Luxury Florida Vacation Homes

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AMI_222 | Island Life Villa Welcome to Island Life Villa, located on the beautiful Anna Maria Island! This 5-bed, 4-bath villa is 3,338 sq. ft, main house and with attached guest residence, and a pool with the view of the bay.

AMI_222 | Island Life Villa

AMI_222 | Island Life Villa

AMI_222 | Island Life Villa

AMI_222 | Island Life Villa

AMI_222 | Island Life Villa

AMI_222 | Island Life Villa

AMI_222 | Island Life Villa

10 guests 5 bed 4 bath 3,338 sq ft

Gulf Coast - Anna Maria Island | Bradenton Beach

Starting at $699 daily

AMI_5002R Happy Place 2

AMI_5002R Happy Place 2

AMI_5002R Happy Place 2

AMI_5002R Happy Place 2

AMI_5002R Happy Place 2

AMI_5002R Happy Place 2

AMI_5002R Happy Place 2

AMI_5002R Happy Place 2

10 guests 5 bed 4 bath 4,000 sq ft

Gulf Coast - Anna Maria Island | Holmes Beach

Recommended Rental Flex30

Starting at $439 daily

CJs on Siesta - 104 The CJs on Siesta Building with the Beautiful Coast in the Background

CJs on Siesta - 104 The CJs on Siesta Complex, Showing Off the 2 Stories and an Outdoor Patio Area.

CJs on Siesta - 104 A Bird's Eye View Showing CJs on Siesta's Location next to the Beach

CJs on Siesta - 104 The Outdoor Patio Area Fitted with Loungers and Tables

CJs on Siesta - 104 A Beach Equipment Docking Area, Each Marked by their Respective Unit

CJs on Siesta - 104 The 2nd Floor Entrance to Unit 274, Sea Angel

CJs on Siesta - 104 Sea Angel's Living Area, Featuring a Pull-Out Sleeper Couch, A Dining Table, A Fully Stocked Kitchen, and a Desk.

CJs on Siesta - 104 Sea Angel's Living Area, Featuring a Pull-Out Sleeper Couch, A Dining Table, and a Large HD TV

24 guests 6 bed 6 bath 3,222 sq ft

Gulf Coast - Siesta Key | Siesta Key

Starting at $1,062 daily

941 Bunker View Dr

941 Bunker View Dr

941 Bunker View Dr

941 Bunker View Dr

941 Bunker View Dr

941 Bunker View Dr

941 Bunker View Dr

941 Bunker View Dr

12 guests 5 bed 4 bath 3,676 sq ft

Gulf Coast - Other | Apollo Beach

Starting at $630 daily

26 Heilwood SUNNY ORANGE STAYS presents… ☀️ Forever Sunshine ➠ 26 Heilwood

26 Heilwood Hosting a family reunion, corporate retreat, or destination wedding? This massive 9-bedroom estate is custom-built for large groups, sleeping up to 26 guests.

26 Heilwood Located just a block from the white sands of Clearwater Beach, this home features a private heated pool, an incredible outdoor entertainment bar

26 Heilwood Rooftop terrace with the Gulf views and enough space for everyone to spread out

26 Heilwood Steps to the Sand – A quick 1.5-minute walk puts you directly on the quiet sands of Clearwater Beach.

26 Heilwood The backyard is designed for parties and gatherings.

26 Heilwood Private Heated Pool– Resort-style pool with a waterfall feature, perfect for kids and adults alike (Heat available for a fee)

26 Heilwood Outdoor Tiki Bar – A massive covered entertainment area with a TV and seating—the group's favorite hangout spot.

26 guests 9 bed 5 bath 2,400 sq ft

Gulf Coast - Clearwater Beach | Clearwater Beach

4.9 (58)

Guest rating

Starting at $1,189 daily

971 Eldorado SUNNY ORANGE STAYS presents… 🌴 Casa Del Mar ➠ 971 Eldorado

971 Eldorado Private Screened Pool – A sparkling oasis with a waterfall feature, fully screened for comfort (Pool heat available for a fee)

971 Eldorado Comprising a spacious main house and a Casita, this property is the ultimate compound for reunions and large groups.

971 Eldorado Gather the whole extended family at this sprawling 6-bedroom coastal estate, located in the uncrowded North Beach neighborhood of Clearwater.

971 Eldorado Main Living: Comfortable seating and a large Smart TV for movie nights.

971 Eldorado Climate Controlled Florida Room – An extra living space to spread out, play games, or relax out of the sun.

971 Eldorado Steps to North Beach – Located directly across the street from a quiet, residential stretch of sand away from the high-rise crowds.

971 Eldorado Parking for 5 Vehicles – Rare for Clearwater Beach, featuring two separate driveways for hassle-free parking.

12 guests 6 bed 4 bath 2,932 sq ft

Gulf Coast - Clearwater Beach | Clearwater Beach

4.9 (21)

Guest rating

Starting at $859 daily

Tranquility - 113 Welcome to Tranquility! A quiet outdoor setting with pool, water features, and layered landscaping.

Tranquility - 113 An aerial view showcasing your homes proximity to the water.

Tranquility - 113 The spa flows into the pool, with multiple seating areas just steps away.

Tranquility - 113 A grand entry with arched architectural details and a paver driveway.

Tranquility - 113 Outdoor seating and dining are arranged around the pool for easy gathering.

Tranquility - 113 The front elevation features Mediterranean-inspired design and mature landscaping.

Tranquility - 113 A welcoming entry opens into a formal dining space with high ceilings and detailed finishes.

Tranquility - 113 The dining table comfortably seats guests for both casual meals and special dinners.

10 guests 4 bed 4 bath 4,008 sq ft

Gulf Coast - Other | Lido Key

Starting at $540 daily

Casa Feliz Private, resort-style oceanfront home designed for luxury living in the Florida Keys.

Casa Feliz Toast marshmallows while watching sunsets over the Atlantic Ocean.

Casa Feliz Heated saltwater pool with cascading waterfalls and spa overflow design.

Casa Feliz A rare private beach retreat in the Keys.

Casa Feliz High-end chef's kitchen with induction cooktop, pizza oven, and premium coffee stations.

Casa Feliz Wake to sunrises and fall asleep to ocean breezes in this unforgettable suite.

Casa Feliz Thoughtfully designed for functionality, comfort, and luxury.

Casa Feliz Sleek countertops, premium appliances, and ample storage make cooking a joy.

10 guests 4 bed 4 bath 1,914 sq ft

The Keys - Marathon | Marathon

5.0 (22)

Guest rating

Starting at $861 daily

GAR4430 Extra large lanai overlooking the canal. Includes sparkling pool, relaxing hot tub, al fresco dining and more. Pool size: 14' x 28' x 6'

GAR4430 Beautiful 4/3 waterfront home with private pool

GAR4430 Gorgeous, bright, open, fully-equipped kitchen

GAR4430 Double suite attached bathroom with walk-in shower, soaking tub, and double vanities

GAR4430 Beautiful 4/3 waterfront home with private pool

GAR4430 Game room in garage with pool table & foosball

8 guests 4 bed 3 bath 1,940 sq ft

Gulf Coast - Charlotte Harbor | Port Charlotte

Starting at $400 daily

800 Lantana Pool, hot tub, outdoor kichen & TV

800 Lantana Stunning home a short walk to Clearwater Beach

800 Lantana Enjoy the sunset views from your private balcony

800 Lantana Beautiful living room area

800 Lantana Ground floor main kitchen with complete equipment and modern appliances

800 Lantana Pool, hot tub, outdoor kichen & TV

800 Lantana Pool, hot tub, outdoor kichen & TV

800 Lantana Pool, hot tub, outdoor kichen & TV

17 guests 4 bed 5 bath 2,663 sq ft

Gulf Coast - Clearwater Beach | Clearwater Beach

5.0 (2)

Guest rating

Starting at $357 daily

20002 Gulf Blvd, PH5 Ocean View

20002 Gulf Blvd, PH5 Incredible Sunsets!!

20002 Gulf Blvd, PH5 Kitchen

20002 Gulf Blvd, PH5 Living Room

20002 Gulf Blvd, PH5 Primary Suite King Bed with sitting chair

20002 Gulf Blvd, PH5 Enclosed Balcony with seating for 4

20002 Gulf Blvd, PH5 Beach and ocean view

20002 Gulf Blvd, PH5 Living Room

12 guests 4 bed 2 bath 2,580 sq ft

Gulf Coast - Indian Rocks Beach | Indian Rocks Beach

4.5 (6)

Guest rating

Starting at $375 daily

The Pearl on the Bay - 1370 Step into serenity as you dip into your private waterfront pool—palm trees swaying, spa bubbles rising, and the waterway sparkling just beyond.

The Pearl on the Bay - 1370 Water everywhere you look—this is life at the edge of paradise, nestled in San Remo's most exclusive corner.

The Pearl on the Bay - 1370 Bird's eye of The Pearl on the Bay—your private retreat framed by tropical palms, with direct access to the shimmering intracoastal.

The Pearl on the Bay - 1370 Feel the warmth of the setting sun reflect off the still waters as you float in the private pool, where the bay stretches endlessly beyond—pure serenity with a golden-hour glow.

The Pearl on the Bay - 1370 Sink into the patio lounge as the fire pit flickers, the pool glistens, and the sun melts into the bay—this is your front-row seat to paradise.

The Pearl on the Bay - 1370 Float above it all—your private dock, shimmering pool, and elegant waterfront home await, nestled perfectly on the edge of the bay.

The Pearl on the Bay - 1370 Second floor balcony where lounge chairs line the sun-drenched deck, your favorite drink in hand and not a care in the world.

The Pearl on the Bay - 1370 Gaze down on your private slice of Siesta Key paradise—where the elegant bayfront home, sparkling pool, and tranquil waters come together in one unforgettable view.

8 guests 4 bed 4 bath 3,506 sq ft

Gulf Coast - Sarasota | Sarasota

Starting at $569 daily

Boaters Paradise - 7767 Your paradise awaits! An infinity pool with baja tanning shelf and water chaise lounges. Al fresco outdoor dining, patio chaise lounges, and a lanai lounge completes your escape!

Boaters Paradise - 7767 Location! The canal leads right into Little Sarasota Bay.

Boaters Paradise - 7767 The aerial view. Glistening pool and patio overlooks the canal.

Boaters Paradise - 7767 Ahh... Everything you could want right in your backyard!

Boaters Paradise - 7767 The outdoor lounge - pure CHILAXIFICATION!

Boaters Paradise - 7767 Your Pitmaster's Paradise. Complete with an outdoor television and wine fridge to keep your beverages frosty!

Boaters Paradise - 7767 Kayaks at your disposal for exploring the canal and beyond.

Boaters Paradise - 7767 Hello to your vacation escape.

8 guests 4 bed 3 bath 2,776 sq ft

Gulf Coast - Sarasota | Sarasota

Starting at $378 daily

Tidal Wave Splash, soak, and sunbathe—the pool is ready whenever you are.

Tidal Wave Just two blocks from the beach, your group getaway is perfectly placed.

Tidal Wave Aerial view reveals your spacious island oasis tucked in the heart of Siesta Key.

Tidal Wave The private backyard is your group's go-to for downtime and BBQs.

Tidal Wave Late-night swims? Morning coffee by the pool? It's all yours.

Tidal Wave Low Tide screened lanai. Step onto the lanai and let the island rhythm slow you down.

Tidal Wave High Tide screened balcony.

Tidal Wave Siesta Beach, palm-lined streets, and island charm stretch out around you.

12 guests 4 bed 4 bath 1,920 sq ft

Gulf Coast - Siesta Key | Sarasota

Starting at $356 daily

Wade n Sea - 329 Bistro lights glow above the water as palm trees light up your private paradise.

Wade n Sea - 329 Just 0.3 miles from Siesta Beach—start your days in soft white sand, end them with dolphins dancing by the dock.

Wade n Sea - 329 Tucked into a quiet Siesta Key cul-de-sac, this is your hidden haven between the Village, the beach, and the bay.

Wade n Sea - 329 Your waterfront escape—this is Siesta Key living at its finest.

Wade n Sea - 329 This dock is your front-row seat to the water.

Wade n Sea - 329 When the sun goes down, the magic turns up—swim under the stars surrounded by glowing palms and twinkling lights.

Wade n Sea - 329 NFL Sunday, sea breezes, and zero bugs—this screened lanai takes lounging to legendary levels.

Wade n Sea - 329 Tie up the paddleboard or drop a line—your dockside perch glows with fish and Florida magic after dark.

6 guests 3 bed 2 bath 1,664 sq ft

Gulf Coast - Siesta Key | Siesta Key

Starting at $330 daily

HZL17163 Gorgeous 3 bedroom, 2 bathroom waterfront home with private pool

HZL17163 Beautiful, bright, open living space

HZL17163 Bright, open, fully-equipped kitchen

HZL17163 Sparkling pool overlooking canal.

HZL17163 Don't forget your boat! Dock size: 34' x 8'. Dock has electricity and water (No boat lift)

HZL17163 Beautiful primary bedroom with king bed, attached bathroom, lanai access and 75-inch Smart TV

HZL17163 Welcoming foyer

HZL17163 Living room overlooking the sparkling pool and canal beyond. Living room features lots of comfy seating and 75-inch Smart TV

6 guests 3 bed 2 bath 2,100 sq ft

Gulf Coast - Charlotte Harbor | Port Charlotte

Starting at $350 daily

The River View 1008

The River View 1008

The River View 1008

The River View 1008

The River View 1008

The River View 1008

The River View 1008

The River View 1008

8 guests 4 bed 3 bath 2,700 sq ft

Gulf Coast - Cape Coral | Cape Coral

Starting at $338 daily

ANC311 Living Room outdoor view

ANC311 Olympic-size Pool

ANC311 Primary Bedroom/King Bed
50" TV / DVD Player/Balcony access

ANC311 View From Beach

ANC311 Living Room With 75" Smart TV

ANC311 Living Room

ANC311 Living Room

8 guests 3 bed 2 bath 2,400 sq ft

Gulf Coast - Siesta Key | Siesta Key

Starting at $340 daily

ANC611 Pool Table

ANC611 Living Room (Angle)

ANC611 Olympic-size Pool

ANC611 Breakfast Bar

ANC611 Master Bedroom
King Bed
32" Smart TV

ANC611 View From Beach

ANC611 Living Room
50" Smart TV

ANC611 Living Room (Angle 2)

6 guests 3 bed 3 bath 2,400 sq ft

Gulf Coast - Siesta Key | Siesta Key

Starting at $350 daily

GA1978 Our Canal Front House offers a fantastic location to the Harbor and thoughtful touches to make your vacation one to remember!

GA1978 A comfortable living room to relax

GA1978 Gorgeous kitchen with plenty of space to prepare any meal

GA1978 Our Canal Front House offers a fantastic location to the Harbor and thoughtful touches to make your vacation one to remember!

GA1978 Our Canal Front House offers a fantastic location to the Harbor and thoughtful touches to make your vacation one to remember!

GA1978 Our Canal Front House offers a fantastic location to the Harbor and thoughtful touches to make your vacation one to remember!

GA1978 A comfortable living room to relax

GA1978 A comfortable living room to relax

8 guests 3 bed 3 bath 2,913 sq ft

Gulf Coast - Other | Englewood

Starting at $345 daily

22 Laurel SUNNY ORANGE STAYS presents… 🌴 Island Time ➠ 22 Laurel

22 Laurel Indoor/Outdoor Bar – A unique kitchen pass-through window with seating for 10—perfect for serving drinks and snacks poolside.

22 Laurel Resort-Style Pool Area – Private heated pool (fee applies) with a covered cabana and outdoor TV.

22 Laurel Quiet Location – Situated in a quiet residential neighborhood on the north end of Clearwater beach.

22 Laurel Steps to the Beach – Walk to the uncrowded North Beach sands in 1-2 minutes.

22 Laurel Massive Parking – Rare private driveway space for 6–7 vehicles.

22 Laurel Private backyard retreat featuring a sparkling pool, cabana, and plenty of space to unwind.

22 Laurel Resort-Style Pool Area – Private heated pool (fee applies) with a covered cabana and outdoor TV.

16 guests 6 bed 4 bath 1,976 sq ft

Gulf Coast - Clearwater Beach | Clearwater Beach

4.9 (26)

Guest rating

Starting at $595 daily

770 Mandalay SUNNY ORANGE STAYS presents… 🌴 Summer Breeze ➠ 770 Mandalay

770 Mandalay 100 Steps to the Beach – Just a 1.5-minute walk to the sugar-white sands of Clearwater Beach.

770 Mandalay Outdoor Tiki Bar – A fun, tropical spot by the pool to serve drinks and hang out.

770 Mandalay Massive Capacity – Sleeps up to 20 guests comfortably with 7 bedrooms and multiple living spaces.

770 Mandalay Single-Level Living – No stairs to navigate, making it perfect for multi-generational families and guests with mobility concerns.

770 Mandalay Cooking for an Army – Equipped with Dual Prep Areas and 3-door full-size fridge to cook for the whole crowd with ease.

770 Mandalay Dining Space for Group Meals

770 Mandalay Comfortable Bedrooms for All

20 guests 7 bed 3 bath 2,500 sq ft

Gulf Coast - Clearwater Beach | Clearwater Beach

4.9 (32)

Guest rating

Starting at $727 daily

TED333 Welcome to Champagne Sunset. Relax, unwind, and enjoy

TED333 Gorgeous, open living space overlooking private pool, canal, and nature preserve beyond. Living room features lots of comfy seating and 70-inch Smart TV

TED333 Beautiful, bright, open, fully-equipped kitchen

TED333 Large primary bedroom with king bed, en suite, lanai access, and 55-inch Roku TV

TED333 14' x 6'. Dock with underwater fish lights (Boat lift not available)

TED333 Welcoming foyer

TED333 Welcoming foyer

TED333 Gorgeous, open living space overlooking private pool, canal, and nature preserve beyond. Living room features lots of comfy seating and 70-inch Smart TV

6 guests 3 bed 3 bath 2,570 sq ft

Gulf Coast - Charlotte Harbor | Punta Gorda

Starting at $400 daily

Tamiami Vice - 2327 As night falls, the heart of Tamiami Vice comes alive — the glow of the pool shimmers like liquid sapphire.

Tamiami Vice - 2327 Caught from a dreamy angle, the evening light dances across the pool's surface as the sleek architecture of Tamiami Vice stretches out before you.

Tamiami Vice - 2327 Every light, every line, every palm-framed detail whispers luxury and invites you to step into your own private paradise under the stars.

Tamiami Vice - 2327 Slip into the soothing warmth of the heated pool.

Tamiami Vice - 2327 Sink into serenity as the glowing pool stretches out before you, flanked by perfectly placed chaise lounges made for stargazing or a quiet glass of wine.

Tamiami Vice - 2327 From above, soak in the privacy and elegance of your tropical retreat — a stunning oasis nestled perfectly for sun-soaked days and starlit nights.

Tamiami Vice - 2327 Breathe in the salty air and soft twilight hues.

Tamiami Vice - 2327 Step inside and feel the calm wash over you — light pours in from every angle, bouncing off sleek finishes and plush furnishings.

10 guests 6 bed 7 bath 3,364 sq ft

Gulf Coast - Sarasota | Sarasota

Starting at $540 daily

MAN8035 Sparkling pool overlooking Lemon Bay

MAN8035 Large, open living space with ample seating, fireplace and 70-inch Smart TV

MAN8035 Large boat dock with power and fish lights (Boat lift is not for guest use.)

MAN8035 Gorgeous, fully-equipped kitchen features high-end stainless-steel appliances, and plenty of storage and counter top space

MAN8035 Stunning 5/4 waterfront home with private pool and beach access on Manasota Key island in Englewood, FL

MAN8035 Lemon Bay & Manasota Key Beach

MAN8035 Large, open living space with ample seating, fireplace and 70-inch Smart TV

MAN8035 Large, open living space with ample seating, fireplace and 70-inch Smart TV

12 guests 4 bed 4 bath 4,560 sq ft

Gulf Coast - Other | Englewood

Starting at $450 daily

806 Lantana Your private backyard oasis features resort-style amenities perfect for relaxing and entertaining.

806 Lantana This spacious coastal home combines luxury, comfort, and resort-style amenities just minutes from the beach.

806 Lantana The fully renovated kitchen offers ample space for preparing meals for large groups.

806 Lantana Designed with comfort in mind, the spacious living room is perfect for movie nights and family time.

806 Lantana Located in a quiet neighborhood just a short walk from the white sands of North Clearwater Beach.

806 Lantana Spend your days lounging poolside and your evenings creating memories with family and friends.

806 Lantana Enjoy easy access to one of Florida's most beautiful beaches while retreating to your private oasis.

806 Lantana Enjoy the perfect blend of privacy and fun in this spacious outdoor retreat.

22 guests 4 bed 4 bath

Gulf Coast - Clearwater Beach | Clearwater Beach

Starting at $100 daily

RVH_254ER Reunion Manor

RVH_254ER Reunion Manor

RVH_254ER Reunion Manor

RVH_254ER Reunion Manor

RVH_254ER Reunion Manor

RVH_254ER Reunion Manor

RVH_254ER Reunion Manor

RVH_254ER Reunion Manor

20 guests 8 bed 5 bath 5,707 sq ft

Orlando - Reunion Resort | Kissimmee

Reunion Membership Recommended Rental Flex30

4.7 (7)

Guest rating

Starting at $899 daily

Starfish Bungalow Behold your entire Longboat Key compound illuminated by the twilight glow, ready to host your group vacation in style.

Starfish Bungalow A truly short walk separates your party from the peaceful, pristine sands of the Gulf, offering the ultimate Longboat Key convenience.

Starfish Bungalow This high view shows the full scope of your private Duplex rental, offering expansive space within the serene Longboat Key community.

Starfish Bungalow Take advantage of the Cedars East pool access for the entire group, ensuring plenty of space for everyone to swim and socialize.

Starfish Bungalow Easily keep up with your fitness routine on the modern cardio equipment inside the exclusive, air-conditioned Cedars East Club gym.

Starfish Bungalow Ready for a bit of competitive fun? Enjoy a spirited match on the Har-Tru courts at the Cedars Club, available just minutes from your door.

Starfish Bungalow Enjoy the ultimate luxury of uncrowded paradise as you stroll along the pristine, wide-open stretch of Longboat Key.

Starfish Bungalow Enjoy the exclusive curb appeal of the entire building, designed to be the perfect, laid-back backdrop for your family reunion.

12 guests 4 bed 3 bath 1,792 sq ft

Gulf Coast - Other | Longboat Key

Starting at $329 daily

RVH_1392ER Whitemarsh Elegance

RVH_1392ER Whitemarsh Elegance

RVH_1392ER Whitemarsh Elegance

RVH_1392ER Whitemarsh Elegance

RVH_1392ER Whitemarsh Elegance

RVH_1392ER Whitemarsh Elegance

RVH_1392ER Whitemarsh Elegance

RVH_1392ER Whitemarsh Elegance - clubs are not provided

22 guests 9 bed 9 bath 5,154 sq ft

Orlando - Reunion Resort | Kissimmee

Reunion Membership Recommended Rental Flex30

Starting at $569 daily

SO_960AR Solara Luxury

SO_960AR Solara Luxury

SO_960AR Solara Luxury

SO_960AR Solara Luxury

SO_960AR Solara Luxury

SO_960AR Solara Luxury

SO_960AR Solara Luxury Tiki bar!

SO_960AR Solara Luxury

13 guests 5 bed 6 bath 3,410 sq ft

Orlando - Solara Resort | Kissimmee

Recommended Rental Flex30

4.8 (12)

Guest rating

Starting at $205 daily

1 2 3 4 5 13