Luxury Florida Vacation Homes

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676 Mandalay 111 Sugar Sand Sanctuary condominium features a prime location: Steps away to Clearwater beach!

676 Mandalay 111 Lounge in the spacious living room that features 2 huge couches, a smart tv, and a lot of natural light.

676 Mandalay 111 Bedroom 1 - Queen sized bed

676 Mandalay 111 Sugar Sand Sanctuary condominium features a prime location: Steps away to Clearwater beach!

676 Mandalay 111 Enjoy your meals in this spacious and cozy dining area that comfortably sits 4.

676 Mandalay 111 Lounge in the spacious living room that features 2 huge couches, a smart tv, and a lot of natural light.

676 Mandalay 111 Lounge in the spacious living room that features 2 huge couches, a smart tv, and a lot of natural light.

676 Mandalay 111 Lounge in the spacious living room that features 2 huge couches, a smart tv, and a lot of natural light.

4 guests 2 bed 2 bath 923 sq ft

Gulf Coast - Clearwater Beach | Clearwater Beach

5.0 (3)

Guest rating

Starting at $238 daily

1015 Eldorado SUNNY ORANGE STAYS presents… 🌊 Sweet Escape ➠ 1015

1015 Eldorado With floor-to-ceiling windows showcasing Gulf views, a private elevator serving all three floors, and dedicated office space

1015 Eldorado Designed specifically for extended stays, this expansive 4,998 sq. ft. residence offers the ultimate "work from paradise" or winter retreat experience.

1015 Eldorado Stunning Gulf Views – Enjoy daily sunsets from the floor-to-ceiling windows on the 2nd and 3rd floors.

1015 Eldorado Unlike typical week-long rentals, this kitchen is built for daily life.

1015 Eldorado Monthly Executive Rental – Exclusively available for stays of 27+ nights —perfect for snowbirds or corporate relocations.

1015 Eldorado Carlouel Neighborhood: Located in the prestigious North Beach residential enclave, away from the heavy tourist foot traffic.

1015 Eldorado Expansive 5BR/5BA Layout – Nearly 5,000 sq ft of living space allows large groups to spread out comfortably.

12 guests 5 bed 5 bath 4,998 sq ft

Gulf Coast - Clearwater Beach | Clearwater Beach

5.0 (2)

Guest rating

Starting at $382 daily

1612 Lakeview SUNNY ORANGE STAYS presents… 🌴Sandy Retreat Pool House

1612 Lakeview Relax in paradise at this spacious Clearwater home

1612 Lakeview Private Swimming Pool – Make a splash in your own backyard oasis (Note: Pool is not heated or gated).

1612 Lakeview Spacious 3BR/3BA Layout – Rare setup with a dedicated bathrooms for each room ensuring maximum comfort for the whole group.

1612 Lakeview Screened Florida Room – The ultimate hangout spot with comfortable outdoor furniture and a TV to catch the game.

1612 Lakeview Modern Interiors – Recently updated with high vaulted wood-beamed ceilings and a bright, airy feel

1612 Lakeview Relax: Settle into the spacious seating area, bust a movie on a large Smart TV and enjoy the ambiance of the indoor fireplace.

1612 Lakeview Designed for togetherness, the open-concept living area features soaring wood ceilings and abundant natural light.

6 guests 3 bed 3 bath

Gulf Coast - Other | Clearwater

5.0 (4)

Guest rating

Starting at $327 daily

ELD509 Bright, open living space

ELD509 Sparkling private pool faces west

ELD509 En suite with large walk-in shower, double vanities and soaking tub

ELD509 The best of Florida outdoor living. Lanai with outdoor kitchen overlooking the sparkling private pool and canal

ELD509 Bright, open living space. Ample seating and 50-inch Smart TV with HD antenna

ELD509 Bright, open living space

6 guests 3 bed 2 bath 1,976 sq ft

Gulf Coast - Charlotte Harbor | Punta Gorda

Starting at $250 daily

E5S831 Gorgeous, large lanai with sparkling pool overlooking the canal. Lanai also features a dining table for 6 and 32-inch Smart TV. Pool size: 22' x 8' x 6'D

E5S831 Gorgeous Englewood Waterfront Home With Private Pool

E5S831 Guest bedroom 4 features 2 twin over twon bunkbeds and 43-inch Smart TV

E5S831 Complimentary kayaks (Boat lift not available)

E5S831 Gorgeous Englewood Waterfront Home With Private Pool (Boat lift not available)

E5S831 Beautiful, fully-equipped kitchen

E5S831 BBQ grill in backyard with path leading to boat dock and canal (Boat lift not available)

E5S831 Large living room overlooking pool. Living room features comfy, ample seating and large 65-inch Smart TV

12 guests 5 bed 3 bath 2,344 sq ft

Gulf Coast - Other | Englewood

Starting at $400 daily

Palm Paradise - 156 Dive into tropical bliss with your private, palm-lined heated pool—designed for sun-soaked days and starry night dips.

Palm Paradise - 156 Overhead drone view reveals your serene island hideaway—nestled among lush greenery, just minutes from Siesta Key's iconic white sand.

Palm Paradise - 156 Soar above your private slice of paradise—this stunning aerial captures Palm Paradise nestled in lush tropical greenery, just moments from Siesta Key's world-famous white sands.

Palm Paradise - 156 Private backyard sanctuary with sparkling water, tall palms, and total seclusion.

Palm Paradise - 156 Stretch out on the chaise lounges and soak up the Florida sun as the gentle island breeze drifts across the deck.

Palm Paradise - 156 Gather for al fresco meals around the outdoor dining table, with the grill sizzling nearby and the scent of fresh barbecue mingling with the sea air.

Palm Paradise - 156 Charming island-style façade with lush tropical landscaping sets the tone for your luxurious coastal escape.

Palm Paradise - 156 Welcoming front entrance hints at the relaxing, light-filled spaces waiting just beyond the door.

10 guests 5 bed 3 bath 2,901 sq ft

Gulf Coast - Sarasota | Sarasota

Starting at $240 daily

Key Life Living Unwind in your own sparkling pool, surrounded by a sun-soaked patio made for family fun or quiet relaxation.

Key Life Living Follow the sunlit path from your private retreat down to soft sands and sparkling waves.

Key Life Living See your entire private retreat from above, where pool, patio, and bright coastal spaces come together beautifully.

Key Life Living Soak in the evening atmosphere where family-friendly spaces meet tranquil twilight charm.

Key Life Living Step into the crystal-clear pool for refreshing dips in a tranquil, exclusive setting.

Key Life Living Key Life Beach, the left side of this duplex.

Key Life Living Step up to a welcoming entrance where coastal charm and bright, open-air vibes invite you inside.

Key Life Living Breathe in the open, sunlit living space where comfort meets coastal style.

12 guests 4 bed 4 bath 2,280 sq ft

Gulf Coast - Siesta Key | Siesta Key

Starting at $310 daily

Casa Del Mar - 5079 Screened-In Pool at twilight.

Casa Del Mar - 5079 Screened-In Pool & Outdoor Patio looking back to home.

Casa Del Mar - 5079 Screened-In Pool

Casa Del Mar - 5079 Screened in Outdoor Sitting Area. Raise Lanai and the bank of chaise lounges.

Casa Del Mar - 5079 Poolside Lanai Dining Area with lounge.

Casa Del Mar - 5079 Front View with ample off street driveway parking.

Casa Del Mar - 5079 Living Room

Casa Del Mar - 5079 Living Room with french doors to patio.

8 guests 3 bed 2 bath 1,770 sq ft

Gulf Coast - Sarasota | Siesta Key

Starting at $257 daily

1465 Satsuma St

1465 Satsuma St

1465 Satsuma St

1465 Satsuma St

1465 Satsuma St

1465 Satsuma St

1465 Satsuma St

1465 Satsuma St

10 guests 4 bed 2 bath 1,958 sq ft

Gulf Coast - Other | Clearwater

4.9 (8)

Guest rating

Starting at $300 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 - Holmes Beach | Holmes Beach

Recommended Rental Flex30

Starting at $439 daily

2631 Cedarglen Drive Bird's Eye View

2631 Cedarglen Drive Kitchen with Island

2631 Cedarglen Drive Living Room

2631 Cedarglen Drive Indoor/Outdoor patio from Primary Bedroom

2631 Cedarglen Drive Game Room with 2 arcade games and a sofa sleeper.

2631 Cedarglen Drive Coffee Bar

2631 Cedarglen Drive Pool

2631 Cedarglen Drive Game room featuring arcade games such as Pac Man, Mrs. Pac Man and more. This room also has a sofa sleeper

10 guests 3 bed 3 bath 1,783 sq ft

Gulf Coast - Other | Dunedin

5.0 (2)

Guest rating

Starting at $215 daily

MER50-7 Beautiful 3 bedroom / 2 bathroom condo on Manasota Key

MER50-7 Large balcony overlooking the beach & Gulf of Mexico. Balcony also features two dining tables seating 8 total.

MER50-7 Beautiful, Bright, Open Living Space

MER50-7 Community Pool

MER50-7 Manasota Key

MER50-7 Primary Bedroom With King Bed, attached bathroom, 50-inch Smart TV, and balcony access

MER50-7 Fully Equipment Kitchen

MER50-7 Beautiful, Bright, Open Living Space

8 guests 3 bed 3 bath 1,737 sq ft

Gulf Coast - Other | Manasota Key

Starting at $347 daily

Wischis Florida Home - The Ranch Wischis Florida Home - The Ranch

Wischis Florida Home - The Ranch Wischis Florida Home - The Ranch

Wischis Florida Home - The Ranch Wischis Florida Home - The Ranch

Wischis Florida Home - The Ranch Wischis Florida Home - The Ranch

Wischis Florida Home - The Ranch

Wischis Florida Home - The Ranch Wischis Florida Home - The Ranch

Wischis Florida Home - The Ranch Wischis Florida Home - The Ranch

Wischis Florida Home - The Ranch Wischis Florida Home - The Ranch

12 guests 6 bed 4 bath 6,000 sq ft

Gulf Coast - Cape Coral | Cape Coral

Starting at $150 daily

Lazy Lagoon 1010

Lazy Lagoon 1010

Lazy Lagoon 1010

Lazy Lagoon 1010

Lazy Lagoon 1010

Lazy Lagoon 1010

Lazy Lagoon 1010

Lazy Lagoon 1010

6 guests 3 bed 2 bath 1,700 sq ft

Gulf Coast - Cape Coral | Cape Coral

Starting at $125 daily

Palm Villa 1009

Palm Villa 1009

Palm Villa 1009

Palm Villa 1009

Palm Villa 1009

Palm Villa 1009

Palm Villa 1009

Palm Villa 1009

8 guests 4 bed 4 bath 3,500 sq ft

Gulf Coast - Cape Coral | Cape Coral

Starting at $308 daily

ANC605 Living Room
65" Smart TV

ANC605 Olympic-size Pool

ANC605 updated, fully-equipped kitchen

ANC605 Master Bedroom
King Bed
55" Smart TV
Attached Bathroom
Balcony Access

ANC605 View From Beach

ANC605 Living Room (Angle)

ANC605 Open floor plan

ANC605 Living Room (Angle 3)

6 guests 2 bed 2 bath 1,250 sq ft

Gulf Coast - Siesta Key | Siesta Key

Starting at $202 daily

ANC506 Living Room with view of intracoastal

ANC506 Outdoor dining

ANC506 full-equipped kitchen

ANC506 Olympic-size heated pool

ANC506 Plenty of seating for everyone

ANC506 Living room with sofa bed

ANC506 Open living space

6 guests 2 bed 2 bath 1,250 sq ft

Gulf Coast - Siesta Key | Siesta Key

Starting at $233 daily

ANC601 Living Room
55" Smart TV

ANC601 Olympic-size Pool

ANC601 Master Bedroom
King Bed
42" TV

ANC601 Living Room (Angle)

ANC601 View From Beach

ANC601 Living Room (Angle 2)

ANC601 Living Room (Angle 3)

6 guests 2 bed 2 bath 1,250 sq ft

Gulf Coast - Siesta Key | Siesta Key

Starting at $202 daily

ANC606 Dining Room (Angle)

ANC606 Olympic-size Pool

ANC606 View From Beach

ANC606 Master Bedroom

ANC606 Bedroom 2

ANC606 Kitchen (Angle)

ANC606 Living Room

ANC606 Living Room (Angle)

6 guests 2 bed 2 bath 1,250 sq ft

Gulf Coast - Siesta Key | Siesta Key

Starting at $202 daily

ANC707 Dining Area (Angle)

ANC707 Olympic-size Pool

ANC707 Master Bedroom
One King Bed
43" Smart TV

ANC707 Bedroom 2
Two Queen Beds
32" TV

ANC707 Siesta Key

ANC707 Living Room (Angle)

ANC707 Living Room / 55" Smart TV

ANC707 Living Room (Angle 2)

6 guests 2 bed 2 bath 1,250 sq ft

Gulf Coast - Siesta Key | Siesta Key

Starting at $212 daily

ANC709 Bright, open living space overlooking the Intracoastal Waterway with ample seating and 75-inch Smart TV. Dining Table seats 6

ANC709 Olympic-size Pool

ANC709 Bright, open living space overlooking the Intracoastal Waterway with ample seating and 75-inch Smart TV. Dining Table seats 6

ANC709 Balcony off of living room

ANC709 The Anchorage on Siesta Key

ANC709 Bright, open living space overlooking the Intracoastal Waterway with ample seating and 75-inch Smart TV. Dining Table seats 6

ANC709 Bright, open living space overlooking the Intracoastal Waterway with ample seating and 75-inch Smart TV. Dining Table seats 6

ANC709 Fully-equipped kitchen

6 guests 2 bed 2 bath 1,250 sq ft

Gulf Coast - Siesta Key | Siesta Key

Starting at $212 daily

ANC805 Beautiful 2 bedroom, 2 bathroom condo on Siesta Key Island

ANC805 Olympic-size Pool

ANC805 Beautifully updated, fully-equipped kitchen overlooking living room/dining room

ANC805 Primary bedroom with king bed, desk, en suite, balcony access, and 43-inch Smart TV

ANC805 Siesta Key

ANC805 Bright, open living space

ANC805 Bright, open living space

ANC805 Bright, open living space. Living room features 65-inch Smart TV.

6 guests 2 bed 2 bath 1,250 sq ft

Gulf Coast - Siesta Key | Siesta Key

Starting at $226 daily

CBS 104 Heated Courtyard Pool — a warm, relaxing haven open year-round.

CBS 104 Relax in the comfortable living area with a Smart TV, plush seating, and a coastal feel that brings the Clearwater Beach experience indoors.

CBS 104 Primary Bedroom: A serene sanctuary featuring a King-sized bed, smart TV and a ceiling fan.

CBS 104 Cheerful dining space with seating for four, perfect for enjoying a morning coffee or sharing a meal after a day in the sun.

CBS 104 Relax in the comfortable living area with a Smart TV, plush seating, and a coastal feel that brings the Clearwater Beach experience indoors.

CBS 104 Clean and bright full bathroom with a fresh, coastal feel, providing a convenient space to get ready for a day at the beach or freshen up after enjoying the sand and surf.

CBS 104 Comfortable bedroom featuring a cozy bed, soft coastal-inspired bedding, a Smart TV, and plenty of natural light.

CBS 104 Our living room features a sofa bed and smart tv, perfect for unwinding.

4 guests 1 bed 1 bath 512 sq ft

Gulf Coast - Clearwater Beach | Clearwater Beach

4.9 (7)

Guest rating

Starting at $165 daily

ANC902 View From Beach

ANC902 Balcony View

ANC902 Olympic-size Pool

ANC902 Breakfast Bar

ANC902 Bedroom #1 Angle
King Bed
36" TV

ANC902 Living Room

ANC902 Living Room Angle
42" Smart TV

ANC902 Living Room Angle

4 guests 2 bed 2 bath 1,250 sq ft

Gulf Coast - Siesta Key | Siesta Key

Starting at $206 daily

ANC-PH8 Sunset view from balcony

ANC-PH8 Living room

ANC-PH8 Primary bedroom with attached bathroom and balcony access

ANC-PH8 The Anchorage on Siesta Key

ANC-PH8 Resort amenities

ANC-PH8 Bright, open living area with balcony access and water view

ANC-PH8 Living room

ANC-PH8 2 bedroom, 2 bathroom condo on Siesta Key

6 guests 2 bed 2 bath 1,250 sq ft

Gulf Coast - Siesta Key | Siesta Key

Starting at $226 daily

CS2115 Gorgeous 3 bedroom, 2 bathroom waterfront home in Punta Gorda with private pool and boat dock

CS2115 Family Room just off the kitchen with cofy sectional sofa and 65" Smart TV

CS2115 Bright, open living space overlooking the pool and canal beyond

CS2115 Primary bedroom with king bed, en suite, lanai access and 58" TV

CS2115 Pool overlooking the canal. Pool size: 27' x 14' 5'

CS2115 Lanai BBQ grill and bar seating. Pool size: 27' x 14' 5'

CS2115 Patch leading to canal and boat dock (boat lift is not for guest use)

CS2115 Formal living room overlooking the sparkling pool and canal beyond

6 guests 3 bed 2 bath 2,092 sq ft

Gulf Coast - Charlotte Harbor | Punta Gorda

Starting at $250 daily

LPC1140 (Boat lift not available)

6 guests 3 bed 3 bath 2,207 sq ft

Gulf Coast - Charlotte Harbor | Punta Gorda

Starting at $250 daily

NPL829 Private Pool/Spa on canal (Boat lift not available)

NPL829 Living room

NPL829 Dining area on Lanai

NPL829 Tiki Bar

NPL829 Poolside patio

NPL829 Breakfast area

NPL829 Gorgeous landscaping

8 guests 3 bed 2 bath 1,599 sq ft

Gulf Coast - Charlotte Harbor | Punta Gorda

Starting at $225 daily

AA15432 Beautiful South Gulf Cove home with private pool, hot tub, and canal access

AA15432 Outdoor dining on the lanai overlooking the sparkling pool & canal

AA15432 Relax on the comfortable sofas in the living room, overlooking the pool and canal
Living Room TV 65'

AA15432 Primary bedroom with king bed, ensuite and lanai access

AA15432 Beautiful South Gulf Cove home with private pool, hot tub, and canal access (Boat lift not available)

AA15432 Formal living room & foyer

AA15432 Formal living room

AA15432 Dining room overlooking pool

11 guests 4 bed 3 bath 2,700 sq ft

Gulf Coast - Charlotte Harbor | Port Charlotte

Starting at $356 daily

BLC200 The Canal House of Punta Gorda Isles offers a fantastic location to the Harbor and thoughtful touches to make your vacation one to remember!

BLC200 The perfect place to spend the day (Boat lift not available)

BLC200 Spacious backyard leading to the boat dock. Dock size 6' x 30' (Boat lift not available)

BLC200 Comfortable living room to relax

BLC200 King master bedroom with ensuite

BLC200 Cozy family room

BLC200 Cozy up in the comfortable family room space

BLC200 Comfortable living room to relax

8 guests 3 bed 2 bath 1,808 sq ft

Gulf Coast - Charlotte Harbor | Punta Gorda

Starting at $250 daily

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