Skip to content

Siesta Key Vacation Rentals, Homes and Condos for Rent near the Beach

Book Your Siesta Key Florida Vacation Rentals Here and Save! Many to choose from, including Rental Homes or Condos with Wi-Fi, Pool, Oceanview, Beachfront and other amenities to make your stay enjoyable.

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

Spacious 2Bed/ 2Bath Beachfront Town Home!!

Siesta Key Private vacation home

DIRECTLY ON NUMBER ONE RATED BEACH IN THE USA SIESTA BEACH !!! Included with your stay: Complimentary Bicycles, Beach chairs, Beach-Towels, Free-rides around Siesta and a 7-day week office for your convenience and guest needs. Beachfront home on Siesta Key Sunset Point. Siesta Key Beach is the number one rated beach in the USA. Walk out of your fro.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 4


Vacation Home


Upgraded Modern Condo on Beautiful Siesta Key!

Siesta Key Condo

This unit (405) is located on the East corridor on the fourth floor, it faces east/south with plenty of sunlight throughout the year.
There are two bedrooms in this unit, each located on the opposite sides of the living/dining room. Each bedroom has its own updated full bathrooms, king sized beds, and flat-screen TVs. Both bedrooms have views of.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 4


Vacation Home


Bright and Airy 4th floor condo at Fisherman's Haven with Private Beach and Stunning Water Views! FH

Siesta Key Condo Star 5.0 Star Review

Bright and Airy 4th floor condo at Fisherman\'s Haven with private beach and stunning water views!

Spacious, open-concept 2 bedroom featuring a roomy kitchen with breakfast bar, large bedrooms, and nicely furnished oversized living room with Bay views. King beds and large closets are provided in both bedrooms, and both have gorgeous views o.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 4


Vacation Home


Private villa, 7 min walk to beach, restaurants, grocery

Siesta Key Villa Star 4.9 Star Review

Amazing private location, steps away from all the action. Seven minute walk to beach, restaurants, grocery store, and boat rentals. This place will feel like your home away from home. Recently renovated with all new furnishings, including a large, fully stocked kitchen and 65-inch TV in living room. Enter this single family, one story, 1200 SF hous.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 7


Vacation Home


Newly Reno Cozy 2BR - Walk to Beach & Village!

Siesta Key Private vacation home

Duplex second floor unit located in best location in Siesta Key! Walk to the beach just across the street or to the Village just 5 mins down the road! This unit has two bedrooms and one full bathroom. Very central location in Siesta Key, close to everything. About 10 miles away from Sarasota airport.

The space
Amenities Included:
- Acr.......read more

2 Bedroom(s)
1 Bath(s) Sleeps 6


Vacation Home


NEW LISTING! Spend your winter in this condo just steps from Siesta Village!

Siesta Key Condo

Enjoy your stay on Siesta Key Beach!

Whispering Sands condo is located right on Siesta Key Beach and just a block from the Siesta Key Village, where you can enjoy countless restaurants, cafes, bars and boutiques.

Kitchen, Living Room and Master Bedroom all have beautiful views of the Gulf of Mexico. Master bedroom has a queen size .......read more

2 Bedroom(s)
2 Bath(s) Sleeps 4


Vacation Home


Steps to the ⭐ Beach, Short Walk to the Village

Siesta Key Private vacation home Star 4.9 Star Review

How far from the Beach? 150 steps or barely a 2 minute walk and you\'re on the Beach! Short walk to Siesta Village loaded with restaurants, bars, shopping, clubs and more!
Welcome to Convenience on Siesta Key - Wonderful, Clean & Cozy 2 bedroom, 2 full bathroom, single-level Villa that comfortably sleeps 4 adults. Enjoy 1000 sf of living s.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 4


Vacation Home


OVER 180 DEGREE VIEW OF THE BEACH AND GULF!!!

Siesta Key Condo Star 4.9 Star Review

Location, view & value. This is the best location, the best value, and absolutely the most stunning view in Siesta Key. There’s even a nice view of Sarasota Bay and the mainland from your kitchen window. Views galore from every room (except for 1 closet).

This 11th floor condo has both panoramic views of the Gulf of Mexico and the bea.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 5


Vacation Home


On Siesta Key Beach!! Sandpiper Beach Club of Siesta Key
Siesta Key, FL USA

Siesta Key Condo

7 night min booking for this 2/2 resort condo directly on Siesta Key Beach with it\'s own private beach! Beach chairs and umbrellas available through resort for a nominal fee. Heated pool and hot tub also included. Many other amenities include onsite gym, tennis and shuffle board. Several grilling stations and seating areas located along the ground.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 6


Vacation Home


Luxury Villa: 2 min walk to beach and The Village. Contact me for <30 day stay.

Siesta Key Villa Star 5.0 Star Review

Enjoy a fantastic experience at this prime Siesta Key location, and beautiful Villa. Luxury Villa is across the street from the Siesta Key beach (beach access #5), the top beach in the USA and noted as a top international beach. Villa is also located via a two minute walk to the Siesta Key Village; various restaurants, bars and shopping. No need .......read more

2 Bedroom(s)
2 Bath(s) Sleeps 6


Vacation Home


Hyatt Residences- High End Condo on #1 Beach in the US!!

Siesta Key Condo Star 5.0 Star Review

No better deal around! Top of the line on Siesta Key! It really doesn\'t get any better than this. This 2 bedroom / 3 bathroom unit has all the top of the line finishes that you would expect, such as Wolf gas stove, Sub Zero refrigerator, flat screen TVs in all rooms, high-speed internet, and more! This over the top unit will amaze you at every tur.......read more

2 Bedroom(s)
3 Bath(s) Sleeps 6


Vacation Home


New Listing! Sea Breeze | Located in Siesta Key Village, Walk to the Beach!

Siesta Key Private vacation home Star 5.0 Star Review

Welcome to Sea Breeze! This private unit is perfect for small families, with the ability to accommodate up to 4 guests, with 1 bedrooms and 1 bathrooms.

Cross the drawbridge from Sarasota to enter the serene island escape of Siesta Key, Florida! With clear blue gulf waters and powdery white sand, Siesta Key\'s world-renowned beaches are the .......read more

1 Bedroom(s)
1 Bath(s) Sleeps 4


Vacation Home


Penthouse suite with ocean views 2 Bed 2 Bath
7 Day Minimum

Siesta Key Condo Star 5.0 Star Review

Newly renovated and Decorated Penthouse with ocean views. This 5th floor unit is located Two blocks from the famous MTV “Siesta Key” Crescent Beach and 4 blocks from the #1 beach in the country Siesta Key Beach. If walking is not your thing you can take the free trolley anywhere on the Island. The master has a new King size bed and its own bath.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 6


Vacation Home


Aloha Kai - Unit 3-close to the pool!

Siesta Key Apartment

Fully furnished villa offering living room, dining area, fully equipped kitchen, two bedrooms and one bathroom. ALOHA KAI is a five acre vacation retreat hosting 68 private villas and apartments, nestled on the powdery-white sands of the Gulf of Mexico. Villas are at ground level, and offers a private parking space directly outside your front door........read more

2 Bedroom(s)
1 Bath(s) Sleeps 5


Vacation Home


Chinaberry 456 - 2 Bedroom Condo with Private Beach with lounge chairs & umbrella provided, 2 Poo...

Siesta Key Condo Star 5.0 Star Review

AMAZING views from this 5th floor 2BR/2BA condo overlooking the Beach and the Gulf! Brand New to our Rental Program! Spacious living, dining, lanai and kitchen, all with views of the water! King bed in master bedroom, full view of the water, with glass sliders out to the lanai. Very spacious master bath with large soaking tub (no shower.) Two twin .......read more

2 Bedroom(s)
2 Bath(s) Sleeps 6


Vacation Home


Siesta Cool : Only Minutes Walk to Siesta Beach!

Siesta Key Apartment Star 5.0 Star Review

Light, bright and cozy in the HEART of Siesta Key Village! Open floor plan including queen-sized murphy bed, Smart TVs, &Strong WIFI. Amazing balcony for the best people watching on Ocean Blvd. Quick & easy three minute walk will put you on the #1 Beach in the USA, Siesta Beach! This beautifully appointed apt. is perfect for those who will not mind.......read more

1 Bedroom(s)
1 Bath(s) Sleeps 3


Vacation Home


Siesta Beach House #312 Minute Walk to Beach

Siesta Key Apartment Star 3.9 Star Review

If you\'re looking for a great vacation location on beautiful Siesta Key, then look no further. This people friendly complex is the perfect place to bring the family for a true holiday get-away at the beach! You can enjoy swimming in the heated pool, take up a game of shuffleboard, stroll along gorgeous white sandy beaches, or swim in the crystal c.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 7


Vacation Home


101-Excelsior- Updated and Full Gulf Front!- 2 week minimum

Siesta Key Condo Star 4.8 Star Review

PERFECT PLACE TO WATCH THE SUNSET!! 2 bedroom/2 bath gulf front condo located on Crescent Beach. Walk out onto your patio and directly down to the courtyard area with a private back entrance for easy access to the pool area and beach access. . This unit features a King bed in the master and 2 Queen beds in the guest room. It\'s only a short walk .......read more

2 Bedroom(s)
2 Bath(s) Sleeps 6


Vacation Home


Our House at the Beach 222, Sleeps 4, 2 Bedroom, Tennis, Heated Pool

Siesta Key Condo Star 4.5 Star Review

There\'s plenty of room for everyone here at Our House. We have a split-level living/dining area, with a large living room made for a crowd! The huge sectional sofa faces our new HDTV with DVD player, so anytime you need a little downtime from all the outdoor fun, settle in with your favorite movie, a bowl of popcorn, and frosty drinks. The kitchen.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 4


Vacation Home


CA403N - 2/2 DIRECTLY ON THE BEACH - 4th Floor Views - Vacation Getaway

Siesta Key Condo Star 4.6 Star Review

403 N.
Last minute specials!
$200 off during the weeks of August 20/2022 to September 3/2022 and September 24 to October 1, 2022.

Come and enjoy the sun and moon light on the Gulf and feel the powder white sands of Siesta Key between your toes, where the sand never gets hot, steps away from your condo.
We are located on the 4th-f.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 6


Vacation Home


Welcome to Paradise! Pet Friendly! Walk to acclaimed Siesta Beach!

Siesta Key Private vacation home

**** APRIL IS THE BEST MONTH TO BE IN PARADISE !!! ****
Ahhh, welcome to Paradise — where sunny, warm weather embraces your soul. Snow, ice, rain, gray days got you down? Cheer up! Come and see why spring is the best time of year to be in Siesta Key, Florida. Enjoy this private 3 bedroom, 2 bath house on Palm Island, the.......read more

3 Bedroom(s)
2 Bath(s) Sleeps 9


Vacation Home


New Listing! Ground floor, easy access to the pool and beach! Siesta Dunes 2-104

Siesta Key Condo Star 4.0 Star Review

This ground floor 2 bedroom, 2 bathroom unit is nicely updated and comfortably furnished with easy access to the pool and the beach. Our Property is managed by the Siesta Dunes Rental Office and the staff is available to assist you during your stay.

Amenities include:

Gulf View, from 1st Floor

King in Master Bedroom

Show.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 4


Vacation Home


Perfect Siesta Village Pool Home! Walk to the beach and hang out in the Village!

Siesta Key Private vacation home Star 4.8 Star Review

This Lovely, fully updated 3 bedroom property that holds 4 Adults and 2kids.Its also is a 3 bath canal home 1 block from Siesta Village! Tropical private pool setting just off the main living area and the grand Master Bedroom. Second Master suite with private bath including soaking tub. All bathrooms completely redone in 2015. Quiet street literall.......read more

3 Bedroom(s)
3 Bath(s) Sleeps 6


Vacation Home


Sunset Royale - 118- Bright and Beachy Across from beautiful Siesta Key Beach!

Siesta Key Apartment Star 4.5 Star Review

Your ultimate vacation getaway! Bright and breezy 2 bedroom/2 bath condo across the street from Beach Access 11 at the world-renowned white sands of Siesta Beach.
Located on the main level, the open floor plan and beachy décor will fill you with good vibes. Enjoy morning coffee or pre dinner cocktails from your private outdoor patio. The maste.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 6


Vacation Home


New Listing! Sea Dream | Located in Siesta Key Village, Walk to the Beach!

Siesta Key Private vacation home Star 5.0 Star Review

Welcome to Sea Dream! This private unit is perfect for small families, with the ability to accommodate up to 4 guests, with 1 bedrooms and 1 bathrooms.

Cross the drawbridge from Sarasota to enter the serene island escape of Siesta Key, Florida! With clear blue gulf waters and powdery white sand, Siesta Key\'s world-renowned beaches are the p.......read more

1 Bedroom(s)
1 Bath(s) Sleeps 4


Vacation Home


Clean and Perfectly Remodeled Townhome, Steps From the Private Beach

Siesta Key Private vacation home Star 4.8 Star Review

Impeccably Clean, the reviews speak for themselves!

Located at Siesta Beach House, 5950 Midnight Pass Road, this luxurious Beach Townhouse, is just steps to its private beach entrance. Totally renovated top to bottom. This 2 bedroom, 2.5 bath Townhome is amazing and the best unit in the complex. Well, 302 is a close tie but that\'s mine .......read more

2 Bedroom(s)
3 Bath(s) Sleeps 5


Vacation Home


Slice of Beach Paradise | Private Wraparound Balcony with Amazing Gulf Views

Siesta Key Private vacation home Star 4.0 Star Review

Beach Road Condo Unit 2

Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click \'Book Now!\'

Perched by the shoreline, this 3BR/2BA townhome is a slice of beach paradise. With the Gulf just a 2-minute walk away, enjoy the stretches of sugar-white sand and turquoise .......read more

3 Bedroom(s)
2 Bath(s) Sleeps 6


Vacation Home


Newly Renovated Family Fun 2BR w/ Pool - Walk to Beach

Siesta Key Private vacation home Star 4.6 Star Review

Newly renovated gated beach access apartment with a pool. This is a two bedroom and two bath apartment that makes up one unit in a quadplex. It is on a very quiet private road that leads to a gated beach access way that only residents on this street have access too.

The house was completely redone and has all new furniture, sheets, pillows,.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 8


Vacation Home


Beautifully Updated Gulf View, 2 Bed, 2 Bath with Loft, Sleeping 6

Siesta Key Condo Star 5.0 Star Review

Beautifully updated 2 bedroom, 2 bathroom with loft, gulf view unit. This unit is new to the Rental Program as of June of 2019. The master features a king size bed, updated bathroom with a shower and side porch with a view of the water. The guest room has a king size bed. For convenience, the washer/dryer is in the guest room closet. The guest bath.......read more

3 Bedroom(s)
2 Bath(s) Sleeps 6


Vacation Home


Aloha Kai - Unit 4-updated and by the pool!

Siesta Key Cottage Star 5.0 Star Review

Fully furnished villas offer living room, dining area, fully equipped kitchens, 1 bedroom/ 1 bathroom. Screened porch. Short walk to the beach or pool. ALOHA KAI is a five acre vacation retreat hosting 68 private villas and apartments, nestled on the powdery-white sands of the Gulf of Mexico. Villas are at ground level, and offers a private parki.......read more

1 Bedroom(s)
1 Bath(s) Sleeps 4


Vacation Home


Aloha Kai - Unit 49-close to the pool!

Siesta Key Cottage Star 4.5 Star Review

This 2 story Villa is just steps from the largest heated pool on Siesta Key and a few minute walk to our wonderful private beach. Featuring 2 bedrooms upstairs, king bed in the master and 2 twins in the guest room with a full bath to share. This Villa also boasts a spacious living/dining area and fully stocked kitchen on the main floor. Sleeps u.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 6


Vacation Home


Stylish escape near the beach with free WiFi, pool, two balconies, & AC

Siesta Key Private vacation home Star 5.0 Star Review

Salt & Serenity

Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click \'Book Now!\'

The relaxed lifestyle of Siesta Key is calling your name for that rejuvenating beach vacation, so pack your favorite bathing suits and make your way to Salt & Serenity. Sitting just.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 6


Vacation Home


New Listing - Bali Hai House - A Siesta Key Water Front Cottage

Siesta Key Private vacation home Star 5.0 Star Review

Everything you\'re looking for in a comfortable and convenient vacation is waiting for you at Bali Hai House! This gorgeous waterfront home is fully equipped with a spacious outdoor patio, fire pit, and private screened in heated pool. Hang out on the hammock and watch boats drift by or take a short walk to Siesta Key Beach. This spot is ideal for.......read more

3 Bedroom(s)
2 Bath(s) Sleeps 8


Vacation Home


Luxurious Waterfront Retreat with bay & city views minutes from Beach

Siesta Key Private vacation home Star 5.0 Star Review

Villa Siesta sits poetically in a walled, gated garden on deep, azure-colored Hansen Bayou with views of Sarasota Bay & City skyline. This architecturally unique 5400 sf villa is built around a spacious tower with winding 3 story staircase opening to each living level.

The romantic residence is located just a few blocks from Shell Beach, les.......read more

4 Bedroom(s)
6 Bath(s) Sleeps 8


Vacation Home


Aloha Kai - 2 beautful unit and close to pool!

Siesta Key Cottage Star 5.0 Star Review

Fully furnished villa offers living room, dining area, fully equipped kitchen, two bedrooms and 2 bathrooms. ALOHA KAI is a five acre vacation retreat hosting 68 private villas and apartments, nestled on the powdery-white sands of the Gulf of Mexico. Villas are at ground level, and offers a private parking space directly outside your front door. T.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 4


Vacation Home


Pet-friendly condo a short walk from private beach & fishing dock on bay

Siesta Key Condo

Get your second wind at A Second Wind! Roomy, quiet and comfortable third-floor condo at beautiful Island Reef. Beach-to-bay complex on the peaceful side of Siesta Key with a pool view. Our private Gulf beach, pools and bay are not crowded at all. Two heated pools, tennis courts, pickleball and sauna. The private beach is just a five-minute walk ac.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 4


Vacation Home


"Safe & Clean" Hide-A-Way Suite, only 60 steps to the Siesta Key Public Beach

Siesta Key Apartment Star 4.7 Star Review

HIDE-A-WAY Suite

This enchanting comfortable and newly refurbished & updated 1 bedroom / 1 bath ground floor apartment, 580 is a strictly non-smoking unit. This apartment offers AC / heat, 1 king and a luxury queen size self inflating air bed for the living room.
All hyper-allergenic bedding, no feathers!
With a maximum occupancy of.......read more

Studio
1 Bath(s) Sleeps 4


Vacation Home


Siesta Key 2 Bedroom Condo

Siesta Key Condo Star 4.6 Star Review

Perfect little condo on siesta key, home of the #1 rated beach in the USA. Just minutes from the beaches and great restaurants.
Wi-fi, TV, full bath, screened in lanai, beach towels & chairs, everything you need for your home away from home. Fully loaded kitchen, coffee maker, micro, etc.
Local shuttle goes by for your convenience. Heated .......read more

2 Bedroom(s)
1 Bath(s) Sleeps 3


Vacation Home


Long Term Discounts! Siesta Key Palm Island Canal-Front House Walk to Beach

Siesta Key Private vacation home Star 4.9 Star Review

Large home with 3 bedrooms and 3 bathrooms. Looks and feels like a Mexican Hacienda. Low ceilings (approx 7 foot) in the living room and bedrooms. Three sliding glass doors open up to a screened in heated pool. Walk down the paver path to a dock on the canal. At night, lights under the water allow you to see the fish swimming in the canal. Le.......read more

3 Bedroom(s)
3 Bath(s)


Vacation Home


Casa Mar - 50- Ground floor unit in Gulf side Complex- studio!

Siesta Key Apartment Star 4.4 Star Review

This studio condo is approx 420 sq feet and offers a king size bed. Play tennis or shuffleboard, then bask in the sun by the swimming pool located steps from your unit. Stroll down palm lined walkway that lead to Siesta Key\'s fine white quartz sand and enjoy one of Florida\'s spectacular sunsets. Lounge chairs are conveniently located on the beach.......read more

1 Bedroom(s)
1 Bath(s) Sleeps 2


Vacation Home


Steps to Village and Beaches! Remodeled, two Private Patios! Casa Tranquilla.

Siesta Key Private vacation home Star 4.9 Star Review

This is Casa Tranquila, a Gertrude Rentals property steps to the Siesta Key Beach and Village! Leave the car behind at this spacious, fully renovated 3BR/2.5 bath home.  Lounge dine and drink while you soak up the sun on two large private patios, or walk 250 feet to a secluded access for amazing fishing, sunsets, and Gulf views including white-san.......read more

3 Bedroom(s)
3 Bath(s) Sleeps 10


Vacation Home


BEACHFRONT CONDO - THREE BEDROOM - HEATED POOL - FREE BOAT DOCKS - RENOVATED

siesta key Condo Star 4.9 Star Review

Beachfront Condo - Three Bedroom - Heated Pool - Free Boat Docks - Upscale - Siesta KeyLocated Next to Turtle Beach on the Southern End of Siesta Key, Sarasota, FL

Top beachfront unit at Fisherman\'s Cove!! Fisherman\'s Cove is a very rare Siesta Key condo where every unit has direct, unobstructed, full Gulf views. The building is one of t.......read more

3 Bedroom(s)
2 Bath(s) Sleeps 8


Vacation Home


Waterfront Condo at The Inlet - Great Views, Heated Pool on the Bay Quiet, Friendly Community #39

Siesta Key Condo Star 3.8 Star Review

Waterfront with Great Views & Large Heated Pool Overlooking the Bay

Cozy 2 bedroom, 3rd floor condo located directly on Turtle Beach Inlet where you can fish, swim, and boat just steps from your door. Condo has just been repainted throughout and features comfortable living room furniture w/sleeper sofa for overnight visitors. New dining set .......read more

2 Bedroom(s)
2 Bath(s) Sleeps 4


Vacation Home


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

Siesta Key Condo Star 5.0 Star Review

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 w.......read more

2 Bedroom(s)
4 Bath(s) Sleeps 6


Vacation Home


2 units next to each other on the #1 Beach in USA. Perfect vacation in Paradise

Siesta Key Condo

Siesta Key gulf side rental on one of the widest and most beautiful stretches of beach in the world. See why siesta key\'s beach has been rated #1 in the USA! There is a one month minimum rental for this property. You could be one of the first to stay here after a gut renovation down to the studs. This 1800 square foot, 2 bedroom 3.5 bath condo has.......read more

3 Bedroom(s)
5 Bath(s) Sleeps 10


Vacation Home


Private Home and Great Location with walking distance to Village and Beach!

Siesta Key Private vacation home Star 5.0 Star Review

Updated home in quiet neighborhood just off the beaten path to the Village and Beach. Walk to all of your favorite restaurants and shops. This is a private home with lush landscaping and surrounding privacy wall. Main Floor Master Suite and guest bedroom, upper level has a second master suite with another guest bedroom. The home sits on a corne.......read more

4 Bedroom(s)
4 Bath(s) Sleeps 8


Vacation Home


Midnight Cove II - 137-bay views and Gulf access!

Siesta Key Condo Star 4.0 Star Review

Enjoy this beautiful condominium in Midnight Cove II! Watch the boats go by from your open 3rd floor Bay front balcony! Updated unit with new kitchen, newly upgraded master bath with walk in shower, and washer and dryer. Enjoy a game of tennis at of their nicely appointed tennis courts, or a dip in the pool at their invitingly large community pool.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 5


Vacation Home


Cozy Family Condo- Beautiful Newly Renovated 2 Bedroom - Near Siesta Key!

Siesta Key Condo

The Dock Holiday is located at the popular Bay Oaks Condominiums in a beautiful, park-like setting on the intracoastal waterway, where you can watch the sunrise. Spacious and updated, second floor, two-story condo with almost 1400 square feet of living space.

The living room is furnished with a large flat-screen TV, including free WiFi, and .......read more

2 Bedroom(s)
3 Bath(s) Sleeps 6


Vacation Home


Walk to Siesta Key Beach, Pool/Spa/Tiki Bar, WiFi, Close to Village Shops, Laundry

Siesta Key Private vacation home Star 4.5 Star Review

If you are looking for a private home on Siesta Key that\'s only 460 feet from the Siesta Key Beach Access; then this is your vacation home to come to! It rests on a quiet street in a beautiful upscale neighborhood on Siesta Key just steps from playing in the sand with your kids, or reading a great novel under an umbrella with a glass of white wi.......read more

3 Bedroom(s)
2 Bath(s) Sleeps 6


Vacation Home


Spectacular Waterfront - Panoramic Views of Intercostal 3Bed- 2 Bath

Siesta Key Condo Star 5.0 Star Review

This spacious first floor waterfront condo has over 1879 sq. of indoor/outdoor living space. Boasting two gigantic elevated private outdoor patio’s with new outdoor furniture, along with water views of the Intercostal, direct access to marina, designated parking and your own private entrance. Siesta Beach #5 in the World #1 in the USA 2017!! P.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 6


Vacation Home


Our House at the Beach E-404 Sugar Sands Beach View!!

Siesta Key Condo Star 4.3 Star Review

Just across the street from the acclaimed #1 Beach in the US. This beautiful two bedroom/ 2 bath condo has all the comforts of home! This condo offers a fully equipped kitchen, spacious living room, dining area, washer and dryer and balconies off of both the living room and dining room. Linens and towels are also provided. The facilities includ.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 6


Vacation Home


Siesta Key Gulf Front Condo

Siesta Key Condo Star 5.0 Star Review

Located at CRESCENT ROYALE CONDOMINIUMS - one of the finest gated communities on Siesta Key. Large HEATED outdoor pool - this 2 bedroom/2 bath PRIVATELY OWNED vacation condo is steps away from world famous, breathtaking Siesta Beach - consistently VOTED #1 BEST BEACH IN THE USA year after year! This condo is nicely situated on the 2nd floor and is .......read more

2 Bedroom(s)
2 Bath(s) Sleeps 6


Vacation Home


Decadence on Siesta Key with private pool and dock

Siesta Key Private vacation home Star 4.5 Star Review

As you enter the property, you will take a walkway along the your private entry and into the private tropical backyard with the world’s smallest pool or the world’s largest jacuzzi, a fish-less pond, and a private dock on the canal where snook jump and manatees have been seen. Lounge chairs, tables, grill and fire pit are yours in the fenced in.......read more

1 Bedroom(s)
1 Bath(s) Sleeps 2


Vacation Home


Beautifully Updated Ground Floor at Gulf & Bay Club. Gulf Front Living at it's Finest!

Siesta Key Condo Star 5.0 Star Review

Beautifully Updated Ground Floor Condo at the Desirable Gulf & Bay Club. Gulf Front Living at it\'s Finest!

Just steps from Crescent Beach, you are sure to fall in love with this beautiful, spacious 2 bedroom, 2 bath ground floor unit with all the amenities the Gulf & Bay Club Resort has to offer. Step out the door of the enclosed lanai and.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 8


Vacation Home


Location. 3 bedroom cottage block from beach and two blocks from Siesta Village

Siesta Key Cottage Star 4.7 Star Review

Location, location, location. Our charming 3-bedroom 2 bath Florida beach cottage, which is over 1000 feet and sleeps 6, which we call the “Manatee Cottage” is across the street from the soft, white sands of the world-famous Siesta Beach which is consistently rated the best beach in the United States (you will be a 5 minute walk from access 7)........read more

3 Bedroom(s)
3 Bath(s) Sleeps 6


Vacation Home


Updated! Walk to SK Beach, 2 Heated Pools, WiFi/Cable, Screened Lanai, Tennis/Pickleball, Gym

Siesta Key Condo Star 5.0 Star Review

New Flooring 12/21...Smashing second story, 3 bedroom town home in popular Siesta Bayside on the Bay and for the best part.....you can walk to Siesta Key Beach...via our private access!! Resort style amenities include TWO heated swimming pools, Clubhouse & Fitness Center, BBQ Grill area with tables, 2 Tennis/Pickle-ball Courts with lights for ni.......read more

3 Bedroom(s)
2 Bath(s) Sleeps 8


Vacation Home


Casa Blanca B08 Villa

Siesta Key Villa Star 5.0 Star Review

2 Bedroom/ 2 Bath Private Villa, Close to Pool, Clubhouse, and Laundry. A few Steps to our Private Beach.

Master Bedroom new, King size pillow-top mattress, a tropical ceiling fan, upscale furnishings and is tastefully decorated for ultimate relaxation and comfort.

Second Bedroom is tastefully furnished with 2 twin beds.

Our v.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 4


Vacation Home


Beautiful 3/2 Home on Siesta Key, Palm Island !

Siesta Key Private vacation home Star 4.0 Star Review

This adorable 3BR/2BA home is located in the quiet neighborhood of Palm Island, just a short walk away from the world famous Siesta Key Beach! It is fully furnished and can sleep up to 6 comfortably! The master and guest bedrooms have queen size beds. The third bedroom has two twin beds. Siesta Key Village is a bike ride away and offers a variety .......read more

3 Bedroom(s)
2 Bath(s) Sleeps 6


Vacation Home


Siesta Key Beach View Condo New Stainless Steel Kitchen Appliances

Siesta Key Condo Star 5.0 Star Review

Looking for a little get away at the Beach? Well, you’ve found it! This recently updated condo features two bedrooms and one full bath which puts you in the perfect location steps away from the world-famous quartz sand of Siesta Key Beach. There is no need to worry about parking, you are a one minute walk to the beach. This 4th floor condo has a .......read more

2 Bedroom(s)
1 Bath(s) Sleeps 4


Vacation Home


Relaxing Siesta Key Condo

Siesta Key Condo Star 4.9 Star Review

Come and enjoy the island lifestyle on Siesta Key in this lovely furnished 3rd floor condo. Enjoy your morning coffee or evening cocktail on the balcony with views of the beautiful inter-coastal waterway from your vacation home. Deeded beach access to Siesta Key’s famous Crescent Beach quartz sand beach is just a short stroll across the street; a.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 4


Vacation Home


Scroll To Top