Properties

A minimum stay of one month is required in accordance with Peppertree Bay Association regulations.

☀️ Dreaming of Winter in Paradise?🌴 Call to book your seasonal stay by December 15th and ask about a 20% discount on select available condos.

42 properties  

6026 | 2 BEDROOM | 2 BATHROOM | GARDEN RETREAT

OwnerRez
2 Bedrooms • 2 Baths • Sleeps 1-4
Internet Pool
Relax and unwind at Peppertree Bay Unit 6026, a spacious 2-bedroom, 2-bath garden condominium on beautiful Siesta Key. Located in the peaceful Bayside section of the community, this inviting retreat features over 1,300 square feet of living space, a private lanai, fully equipped kitchen, in-unit washer and dryer, complimentary Wi-Fi. Guests enjoy exclusive access to Peppertree Bay's private beach, two heated pools, tennis and pickleball courts, fishing pier, and beautifully maintained tropical grounds. Just minutes from Siesta Key Village, it's the perfect destination for an unforgettable extended stay.

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1160 | 2BEDROOM | 2 BATHROOM | CRESCENT BEACH

OwnerRez
2 Bedrooms • 2 Baths • Sleeps 1-4
Internet Pool
Escape to Siesta Key in this inviting 2-bedroom, 2-bathroom Gulf side garden condo at Peppertree Bay, approximately 200 yards from Crescent Beach. Enjoy an updated kitchen with granite countertops, comfortable living spaces, a bright enclosed lanai, and king and queen bedrooms. Take advantage of private community beach access, two heated swimming pools, tennis courts, and fitness facilities. Perfect for a relaxing monthly getaway. Sleeps 4.

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1140 | 2 BEDROOM | 2 BATHROOM | SMALL GARDEN

OwnerRez
2 Bedrooms • 2 Baths • Sleeps 1-4
Internet Pool
Relax and settle into Siesta Key living in this comfortable 2-bedroom, 2-bath residence at Peppertree Bay. Featuring a king primary bedroom, 2 twin bed guest bedroom, full kitchen, in-unit laundry, and inviting living and dining areas, Unit 1140 is well suited for couples, families, and extended stays. Enjoy Peppertree Bay's private beach access, pools, tennis, fitness center, fishing pier, grilling areas, and beautiful Gulf-to-Bay community.

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6053 | 2 BEDROOM | 2 BATHROOM | GARDEN & BAY VIEW

OwnerRez
2 Bedrooms • 2 Baths • Sleeps 1-4
Internet Pool
Relax into island living at this beautifully updated 2-bedroom, 2-bath Peppertree Bay condo on Siesta Key. Enjoy peaceful garden and bay views from the enclosed sunroom, two queen bedrooms, two full baths, a fully equipped kitchen, in-unit laundry, Wi-Fi, and access to Peppertree Bay's private Crescent Beach, two heated pools, tennis/pickleball, fitness center and bayfront fishing pier. 30-night minimum.

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6061 | 2 BEDROOM | 2 BATHROOM | TOWNHOUSE

OwnerRez
2 Bedrooms • Sleeps 1-4
Internet Pool
Spacious 2BR, 2BA bayside residence offering comfortable island living and private beach access. Enjoy two heated pools, tennis and pickleball courts, fitness center, fishing pier, tropical grounds, and Peppertree Bay’s resort-style amenities during your relaxing 30-night stay on beautiful Siesta Key.

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1055-803 | 2 BEDROOM | 2 BATHROOM | PENTHOUSE

OwnerRez
2 Bedrooms • Sleeps 1-4
Accessible Internet Ocean View Pool
Luxury 2BR, 2BA eighth-floor Gulf view condominium featuring an expansive enclosed lanai, fully equipped kitchen, king primary suite, queen guest bedroom, and private beach access. Enjoy panoramic sunsets, two heated pools, tennis and pickleball courts, fitness center, fishing pier, covered parking, and all of Peppertree Bay's premier resort amenities during your relaxing 30-night stay on beautiful Siesta Key.

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1055-805 | 2 BEDROOM | 2 BATHROOM | MIDRISE

OwnerRez
2 Bedrooms • Sleeps 1-4
Accessible Internet Near Ocean Pool
Spacious and comfortable Siesta Key retreat for up to 4 guests. Enjoy a bright living space, full kitchen, two bedrooms and two bathrooms, plus access to the beautiful Peppertree Bay community and its convenient location near the beach, dining, shopping, and Siesta Key Village.

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1201 | 3 BEDROOM | 2 BATHROOM | TOWNHOUSE

OwnerRez
3 Bedrooms • 2 Baths • Sleeps 1-7
Internet Near Ocean Pool
Spacious 3-bedroom, 2 bath two-story townhouse at Peppertree Bay on Siesta Key. With approximately 1,686 square feet of living space and room for up to seven guests, Unit 1201 offers the comfort and space needed for an extended island stay, along with access to Peppertree Bay's beach, pools, tennis, fitness facilities, and tropical grounds.

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1255-101 | 2 BEDROOM | 2 BATHROOM | MIDRISE

OwnerRez
2 Bedrooms • Sleeps 1-4
Accessible Internet Pool
Enjoy your Siesta Key stay in this spacious first-floor bayside 2-bedroom, 2-bath condo at Peppertree Bay. Unit 1255-101 sleeps 4 with a king primary bedroom and two twin beds in the guest room. Enjoy an enclosed lanai, full kitchen, in-unit laundry, Wi-Fi, covered parking, private beach access, heated pools, tennis, pickleball, fitness facilities, and fishing pier. 30-night minimum.

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1055-207 | 2 BEDROOM | 2 BATHROOM | MIDRISE

OwnerRez
2 Bedrooms • Sleeps 1-4
Accessible Internet Near Ocean Pool
Relax and enjoy Siesta Key from this comfortable 2-bedroom, 2-bathroom second-floor condo at Peppertree Bay. Perfect for up to four guests, Unit 1055-207 features a full kitchen, in-unit laundry, Wi-Fi, elevator access, and free parking. Guests also enjoy Peppertree Bay’s private beach access, pools, tennis, fitness facilities, marina, fishing areas, and tropical community grounds. An ideal choice for an extended Siesta Key stay.

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1055-302 | 2 BEDROOM | 2 BATHROOM | MIDRISE

OwnerRez
2 Bedrooms • 2 Baths • Sleeps 1-4
Accessible Internet Near Ocean Pool
Bedding:
Master Bedroom: 1 King
Guest Bedroom: 1 Queen
Sleeper Sofa: No
Electronics:
Livingroom: 40'' TV
Master Bedroom: 32'' TV
Guest Bedroom: 32" TV
Bathrooms:
Master: bath tub - with grab bars
Guest: walk-in shower - with grab bars - without a shower seat

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1055-503 | 2 BEDROOM | 2 BATHROOM | MIDRISE

OwnerRez
2 Bedrooms • 2 Baths • Sleeps 1-4
Internet Pool
Luxurious fifth-floor Gulf-view condo featuring two king bedrooms, a renovated kitchen, expansive lanai, and private beach access. Enjoy Peppertree Bay's heated pools, tennis courts, fitness center, fishing pier, and resort amenities—all just steps from the world-famous white sands of Crescent Beach. Perfect for a relaxing 30-night stay on beautiful Siesta Key.

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