAL LOCATION BEACH, VILLAGE, HEATED POOL

2 week rental minimum from April through December. January, February March, are monthly rentals please select the first day and last day of the month when booking. There is currently January 2026 still available.

Siesta Key Beach Vacation Rental: Location- location-location-BEACH, VILLAGE, HEATED POOL.

Walk across the street to the beach, walk or take the free trolley to the village, or decide to sit in a heated saltwater swimming pool!

STAY AT THE CENTER OF IT ALL! Ma.......

Condo in Siesta Key
1 Bedroom Sleeps 4
Pet Friendly Pets Allowed

Siesta Key Beach Views – 2BR Oceanfront

Serenity
Your tranquil escape is found at the Serenity Beach Condo at the Beachfront Suites on Siesta Key. Enjoy your peaceful escape to the world-famous Siesta Key Beach, in this lovely 2 bedrooms 2nd-floor condo on the 2nd floor of the Beachfront Suites on Siesta Key, located directly on the beach. Enjoy your morning coffee on the private balcony as the stress of the world falls from your shoulder and you sink into the calming aesthetic of the Serenity Condo. Complete with everything you ne.......

Apartment in Siesta Key
2 Bedroom Sleeps 5
Pet Friendly Pets Allowed

2 BR Condo-Short Walk to Siesta Beach/ One 25 lbs Dog Allowed

Beautifully furnished, newly renovated 2BR (one king size & 2 single beds) + convertible sofa bed, 2 Bathrooms 2nd floor condo (sleeps 4-6), and with all the amenities of a comfortable home. Located in White Sands Village with 7 acres of lush tropical surroundings & paving stones carports parking, our air-conditioned condo offers two large newly installed wood-like flooring bedrooms with 2 full baths (in-suite master bathroom with new vanity & ceramics), a comfortable living room, fully equipped.......

Condo in Siesta Key
2 Bedroom Sleeps 6
Pet Friendly Pets Allowed

Siesta Key vacation rental home close to village with swimming pool and free wifi

When you can't wait to enjoy a well-earned getaway to sunny Siesta Key, make the most of your island adventure by booking Oxford House as your home away from home during your stay. This 2-bed, 2-bath property can welcome up to 7 guests at a time and puts visitors right in the heart of a barrier island experience. Oxford House is surrounded by lush tropical foliage and sits within reach of area attractions and activities too. Booking a stay here provides a refreshing balance between desirable isl.......

Vacation Home in Siesta Key
2 Bedroom Sleeps 10
Pet Friendly Pets Allowed

Romantic 1BR - Siesta Key Beach Sunset View

The Property
The best view on Siesta Key is found at the Dreamview Beach Front Condo. Find your romantic getaway at our 1 Bedroom, 1-1/2 Bath suite on the 3rd floor of the Beachfront Suites on Siesta Key, where you are only steps away from digging your toes into the sugary sand of the #1 Beach. The bright and airy space is warm and inviting, featuring comfortable living room furniture, a large fully stocked kitchen, a plush king bed with high-end bedding, and a private balcony for you to enjo.......

Condo in Siesta Key
1 Bedroom Sleeps 3
Pet Friendly Pets Allowed

Short 0.3 Mile Walk to #1 Siesta Beach, Heated Pool, Wifi, Covered Parking.

White Sands Village Condominium is the ideal place to enjoy your stay on tropical Siesta Key, Florida. Situated just a short walk from the world-renowned Siesta Key Public Beach, it’s a great place for a two-week vacation or for an extended stay.
Please note: THE MINIMUM RENTAL PERIOD IS 14 DAYS.
Our condominium is privately owned and decorated, unique and beautifully maintained. Check out the amenities and photos!
Our unit has an assigned carport.
Why just go to Florida when you .......

Condo in Siesta Key
2 Bedroom Sleeps 6
Pet Friendly Pets Allowed

Super 2 Bed/2 Bath Ground Floor,#1 Siesta Beach

White Sands Village Condominium is the ideal place to enjoy your stay on tropical Siesta Key, Florida. Situated just a short walk from the world-renowned Siesta Key Public Beach, it’s a great place for a two-week vacation or for an extended stay.
Please note: THE MINIMUM RENTAL PERIOD IS 14 DAYS.
Our condominium is privately owned and decorated, unique and beautifully maintained. Check out the amenities and photos!
Our unit has an assigned carport.
Why just go to Florida when you .......

Condo in Siesta Key
2 Bedroom Sleeps 4
Pet Friendly Pets Allowed

Walk to Siesta Key beach. 2 BR/2 Bath. Washer/Dryer. Heated Pool. Gas Grills.

You will love the grounds with 7 acres of lush tropical landscaping. Our unit is complete with coastal décor, newer appliances and washer/dryer in the unit. Walk to Siesta Key Beach or swim in the heated pool. We have several grills, a clubhouse with library, and a peaceful lagoon. Siesta Key Village is filled with restaurants and shops. There is no worry about parking when you take the free trolley! Siesta Key Beach has tennis and pickleball courts, playground, volleyball courts, concession st.......

Condo in Siesta Key
2 Bedroom Sleeps 6
Pet Friendly Pets Allowed