Vacation rentals with breakfast in Southside, Jacksonville

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Top-rated breakfast rentals in Southside, Jacksonville

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Guest favorite

Home in Ponte Vedra Beach

5 out of 5 average rating, 38 reviews

Direct Beachfront Private House 11 steps to beach

🐚Serenity awaits at this DIRECT oceanfront home on prestigious PV Beach, miles from public access. 🌟🌟🌟🌟🌟Hospitality is our passion! FREE welcome gift, breakfast starters, waters! Relax to soothing waves in hammocks yet close to spas, golf, parks dining and St. Augustine or TPC golf. We provide FLEX bedrooms- ASK two weeks before. ☕️This home is designed for your comforts, FAST WiFi & workspace, FREE parking & great amenities, HUGE deck & beach supplies! Stocked kitchen, coffee/tea bar, smart TVs🐬

Top guest favorite

A vibrant fountain display features streams of water illuminated in various shades of blue, enhancing the nighttime view of the skyline. Surrounding palm trees provide a tropical touch, while the city lights reflect off the water, creating a serene urban atmosphere.

Home in San Marco

4.98 out of 5 average rating, 261 reviews

Luxurious Craftsman in Historic San Marco

Never Drive Again! Immaculately renovated San Marco Bungalow, just a minute from excellent restaurants, retail, entertainment, hospitals & easy transit (via San Marco's FREE Beachside Buggy App) to everything else. Features include an inviting front porch, interior foyer, charming living room w/gas fireplace, new kitchen w/SS and granite, indoor laundry, historic architectural features, and private backyard w/ sitting area, fire pit, games & BBQ! Incredible location with unmatched walkability!

Guest favorite

A bathroom features a double sink vanity with wooden cabinetry and a large garden tub beside a window covered by light gray curtains. Natural light filters through, illuminating floral wall accents, while white towels hang neatly on the side.

Home in St. Augustine

4.98 out of 5 average rating, 49 reviews

Twin Oaks Family Retreat, Sleeps 8, N St Augustine

Cleaning fees the same as when we opened in 2019! Spacious 1412 sf home conveniently located 10-15 minutes by car to Vilano beach and nation's oldest city. Large backyard with grill and furniture. Off street parking. Master has King and bath with double sink, shower, garden tub. Queen bedroom and full bedroom separated by second bath with shower/tub combo at opposite end of house. Two family rooms one with 2 Twin/1King, other with full pullout sofa, Queen airbed available. Now with solar panels!

Guest favorite

Home in St. Augustine

4.87 out of 5 average rating, 127 reviews

St. Augustine's Sea Pearl~ BEACH HOUSE ~ Sleeps 10

WELCOME! Ready to wake up to the SUNRISE over the ATLANTIC OCEAN? Vacationers - no party? We love you guys, too! No Extra Fees if 10 people or under. EVENTS/Parties & WEDDINGS $7777= Beach House 4 NIGHTS All Decor Included in your colors/style. Ask about Payment Plans SeaSide Bar & Grill ~ Indoor Tiki Bar ~ 4 Bedrooms ~ Beach Ceremony ~ Beachside Dining for 50 ~ Dinner Garden holds 100 people. Bridal Dressing Room ~ Romantic Lighting ~ Hosting Beautiful Weddings is Our Super Power

Top guest favorite

A spacious backyard is featured, showcasing a fire pit surrounded by four adirondack chairs on lush green grass. A wooden fence provides privacy, enhancing the peaceful outdoor setting.

Home in Riverside

4.98 out of 5 average rating, 151 reviews

King bed home with bikes, arcade games and a BARn!

This super fun house is perfectly located in Riverside; Jacksonville's most fun neighborhood. It features two bikes, full-size arcade games, board games, darts, Wii, and a unique country western BARn in the backyard! Our backyard also has a firepit with adirondack chairs, a grill, horse shoes, a lasso game, and (obviously) 'smores kits! Walk to bars, restaurants, yoga studios, shops, & more. We'll also send you our local guidebook with things to do, where to shop, & where to eat and drink.

Guest favorite

Home in Jacksonville

4.8 out of 5 average rating, 94 reviews

The entire Wonderwood beach house! 3br / Hot Tub.

Welcome to “Wonderwood” where your beach adventure begins. Although the house is located in a populated area It feels like you are located in a tropical forest with no neighbors. This property is bounded on 4 sides by protected parks and savannahs. One block from Hanna Park, you are moments from the ocean surf and it’s ecological preserve. The house was completely renovated recently and is sterilized / ready for your arrival. 2 bicycles / hot tub included! It’s the closest Airbnb to NAS!

Top guest favorite

A woven basket contains two colorful beach towels and three pairs of flip-flops in varying designs. A bottle of sunscreen is positioned centrally, highlighting the beach essentials provided for guests.

Apartment in Southwest Jacksonville

4.97 out of 5 average rating, 140 reviews

Val's Sanctuary. In-law-suite, private unit.

Take it easy at this unique and tranquil getaway with private entrance. Enjoy this peaceful rural country area on the screened porch with an evening tea. You can play some games or puzzles if you want to stay inside or Crochet on the front lawn to enjoy some fresh air & sunshine. We are 2.5 Miles from the WW Ranch Motorcross park. We don't have anything new but I can assure you it will be clean. Sorry we are not suited for children or pets, 2 guests Max. and check-in must be before 9PM.

Top guest favorite

Home in San Marco

5 out of 5 average rating, 30 reviews

Snuggle up at The Happy Hearth •Sunset, Dine, Shop

IMPORTANT NOTE: This is a duplex—this listing is for the downstairs unit. Welcome to our charming historical duplex located in the heart of San Marco, Jacksonville, Florida! Just 2 blocks from the square and a short 3-minute walk to the St. John’s River and Landon Park, you’ll find the perfect balance of convenience and charm. Minutes away from downtown and Riverside, this unit offers modern comforts in an unbeatable location. Make this rental your ultimate retreat for a memorable getaway!

Top guest favorite

A spacious outdoor deck features comfortable seating and a dining area, surrounded by greenery. A grill is positioned for outdoor cooking, with bright flower pots adding color to the space. French doors lead into the interior, enhancing seamless indoor-outdoor living.

Home in St. Augustine

5 out of 5 average rating, 34 reviews

Steps to Private Beach Access-Game Room-Hot Tub

☀️Please Read Below/The Space☀️ -Garage renovated into Game Room-Simpsons arcade game-ping pong table/darts/TV/Playstation4&Nintendo64 /Air-conditioned. -Less than 1min walk to beach(pic#3) -Private hot tub off master suite -Newly built home -Private beach access/NOTcrowded -Indoor/outdoor living space-large deck&grill -Semi-private tropical outdoor shower -Yard completely fenced in 100x100 lot -Never flooded -5min from Publix Grocery -Vilano spots to eat-5min away-Beach/Intercoastal views

Guest favorite

The kitchen is equipped with modern white cabinetry, featuring a spacious granite countertop and a deep sink. A stylish hexagonal backsplash contrasts with the bright surfaces. Appliances, including a refrigerator and coffee maker, are present, while ample natural light enhances the open layout.

Home in Beaches

4.79 out of 5 average rating, 56 reviews

Seabreeze Gardens Bungalow

Beautifully renovated beach bungalow only 7 blocks from the Beach. Upscale finishes & furniture throughout. This 3 bedroom 2 bathroom single story makes you feel right at home. From the beautifully landscaped front and backyards to the ample amount of seating for guests, this property truly has it all. Kitchen essentials, laundry room with full sized washer/dryer. New wood deck outside for those perfect summer BBQs. Close to amazing restaurants, bars, public parks, and beach. $75 pet fee.

Guest favorite

A spacious lobby welcomes guests with high wooden ceilings and stone accents. Comfortable blue seating is arranged around wooden coffee tables, complemented by decorative plants. Natural light fills the area through large windows, creating an inviting environment for relaxation.

Condo in St. Augustine

4.97 out of 5 average rating, 64 reviews

Luxury Golf & Spa condo in Beautiful St. Augustine

Beautiful 1 bedroom pristine condo unit has it all. Comfortable king size bed, privacy, full bathroom with roman bathtub, washer/dryer, full kitchen with all the utensils you will need, two flat screen tv's, fast free wifi, private balcony overlooking lush gardens with a fountain. The Laterra resort boasts a plethora of amenities right outside your doorstep. Heated pool, pool with waterfall feature, hot tub, tennis courts, award winning Golf and restaurants nearby!

Top guest favorite

Home in Southwest Jacksonville

5 out of 5 average rating, 25 reviews

Cottontail Manor Ortega 4BR across from River

Welcome to the Cottontail Manor! Indulge in this luxurious large, serene space. Beautifully appointed 1 story (open floor plan) on one of the most desirable streets in Jax across from Ortega River & very close to Timuquana CC/Riverside/Avondale. Great for large family & special gatherings, or for those just wanting to get away and enjoy each other. A gift basket, spa robes & special coffees/tea await you! Extra comfortable beds with organic linens and soaps.