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 September 01, 2025.
1. Two-bedroom condo with tennis courts and a fitness room (from USD 299)
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.
Siesta Key, Florida, United States
2.14 km (1.4 mi) from Siesta Key Watersports
Top guest reviews
Host:
the host was very responsive to our questionsthe owner is very responsive to calls and textjd was very responsive to any text we sent to himvery easy having direct communication with the owner jdLocation:
highly recommend this location when visiting siesta keyit is in an excellent location with access to the beach and a short drive to the villageit’s also an easy walk to the beach about a 5 to 10 minute walkthe location near the pool was also a benefit that we enjoyedand the location could not be beat place would benefit from some newer upholstery and rugsCleanliness:
it is right next to the pool and the pool area is very nice clean and quietoverall we absolutely loved this place and its location and how clean the property wasthe beds were comfortable and everything was fully stocked and cleanour entire family had a great stay - very clean - great location - owner jd very responsiveRead more reviewsAmenities & Room:
the location nice iis next to one of the pools tennis courts and gas grillsthe positives for us were new beds sleeper sofa linens and kitchen itemsthe living space itself was very comfortable and well-cared for with everything we needed and lots of lightthis property had plenty of room for 3-4 adults - and a lovely screened-in porch
2. Condo with private beach access (from USD 238)
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.
Siesta Key, Florida, United States
1.85 km (1.2 mi) from Siesta Key Watersports
Top guest reviews
Location:
great location clean & good walk/drive to beachthe room was comfortable and close to everythinggreat location and loved the gulf & bay bayside communitygreat location access to the beach + pool + bayCleanliness:
is was very clean pool was very clean and warmRead more reviewsAmenities & Room:
the location in siesta key itself is very nice and the pools on the property are great
3. Condo surrounded by tropical landscapes (from USD 317)
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.
Siesta Key, Florida, United States
1.85 km (1.2 mi) from Siesta Key Watersports
Top guest reviews
Location:
nice neighborhood close to the beachthe location was great and we enjoyed the access to the private beachit’s about an 8 minute walk to the private beach but it was well worth itthe community is nice and friendly and a very short walk/drive to many attractions restaurants/barsthanks for a nice experience place was a great location and was cleanCleanliness:
the property was clean updated and very nicethe place was very cleanthe space in the condo was clean and felt like home we would stay there againother than that this was by far the best rental we’ve had and was very cleanRead more reviewsAmenities & Room:
pools were nice and neighborhood was perfectwe had enough space for 3 teenagers and 2 adults and it was very comfortableboth pools are very nice and it’s a short walk to the private beach
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.
Siesta Key, FL, US
5. Two-bedroom condo with a direct access to Siesta Key Beach
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.
1.85 km (1.2 mi) from Siesta Key WatersportsAccommodates: 4
Minimum Nights: 1
Refund Policy : 100% refund if you cancel at least 60 days before check-in.
Top guest reviews
Location:
good location access to beach across the stand a short walk to public beach would definitely stay againnice property and location between bay and ocean nicely furnishedRead more reviewsAmenities & Room:
the pools were both great2 pools larger one very nicei enjoyed sitting in the enclosed patio every morning eating breakfastthe room was clean other than some stains on the carpet that was addressed during our stay
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.
Siesta Key, FL, US
7. Serene and private two-bedroom condo
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.
2.19 km (1.4 mi) from Siesta Key WatersportsAccommodates: 6
Minimum Nights: 1
Refund Policy : 100% refund if you cancel at least 60 days before check-in.
8. Beachfront getaway for couples
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.
1.73 km (1.1 mi) from Siesta Key WatersportsAccommodates: 4
Minimum Nights: 0
Refund Policy : 100% refund if you cancel at least 60 days before check-in.
9. Enjoy access to a private beach and poolside views (from USD 209)
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.
Siesta Key, Florida, United States
1.58 km (1.0 mi) from Siesta Key Watersports
Top guest reviews
Host:
welcoming, friendly peoplewe had the most amazing experience during our staythe owner, chris, responded quickly during the booking of our stay - made us feel welcome and comfortable by answering all the questions we had up frontgreat manager (ania) and cooperative, caring and responsive owner (chris)the gulf-side property has a laid back, relaxed vibeLocation:
location is close to beach, shopping and restaurantscharming, key-west village nearbygreat beachanother good pointit's ground level so we could walk right in and not deal with stairs or wait on an elevatorCleanliness:
the villa & accompanying carport area was clean and well-keptthis unit is so clean and comfortablebeautifully decoratedthe villa was beautifully decorated, attention to detail was on point - it exceeded our expectationswe were over the top thrilled with this rental and thought it was professionally decorated until chris told us they did it themselvesRead more reviewsAmenities & 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 occasionsthe kitchen was gorgeously remodeled, had all the bells and whistlesa spacious, quiet, warm beachside place to besettle in (and everything you might need is there),and head off to the pool and ocean, both a walk awaythe built in bar invites you to concoct your favorite cocktail and the gorgeous granite top counters, new appliances
10. Bright and well-furnished unit near the beach
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.
2.11 km (1.4 mi) from Siesta Key WatersportsAccommodates: 6
Minimum Nights: 0
Refund Policy : 100% refund if you cancel at least 60 days before check-in.
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.
2.19 km (1.4 mi) from Siesta Key WatersportsAccommodates: 4
Minimum Nights: 1
Refund Policy : 100% refund if you cancel at least 60 days before check-in.
Top guest reviews
Host:
The weather was great and we rebooked for next yearRead more reviewsAmenities & Room:
Loved the accommodations the ease to get to the beach
12. Elegant beachfront condo
Check out this elegant two-bedroom and two-bathroom condo nestled in the Siesta Key Beach. The condo is fully equipped with basic amenities for use during your stay. Accommodating a total of six guests you can enjoy all the facilities provided in the premise including a state-of-the-art fitness center, saunas, three heated swimming pools, tennis courts, grilling areas, and clubhouses. Enjoy some quality time at the beach where you get to experience great sunset views in the evening.
2.05 km (1.3 mi) from Siesta Key Watersports
13. Cozy vacation retreat
A perfect retreat located just steps away from Siesta Key Beach. This two-bedroom unit is generously spaced and includes a large dining table, a laundry room and an expansive family room with large-screen flat TV. The bedrooms have a bathroom each. Enjoy all the facilities provided including access to the heated pools, state-of-the-art fitness center and access to WiFi. The unit accommodates four guests.
2.07 km (1.3 mi) from Siesta Key WatersportsTop guest reviews
Host:
the unit was also terrificManager and owner very responsivethe best recommendation I can give is that we have booked again for next yearComfortable near pool GulfGulf and Bay is terrificLocation:
Have stayed here many times and its the best location in the complexExternally the complex has swimming BBQ gym and walking facilities together with a magnificent beach If you are looking for a sunny seaside holidaybut you could tell they've kept it in really good shapeRead more reviewsAmenities & Room:
Very comfortable Lots of kitchen stuffThe condo it fully furnished and has everything you will needAll the usual kitchen laundry equipment is provided A dedicated car parking facility is available adjacent to the propertyThis unit might not be renovated with granite countertopsThe accommodation compromises two bedrooms two bathrooms kitchen combined dining/sitting area with a covered/enclosed external sun room
14. A spacious beachfront condo
A charming three-bedroom accommodation is available at the Siesta Key Beach. Comfortable and posh, the accommodation can comfortably house eight guests. The rental has a large dining table while the main living room offers a flat-screen TV and bar. After a long and lazy day at the beach, retreat to a sumptuous master bedroom suite with a bathtub. Enjoy 24-hour security, with picturesque views of the beach and pool from the enclosed patio. Enjoy the Gulf and Bay complex with 24-hour security guards and featuring three swimming pools, courts, indoor hot tub, and two state-of-the-art fitness centers.
2.12 km (1.4 mi) from Siesta Key WatersportsTop guest reviews
Host:
the owners were extremely considerate and attentive hostsyou can tell the owner cares about your experiencethe gulf and bay staff from gate attendants to grounds keepers are welcoming and pleasantthe owner was very thoughtful and easy to contactthe owners are easily accessible and very pleasantLocation:
amazing set up in the perfect locationCleanliness:
the pools were clean and the beach always ready for our enjoymentRead more reviewsAmenities & Room:
all of the furniture is comfortablebed & couches & even beach chairs on patio very comfortablework out rooms were easy to access and enjoy
15. Appreciate beautiful views from this condo
Check out this waterfront spacious unit surrounded by lush, tropical landscaping, shell paths, and quiet lakes with soothing fountains. The two-bedroom condo provides you with a private garage and is the perfect choice for a quiet and comfortable vacation stay. The rental is air-conditioned with large glass sliding doors that invite pure and fresh tropical air into the house. Enjoy the Gulf & Bay Club in the best possible way while staying in this accommodation.
1.85 km (1.2 mi) from Siesta Key Watersports
16. Spacious two-bedroom vacation home
This two-bedroom condo comfortably accommodates six guests and is situated near the best of Gulf & Bay. Its spacious living area is great for relaxing and features a brand-new leather love seat and couch, cable TV and DVD player. The dining area is well appointed while the master bedroom is a comfortable haven for a good night’s sleep and features a king-sized bed, Papasan chair, big TV, and desk. This unit is great for your vacation.
1.85 km (1.2 mi) from Siesta Key WatersportsTop guest reviews
Host:
but the owner had beach chairs and a wagon for transporting them in the garageand she told me a long list of things people stealI would expect more As I said everything else met or exceeded expectationsWe have had a nice time there Really convenient and close to the beachWe drove parked and had a great time on the beachLocation:
just a few minutes walkjust a 5 minute walk30 minute walk Apart from 3 Daysyou just really want to partake in the funThe walk to the beach is about 5 minutesCleanliness:
The townhouse was very cleanTotally enjoyed our stay Very comfortable and clean condoThe property next to ours had two bicyles in the garage for use by guestsRead more reviewsAmenities & Room:
The apartment is great for allBayside Because it is not gulf sideThe apartment has a great kitchen with mod con appliancesso we had to watch the TV in our bedroomI did however have 1 major issue that should be corrected The king mattress in the master BR and
Properties available nearby
17. Charming cottage in Sea Club II Resort
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.
Siesta Key, Florida, United States
1.46 km (1.0 mi) from Siesta Key Watersports
Top guest reviews
Host:
property manager rae is very responsive to any questions or requestsLocation:
cute little cottage in a nice location not far from the beachthere also are free shuttle buseslocation by the water and pool is greatold florida charm :)cozy cottage close to main beachCleanliness:
house was very clean as well as the groundsRead more reviewsAmenities & Room:
pool area was great with beautiful views of the intercoastal waterwayvery comfortable unit in an exceptional setting
18. Lovely condo unit in Palm Bay Club
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.
1.48 km (1.0 mi) from Siesta Key WatersportsAccommodates: 6
Minimum Nights: 3
Refund Policy : 100% refund if you cancel at least 30 days before check-in.
Top guest reviews
Host:
owner easy to communicate withowner said thanks for letting him know and didn’t offer any compensation or even an apologythe staff and security were very nice and other guest were friendlythe security guard named charlie was very helpful when we arrivedhe was very friendly when we would see him during our stayLocation:
the location was beautifulsuper close to the pool and a short walk to the beachthis condo and it’s location will not disappointgreat location for beach during the day and restaurants/ night life at nightgreat location well kept great stay over allCleanliness:
well maintained/clean on the bayside with the feel of home it never gets old staying hereRead more reviewsAmenities & Room:
great beach access and pools were lovelythe pools were clean and warmthe room satisfied all our needspool and hot tub are a great perk as well
19. Cozy townhouse along Siesta Bayside Drive (from USD 318)
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.
Siesta Key, Florida, United States
1.85 km (1.2 mi) from Siesta Key Watersports
Top guest reviews
Host:
the staff was friendly and the owner easy to communicate with and very accommodatingwe had great communication with the owners who have it all togetherLocation:
loved the location of this condofamily and kid friendly locationshort walk to the beach which was beautifulclose to the beach and in a quiet neighborhood with good amenitiesCleanliness:
very clean and moderngreat place very updated and clean close to pool and beach access good communication thanksRead more reviewsAmenities & Room:
we enjoyed the pool and cooking out on the grills for dinner a couple evenings
20. Bayside dwelling in Palm Bay Club (from USD 305)
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.
Siesta Key, Florida, United States
1.41 km (0.9 mi) from Siesta Key Watersports
Top guest reviews
Host:
thank you so much to the owners for their generous welcome care package of goodies they left usall the staff and vacationers were friendly area restaurants-great servicethe owners welcomed us with all kinds of snacks and bottled waterrental property was very clean had everything we needed owners had a generous care package when we arrivedthe communication with the hosts was wonderfulLocation:
the location is fabulousexcellent location free shuttle was just a few steps awaygreat condo and great locationthis is a great condo with an easy walk to the beachthe access is great but it is a bit of a walkCleanliness:
very clean beautiful propertythe place was clean and comfortablethe place was very clean and had everything we neededthe condo was clean and had everything we needed for our short tripthe condo was very well equipped with high quality items and exceptionally cleanRead more reviewsAmenities & Room:
the 2 pools were wonderful and crescent beach is the bestthe place has a nice swimming pool and hot tub one side and the beautiful beach on the other
21. 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.
Sarasota, FL, US
22. Lakeside condo with an old Key West charm
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.
Sarasota, FL, US
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!
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