Resort holiday rentals in Hillsborough County

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Top-rated resort stays in Hillsborough County

Guests agree: These resort stays are highly rated for location, cleanliness and more.

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Top Guest favourite

A modern kitchenette is equipped with a stainless steel sink, a black coffee maker, and a built-in flat top electric stove. A microwave is mounted above, and textured tile backsplash adds a subtle design element.

Resort in Ruskin

4.9 out of 5 average rating, 68 reviews

Little Harbor Hideaway

Welcome to Little Harbor Hideaway! Enjoy the Beach, 2 pools,Hot Tub & Kayaking on Cabbage Creek. We also have 2 restaurants on property. * New PickleBall courts & CornHole boards Our Unit has a very nice king bed as well as a sectional couch with pull out full bed. This unit has a full refrigerator and also has a built in flat top electric stove. 50in Sony Smart TV for Netflix etc +cable New A/C in late 2023 This is a 2nd FL unit w/ large Balcony new Washer & Dryer in common area near steps.

Guest favourite

A vibrant sunset fills the sky with hues of orange, pink, and blue, reflecting on the water's surface. Silhouettes of wooden piers extend into the water, and tables with umbrellas are positioned in the foreground, creating a serene scenic view.

Resort in Dunedin

4.94 out of 5 average rating, 66 reviews

Best of Beso Suite Water View ADA 2Balcony/1BR/2BA

Stay in the heart of it all at this one-of-a-kind, unique double unit condo, which boasts views from 2 balconies, has 2 full bathrooms & a private bedroom suite. This upscale, tropical oasis is located right off the Gulf of Mexico’s St. Joseph Sound! RELAX & ENJOY the jacuzzi, dolphin watching & barbecuing, from Beso Del Sol Resort’s Waterfront Guest Pool Deck. Bask in the splendor of Delightful Dunedin’s Premier Resort’s Spectacular Sunset with a complimentary shot from Marker 8 Tiki Bar!

This beachfront guest room features two spacious beds with crisp linens. A seating area includes two red chairs paired with a small table. Large windows overlook palm trees and the beach. Artwork on the walls adds a pop of color, while a ceiling fan enhances comfort.

Resort in Treasure Island

3.5 out of 5 average rating, 4 reviews

Beachfront Traditional

Located in the Shells building. Enjoy breathtaking sunset views from your large picture window which overlooks Treasure Island’s wide sandy beaches along the Gulf of Mexico. This 297 Sq. Ft. beachfront guest room features (2) Queen Pillow Top Beds. Other features include: * 55” LCD Flat Panel TV * Mini Refrigerator * Microwave * Coffee Maker * Toaster * AM/FM Clock Radio * Hairdryer * Iron, Ironing Board * Electronic Safe * Ceiling Fan * Beach Towels

An aerial view captures the vibrant coastal landscape, highlighting the long stretch of white sandy beaches and turquoise waters. The layout of the small island showcases various buildings and neighborhoods, with roads and waterways interspersed throughout the scene.

Resort in Clearwater

4.62 out of 5 average rating, 21 reviews

Adorable Affordable Beach Efficiency

A Beach Adventure Awaits You..Come Play Or Relax @ the Coral Resort Clearwater Beach, Fl This small , lovely island is all water, beaches, restaurants and fun. NO CAR NEEDED. Bike or walk the beach. Visit: Winter the dolphin is right here... White sand will surround you on all these public beaches . Free parking/ internet. Managers onsite. 24 hr Fishing Pier on site. Rent jetski/boats in walking distance. YOLO Note: Unit A5 is a second floor/no elevator.

Guest favourite

A serene beach scene is captured, showcasing fine white sand and gentle waves. Colorful beach umbrellas dot the shoreline, while a wooden walkway leads to the beach from the grassy dunes. The clear blue sky enhances the tranquil atmosphere over the coastal view.

Resort in Treasure Island

4.94 out of 5 average rating, 83 reviews

Treasure Island Beachfront Resort with pool

Amazing beach views from your vacation condo unit and from your private balcony. Newly refreshed privately owned condo at the Island Inn Beach Resort in Treasure Island Florida. Treasure Island is next to St. Pete Beach, south of John's Pass, Madeira Beach, Indian Rocks and Clearwater beaches. Pool bar, heated pool on beach, kitchen with two burner hot plate, pots, pans, coffee maker, microwave and more.

Superhost

A relaxing bedroom features a spacious bed adorned with a light floral pattern. Natural light enters through a nearby window with blinds. Artwork and decorative fish embellish the walls, while a bedside table with a lamp adds functionality.

Resort in Anna Maria

Grand Suite 8

2+ Guests (*2 non-sleeper sofas) Beds : Queen Living Rm, Indoor/ Outdoor Dining for 15 Private 40’ Water Facing Deck, Outdoor Grills Marble Tub/Shower Combination plus ½ Bath Chef Kitchen: 3 Ovens, Side by Side Refrigerator Coffeemaker, Toaster, Microwave, Dishwasher Beach Towels, Spa Robes 2 -TV’s, Secure WIFI, and Cable Rm Temp Control, Fan, Dual Dark/Light Shades

Superhost

The living area features a light-colored leather sofa complemented by colorful armchairs. A modern kitchen with stainless steel appliances and granite countertops is visible. A large wall-mounted TV sits above a stylish console, while natural light flows through nearby windows, enhancing the inviting layout.

Resort in Anna Maria

Grand Suite 6

2 - 6 Guests Beds : RM 1- King, RM 2 - Full, Twin/Twin Bunk Living Room, Leather Sofa, Dining Bar Marble Bathrooms and Oversized Shower Full Refrigerator, Dishwasher, Oven, W/D Coffeemaker, Toaster, Microwave, Hair Dryer Complimentary Coffee/Condiments/Toiletries Beach Towels, Spa Robes 3 -TV’s, Secure WIFI, and Cable Rm Temp Control, Fan, Dual Dark/Light Shades

Guest favourite

A well-appointed bedroom features a king-sized bed adorned with a colorful, patterned quilt. Bright artwork depicting beach scenes is displayed above the bed. A ceiling fan helps maintain a comfortable atmosphere, while natural light streams in from a door that opens to the outside.

Resort in Anna Maria

5 out of 5 average rating, 6 reviews

Suite 2

2 - 6 Guests Beds : RM 1- King, RM 2 - Full, Twin/Twin Bunk Marble Tub and Shower Combination Fully Stocked Efficiency Kitchenette Keurig K-Cup, Refrigerator, Micro/Conv Oven Toaster, Complimentary Coffee/Condiments Hair Dryer, Complimentary Toiletries Beach Towels, Spa Robes 2-TV’s, Secure WIFI, and Cable Rm Temp Control, Fan, Dual Dark/Light Shades

Superhost

A cozy sleeping area features a queen bed adorned with colorful bedding and light wood furnishings. A leather seating area is positioned beside the bed, complemented by a wicker storage table. Natural light enters through the nearby windows, enhancing the welcoming ambiance.

Resort in Anna Maria

4.86 out of 5 average rating, 7 reviews

Suite 5

2 Guests - Bed : Queen Dining Bar and Leather Seating Area Marble Bathroom and Shower Fully Stocked Efficiency Kitchenette Keurig K-Cup, Refrigerator, Micro/Conv Oven Toaster, Complimentary Coffee/Condiments Hair Dryer, Complimentary Toiletries Beach Towels, Spa Robes 1-TV, Secure WIFI, and Cable Rm Temp Control, Fan, Dual Dark/Light Shades

Suite 4

Suite 3

2 - 6 Guests Beds : Queen, Queen, Full/Twin Bunk Marble Tub and Shower Combination Fully Stocked Efficiency Kitchenette Keurig K-Cup, Refrigerator, Micro/Conv Oven Toaster, Complimentary Coffee/Condiments Hair Dryer, Complimentary Toiletries Beach Towels, Spa Robes 2-TV’s, Secure WIFI, and Cable Rm Temp Control, Fan, Dual Dark/Light Shades

Superhost

A bright bedroom features a spacious bed adorned with colorful floral bedding and decorative pillows. Flanking the bed are two bedside lamps and a mirrored nightstand. A piece of beach-themed artwork is displayed on the wall, while a door leads to a marble-finished bathroom.

Resort in Anna Maria

4.78 out of 5 average rating, 9 reviews

Suite 1 - Rod and Reel Resort

2 Guests - Queen Bed; Marble European Oversized Shower, Dual Wardrobe and Built-in TV, Keurig Coffee Maker, Hairdryer, Outdoor Refrigerator for Drinks, Complimentary Toiletries, Complimentary Coffee and Condiments, Beach Towels, Spa Robes Secure WI-FI, and Cable Rm Temp Control, Fan, Dual Dark/Light Shades, and Complimentary Bicycles.