17 Best Vrbo Vacation Rentals In Gulf And Bay Club, Siesta Key, Florida - Updated 2024

Daniel
Daniel  
Updated
| 5 min read

The Gulf & Bay Club complex is a nest of luxurious accommodations and boasts of facilities that guarantee a lot of fun. This vacation includes visits to the beach so remember to pack your swimsuit. Featuring true resort-style vacation rentals with the breathtaking Gulf of Mexico and soothing lagoon views, once here you can indulge in many exciting activities like para-sailing or kayaking, canoeing or simply watch dolphins frolic in the surf. Other trips you can make include a visit to the art and circus museums, Ca’ d’Zan and the Mote Aquarium and check out the aquatic life including sharks, sea turtles, and other marine animals. Scroll below for the best Vrbo accommodations in Gulf And Bay Club, Siesta Key, Florida.

We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on March 02, 2024.

1. Two-bedroom condo with tennis courts and a fitness room (from USD 180)

A soothing bayside getaway awaits any guest who books a stay in this two-bedroom condominium unit. Perfect for families of up to six people, the condo features a plethora of family-friendly amenities like two outdoor tennis courts and a fitness room. The kitchen has an ice maker, stove, and oven. There are also beach chairs and beach towels as well for guests’ beach needs. Guests also have access to the communal pool and bayside dock.

As for nearby places to visit, the condo is only 0.1 mi (0.1 km) from Siesta Key Beach, 1.1 mi (1.7 km) from Siesta Key Marina, 1.5 mi (2.4 km) from Point of Rocks, and 2.5 mi (4 km) from Coconut Family Entertainment Center.

Stayed at this property?

1.91 km (1.2 mi) from Siesta Key Watersports
12 reviews   Wifi Available
condo 6 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 6
Minimum Nights: 7
Refund Policy : 100% refund if you cancel at least 60 days before check-in.

Top guest reviews
Amenities & Room:
the location nice iis next to one of the pools tennis courts and gas grills
the positives for us were new beds sleeper sofa linens and kitchen items
the living space itself was very comfortable and well-cared for with everything we needed and lots of light
this property had plenty of room for 3-4 adults - and a lovely screened-in porch
Cleanliness:
it is right next to the pool and the pool area is very nice clean and quiet
overall we absolutely loved this place and its location and how clean the property was
the beds were comfortable and everything was fully stocked and clean
our entire family had a great stay - very clean - great location - owner jd very responsive
Host:
the host was very responsive to our questions
the owner is very responsive to calls and text
jd was very responsive to any text we sent to him
very easy having direct communication with the owner jd
Location:
highly recommend this location when visiting siesta key
it is in an excellent location with access to the beach and a short drive to the village
it’s also an easy walk to the beach about a 5 to 10 minute walk
the location near the pool was also a benefit that we enjoyed
and the location could not be beat place would benefit from some newer upholstery and rugs
Read more reviews
Earn OneKeyCash for every dollar spent on eligible hotels, vacation rentals, flights, car rentals, and more when you book across our family of brands.

2. Condo with private beach access (from USD 170)

If it’s a beachside vacation that you’re after, then this two-bedroom condominium unit is a great place to consider. It features a private access to the beach, which is only five minutes away. There are also two heated swimming pools and a fishing dock available to further enhance your beachside getaway. The condo also has a screened-in lanai that showcases a lovely view of the area. For guests bringing their cars, there is a private garage available.

Other than the beach, the condo is close to various magnificent locations such as Point of Rocks, Gulf Gate Golf Club, Coconuts Family Entertainment Center, South Lido Park, and Sarasota Square.

Stayed at this property?

1.85 km (1.2 mi) from Siesta Key Watersports
14 reviews  
condo 6 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 6
Minimum Nights: 7
Refund Policy : 100% refund if you cancel at least 60 days before check-in.

Top guest reviews
Amenities & Room:
the location in siesta key itself is very nice and the pools on the property are great
Cleanliness:
is was very clean pool was very clean and warm
Location:
great location clean & good walk/drive to beach
the room was comfortable and close to everything
great location and loved the gulf & bay bayside community
great location access to the beach + pool + bay
Read more reviews
Earn OneKeyCash for every dollar spent on eligible hotels, vacation rentals, flights, car rentals, and more when you book across our family of brands.

3. Condo surrounded by tropical landscapes (from USD 335)

Located in a resort-style gated community, this three-bedroom condominium unit offers a serene and tropical getaway for its guests. The condo features a screened balcony that showcases the lush landscape and lakes that surround it. The living area is spacious and comes with a 55-inch flat-screen TV. The eat-in style kitchen has a breakfast bar, stove, and an oven. Do know that the condo requires a minimum of one week stay for any potential bookings.

As for nearby locations, the condo is only 0.1 mi (0.1 km) from Siesta Key Beach, 1.5 mi (2.4 km) from Point of Rocks, and 2.5 mi (4 km) from Coconuts Family Entertainment Center.

Stayed at this property?

1.57 km (1.0 mi) from Siesta Key Watersports
12 reviews   Wifi Available
condo 7 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 7
Minimum Nights: 0
Refund Policy : 100% refund if you cancel at least 60 days before check-in.

Top guest reviews
Amenities & Room:
pools were nice and neighborhood was perfect
we had enough space for 3 teenagers and 2 adults and it was very comfortable
both pools are very nice and it’s a short walk to the private beach
Cleanliness:
the property was clean updated and very nice
the place was very clean
the space in the condo was clean and felt like home we would stay there again
other than that this was by far the best rental we’ve had and was very clean
Location:
nice neighborhood close to the beach
the location was great and we enjoyed the access to the private beach
it’s about an 8 minute walk to the private beach but it was well worth it
the community is nice and friendly and a very short walk/drive to many attractions restaurants/bars
thanks for a nice experience place was a great location and was clean
Read more reviews
Earn OneKeyCash for every dollar spent on eligible hotels, vacation rentals, flights, car rentals, and more when you book across our family of brands.

4. Two-bedroom villa with private beach access (from USD 196)

Proudly exclaiming that it showcases the best of both worlds, this two-bedroom villa showcases a beautiful view of the intercoastal and neighboring yacht club marina. Because of this, the villa offers a private access to the beach, which is only a short walk away.

Amenities-wise, the villa includes a fireplace, satellite TV, DVD player, and various children’s games. Fishermen are in for a treat as guests are also provided two fishing poles, a tackle box, and a shrimp bait bucket. There is also a communal pool, two tennis courts, and a fitness room available.

Stayed at this property?
Siesta Key, FL, US
4 Guests 2 Bedrooms 2 Bathrooms
Earn OneKeyCash for every dollar spent on eligible hotels, vacation rentals, flights, car rentals, and more when you book across our family of brands.

5. Two-bedroom condo with a direct access to Siesta Key Beach (from USD 170)

Have a memorable beachside getaway in this two-bedroom condominium unit. Enjoy the serenity and charm of the surrounding area courtesy of the lush tropical landscape, shell paths, and quiet lakes with soothing fountains that are placed around the property. The condo features a direct access to the world-famous Siesta Key Beach.

As for amenities, the condo has a satellite TV, DVD player, stereo system, air conditioning, and a kitchen with a stove and oven. There is also a fishing dock, two heated pools, two tennis courts, and an exercise room available.

Stayed at this property?

1.85 km (1.2 mi) from Siesta Key Watersports
14 reviews  
condo 4 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 4
Minimum Nights: 1
Refund Policy : 100% refund if you cancel at least 60 days before check-in.

Top guest reviews
Amenities & Room:
the pools were both great
2 pools larger one very nice
i enjoyed sitting in the enclosed patio every morning eating breakfast
the room was clean other than some stains on the carpet that was addressed during our stay
Location:
good location access to beach across the st
and a short walk to public beach would definitely stay again
nice property and location between bay and ocean nicely furnished
Read more reviews
Earn OneKeyCash for every dollar spent on eligible hotels, vacation rentals, flights, car rentals, and more when you book across our family of brands.

6. Condo unit boasting panoramic seascapes (from USD 743)

For a Siesta Key vacation that’s filled with panoramic ocean views, book this fourth-floor unit that has a wraparound beachfront lanai. Featuring floor-to-ceiling windows, this bright rental is designed with an open layout interior to maximize the outdoor views. You can either lounge in the living area with comfy sofas or whip up great recipes in the well-equipped kitchen and you’ll still be able to enjoy the beach views in every direction. It is also readily equipped with cable TV and WiFi to keep you entertained. An ideal space for a group of eight, the unit has three bedrooms with single to king-size beds.

Before you head out and try the resort amenities, check out the bathroom’s inviting hot tub first. Your booking also grants you access to an Olympic-sized pool, a sauna, sports courts, a fitness facility, and more.

Stayed at this property?
Siesta Key, FL, US
8 Guests 3 Bedrooms 3 Bathrooms
Earn OneKeyCash for every dollar spent on eligible hotels, vacation rentals, flights, car rentals, and more when you book across our family of brands.

7. Serene and private two-bedroom condo (from USD 254)

This Gulf & Bay Club condo features two en-suite bedrooms. The master bedroom has a spacious king-sized bed that guarantees a great night’s sleep while also provides flat-screen TV for entertainment. The second bedroom has a pair of twin beds while in the living room the sofa converts to a bed for two to provide enough beds for extra guests. Enjoy all the facilities provided including pools, a hot tub, tennis courts, and a fitness center. Visit the picnic island with tiki huts for dining or you can decide to spend the day on the sandy beach right behind the rental.

Stayed at this property?

2.19 km (1.4 mi) from Siesta Key Watersports
Wifi Available
condo 6 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 6
Minimum Nights: 1
Refund Policy : 100% refund if you cancel at least 60 days before check-in.

Earn OneKeyCash for every dollar spent on eligible hotels, vacation rentals, flights, car rentals, and more when you book across our family of brands.

8. Beachfront getaway for couples (from USD 193)

Enjoy the comfort and luxury provided by this elegant beach house with two bedrooms and two bathrooms. The unit is able to accommodate four guests. It is well-equipped with a kitchen with granitic countertops, custom cabinets and rooms with crown moldings. Both bedrooms and the living room has cable TV as well as WiFi, provided throughout the unit. The master bedroom features a king size bed and a double sink bathroom and a walk-in closet. The guest bedroom has a king size pull-down bed with a large desk area and the adjoining bathroom has a deep tub with whirlpool jets.

Stayed at this property?

1.73 km (1.1 mi) from Siesta Key Watersports
condo 4 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 4
Minimum Nights: 0
Refund Policy : 100% refund if you cancel at least 60 days before check-in.

Earn OneKeyCash for every dollar spent on eligible hotels, vacation rentals, flights, car rentals, and more when you book across our family of brands.

9. Enjoy access to a private beach and poolside views (from USD 142)

Featuring brand new appliances and furnishings is this remodeled villa with stunning beach and pool views. A beachfront open-floor plan characterizes this picture-perfect vacation rental with a washer and dryer, two large flat-screen TVs, a provision of high-speed WiFi access, and a high-top dining table for four. Twin large beds are provided for guests. You and your family of four can enjoy a great experience at the refreshing azure waters of the Gulf and the sandy private beach. Other highlights include a breakfast bar with seating for four, a spacious stand-up shower in the spotless bathroom, a leather pull-out sofa, and parking space for one car.

Stayed at this property?
Siesta Key, FL, US
1.71 km (1.1 mi) from Siesta Key Watersports
7 reviews  
villa 4 Guests 1 Bedroom 1 Bathroom
Top guest reviews
Amenities & Room:
the clubhouse by the pool was so convenient, with a full kitchen and bathroom amenities, we were able to hang by the pool all day long, on many occasions
the kitchen was gorgeously remodeled, had all the bells and whistles
a spacious, quiet, warm beachside place to be
settle in (and everything you might need is there),and head off to the pool and ocean, both a walk away
the built in bar invites you to concoct your favorite cocktail and the gorgeous granite top counters, new appliances
Cleanliness:
the villa & accompanying carport area was clean and well-kept
this unit is so clean and comfortable
beautifully decorated
the villa was beautifully decorated, attention to detail was on point - it exceeded our expectations
we were over the top thrilled with this rental and thought it was professionally decorated until chris told us they did it themselves
Host:
welcoming, friendly people
we had the most amazing experience during our stay
the owner, chris, responded quickly during the booking of our stay - made us feel welcome and comfortable by answering all the questions we had up front
great manager (ania) and cooperative, caring and responsive owner (chris)
the gulf-side property has a laid back, relaxed vibe
Location:
location is close to beach, shopping and restaurants
charming, key-west village nearby
great beach
another good point
it's ground level so we could walk right in and not deal with stairs or wait on an elevator
Read more reviews
Earn OneKeyCash for every dollar spent on eligible hotels, vacation rentals, flights, car rentals, and more when you book across our family of brands.

10. Bright and well-furnished unit near the beach (from USD 193)

Enjoy the breathtaking views of the beach and the Gulf from this two-bedroom unit. It is well equipped with an updated kitchen and new furnishings in the living room. The bedrooms each have a bathroom which is newly redesigned. The unit is just steps from the sparkling white-quartz beach. Enjoy the most luxurious condo communities on Siesta Key, with top facilities within a resort that also has a freshwater lagoon with a footbridge towards an island in its midst.

Stayed at this property?

2.11 km (1.4 mi) from Siesta Key Watersports
condo 6 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 6
Minimum Nights: 0
Refund Policy : 100% refund if you cancel at least 60 days before check-in.

Earn OneKeyCash for every dollar spent on eligible hotels, vacation rentals, flights, car rentals, and more when you book across our family of brands.

11. Garden condo with great furnishing

This luxury garden condo includes two bedrooms and two bathrooms. The elegant interior décor includes beautiful furnishings and a warm cozy living room with large glass doors with a view of the outside patio and large windows which fill the room with natural light. The condo provides a home-away-from-home experience with the provision of a stunning living room, a large dining room with a seating table and a fully equipped kitchen.

Stayed at this property?

2.19 km (1.4 mi) from Siesta Key Watersports
4 reviews   Wifi Available
condo 4 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 4
Minimum Nights: 1
Refund Policy : 100% refund if you cancel at least 60 days before check-in.

Top guest reviews
Amenities & Room:
Loved the accommodations the ease to get to the beach
Host:
The weather was great and we rebooked for next year
Read more reviews
Oops, this listing is currently inactive. Check out these alternative properties in the same location.
Earn OneKeyCash for every dollar spent on eligible hotels, vacation rentals, flights, car rentals, and more when you book across our family of brands.

Properties available nearby

12. Charming cottage in Sea Club II Resort (from USD 153)

This quaint cottage in Sea Club II Resort that radiates the Old Florida ambiance will make for a tranquil escape in Siesta Key. It is equipped with a 42-inch cable TV, WiFi, and a queen-size bed for a convenient stay. The well-stocked kitchen has everything you could need to create your getaway favorites. You’ll have two private outdoor areas where you can experience alfresco dining under the canopy of trees.

Aside from your cottage amenities, you’ll also benefit from the resort’s facilities such as a heated pool, Tiki hut, fishing pier, picnic area, and clubhouse. You might also want to dedicate some days to exploring nearby sights including the beachfront, shops, and restaurants—all within short walking distance. This property is about two minutes from Gulf & Bay Club Condominiums.

Stayed at this property?
Siesta Key, Florida, United States
1.46 km (1.0 mi) from Siesta Key Watersports
cottage 2 Guests 1 Bedroom 1 Bathroom

Top guest reviews
Amenities & Room:
pool area was great with beautiful views of the intercoastal waterway
very comfortable unit in an exceptional setting
Cleanliness:
house was very clean as well as the grounds
Host:
property manager rae is very responsive to any questions or requests
Location:
cute little cottage in a nice location not far from the beach
there also are free shuttle buses
location by the water and pool is great
old florida charm :)cozy cottage close to main beach
Read more reviews
Earn OneKeyCash for every dollar spent on eligible hotels, vacation rentals, flights, car rentals, and more when you book across our family of brands.

13. Lovely condo unit in Palm Bay Club (from USD 126)

If you want a great view of Sarasota Bay from your accommodation, look no further for a vacation rental. This two-bedroom condo unit in Palm Bay Club, located half a mile (0.8 kilometers) from Gulf And Bay Club, is positioned on the peaceful bayside so you can watch the boats sail by the pier.

With its resort location, prepare to gain access to the club amenities such as heated pools, a fishing pier, a custom hot tub, a recreation room, and more.

During idle days, you can simply relax in the living room to catch a big game or watch your favorite shows on the HDTV with premium cable channels. Both of the bedrooms are also equipped with TVs and the vacation home has free WiFi installed. You can be your own chef in the fully furnished kitchen when it’s to fill the stomach.

Stayed at this property?

1.48 km (1.0 mi) from Siesta Key Watersports
129 reviews  
condo 6 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 6
Minimum Nights: 3
Refund Policy : 100% refund if you cancel at least 30 days before check-in.

Top guest reviews
Amenities & Room:
great beach access and pools were lovely
the pools were clean and warm
the room satisfied all our needs
pool and hot tub are a great perk as well
Cleanliness:
well maintained/clean on the bayside with the feel of home it never gets old staying here
Host:
owner easy to communicate with
owner said thanks for letting him know and didn’t offer any compensation or even an apology
the staff and security were very nice and other guest were friendly
the security guard named charlie was very helpful when we arrived
he was very friendly when we would see him during our stay
Location:
the location was beautiful
super close to the pool and a short walk to the beach
this condo and it’s location will not disappoint
great location for beach during the day and restaurants/ night life at night
great location well kept great stay over all
Read more reviews
Earn OneKeyCash for every dollar spent on eligible hotels, vacation rentals, flights, car rentals, and more when you book across our family of brands.

14. Cozy townhouse along Siesta Bayside Drive (from USD 270)

This newly renovated townhouse along Siesta Bayside Drive is the ideal refuge for binge-watchers. With three smart TVs, you’ll never miss out on your favorite shows. High-speed WiFi is on-hand to enable your streaming pleasures. The cozy home also highlights its modern interiors, especially the equipped kitchen area that can facilitate all your cooking adventures.

The property is just a short walk to the beach, perfect for soaking up the sun or admiring the glorious sunsets when welcoming the evening. When taking a break from the shores, you can make a splash on the communal pool. Note that the unit can comfortably sleep up to six people but the base rate is priced for four guests only. Additional charge applies to the extra guests.

Stayed at this property?

1.85 km (1.2 mi) from Siesta Key Watersports
55 reviews   Wifi Available
townhome 6 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 6
Minimum Nights: 7
Refund Policy : 100% refund if you cancel at least 60 days before check-in.

Top guest reviews
Amenities & Room:
we enjoyed the pool and cooking out on the grills for dinner a couple evenings
Cleanliness:
very clean and modern
great place very updated and clean close to pool and beach access good communication thanks
Host:
the staff was friendly and the owner easy to communicate with and very accommodating
we had great communication with the owners who have it all together
Location:
loved the location of this condo
family and kid friendly location
short walk to the beach which was beautiful
close to the beach and in a quiet neighborhood with good amenities
Read more reviews
Earn OneKeyCash for every dollar spent on eligible hotels, vacation rentals, flights, car rentals, and more when you book across our family of brands.

15. Bayside dwelling in Palm Bay Club (from USD 176)

Get the best of both worlds when you stay in this bayside condo unit at Palm Bay Club, offering a great location and value for money. You’ll get to spend your vacation in a resort-style complex without breaking the bank. Make your stay count by maximizing all the great amenities of the resort such as pools, a boat and fishing dock, a recreation facility, and more.

For days when you simply want to stay indoors, you can recline in the living room with leather furniture or take a full rest in either of the two bedrooms appointed with single and king-size beds. There’s also a fully equipped kitchen that can cater to your skillful cooking. Your stay is also made more convenient by the availability of flat-screen HDTVs, WiFi, and free local and long-distance calls throughout the US.

Stayed at this property?

1.41 km (0.9 mi) from Siesta Key Watersports
92 reviews   Wifi Available
condo 4 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 4
Minimum Nights: 3
Refund Policy :

Top guest reviews
Amenities & Room:
the 2 pools were wonderful and crescent beach is the best
the place has a nice swimming pool and hot tub one side and the beautiful beach on the other
Cleanliness:
very clean beautiful property
the place was clean and comfortable
the place was very clean and had everything we needed
the condo was clean and had everything we needed for our short trip
the condo was very well equipped with high quality items and exceptionally clean
Host:
thank you so much to the owners for their generous welcome care package of goodies they left us
all the staff and vacationers were friendly area restaurants-great service
the owners welcomed us with all kinds of snacks and bottled water
rental property was very clean had everything we needed owners had a generous care package when we arrived
the communication with the hosts was wonderful
Location:
the location is fabulous
excellent location free shuttle was just a few steps away
great condo and great location
this is a great condo with an easy walk to the beach
the access is great but it is a bit of a walk
Read more reviews
Earn OneKeyCash for every dollar spent on eligible hotels, vacation rentals, flights, car rentals, and more when you book across our family of brands.

16. Spacious condo unit in Sarasota Surf and Racquet Club (from USD 295)

Score all the amenities of the club resort without the heavy price tag at this spacious rental with breathtaking beach views. A spacious 1500-sq-ft (139.4-sq-m) condo unit, the property features an open layout living room with a 55-inch flat-screen TV, a 4-seater dining table, and a fully equipped kitchen with a bar for extra eating space. It has two bedrooms, which are fitted with plush king and double-size beds and 40-inch flat-screen TVs for the days that you feel like binge-watching all day. But by no means stay indoors as the pristine white-sand beach awaits.

While the beach cabana, canopies, and umbrellas are for rent, you can enjoy basking under the sun on the complimentary beach chairs. You’ll also have access to Sarasota Surf and Racquet Club’s two heated pools, pickleball and tennis courts, and fitness room.

Stayed at this property?
Sarasota, FL, US
6 Guests 2 Bedrooms 2 Bathrooms
Earn OneKeyCash for every dollar spent on eligible hotels, vacation rentals, flights, car rentals, and more when you book across our family of brands.

17. Lakeside condo with an old Key West charm (from USD 188)

This lakeside condo on Siesta Key is the perfect hideaway for a group of four that wants a home-away-from-home experience. The property syncs the old Key West village condo vibe and modern amenities for a trouble-free stay. Enjoy the comforts of contemporary equipment including a 50-inch smart TV, a Bluetooth soundbar, and reliable WiFi. You’ll also have two bedrooms that are appointed with snug beds, just make sure to check out the rooms first to call dibs on the one that features a bathtub.

For your culinary pursuits, there’s a well-equipped kitchen to facilitate your delicious cooking. The spacious ground floor also overlooks a tranquil pond with a fountain that’s perfect for quiet moments with your favorite drink. Note that this listing requires a minimum of 7-night stays in the off-peak season and 14 nights in peak season.

Stayed at this property?
Sarasota, FL, US
4 Guests 2 Bedrooms 2 Bathrooms
Earn OneKeyCash for every dollar spent on eligible hotels, vacation rentals, flights, car rentals, and more when you book across our family of brands.

Enjoy at the Gulf And Bay Club

Enjoy all that Gulf And Bay Club has to offer while staying in the most comfortable and luxurious accommodations with the best views and facilities. You will not be disappointed. Take the chance and book now!

Any must-sees we missed? Tell us about them in the comments section or write a post here to help out fellow travelers!
Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

History


Get Trip101 in your inbox

Unsubscribe in one click. See our Privacy Policy for more information on how we use your data

Daniel, a sports enthusiast with a passion for football, finds enjoyment in exploring new places, listening to music, and reading novels.

 Want to contribute as a Local Expert?
Explore Siesta Key
x
Good things are meant to be shared!
Back to top
Visited any of these places? Click this button to activate our "Add a Tip" feature to share your experience.